Skip to main content

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 101))

Abstract

In recent decades, annonaceous acetogenins have become highly studied plant secondary metabolites in terms of their isolation, structure elucidation, synthesis, biological evaluation, mechanism of action, and toxicity. The aim of the present contribution is to summarize chemical and biological reports published since 1997 on annonaceous acetogenins and synthetic acetogenin mimics. The compounds are considered biologically in terms of their cytotoxicity for cancer cell lines, neurotoxicity, pesticidal effects, and miscellaneous activities.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Jolad SD, Hoffmann JJ, Schram KH, Cole JR, Tempesta MS, Kreik GR, Bates RB (1982) Uvaricin, a new antitumor agent from Uvaria acuminata (Annonaceae). J Org Chem 47:3151

    Article  Google Scholar 

  2. Cavé A, Figadère B, Laurens A, Cortes D (1997) Acetogenins from Annonaceae. Prog Chem Org Nat Prod 70:81

    Google Scholar 

  3. Hollerhage M, Matusch A, Champy P, Lombes A, Ruberg M, Oertel WH, Hoglinger GU (2009) Natural lipophilic inhibitors of mitochondrial complex I are candidate toxins for sporadic neurodegenerative tau pathologies. Exp Neurol 220:133

    Article  CAS  Google Scholar 

  4. Londershausen M, Leicht W, Lieb F, Moeschler H, Weiss H (1991) Molecular mode of action of annonins. Pestic Sci 33:427

    Article  CAS  Google Scholar 

  5. Gu ZM, Fang XP, Miesbauer LR, Smith DL, McLaughlin JL (1993) 30-, 31-, and 32-Hydroxybullatacinones: bioactive terminally hydroxylated annonaceous acetogenins from Annona bullata. J Nat Prod 56:870

    Article  CAS  Google Scholar 

  6. Gu ZM, Fang XP, Rieser MJ, Hui YH, Miesbauer LR, Smith DL, Wood KV, McLaughlin JL (1993) New cytotoxic annonaceous acetogenins: bullatanocin and cis- and trans-bullatanocinone, from Annona bullata (Annonaceae). Tetrahedron 49:747

    Article  CAS  Google Scholar 

  7. Gu ZM, Fang XP, Zeng L, Wood KV, McLaughlin JL (1993) Bullacin: a new cytotoxic annonaceous acetogenin from Annona bullata. Heterocycles 36:2221

    Article  CAS  Google Scholar 

  8. Zafra-Polo MC, Figadère B, Gallardo T, Tormo JR, Cortes D (1998) Natural acetogenins from Annonaceae, synthesis and mechanisms of action. Phytochemistry 48:1087

    Article  CAS  Google Scholar 

  9. Duret P, Laurens A, Hocquemiller R, Cortes D, Cavé A (1994) Acetogenins of Annonaceae. 34. Isoacetogenins, artifacts issued from translactonization from annonaceous acetogenins. Heterocycles 39:741

    Article  CAS  Google Scholar 

  10. Duret P, Fagadère B, Hocquemiller R, Cavé A (1997) Epimerization of annonaceous acetogenins under basic conditions. Tetrahedron Lett 38:8849

    Article  CAS  Google Scholar 

  11. Colman-Saizarbitoria T, Johnson HA, Alali FQ, Hopp DC, Rogers LL, McLaughlin JL (1998) Annojahnin from Annona jahnii: a possible precursor of mono-tetrahydrofuran acetogenins. Phytochemistry 49:1609

    Article  CAS  Google Scholar 

  12. Colman-Saizarbitoria T, Liu X, Hopp DC, Johnson HA, Alali FQ, Rogers LL, McLaughlin JL (1999) Annodienin and jahnonacin: new bioactive nontetrahydrofuran annonaceous acetogenins from the twigs of Annona jahnii. Nat Prod Lett 14:65

    Article  CAS  Google Scholar 

  13. Gleye C, Raynaud S, Hocquemiller R, Laurens A, Fourneau C, Serani L, Laprevote O, Roblot F, Leboeuf M, Fournet A, de Arias AR, Figadère B, Cavé A (1998) Acetogenins of Annonaceae: part 67. Muricadienin, muridienins and chatenaytrienins, the early precursors of annonaceous acetogenins. Phytochemistry 47:749

    Article  CAS  Google Scholar 

  14. Wong HF, Brown GD (2002) β-Methoxy-γ-methylene-α,β-unsaturated-γ-butyrolactones from Artabotrys hexapetalus. Phytochemistry 59:99

    Article  CAS  Google Scholar 

  15. Wongsa N, Kanokmedhakul S, Kanokmedhakul K (2011) Cananginones A-I, linear acetogenins from the stem bark of Cananga latifolia. Phytochemistry 72:1859

    Article  CAS  Google Scholar 

  16. Sinz A, Matusch R, Kaempchen T, Fiedler W, Schmidt J, Santisuk T, Wangcharoentrakul S, Chaichana S, Reutrakul V (1998) Novel acetogenins from the leaves of Dasymaschalon sootepense. Helv Chim Acta 81:1608

    Article  CAS  Google Scholar 

  17. Ee GCL, Chuah CH, Sha CK, Goh SH (1996) Disepalin, a new acetogenin from Disepalum anomalum (Annonaceae). J Nat Prod 9:141

    CAS  Google Scholar 

  18. Eparvier V, van Nguyen H, Thoison O, Martin MT, Sévenet T, Guéritte F (2006) Cytotoxic monotetrahydrofuran acetogenins from Disepalum plagioneurum. J Nat Prod 69:1289

    Article  CAS  Google Scholar 

  19. Jiang Z, Chen Y, Chen RY, Yu DQ (1997) Mono-tetrahydrofuran ring acetogenins from Goniothalamus donnaiensis. Phytochemistry 46:327

    Article  CAS  Google Scholar 

  20. Jiang Z, Yu DQ (1997) New type of mono-tetrahydrofuran ring acetogenins from Goniothalamus donnaiensis. J Nat Prod 60:122

    Article  CAS  Google Scholar 

  21. Jiang Z, Yu DQ (1997) Donhexocin, a new non-tetrahydrofuran acetogenin from Goniothalamus donnaiensis. Chin Chem Lett 8:233

    CAS  Google Scholar 

  22. Tantithanaporn S, Wattanapiromsakul C, Itharat A, Keawpradub N (2011) Cytotoxic activity of acetogenins and styryl lactones isolated from Goniothalamus undulatus Ridl. root extracts against a lung cancer cell line (COR-L23). Phytomedicine 18:486

    Article  CAS  Google Scholar 

  23. Li C, Lee D, Graf TN, Phifer SS, Nakanishi Y, Riswan S, Setyowati FM, Saribi AM, Soejarto DD, Farnsworth NR, Falkinham JO III, Kroll DJ, Kinghorn AD, Wani MC, Oberlies NH (2009) Bioactive constituents of the stem bark of Mitrephora glabra. J Nat Prod 72:1949

    Article  CAS  Google Scholar 

  24. Zhang Q, Di YT, He H-P, Li S-L, Hao X-J (2010) Mitregenin, a new annonaceous acetogenin from Mitrephora maingayi. Nat Prod Commun 5:1793

    CAS  Google Scholar 

  25. Sung’hwa F, Mgina CA, Jonker SA, Nkunya MHH, Waibel R, Achenbach H (1999) Constituents of tropical medicinal plants. Part 88. Ophrypetalin and other annonaceous acetogenins from Ophrypetalum odoratum. Nat Prod Lett 13:195

    Article  Google Scholar 

  26. Panthama N, Kanokmedhakul S, Kanokmedhakul K (2010) Polyacetylenes from the roots of Polyalthia debilis. J Nat Prod 73:1366

    Article  CAS  Google Scholar 

  27. Fevrier A, Ferreira ME, Fournet A, Yaluff G, Inchausti A, Rojas de Arias A, Hocquemiller R, Waechter AI (1999) Acetogenins and other compounds from Rollinia emarginata and their antiprotozoal activities. Planta Med 65:47

    Article  CAS  Google Scholar 

  28. Wang ML, Du J, Zhang PC, Chen RY, Xie FZ, Zhao B, Yu DQ (2002) Saccopetrins A and B, two novel γ-lactones from Saccopetalum prolificum. Planta Med 68:719

    Article  CAS  Google Scholar 

  29. Qin Y, Pan X, Chen R, Yu D (1996) New annonaceous acetogenins from Uvaria boniana. Acta Pharm Sin 31:381

    CAS  Google Scholar 

  30. Zhou GX, Zhou LE, Chen RY, Yu DQ (1999) Calamistrins A and B, two new cytotoxic monotetrahydrofuran annonaceous acetogenins from Uvaria calamistrata. J Nat Prod 62:261

    Article  CAS  Google Scholar 

  31. Raynaud S, Fourneau C, Hocquemiller R, Sévenet T, Hadi HA, Cavé A (1997) Acetogenins of Annonaceae. Part 54. Acetogenins from the bark of Uvaria pauci-ovulata. Phytochemistry 46:321

    Article  CAS  Google Scholar 

  32. Chen Y, Yu DQ (1997) Absolute configurations of tonkinin A and B: two new acetogenins from Uvaria tonkinensis. Chin Chem Lett 8:789

    CAS  Google Scholar 

  33. Colman-Saizarbitoria T, Montilla L, Rodriguez M, Castillo A, Hasegawa M (2009) Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae. Rev Bras Farm 19:871

    Article  CAS  Google Scholar 

  34. Pettit GR, Mukku VJRV, Cragg G, Herald DL, Knight JC, Herald CL, Chapuis JC (2008) Antineoplastic agents. 558. Ampelocissus sp. cancer cell growth inhibitory constituents. J Nat Prod 71:130

    Article  CAS  Google Scholar 

  35. Hopp DC, Conway WD, McLaughlin JL (1999) Using countercurrent chromatography to assist in the purification of new annonaceous acetogenins from Annona squamosa. Phytochem Anal 10:339

    Article  CAS  Google Scholar 

  36. Duret P, Waechter AI, Margraff R, Foucault A, Hocquemiller R, Cavé A (1997) High-speed countercurrent chromatography: a promising method for the separation of the annonaceous acetogenins. J Liq Chromatogr Relat Technol 20:627

    Article  CAS  Google Scholar 

  37. Liaw CC, Yang YL, Chen M, Chang FR, Chen SL, Wu SH, Wu YC (2008) Mono-tetrahydrofuran annonaceous acetogenins from Annona squamosa as cytotoxic agents and calcium ion chelators. J Nat Prod 71:764

    Article  CAS  Google Scholar 

  38. Gawronski J, Wu YC (1999) A note on the determination of absolute configuration of acetogenins by circular dichroism. Pol J Chem 73:241

    CAS  Google Scholar 

  39. Duret P, Waechter AI, Figadère B, Hocquemiller R, Cavé A (1998) Determination of absolute configurations of carbinols of annonaceous acetogenins with 2-naphthylmethoxyacetic acid esters. J Org Chem 63:4717–4720

    Article  CAS  Google Scholar 

  40. Hirayama K, Akashi S, Yuji R, Niitsu U, Fujimoto Y (1993) Structural studies of polyhydroxybis(tetrahydrofuran) acetogenins from Annona squamosa using the combination of chemical derivatization and precursor-ion scanning mass spectrometry. Org Mass Spectrom 28:1516

    Article  CAS  Google Scholar 

  41. Gu ZM, Zhou D, Wu J, Shi G, Zeng L, McLaughlin JL (1997) Screening for annonaceous acetogenins in bioactive plant extracts by liquid chromatography/mass spectrometry. J Nat Prod 60:242

    Article  CAS  Google Scholar 

  42. Alali FQ, Liu XX, McLaughlin JL (1999) Annonaceous acetogenins: recent progress. J Nat Prod 62:504

    Article  CAS  Google Scholar 

  43. Chang FR, Chen JL, Lin CY, Chiu HF, Wu MJ, Wu YC (1999) Bioactive acetogenins from the seeds of Annona atemoya. Phytochemistry 51:883

    Article  CAS  Google Scholar 

  44. Gleye C, Laurens A, Hocquemiller R, Laprévote O, Serani L, Cavé A (1997) Cohibins A and B, acetogenins from roots of Annona muricata. Phytochemistry 44:1541

    Article  CAS  Google Scholar 

  45. Gleye C, Raynaud S, Fourneau C, Laurens A, Laprévote O, Serani L, Fournet A, Hocquemiller R (2000) Cohibins C and D, two important metabolites in the biogenesis of acetogenins from Annona muricata and Annona nutans. J Nat Prod 63:1192

    Article  CAS  Google Scholar 

  46. Gleye C, Akendengue B, Laurens A, Hocquemiller R (2001) Coronin from roots of Annona muricata, a putative intermediate in acetogenin biosynthesis (1). Planta Med 67:570

    Article  CAS  Google Scholar 

  47. Sahpaz S, Hocquemiller R, Cavé A, Saez J, Cortes D (1997) Diepoxyrollin and diepomuricanin B: two new diepoxyacetogenins from Rollinia membranacea seeds. J Nat Prod 60:199

    Article  CAS  Google Scholar 

  48. ba Ndob IB, Champy P, Gleye C, Lewin G, Akendengue B (2009) Annonaceous acetogenins: precursors from the seeds of Annona squamosa. Phytochem Lett 2:72

    Article  CAS  Google Scholar 

  49. Jiang Z, Chen Y, Chen RY, Yu DQ (1998) Linear acetogenins from Goniothalamus donnaiensis. Phytochemistry 49:769

    Article  CAS  Google Scholar 

  50. Melot A, Fall D, Gleye C, Champy P (2009) Apolar annonaceous acetogenins from the fruit pulp of Annona muricata. Molecules 14:43875

    Article  CAS  Google Scholar 

  51. Chen Y, Jiang Z, Chen RR, Yu DQ (1998) Two linear acetogenins from Goniothalamus gardneri. Phytochemistry 49:1317

    Article  CAS  Google Scholar 

  52. Seidel V, Bailleul F, Waterman PG (1999) Goniothalamusin, a linear acetogenin from Goniothalamus gardneri. Phytochemistry 52:1101

    Article  CAS  Google Scholar 

  53. Liaw CC, Chang FR, Chen SL, Wu CC, Lee KH, Wu YC (2005) Novel cytotoxic monotetrahydrofuranic annonaceous acetogenins from Annona montana. Bioorg Med Chem 13:4767

    Article  CAS  Google Scholar 

  54. Gleye C, Laurens A, Hocquemiller R, Cavé A, Laprévote O, Serani L (1997) Isolation of montecristin, a key metabolite in biogenesis of acetogenins from Annona muricata and its structure elucidation by using tandem mass spectrometry. J Org Chem 62:510

    Article  CAS  Google Scholar 

  55. Yu JG, Gui HQ, Luo XZ, Sun L (1998) Murihexol, a linear acetogenin from Annona muricata. Phytochemistry 49:1689

    Article  CAS  Google Scholar 

  56. Gleye C, Laurens A, Laprevote O, Serani L, Hocquemiller R (1999) Acetogenins of the Annonaceae. Part 81. Isolation and structure elucidation of sabadelin, an acetogenin from roots of Annona muricata. Phytochemistry 52:1403

    Article  CAS  Google Scholar 

  57. Yu JG, Luo XZ, Sun L, Li DY, Huang WH, Liu CY (2005) Chemical constituents from the seeds of Annona squamosa. Acta Pharm Sin 40:153

    CAS  Google Scholar 

  58. Mootoo BS, Ali A, Khan A, Reynolds WF, McLean S (2000) Three novel monotetrahydrofuran annonaceous acetogenins from Annona montana. J Nat Prod 63:807

    Article  CAS  Google Scholar 

  59. Kim DH, Ma ES, Suk KD, Son JK, Lee JS, Woo MH (2001) Annomolin and annocherimolin, new cytotoxic annonaceous acetogenins from Annona cherimola seeds. J Nat Prod 64:502

    Article  CAS  Google Scholar 

  60. Liaw CC, Chang FR, Lin CY, Chou CJ, Chiu HF, Wu MJ, Wu YC (2002) New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata. J Nat Prod 65:470

    Article  CAS  Google Scholar 

  61. Woo MH, Kim DH, Fotopoulos SS, McLaughlin JL (1999) Annocherin and (2,4)-cis- and trans-annocherinones, monotetrahydrofuran annonaceous acetogenins with a C-7 carbonyl group from Annona cherimola seeds. J Nat Prod 62:1250

    Article  CAS  Google Scholar 

  62. Liu XX, Alali FQ, Pilarinou E, McLaughlin JL (1999) Two bioactive mono-tetrahydrofuran acetogenins, annoglacins A and B, from Annona glabra. Phytochemistry 50:815

    Article  CAS  Google Scholar 

  63. Liu XX, Pilarinou E, McLaughlin JL (1999) Two novel acetogenins, annoglaxin and 27-hydroxybullatacin, from Annona glabra. J Nat Prod 62:848

    Article  CAS  Google Scholar 

  64. Kim DH, Son JK, Woo MH (2001) Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimola seeds. Arch Pharm Res 24:300

    Article  CAS  Google Scholar 

  65. Son JK, Kim DH, Woo MH (2003) Two new epimeric pairs of acetogenins bearing a carbonyl group from Annona cherimola seeds. J Nat Prod 66:1369

    Article  CAS  Google Scholar 

  66. Alali F, Zeng L, Zhang Y, Ye Q, Hopp DC, Schwedler JT, McLaughlin JL (1997) 4-Deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteus. Bioorg Med Chem 5:549

    Article  CAS  Google Scholar 

  67. Kim GS, Zeng L, Alali F, Rogers LL, Wu FE, McLaughlin JL, Sastrodihardjo S (1998) Two new mono-tetrahydrofuran ring acetogenins, annomuricin E and muricapentocin, from the leaves of Annona muricata. J Nat Prod 61:432

    Article  CAS  Google Scholar 

  68. Liaw CC, Chang FR, Wu CC, Chen SL, Bastow KF, Hayashi K, Nozaki H, Lee KH, Wu YC (2004) Nine new cytotoxic monotetrahydrofuranic annonaceous acetogenins from Annona montana. Planta Med 70:948

    Article  CAS  Google Scholar 

  69. Hopp DC, Alali FQ, Gu ZM, McLaughlin JL (1998) Mono-THF ring acetogenins from Annona squamosa. Phytochemistry 47:803

    Article  CAS  Google Scholar 

  70. Woo MH, Kim DH, McLaughlin JL (1999) Asitrilobins A and B: cytotoxic mono-THF Annonaceous acetogenins from the seeds of Asimina triloba. Phytochemistry 50:1033

    Article  CAS  Google Scholar 

  71. Woo MH, Chung SO, Kim DH (2000) Asitrilobins C and D: two new cytotoxic mono-tetrahydrofuran Annonaceous acetogenins from Asimina triloba seeds. Bioorg Med Chem 8:285

    Article  CAS  Google Scholar 

  72. Kim EJ, Tian F, Woo MH (2000) Asitrocin, (2,4)-cis- and trans-asitrocinones: novel bioactive mono-tetrahydrofuran acetogenins from Asimina triloba seeds. J Nat Prod 63:1503

    Article  CAS  Google Scholar 

  73. Zhou GX, Chen RY, Zhang YJ, Yu DQ (2000) New annonaceous acetogenins from the roots of Uvaria calamistrata. J Nat Prod 63:1201

    Article  CAS  Google Scholar 

  74. Meneses Da Silva EL, Roblot F, Laprévote O, Serani L, Cavé A (1997) Coriaheptocins A and B, the first heptahydroxylated acetogenins, isolated from the roots of Annona coriacea. J Nat Prod 60:162

    Article  CAS  Google Scholar 

  75. Sun L, Zhu J, Yu J, Yu D, Li D, Zhou L (2003) Chemical constituents from the seeds of Annona glabra. Acta Pharm Sin 38:32

    CAS  Google Scholar 

  76. Liu XX, Alali FQ, Pilarinou E, McLaughlin JL (1998) Glacins A and B: two novel bioactive mono-tetrahydrofuran acetogenins from Annona glabra. J Nat Prod 61:620

    Article  CAS  Google Scholar 

  77. Waechter AI, Szlosek M, Hocquemiller R, Laurens A, Cavé A (1998) Acetogenins of Annonaceae. 65. Glaucabellin and glaucaflorin, two acetogenins from Annona glauca. Phytochemistry 48:141

    Article  CAS  Google Scholar 

  78. Alali FQ, Zhang Y, Rogers L, McLaughlin JL (1998) Mono-tetrahydrofuran acetogenins from Goniothalamus giganteus. Phytochemistry 49:761

    Article  CAS  Google Scholar 

  79. Chang FR, Chen JL, Chiu HF, Wu MJ, Wu YC (1998) Acetogenins from seeds of Annona reticulata. Phytochemistry 47:1057

    Article  CAS  Google Scholar 

  80. Chávez D, Acevedo LA, Mata R (1998) Jimenezin, a novel annonaceous acetogenin from the seeds of Rollinia mucosa containing adjacent tetrahydrofuran-tetrahydropyran ring systems. J Nat Prod 61:419

    Article  Google Scholar 

  81. Liaw CC, Chang FR, Wu YC, Wang HK, Nakanishi Y, Bastow KF, Lee KH (2004) Montacin and cis-montacin, two new cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona montana. J Nat Prod 67:1804

    Article  CAS  Google Scholar 

  82. Wang LQ, Nakamura N, Meselhy MR, Hattori M, Zhao WM, Cheng KF, Yang RZ, Qin GW (2000) Four mono-tetrahydrofuran ring acetogenins, montanacins B-E, from Annona montana. Chem Pharm Bull 48:1109

    Article  CAS  Google Scholar 

  83. Wang LQ, Min BS, Li Y, Nakamura N, Qin GW, Li CJ, Hattori M (2002) Annonaceous acetogenins from the leaves of Annona montana. Bioorg Med Chem 10:561

    Article  CAS  Google Scholar 

  84. Wang LQ, Li Y, Min BS, Nakamura N, Qin GW, Li CJ, Hattori M (2001) Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana. Planta Med 67:847

    Article  CAS  Google Scholar 

  85. Hopp DC, Zeng L, Gu ZM, Kozlowski JF, McLaughlin JL (1997) Novel mono-tetrahydrofuran ring acetogenins, from the bark of Annona squamosa, showing cytotoxic selectivities for the human pancreatic carcinoma cell line, PACA-2. J Nat Prod 60:581

    Article  CAS  Google Scholar 

  86. Chang FR, Wu YC (2001) Novel cytotoxic annonaceous acetogenins from Annona muricata. J Nat Prod 64:925

    Article  CAS  Google Scholar 

  87. Kim GS, Lu Z, Alali F, Rogers LL, Wu F-E, Sastrodihardjo S, McLaughlin JL (1998) Muricoreacin and murihexocin C, monotetrahydrofuran acetogenins, from the leaves of Annona muricata. Phytochemistry 49:565

    Article  CAS  Google Scholar 

  88. Gleye C, Duret P, Laurens A, Hocquemiller R, Cavé A (1998) cis-Monotetrahydrofuran acetogenins from the roots of Annona muricata. J Nat Prod 61:576

    Article  CAS  Google Scholar 

  89. Queiroz EF, Roblot F, Laprevote O, de Paulo M, Hocquemiller R (2003) Two unusual acetogenins from the roots of Annona salzmanii. J Nat Prod 66:755

    Article  CAS  Google Scholar 

  90. Liaw CC, Chang FR, Chen YY, Chiu HF, Wu MJ, Wu YC (1999) New annonaceous acetogenins from Rollinia mucosa. J Nat Prod 62:1613

    Article  CAS  Google Scholar 

  91. Liaw CC, Chang FR, Wu MJ, Wu YC (2003) A novel constituent from Rollinia mucosa, rollicosin, and a new approach to develop annonaceous acetogenins as potential antitumor agents. J Nat Prod 66:279

    Article  CAS  Google Scholar 

  92. Alvarez Colom O, Neske A, Chahboune N, Zafra-Polo MC, Bardon A (2009) Tucupentol, a novel mono-tetrahydrofuranic acetogenin from Annona montana, as a potent inhibitor of mitochondrial complex I. Chem Biodivers 6:335

    Article  Google Scholar 

  93. Alali FQ, Rogers L, Zhang Y, McLaughlin JL (1999) Goniotriocin and (2,4-cis- and -trans)-xylomaticinones, bioactive annonaceous acetogenins from Goniothalamus giganteus. J Nat Prod 62:31

    Article  CAS  Google Scholar 

  94. Chang FR, Liaw CC, Lin CY, Chou CJ, Chiu HF, Wu YC (2003) New adjacent bis-tetrahydrofuran annonaceous acetogenins from Annona muricata. Planta Med 69:241

    Article  CAS  Google Scholar 

  95. Duret P, Hocquemiller R, Cavé A (1997) Acetogenins from Annonaceae. Part 55. Annonisin, a bis-tetrahydrofuran acetogenin from Annona atemoya seeds. Phytochemistry 45:1423

    Article  CAS  Google Scholar 

  96. Chen Y, Chen JW, Wang Y, Xu SS, Li X (2012) Six cytotoxic annonaceous acetogenins from Annona squamosa seeds. Food Chem 135:960

    Article  CAS  Google Scholar 

  97. Chen Y, Chen JW, Li X (2011) Cytotoxic bistetrahydrofuran annonaceous acetogenins from the seeds of Annona squamosa. J Nat Prod 74:2477

    Article  CAS  Google Scholar 

  98. Hopp DC, Alali FQ, Gu ZM, McLaughlin JL (1998) Three new bioactive bis-adjacent THF-ring acetogenins from the bark of Annona squamosa. Bioorg Med Chem 6:569

    Article  CAS  Google Scholar 

  99. Kim EJ, Suh KM, Kim DH, Jung EJ, Seo CS, Son JK, Woo MH, McLaughlin JL (2005) Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring. J Nat Prod 68:194

    Article  CAS  Google Scholar 

  100. Duret P, Hocquemiller R, Cavé A (1998) Acetogenins from Annonaceae. Part 66. Bulladecin and atemotetrolin, two bis-tetrahydrofuran acetogenins from Annona atemoya seeds. Phytochemistry 48:499

    Article  CAS  Google Scholar 

  101. Queiroz EF, Roblot F, Figadère B, Laurens A, Duret P, Hocquemiller R, Cavé A, Serani L, Laprévote O, Cotte-Laffitte J, Quéro AM (1998) Three new bistetrahydrofuran acetogenins from the seeds of Annona spinescens. J Nat Prod 61:34

    Article  CAS  Google Scholar 

  102. Fall D, Duval Romain A, Gleye C, Laurens A, Hocquemiller R (2004) Chamuvarinin, an acetogenin bearing a tetrahydropyran ring from the roots of Uvaria chamae. J Nat Prod 67:1041

    Article  CAS  Google Scholar 

  103. Rodrigues dos Santos LA, Boaventura MAD, Pimenta LPS (2006) Cornifolin, a new bis-tetrahydrofuran annonaceous acetogenin from Annona cornifolia. Biochem Syst Ecol 34:78

    Article  CAS  Google Scholar 

  104. dos Santos Lima LAR, Pimenta LPS, Boaventura MAD (2009) Two new adjacent bis-tetrahydrofuran annonaceous acetogenins from seeds of Annona cornifolia. Planta Med 75:80

    Article  Google Scholar 

  105. Liu XX, Alali FQ, Hopp DC, Rogers LL, Pilarinou E, McLaughlin JL (1998) Glabracins A and B, two new acetogenins from Annona glabra. Bioorg Med Chem 6:959

    Article  CAS  Google Scholar 

  106. Chahboune N, Barrachina I, Royo I, Romero V, Saez J, Tormo JR, De Pedro N, Estornell E, Zafra-Polo MC, Pelaez F, Cortes D (2006) Guanaconetins, new antitumoral acetogenins, mitochondrial complex I and tumor cell growth inhibitors. Bioorg Med Chem 14:1089

    Article  CAS  Google Scholar 

  107. Fall D, Pimentel L, Champy P, Gleye C, Laurens A, Hocquemiller R (2006) A new adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Uvaria chamae. Planta Med 72:938

    Article  CAS  Google Scholar 

  108. Chávez D, Mata R (1999) Chemical studies on Mexican plants used in traditional medicine. 36. Purpuracenin: a new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Annona purpurea. Phytochemistry 50:823

    Article  Google Scholar 

  109. Chávez D, Mata R (1998) Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea. J Nat Prod 61:580

    Article  Google Scholar 

  110. Gu ZM, Zhou D, Lewis NJ, Wu J, Shi G, McLaughlin JL (1997) Isolation of new bioactive annonaceous acetogenins from Rollinia mucosa guided by liquid chromatography/mass spectrometry. Bioorg Med Chem 5:1911

    Article  CAS  Google Scholar 

  111. Shi G, MacDougal JM, McLaughlin JL (1997) Bioactive annonaceous acetogenins from Rollinia mucosa. Phytochemistry 45:719

    Article  CAS  Google Scholar 

  112. Araya H, Sahai M, Singh S, Singh AK, Yoshida M, Hara N, Fujimoto Y (2002) Squamocin-O1 and squamocin-O2, new adjacent bis-tetrahydrofuran acetogenins from the seeds of Annona squamosa. Phytochemistry 61:999

    Article  CAS  Google Scholar 

  113. He K, Zhao GX, Shi G, Zeng L, Chao JF, McLaughlin JL (1997) Additional bioactive annonaceous acetogenins from Asimina triloba (Annonaceae). Bioorg Med Chem 5:501

    Article  CAS  Google Scholar 

  114. Barrachina I, Neske A, Granell S, Bermejo A, Chahboune N, El Aouad N, Alvarez O, Bardon A, Zafra-Polo MC (2004) Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimola, is a potent inhibitor of mitochondrial complex I. Planta Med 70:866–868

    Article  CAS  Google Scholar 

  115. Souza MMC, Bevilaqua CML, Morais SM, Costa CTC, Silva ARA, Braz-Filho R (2008) Anthelmintic acetogenin from Annona squamosa L. seeds. An Acad Bras Cienc 80:271

    Article  CAS  Google Scholar 

  116. Chen CY, Chang FR, Chiu HF, Wu MJ, Wu YC (1999) Aromin-A, an annonaceous acetogenin from Annona cherimola. Phytochemistry 51:429

    Article  CAS  Google Scholar 

  117. Alali FQ, Zhang Y, Rogers L, McLaughlin JL (1997) (2,4-cis and trans)-Gigantecinone and 4-deoxygigantecin, bioactive nonadjacent bis-tetrahydrofuran annonaceous acetogenins, from Goniothalamus giganteus. J Nat Prod 60:929

    Article  CAS  Google Scholar 

  118. Yang HJ, Li X, Zhang N, Chen JW, Wang MY (2009) Two new cytotoxic acetogenins from Annona squamosa. J Asian Nat Prod Res 11:250

    Article  CAS  Google Scholar 

  119. Yang HJ, Zhang N, Li X, He L, Chen J (2009) New nonadjacent bis-THF ring acetogenins from the seeds of Annona squamosa. Fitoterapia 80:1771

    Google Scholar 

  120. Alfonso D, Colman-Saizarbitoria T, Zhao GX, Shi G, Ye Q, Schwedler JT, McLaughlin JL (1996) Aromin and aromicin, two new bioactive annonaceous acetogenins, possessing an unusual bis-THF ring structure, from Xylopia aromatica (Annonaceae). Tetrahedron 52:4215

    Article  CAS  Google Scholar 

  121. Xie HH, Wei XY, Wang JD, Liu MF, Yang RZ (2003) A new cytotoxic acetogenin from the seeds of Annona squamosa. Chin Chem Lett 14:588

    CAS  Google Scholar 

  122. Rieser MJ, Kozlowski JF, Wood KV, McLaughlin JL (1991) Muricatacin: a simple biologically active acetogenin derivative from the seeds of Annona muricata (Annonaceae). Tetrahedron Lett 32:1137

    Article  CAS  Google Scholar 

  123. Myint SH, Laurens A, Hocquemiller R, Cavé A, Davoust D, Cortes D (1990) Murisolin: a new cytotoxic mono-tetrahydrofuran-γ-lactone from Annona muricata. Heterocycles 31:861

    Article  CAS  Google Scholar 

  124. Hattori Y, Kimura Y, Moroda A, Konno H, Abe M, Miyoshi H, Goto T, Makabe H (2006) Synthesis of murisolin, (15R,16R,19R,20S)-murisolin A, and (15R,16R, 19S,20S)-16,19-cis-murisolin and their inhibitory action with bovine heart mitochondrial complex I. Chem Asian J 1:894

    Article  CAS  Google Scholar 

  125. Ye Q, Zeng L, Zhang Y, Zhao GX, McLaughlin JL, Woo MH, Evert DR (1995) Longicin and goniothalamicinone: novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia. J Nat Prod 58:1398

    Article  CAS  Google Scholar 

  126. Hanessian S, Giroux S, Buffat M (2005) Total synthesis and structural confirmation of (+)-longicin. Org Lett 7:3989

    Article  CAS  Google Scholar 

  127. Goksel H, Stark CBW (2006) Total synthesis of cis-solamin: exploiting the RuO4-catalyzed oxidative cyclization of dienes. Org Lett 8:3433

    Article  CAS  Google Scholar 

  128. Zhao H, Gorman JST, Pagenkopf BL (2006) Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin. Org Lett 8:4379

    Article  CAS  Google Scholar 

  129. Pettit GR, Cragg GM, Polonsky J, Herald DL, Goswami A, Smith CR, Moretti C, Schmidt JM, Weisleder D (1987) Isolation and structure of rolliniastatin 1 from the South American tree Rollinia mucosa. Can J Chem 65:1433

    Article  CAS  Google Scholar 

  130. Keum G, Hwang CH, Kang SB, Kim Y, Lee E (2005) Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin. J Am Chem Soc 127:10396

    Article  CAS  Google Scholar 

  131. Gonzalez MC, Tormo JR, Bermejo A, Zafra-Polo MC, Estornell E, Cortes D (1997) Rollimembrin, a novel acetogenin inhibitor of mammalian mitochondrial complex I. Bioorg Med Chem Lett 7:1113

    Article  CAS  Google Scholar 

  132. Yang SW, Shen YC, Chen CH (1996) Steroids and triterpenoids of Antodia cinnamomea–a fungus parasitic on Cinnamomum micranthum. Phytochemistry 41:1389

    Article  CAS  Google Scholar 

  133. Nattrass GL, Diez E, McLachlan MM, Dixon DJ, Ley SV (2005) The total synthesis of the annonaceous acetogenin 10-hydroxyasimicin. Angew Chem Int Ed 44:580–584

    Article  CAS  Google Scholar 

  134. Saez J, Sahpaz S, Villaescusa L, Hocquemiller R, Cavé A, Cortes D (1993) Acetogenins of the Annonaceae. 18. Rioclarin and membranacin, two new bis-tetrahydrofuran acetogenins of the seeds of Rollinia membranacea. J Nat Prod 56:351

    Article  CAS  Google Scholar 

  135. Rupprecht JK, Chang CJ, Cassady JM, McLaughlin JL, Mikolajczak KL, Weisleder D (1986) Asimicin, a new cytotoxic and pesticidal acetogenin from the paw paw, Asimina triloba (Annonaceae). Heterocycles 24:1197

    Article  CAS  Google Scholar 

  136. Marshall JA, Sabatini JJ (2006) An outside-in approach to adjacent bistetrahydrofuran annonaceous acetogenins with C 2 core symmetry. Total synthesis of asimicin and a C32 analogue. Org Lett 8:3557

    Article  CAS  Google Scholar 

  137. Ye Q, He K, Oberlies NH, Zeng L, Shi G, Evert D, McLaughlin JL (1996) Longimicins A-D: novel bioactive acetogenins from Asimina longifolia (Annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins. J Med Chem 39:1790

    Article  CAS  Google Scholar 

  138. Tominaga H, Maezaki N, Yanai M, Kojima N, Urabe D, Ueki R, Tanaka T (2006) First total synthesis of longimicin D. Eur J Org Chem 2006:1422

    Article  CAS  Google Scholar 

  139. Shi G, Kozlowski JF, Schwedler JT, Wood KV, MacDougal JM, McLaughlin JL (1996) Muconin and mucoxin: additional nonclassical bioactive acetogenins from Rollinia mucosa. J Org Chem 61:7988

    Article  CAS  Google Scholar 

  140. Narayan RS, Borhan B (2006) Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies. J Org Chem 71:1416

    Article  CAS  Google Scholar 

  141. Shi G, Zheng L, Gu ZM, MacDougal JM, McLaughlin JL (1995) Absolute stereochemistries of sylvaticin and 12,15-cis-sylvaticin, bioactive C-20,23-cis nonadjacent bistetrahydrofuran annonaceous acetogenins, from Rollinia mucosa. Heterocycles 41:1785

    Article  CAS  Google Scholar 

  142. Donohoe TJ, Harris RM, Burrows J, Parker J (2006) Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmium. J Am Chem Soc 128:13704

    Article  CAS  Google Scholar 

  143. Alkofahi A, Rupprecht JK, Liu YM, Chang CJ, Smith DL, McLaughlin JL (1990) Gigantecin: a novel antimitotic and cytotoxic acetogenin, with nonadjacent tetrahydrofuran rings, from Goniothalamus giganteus (Annonaceae). Experientia 46:539

    Article  CAS  Google Scholar 

  144. Hoye TR, Eklov BM, Jeon J, Khoroosi M (2006) Sequencing of three-component olefin metatheses: total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin. Org Lett 8:3383

    Article  CAS  Google Scholar 

  145. Bandur NG, Bruckner D, Hoffmann RW, Koert U (2006) Total synthesis of jimenezin via an intramolecular allylboration. Org Lett 8:3829

    Article  CAS  Google Scholar 

  146. Shi G, Alfonso D, Fatope MO, Zeng L, Gu ZM, Zhao GX, He K, MacDougal JM, McLaughlin JL (1995) Mucocin: A new annonaceous acetogenin bearing a tetrahydropyran ring. J Am Chem Soc 117:10409

    Article  CAS  Google Scholar 

  147. Crimmins MT, Zhang Y, Diaz FA (2006) Total synthesis of (–)-mucocin. Org Lett 8:2369

    Article  CAS  Google Scholar 

  148. Alali FQ, Rogers L, Zhang Y, McLaughlin JL (1998) Unusual bioactive annonaceous acetogenins from Goniothalamus giganteus. Tetrahedron 54:5833

    Article  CAS  Google Scholar 

  149. Strand D, Rein T (2004) Total synthesis of pyranicin. Org Lett 7:199

    Article  CAS  Google Scholar 

  150. Strand D, Rein T (2005) Synthesis of pyragonicin. Org Lett 7:2779

    Article  CAS  Google Scholar 

  151. Takahashi S, Ogawa N, Koshino H, Nakata T (2005) Total synthesis of the proposed structure for pyragonicin. Org Lett 7:2783

    Article  CAS  Google Scholar 

  152. Quinn KJ, Isaacs AK, DeChristopher BA, Szklarz SC, Arvary RA (2005) Asymmetric total synthesis of rollicosin. Org Lett 7:1243

    Article  CAS  Google Scholar 

  153. Makabe H, Kimura Y, Higuchi M, Konno H, Murai M, Miyoshi H (2006) Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I. Bioorg Med Chem 14:3119

    Article  CAS  Google Scholar 

  154. Harcken C, Bruckner R (2001) Elucidation of the stereostructure of the annonaceous acetogenin (+)-montecristin through total synthesis. New J Chem 25:40

    Article  CAS  Google Scholar 

  155. Solladie G, Hanquet G, Izzo I, Crumbie R (1999) Asymmetric synthesis of syn and anti 1,2-diols from diethyl oxalate using the stereoselective sulfoxide directed reduction of 1,2-diketone derivatives. Tetrahedron Lett 40:3071

    Article  CAS  Google Scholar 

  156. Baylon C, Prestat G, Heck MP, Mioskowski C (2000) Synthesis of (–)-(4R,5R)-muricatacin using a regio- and stereospecific ring-opening of a vinyl epoxide. Tetrahedron Lett 41:3833

    Article  CAS  Google Scholar 

  157. Konno H, Hiura N, Yanaru M (2002) Syntheses of (4R,5S)- and (4S,5R)-muricatacins, and (4S,5R)-aza-muricatacin, unnatural analogues of the annonaceous acetogenin. Heterocycles 57:1793

    Article  CAS  Google Scholar 

  158. Chandrasekhar M, Chandra KL, Singh VK (2002) An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from d-mannitol: total synthesis of (–)-muricatacin. Tetrahedron Lett 43:2773

    Article  CAS  Google Scholar 

  159. Bernard AM, Frongia A, Piras PP, Secci F (2003) Unexpected stereochemistry in the lithium salt catalyzed ring expansion of nonracemic oxaspiropentanes. Formal syntheses of (−)-(4R,5R)-muricatacin and the pheromone (R)-japonilure. Org Lett 5:2923

    Article  CAS  Google Scholar 

  160. Chen Y, Yu DQ (1996) Tonkinelin, a novel annonaceous acetogenin from Uvaria tonkinesis. Planta Med 62:512

    Article  CAS  Google Scholar 

  161. Hattori T, Konno H, Abe M, Miyoshi H, Goto T, Makabe H (2007) Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I. Bioorg Med Chem 15:3026

    Article  CAS  Google Scholar 

  162. Hu TS, Wu YL, Wu Y (2000) The first total synthesis of annonacin, the most typical monotetrahydrofuran annonaceous acetogenins. Org Lett 2:887

    Article  CAS  Google Scholar 

  163. Hu TS, Yu Q, Wu YL, Wu Y (2001) Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. J Org Chem 66:853

    Article  CAS  Google Scholar 

  164. Yu Q, Yao ZJ, Chen XG, Wu YL (1999) Total synthesis of (10R)- and (10S)-corossolin: Determination of the stereochemistry at C-10 of the natural corossolin and the differential toxicity toward cancer cells caused by the configuration at C-10. J Org Chem 64:2440

    Article  CAS  Google Scholar 

  165. Wang F, Kawamura A, Mootoo DR (2008) Synthesis and antitumor activity of C-9 epimers of the tetrahydrofuran containing acetogenin 4-deoxyannoreticuin. Bioorg Med Chem 16:8413

    Article  CAS  Google Scholar 

  166. Yu Q, Wu Y, Ding H, Wu YL (1999) The first total synthesis of 4-deoxyannomontacin. J Chem Soc Perkin Trans 1:1183

    Article  Google Scholar 

  167. Orru RVA, Groenendaal B, Heyst JV, Hunting M, Wesseling C, Schmitz RF, Mayer SF, Faber K (2003) Biomimetic approach to the stereoselective synthesis of acetogenins. Pure Appl Chem 75:259

    Article  CAS  Google Scholar 

  168. Wang ZM, Tian SK, Shi M (2000) Total synthesis of gigantetrocin A. Chirality 12:581

    Article  CAS  Google Scholar 

  169. Wang ZM, Tian SK, Shi M (1999) A facile route to the total synthesis of gigantetrocin A. Tetrahedron Asymmetry 10:667

    Article  CAS  Google Scholar 

  170. Marshall JA, Jiang H (1998) Total synthesis of the threo, trans, threo-monotetrahydrofuran annonaceous acetogenin longifolicin. Tetrahedron Lett 39:1493

    Article  CAS  Google Scholar 

  171. Maezaki N, Kojima N, Sakamoto A, Iwata C, Tanaka T (2001) First total synthesis of mosin B. Org Lett 3:429

    Article  CAS  Google Scholar 

  172. Maezaki N, Kojima N, Sakamoto A, Tominaga H, Iwata C, Tanaka T, Monden M, Damdinsuren B, Nakamori S (2003) Total synthesis of the antitumor acetogenin mosin B: desymmetrization approach to the stereodivergent synthesis of threo/trans/erythro-type acetogenins. Chem Eur J 9:389

    Article  CAS  Google Scholar 

  173. Dixon DJ, Ley SV, Reynolds DJ (2002) The total synthesis of the annonaceous acetogenin, muricatetrocin C. Chem Eur J 8:1621

    Article  CAS  Google Scholar 

  174. Dixon DJ, Ley SV, Reynolds DJ (2000) The total synthesis of the annonaceous acetogenin, muricatetrocin C. Angew Chem Int Ed 39:3622

    Article  CAS  Google Scholar 

  175. Maezaki N, Tominaga H, Kojima N, Yanai M, Urabe D, Ueki R, Tanaka T, Yamori T (2005) Total synthesis of murisolins and evaluation of tumor-growth inhibitory activity. Chem Eur J 11:6237

    Article  CAS  Google Scholar 

  176. Hanessian S, Grillo TA (1998) Stereocontrolled total synthesis of an annonacin A-type acetogenin: pseudoannonacin A? J Org Chem 63:1049

    Article  CAS  Google Scholar 

  177. Makabe H, Miyawaki A, Takahashi R, Hattori Y, Konno H, Abe M, Miyoshi H (2004) Synthesis of two possible diastereomers of reticulatain-1. Tetrahedron Lett 45:973

    Article  CAS  Google Scholar 

  178. Kuriyama W, Ishigami K, Kitahara T (1999) Synthesis of solamin. Heterocycles 50:981

    Article  CAS  Google Scholar 

  179. Cecil ARL, Brown RCD (2002) Synthesis of cis-solamin using a permanganate-mediated oxidative cyclization. Org Lett 4:3715

    Article  CAS  Google Scholar 

  180. Makabe H, Hattori Y, Tanaka A, Oritani T (2002) Total synthesis of cis-solamin. Org Lett 4:1083

    Article  CAS  Google Scholar 

  181. Makabe H, Hattori Y, Kimura Y, Konno H, Abe M, Miyoshi H, Tanaka A, Oritani T (2004) Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I. Tetrahedron 60:10651–10657

    Article  CAS  Google Scholar 

  182. Prestat G, Baylon C, Heck MP, Grasa GA, Nolan SP, Mioskowski C (2004) New strategy for the construction of a monotetrahydrofuran ring in annonaceous acetogenin based on a ruthenium ring-closing metathesis: application to the synthesis of solamin. J Org Chem 69:5770

    Article  CAS  Google Scholar 

  183. Konno H, Okuno Y, Makabe H, Nosaka K, Onishi A, Abe Y, Sugimoto A, Akaji K (2008) Total synthesis of cis-solamin A, a mono-tetrahydrofuran acetogenin isolated from Annona muricata. Tetrahedron Lett 49:782–785

    Article  CAS  Google Scholar 

  184. Konno H, Makabe H, Hattori Y, Nosaka K, Akaji K (2010) Synthesis of solamin type mono-THF acetogenins using cross-metathesis. Tetrahedron 66:7946

    Article  CAS  Google Scholar 

  185. Wang M, Chen Y, Lou L, Tang W, Wang X, Shen J (2005) Synthesis of pyrrolidine analogues of solamin. Tetrahedron Lett 46:5309

    Article  CAS  Google Scholar 

  186. Hu TS, Yu Q, Lin Q, Wu YL, Wu Y (1999) The first synthesis of tonkinecin, an annonaceous acetogenin with a C-5 carbinol center. Org Lett 1:399

    Article  CAS  Google Scholar 

  187. Avedissian H, Sinha SC, Yazbak A, Sinha A, Neogi P, Sinha SC, Keinan E (2000) Total synthesis of asimicin and bullatacin. J Org Chem 65:6035

    Article  CAS  Google Scholar 

  188. Mertz E, Tinsley JM, Roush WR (2005) [3 + 2]-Annulation reactions of chiral allylsilanes and chiral aldehydes. Studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins. J Org Chem 70:8035

    Article  CAS  Google Scholar 

  189. Marshall JA, Sabatini JJ, Valeriote F (2007) ABC synthesis and antitumor activity of a series of annonaceous acetogenin analogs with a threo, trans, threo, trans, threo-bis-tetrahydrofuran core unit. Bioorg Med Chem Lett 17:2434

    Article  CAS  Google Scholar 

  190. Wang ZM, Tian SK, Shi M (1999) The synthesis of asimilobin and the correction of its tetrahydrofuran segment’s configuration. Tetrahedron Lett 40:977

    Article  CAS  Google Scholar 

  191. Wang ZM, Tian SK, Shi M (2000) A facile route to bulladecin-type acetogenins – total synthesis of asimilobin and correction of the configuration of its tetrahydrofuran segment. Eur J Org Chem 2000:349

    Article  Google Scholar 

  192. Marshall JA, Jiang H (1999) Total synthesis of the cytotoxic threo, trans, threo, trans, threo annonaceous acetogenin asimin and its C-10 epimer: unambiguous confirmation of absolute stereochemistry. J Nat Prod 62:1123

    Article  CAS  Google Scholar 

  193. Mohapatra DK, Nayak S, Mohapatra S, Chorghade MS, Gurjar MK (2007) Double intramolecular oxymercuration: the first stereoselective synthesis of the C10-34 fragment of asimitrin. Tetrahedron Lett 48:5197

    Article  CAS  Google Scholar 

  194. Marshall JA, Hinkle KW (1998) Total synthesis of the cytotoxic annonaceous acetogenin (30S)-bullanin. Tetrahedron Lett 39:1303

    Article  CAS  Google Scholar 

  195. Tinsley JM, Mertz E, Chong PY, Rarig RAF, Roush WR (2005) Synthesis of (+)-bullatacin via the highly diastereoselective [3 + 2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane. Org Lett 7:4245

    Article  CAS  Google Scholar 

  196. Marshall JA, Piettre A, Paige MA, Valeriote F (2003) Total synthesis and structure confirmation of the annonaceous acetogenins (30S)-hydroxybullatacin, uvarigrandin A, and 5(R)-uvarigrandin A (narumicin I?). J Org Chem 68:1780

    Article  CAS  Google Scholar 

  197. Huh CW, Roush WR (2008) Highly stereoselective and modular syntheses of 10-hydroxytrilobacin and three diastereomers via stereodivergent (3 + 2)-annulation reactions. Org Lett 10:3371

    Article  CAS  Google Scholar 

  198. He YT, Xue S, Hu TS, Yao ZJ (2005) An iterative acetylene–epoxide coupling strategy for the total synthesis of longimicin C. Tetrahedron Lett 46:5393

    Article  CAS  Google Scholar 

  199. Head GD, Whittingham WG, Brown RCD (2004) Synthesis of membranacin. Synlett 8:1437

    Google Scholar 

  200. Ruan Z, Dabideen D, Blumenstein M, Mootoo DR (2000) A modular synthesis of the bis-tetrahydrofuran core of rolliniastatin from pyranoside precursors. Tetrahedron 56:9203

    Article  CAS  Google Scholar 

  201. Emde U, Koert U (2000) Total syntheses of squamocin A and squamocin D, bi-tetrahydrofuran acetogenins from Annonaceae. Eur J Org Chem 2000:1889

    Article  Google Scholar 

  202. Emde U, Koert U (1999) Total syntheses of squamocin A and squamocin D. Tetrahedron Lett 40:5979

    Article  CAS  Google Scholar 

  203. Sinha SC, Keinan E (1999) Total synthesis of squamotacin. J Org Chem 64:7067

    Article  CAS  Google Scholar 

  204. Das S, Li LS, Abraham S, Chen Z, Sinha SC (2005) A bidirectional approach to the synthesis of a complete library of adjacent-bis-THF annonaceous acetogenins. J Org Chem 70:5922

    Article  CAS  Google Scholar 

  205. Ruan ZM, Mootoo DR (1999) A novel desymmetrization reaction of an acetogenin precursor: a formal synthesis of trilobacin and asimicin. Tetrahedron Lett 40:49

    Article  CAS  Google Scholar 

  206. Marshall JA, Jiang H (1999) Total synthesis of the cytotoxic threo, trans, erythro, cis, threo annonaceous acetogenin trilobin. J Org Chem 64:971

    Article  CAS  Google Scholar 

  207. Sinha A, Sinha SC, Sinha SC, Keinan E (1999) Total synthesis of trilobin. J Org Chem 64:2381

    Article  CAS  Google Scholar 

  208. Burke SD, Jiang L (2001) Formal synthesis of uvaricin via palladium-mediated double cyclization. Org Lett 3:1953

    Article  CAS  Google Scholar 

  209. Yazbak A, Sinha SC, Keinan E (1998) Total synthesis of uvaricin. J Org Chem 63:5863

    Article  CAS  Google Scholar 

  210. Marshall JA, Piettre A, Paige MA, Valeriote F (2003) A modular synthesis of annonaceous acetogenins. J Org Chem 68:1771

    Article  CAS  Google Scholar 

  211. Gu Z-M, Zeng L, Schwedler JT, Wood KV, McLaughlin JL (1995) New bioactive adjacent bis-THF annonaceous acetogenins from Annona bullata. Phytochemistry 40:467

    Article  CAS  Google Scholar 

  212. Pan X, Yu D (1997) Studies on new cytotoxic annonaceous acetogenins from Uvaria grandiflora and absolute configurations. Acta Pharmacol Sin 32:286

    CAS  Google Scholar 

  213. Zhu L, Mootoo DR (2003) Synthesis of nonadjacently linked tetrahydrofurans: an iodoetherification and olefin metathesis approach. Org Lett 5:3475

    Article  CAS  Google Scholar 

  214. Zhu L, Mootoo DR (2004) Total synthesis of the nonadjacently linked bis-tetrahydrofuran acetogenin bullatanocin (squamostatin C). J Org Chem 69:3154

    Article  CAS  Google Scholar 

  215. Makabe H, Tanaka A, Oritan T (1998) Total synthesis of (+)-4-deoxygigantecin. Tetrahedron 54:6329

    Article  CAS  Google Scholar 

  216. Crimmins MT, She J (2004) Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction. J Am Chem Soc 126:12790

    Article  CAS  Google Scholar 

  217. Marshall JA, Jiang H (1998) Total synthesis of the nonadjacent bis-tetrahydrofuran annonaceous acetogenin squamostatin-D. J Org Chem 63:7066

    Article  CAS  Google Scholar 

  218. Donohoe TJ, Harris RM, Williams O, Hargaden GC, Burrows J, Parker J (2009) Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin. J Am Chem Soc 131:12854

    Article  CAS  Google Scholar 

  219. Quinn KJ, Smith AG, Cammarano CM (2007) Convergent total synthesis of squamostolide. Tetrahedron 63:4881

    Article  CAS  Google Scholar 

  220. Makabe H, Tanaka A, Oritani T (1997) Total synthesis of (+)-4-deoxygigantecin. Tetrahedron Lett 38:4247

    Article  CAS  Google Scholar 

  221. Donohoe TJ, Williams O, Churchill GH (2008) Hydride shift generated oxonium ions: evidence for mechanism and intramolecular trapping experiments to form trans THF derivatives. Angew Chem Int Ed 47:2869

    Article  CAS  Google Scholar 

  222. Takahashi S, Maeda K, Hirota S, Nakata T (1999) Total synthesis of a new cytotoxic acetogenin, jimenezin, and the revised structure. Org Lett 1:2025

    Article  CAS  Google Scholar 

  223. Takahashi S, Maeda K, Hirota S, Nakata T (2000) Total synthesis of antitumor acetogenin, jimenzein, and the revised structure. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 129:769

    Google Scholar 

  224. Schaus SE, Brånalt J, Jacobsen EN (1998) Total synthesis of muconin by efficient assembly of chiral building blocks. J Org Chem 63:4876

    Article  CAS  Google Scholar 

  225. Yang WQ, Kitahara T (1999) Convergent synthesis of (+)-muconin. Tetrahedron Lett 40:7827

    Article  CAS  Google Scholar 

  226. Yang WQ, Kitahara T (2000) Total synthesis of a nonclassical bioactive acetogenin, (+)-muconin. Tetrahedron 56:1451

    Article  CAS  Google Scholar 

  227. Takahashi S, Kubota A, Nakata T (2002) Total synthesis of muconin. Tetrahedron Lett 43:8661

    Article  CAS  Google Scholar 

  228. Takahashi S, Kubota A, Nakata T (2003) Stereoselective total synthesis of muconin. Tetrahedron 59:1627

    Article  CAS  Google Scholar 

  229. Yoshimitsu T, Makino T, Nagaoka H (2004) Total synthesis of (+)-muconin. J Org Chem 69:1993

    Article  CAS  Google Scholar 

  230. Crisóstomo FRP, Carrillo R, León LG, Matrín T, Padón JM, Martín VS (2006) Molecular simplification in bioactive molecules: formal synthesis of (+)-muconin. J Org Chem 71:2339

    Article  CAS  Google Scholar 

  231. Takahashi S, Hongo Y, Tsukagoshi Y, Koshino H (2008) Structural determination of montanacin D by total synthesis. Org Lett 10:4223

    Article  CAS  Google Scholar 

  232. Neogi P, Doundoulakis T, Yazbak A, Sinha SC, Sinha SC, Keinan E (1998) Total synthesis of mucocin. J Am Chem Soc 120:11279

    Article  CAS  Google Scholar 

  233. Takahashi S, Nakata T (1998) Total synthesis of an anticancer agent, mucocin. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 40th, p. 637

    Google Scholar 

  234. Takahashi S, Nakata T (1999) Total synthesis of an anticancer agent, mucocin. 2. A novel approach to a gamma-hydroxy butenolide derivative and completion of total synthesis. Tetrahedron Lett 40:727

    Article  CAS  Google Scholar 

  235. Takahashi S, Nakata T (1999) Total synthesis of an anticancer agent, mucocin. 1. Stereoselective synthesis of the left-half segment. Tetrahedron Lett 40:723

    Article  CAS  Google Scholar 

  236. Takahashi S, Nakata T (2002) Total synthesis of an antitumor agent, mucocin, based on the “chiron approach”. J Org Chem 67:5739

    Article  CAS  Google Scholar 

  237. Bäurle S, Hoppen S, Koert U (1999) Total synthesis of (−)-mucocin. Angew Chem Int Ed 38:1263

    Article  Google Scholar 

  238. Hoppen S, Bäurle S, Koert U (2000) A convergent total synthesis of (−)-mucocin: an acetogenin from Annonaceae. Chem Eur J 6:2382

    Article  CAS  Google Scholar 

  239. Evans PA, Cui J, Gharpure SJ, Polosukhin A, Zhang HR (2003) Enantioselective total synthesis of the potent antitumor agent (−)-mucocin using a temporary silicon-tethered ring-closing metathesis cross-coupling reaction. J Am Chem Soc 125:14702

    Article  CAS  Google Scholar 

  240. Zhu L, Mootoo DR (2005) Synthesis of the non-classical acetogenin mucocin: a modular approach based on olefinic coupling reactions. Org Biomol Chem 3:2750

    Article  CAS  Google Scholar 

  241. Takahashi S, Hongo Y, Ogawa N, Koshino H, Nakata T (2006) Convergent synthesis of pyragonicin. J Org Chem 71:6305

    Article  CAS  Google Scholar 

  242. Takahashi S, Kubota A, Nakata T (2006) Total synthesis of a cytotoxic acetogenin, pyranicin. Org Lett 5:1353

    Article  CAS  Google Scholar 

  243. Strand D, Norrby PO, Rein T (2006) Divergence en route to nonclassical annonaceous acetogenins, synthesis of pyranicin and pyragonicin. J Org Chem 71:1879

    Article  CAS  Google Scholar 

  244. Griggs ND, Phillips AJ (2008) A concise and modular synthesis of pyranicin. Org Lett 10:4955

    Article  CAS  Google Scholar 

  245. Sinha SC, Sinha A, Sinha SC, Keinan E (1997) Tandem oxidative cyclization with rhenium oxide. Total synthesis of 17,18-bisepi-goniocin. J Am Chem Soc 119:12014

    Article  CAS  Google Scholar 

  246. Owens GS, Arias J, Abu-Omar MM (2000) Rhenium oxo complexes in catalytic oxidations. Catal Today 55:317

    Article  CAS  Google Scholar 

  247. Sinha SC, Sinha A, Sinha SC, Keinan E (1998) Goniocin and its heptaepimer, cyclogoniodenin T. Unique biosynthetic implications. J Am Chem Soc 120:4017

    Article  CAS  Google Scholar 

  248. Makabe H, Higuchi M, Konno H, Murai M, Miyoshi H (2005) Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin. Tetrahedron Lett 46:4671

    Article  CAS  Google Scholar 

  249. Wolvetang EJ, Johnson KL, Krauer K, Ralph SJ, Linnane AW (1994) Mitochondrial respiratory chain inhibitors induce apoptosis. FEBS Lett 339:40

    Article  CAS  Google Scholar 

  250. Chih HW, Chiu HF, Tang KS, Chang FR, Wu YC (2001) Bullatacin, a potent antitumor annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction. Life Sci 69:1321

    Article  CAS  Google Scholar 

  251. Cartagena E, Colom OA, Neske A, Valdez JC, Bardon A (2007) Effects of plant lactones on the production of biofilm of Pseudomonas aeruginosa. Chem Pharm Bull 55:22

    Article  CAS  Google Scholar 

  252. Morton JF (1987) Fruits of warm climates. Media, Inc., Greensboro, NC, p 65

    Google Scholar 

  253. Rupprecht JK, Hui YH, McLaughlin JL (1990) Annonaceous acetogenins: a review. J Nat Prod 53:237

    Article  CAS  Google Scholar 

  254. Hui YH, Rupprecht JK, Liu YM, Anderson JE, Smith DL, Chang CJ, McLaughlin JL (1989) Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata. J Nat Prod 52:463

    Article  CAS  Google Scholar 

  255. Ratnayake S, Rupprecht JK, Potter WM, McLaughlin JL (1992) Evaluation of various parts of the paw paw tree, Asimina triloba (Annonaceae), as commercial sources of the pesticidal annonaceous acetogenins. J Econ Entomol 85:2353

    Article  CAS  Google Scholar 

  256. He K, Zeng L, Ye Q, Shi G, Oberlies NH, Zhao GX, Njoku CJ, McLaughlin JL (1997) Comparative structure-activity relationship evaluations of annonaceous acetogenins for pesticidal activity. Pestic Sci 49:372

    Article  CAS  Google Scholar 

  257. Alali FQ, Kaakeh W, Bennett GW, McLaughlin JL (1998) Annonaceous acetogenins as natural pesticides: potent toxicity against insecticide-susceptible and -resistant German cockroaches (Dictyoptera: Blattellidae). J Econ Entomol 91:641

    Article  CAS  Google Scholar 

  258. Ohsawa K, Atsuzawa S, Mitsui T, Yamamoto I (1991) Isolation and insecticidal activity of three acetogenins from seeds of pond apple, Annona glabra L. Nippon Noyaku Gakkaishi 16:93

    CAS  Google Scholar 

  259. Guadano A, Gutierrez C, de La Pena E, Cortes D, Gonzalez-Coloma A (2000) Insecticidal and mutagenic evaluation of two annonaceous acetogenins. J Nat Prod 63:773

    Article  CAS  Google Scholar 

  260. Lewis MA, Arnason JT, Philogene BJR, Rupprecht JK, McLaughlin JL (1993) Inhibition of respiration at site I by asimicin, an insecticidal acetogenin of the pawpaw, Asimina triloba (Annonaceae). Pestic Biochem Physiol 45:15

    Article  CAS  Google Scholar 

  261. Friedrich T, Ohnishi T, Forche E, Kunze B, Jansen R, Trowitzsch W, Hofle G, Reichenbach H, Weiss H (1994) Two binding sites for naturally occurring inhibitors in mitochondrial and bacterial NADH:ubiquinone oxidoreductase (complex I). Biochem Soc Trans 22:226

    Article  CAS  Google Scholar 

  262. Hollingworth RM, Ahammadsahib KI, Gadelhak G, McLaughlin JL (1994) New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides. Biochem Soc Trans 22:230

    Article  CAS  Google Scholar 

  263. Vila-Nova NS, Morais SM, Falcao MJC, Machado Lyeghyna KAA, Bevilaqua CMLL, Costa IRS, de Brasil NVGPS, Andrade HF (2011) Leishmanicidal activity and cytotoxicity of compounds from two Annonaceae species cultivated in Northeastern Brazil. Rev Soc Bras Med Trop 44:567

    Article  Google Scholar 

  264. Ahammadsahib KI, Hollingworth RM, McGovren JP, Hui YH, McLaughlin JL (1993) Mode of action of bullatacin: a potent antitumor and pesticidal annonaceous acetogenin. Life Sci 53:1113

    Article  CAS  Google Scholar 

  265. Degli Esposti M, Ghelli A, Ratta M, Cortes D, Estornell E (1994) Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (complex I). Biochem J 301:161

    Article  CAS  Google Scholar 

  266. Oberlies NH, Jones JL, Corbett TH, Fotopoulos SS, McLaughlin JL (1995) Tumor cell growth inhibition by several annonaceous acetogenins in an in vitro disk diffusion assay. Cancer Lett 96:55

    Article  CAS  Google Scholar 

  267. Oberlies NH, Croy VL, Harrison ML, McLaughlin JL (1997) The annonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells. Cancer Lett 115:73

    Article  CAS  Google Scholar 

  268. Shimada H, Grutzner JB, Kozlowski JF, McLaughlin JL (1998) Membrane conformations and their relation to cytotoxicity of asimicin and its analogs. Biochemistry 37:854

    Article  CAS  Google Scholar 

  269. Kuwabara K, Takada M, Iwata J, Tatsumoto K, Sakamoto K, Iwamura H, Miyoshi H (2000) Design syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics. Eur J Biochem 267:2538

    Article  CAS  Google Scholar 

  270. Yuan SSF, Chang HL, Chen HW, Yeh YT, Kao YH, Lin KH, Wu YC, Su JH (2003) Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway. Life Sci 72:2853

    Article  CAS  Google Scholar 

  271. Lu MC, Yang SH, Hwang SL, Lu YJ, Lin YH, Wang SR, Wu YC, Lin SR (2006) Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells. Life Sci 78:2378

    Article  CAS  Google Scholar 

  272. Caparros-Lefebvre D, Elbaz A (1999) Possible relation of atypical parkinsonism in the French West Indies with consumption of tropical plants: a case-control study. Lancet 354:281

    Article  CAS  Google Scholar 

  273. Chaudhuri KR, Hu MTM, Brooks DJ (2000) Atypical parkinsonism in Afro-Caribbean and Indian origin immigrants to the UK. Mov Disord 15:18

    Article  CAS  Google Scholar 

  274. Caparros-Lefebvre D, Steele J (2005) Atypical parkinsonism on Guadeloupe, comparison with the parkinsonism-dementia complex of Guam, and environmental toxic hypotheses. Environ Toxicol Pharmacol 19:407

    Article  CAS  Google Scholar 

  275. Lannuzel A, Michel PP, Caparros-Lefebvre D, Abaul J, Hocquemiller R, Ruberg M (2002) Toxicity of Annonaceae for dopaminergic neurons: potential role in atypical parkinsonism in Guadeloupe. Mov Disord 17:84

    Article  Google Scholar 

  276. Lannuzel A, Michel PP, Hoglinger GU, Champy P, Jousset A, Medja F, Lombes A, Darios F, Gleye C, Laurens A, Hocquemiller R, Hirsch EC, Ruberg M (2003) The mitochondrial complex I inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism. Neuroscience 121:287

    Article  CAS  Google Scholar 

  277. Champy P, Hoglinger Gunter U, Feger J, Gleye C, Hocquemiller R, Laurens A, Guerineau V, Laprevote O, Medja F, Lombes A, Michel PP, Lannuzel A, Hirsch Etienne C, Ruberg M (2004) Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: possible relevance for atypical parkinsonism in Guadeloupe. J Neurochem 88:63

    Article  CAS  Google Scholar 

  278. Angibaud G, Gaultier C, Rascol O (2004) Atypical parkinsonism and Annonaceae consumption in New Caledonia. Mov Disord 19:603

    Article  Google Scholar 

  279. Potts LF, Luzzio FA, Smith SC, Hetman M, Champy P, Litvan I (2012) Annonacin in Asimina triloba fruit: implication for neurotoxicity. NeuroToxicology 33:53

    Article  CAS  Google Scholar 

  280. Wu TY, Yang IH, Tsai YT, Wang JY, Shiurba R, Hsieh TJ, Chang FR, Chang WC (2012) Isodesacetyluvaricin, an annonaceous acetogenin, specifically inhibits gene expression of cyclooxygenase-2. J Nat Prod 75:572

    Article  CAS  Google Scholar 

  281. Parellada EA, Ramos AN, Ferrero M, Cartagena E, Bardon A, Valdez JC, Neske A (2011) Squamocin mode of action to stimulate biofilm formation of Pseudomonas plecoglossicida J26, a PAHs degrading bacterium. Int Biodeterior Biodegrad 65:1066

    Article  CAS  Google Scholar 

  282. Parellada EA, Ramos AN, Ferrero M, Cartagena E, Bardon A, Neske A (2012) Effect of the annonaceous acetogenins, squamocin and laherradurin, on the degradation of naphthalene mediated by Pseudomonas plecoglossicida J26. Int Biodeterior Biodegrad 72:82

    Article  CAS  Google Scholar 

  283. Bombasaro JA, Blessing LDT, Diaz S, Neske A, Suvire FD, Enriz RD, Rodriguez AM (2011) Theoretical and experimental study of the interactions of annonaceous acetogenins with artificial lipid bilayers. J Mol Struct 1003:87

    Article  CAS  Google Scholar 

  284. Marsh D (1996) Lateral pressure in membranes. Biochim Biophys Acta 1286:183

    Article  CAS  Google Scholar 

  285. Zafra-Polo MC, Gonzalez MC, Estornell E, Sahpaz S, Cortes D (1996) Acetogenins from Annonaceae, inhibitors of mitochondrial complex I. Phytochemistry 42:253

    Article  CAS  Google Scholar 

  286. Sasaki S, Naito H, Maruta K, Kawahara E, Maeda M (1994) Novel calcium ionophores: supramolecular complexation by the hydroxylated-bistetrahydrofuran skeleton of potent antitumor annonaceous acetogenins. Tetrahedron Lett 35:3337

    Article  CAS  Google Scholar 

  287. Araya H, Fujimoto Y, Hirayama K (1994) Structural elucidation of tetrahydrofuranic acetogenins by means of precursor-ion scanning method. J Synth Org Chem Jpn 52:765

    Article  CAS  Google Scholar 

  288. Sasaki S, Maruta K, Naito H, Sugihara H, Hiratani K, Maeda M (1995) New calcium-selective electrodes based on annonaceous acetogenins and their analogs with neighboring bistetrahydrofuran. Tetrahedron Lett 36:5571

    Article  CAS  Google Scholar 

  289. Sasaki S, Maruta K, Naito H, Maemura R, Kawahara E, Maeda M (1998) Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural annonaceous acetogenins. Tetrahedron 54:2401

    Article  CAS  Google Scholar 

  290. Peyrat JF, Mahuteau J, Figadère B, Cavé A (1997) NMR Studies of Ca2+ complexes of annonaceous acetogenins. J Org Chem 62:4811

    Article  CAS  Google Scholar 

  291. Wu SN, Chiang HT, Chang FR, Liaw CC, Wu YC (2003) Stimulatory effects of squamocin, an annonaceous acetogenin, on Ca(2+)-activated K+ current in cultured smooth muscle cells of human coronary artery. Chem Res Toxicol 16:15

    Article  CAS  Google Scholar 

  292. Liaw CC, Liao WY, Chen CS, Jao SC, Wu YC, Shen CN, Wu SH (2011) The calcium-chelating capability of tetrahydrofuranic moieties modulates the cytotoxicity of annonaceous acetogenins. Angew Chem Int Ed 50:7885

    Article  CAS  Google Scholar 

  293. Miyoshi H, Ohshima M, Shimada H, Akagi T, Iwamura H, McLaughlin JL (1998) Essential structural factors of annonaceous acetogenins as potent inhibitors of mitochondrial complex I. Biochim Biophys Acta 1365:443–452

    Article  CAS  Google Scholar 

  294. Miyoshi H (2005) Inhibitors of mitochondrial respiratory enzymes. J Pestic Sci 30:127

    Article  Google Scholar 

  295. Takada M, Kuwabara K, Nakato H, Tanaka A, Iwamura H, Miyoshi H (2000) Definition of crucial structural factors of acetogenins, potent inhibitors of mitochondrial complex I. Biochim Biophys Acta 1460:302

    Article  CAS  Google Scholar 

  296. Murai M, Ichimaru N, Abe M, Nishioka T, Miyoshi H (2006) Synthesis of photolabile Δlac-acetogenin for photoaffinity labeling of mitochondrial complex I. J Pestic Sci 31:156

    Article  CAS  Google Scholar 

  297. Ichimaru N, Murai M, Abe M, Hamada T, Yamada Y, Makino S, Nishioka T, Makabe H, Makino A, Kobayashi T, Miyoshi H (2005) Synthesis and inhibition mechanism of Δlac-acetogenins, a novel type of inhibitor of bovine heart mitochondrial complex I. Biochemistry 44:816

    Article  CAS  Google Scholar 

  298. Hoppen S, Emde U, Friedrich T, Grubert L, Koert U (2000) Natural-product hybrids: design, synthesis, and biological evaluation of quinone-annonaceous acetogenins. Angew Chem Int Ed 39:2099

    Article  CAS  Google Scholar 

  299. Arndt S, Emde U, Baurle S, Friedrich T, Grubert L, Koert U (2001) Quinone-annonaceous acetogenins: synthesis and complex I inhibition studies of a new class of natural product hybrids. Chem Eur J 7:993

    Article  CAS  Google Scholar 

  300. Duval R, Lewin G, Hocquemiller R (2003) Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction. Bioorg Med Chem 11:3439

    Article  CAS  Google Scholar 

  301. Duval RA, Lewin G, Peris E, Chahboune N, Garofano A, Droese S, Cortes D, Brandt U, Hocquemiller R (2006) Heterocyclic analogues of squamocin as inhibitors of mitochondrial complex I. On the role of the terminal lactone of annonaceous acetogenins. Biochemistry 45:2721

    Article  CAS  Google Scholar 

  302. Duval RA, Poupon E, Romero V, Peris E, Lewin G, Cortes D, Brandt U, Hocquemiller R (2006) Analogues of cytotoxic squamocin using reliable reactions: new insights into the reactivity and role of the α,β-unsaturated lactone of the annonaceous acetogenins. Tetrahedron 62:6248

    Article  CAS  Google Scholar 

  303. Kojima N, Fushimi T, Maezaki N, Tanaka T, Yamori T (2008) Synthesis of hybrid acetogenins, α,β-unsaturated-γ-lactone-free nitrogen-containing heterocyclic analogues, and their cytotoxicity against human cancer cell lines. Bioorg Med Chem Lett 18:1637

    Article  CAS  Google Scholar 

  304. Zeng BB, Wu Y, Yu Q, Wu YL, Li Y, Chen XG (2000) Enantiopure simple analogues of annonaceous acetogenins with remarkable selective cytotoxicity towards tumor cell lines. Angew Chem Int Ed 39:1934

    Article  CAS  Google Scholar 

  305. Rodier S, Le Huerou Y, Renoux B, Doyon J, Renard P, Pierre A, Gesson JP, Gree R (2000) Synthesis and cytotoxic activity of acetogenin analogues. Bioorg Med Chem Lett 10:1373

    Article  CAS  Google Scholar 

  306. Yao ZJ, Wu HP, Wu YL (2000) Polyether mimics of naturally occurring cytotoxic annonaceous acetogenins. J Med Chem 43:2484

    Article  CAS  Google Scholar 

  307. Liu YQ, Cheng X, Guo LX, Mao C, Chen YJ, Liu HX, Xiao QC, Jiang S, Yao ZJ, Zhou GB (2012) Identification of an annonaceous acetogenin mimetic, AA005, as an AMPK activator and autophagy inducer in colon cancer cells. PLoS One 7:e47049

    Article  CAS  Google Scholar 

  308. Zeng BB, Wu Y, Jiang S, Yu Q, Yao ZJ, Liu ZH, Li HY, Li Y, Chen XG, Wu YL (2003) Studies on mimicry of naturally occurring annonaceous acetogenins: non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells. Chem Eur J 9:282

    Article  CAS  Google Scholar 

  309. Rodier S, Le Huerou Y, Renoux B, Doyon J, Renard P, Pierre A, Gesson JP, Gree R (2001) New cytotoxic analogues of annonaceous acetogenins. Anticancer Drug Des 16:109

    CAS  Google Scholar 

  310. Fujita D, Ichimaru N, Abe M, Murai M, Hamada T, Nishioka T, Miyoshi H (2005) Synthesis of non-THF analogs of acetogenin toward simplified mimics. Tetrahedron Lett 46:5775

    Article  CAS  Google Scholar 

  311. Liu HX, Huang GR, Zhang HM, Wu JR, Yao ZJ (2007) annonaceous acetogenin mimics bearing a terminal lactam and their cytotoxicity against cancer cells. Bioorg Med Chem Lett 17:3426

    Article  CAS  Google Scholar 

  312. Xiao Q, Liu Y, Qiu Y, Zhou G, Mao C, Li Z, Yao ZJ, Jiang S (2011) Potent antitumor mimetics of annonaceous acetogenins embedded with an aromatic moiety in the left hydrocarbon chain part. J Med Chem 54:525

    Article  CAS  Google Scholar 

  313. Ye Q, Shi G, He K, McLaughlin JL (1996) Chlorinated annonaceous acetogenins and their bioactivities. J Nat Prod 59:994

    Article  CAS  Google Scholar 

  314. Kojima N, Hayashi H, Suzuki S, Tominaga H, Maezaki N, Tanaka T, Yamori T (2008) Synthesis of C4-fluorinated solamins and their growth inhibitory activity against human cancer cell lines. Bioorg Med Chem Lett 18:6451

    Article  CAS  Google Scholar 

  315. Gallardo T, Saez J, Granados H, Tormo JR, Velez ID, Brun N, Torres B, Cortes D (1998) 10-Oximeguanacone, the first nitrogenated acetogenin derivative found to be a potent inhibitor of mitochondrial complex I. J Nat Prod 61:1001

    Article  CAS  Google Scholar 

  316. Duret P, Hocquemiller R, Gantier JC, Figadère B (1999) Semisynthesis and cytotoxicity of amino acetogenins and derivatives. Bioorg Med Chem 7:1821

    Article  CAS  Google Scholar 

  317. Derbre S, Roue G, Poupon E, Susin Santos A, Hocquemiller R (2005) Annonaceous acetogenins: the hydroxyl groups and THF rings are crucial structural elements for targeting the mitochondria, demonstration with the synthesis of fluorescent squamocin analogues. ChemBioChem 6:979

    Article  CAS  Google Scholar 

  318. Alexander MD, Burkart MD, Leonard MS, Portonovo P, Liang B, Ding X, Joullie MM, Gulledge BM, Aggen JB, Chamberlin AR, Sandler J, Fenical W, Cui J, Gharpure SJ, Polosukhin A, Zhang HR, Evans PA, Richardson AD, Harper MK, Ireland CM, Vong BG, Brady TP, Theodorakis EA, La Clair JJ (2006) A central strategy for converting natural products into fluorescent probes. ChemBioChem 7:409

    Article  CAS  Google Scholar 

  319. Maezaki N, Urabe D, Yano M, Tominaga H, Morioka T, Kojima N, Tanaka T (2007) Synthesis of fluorescent solamin for visualization of cell distribution. Heterocycles 73:159

    Article  CAS  Google Scholar 

  320. Kojima N, Morioka T, Yano M, Suga Y, Maezaki N, Tanaka T (2009) Convergent synthesis of fluorescence labeled solamin. Heterocycles 79:387

    Article  CAS  Google Scholar 

  321. Liu HX, Huang GR, Zhang HM, Jiang S, Wu JR, Yao ZJ (2007) A structure-activity guided strategy for fluorescent labeling of annonaceous acetogenin mimetics and their application in cell biology. ChemBioChem 8:172

    Article  CAS  Google Scholar 

  322. Mao C, Han B, Wang LS, Wang S, Yao ZJ (2011) Modular assembly of cytotoxic acetogenin mimetics by click linkage with nitrogen functionalities. MedChemComm 2:918

    Article  CAS  Google Scholar 

  323. Xiao Q, Liu Y, Qiu Y, Yao Z, Zhou G, Yao ZJ, Jiang S (2011) Design, synthesis of symmetrical bivalent mimetics of annonaceous acetogenins and their cytotoxicities. Bioorg Med Chem Lett 21:3613

    Article  CAS  Google Scholar 

  324. Le Ven J, Schmitz-Afonso I, Lewin G, Brunelle A, Touboul D, Champy P (2014) Identification of the environmental neurotoxins annonaceous acetogenins in an Annona cherimola Mill. alcoholic beverage using HPLC-ESI-LTQ-orbitrap. J Agric Food Chem 62:8696

    Article  CAS  Google Scholar 

  325. McLaughlin JL (2008) Paw paw and cancer: annonaceous acetogenins from discovery to commercial products. J Nat Prod 71:1311

    Article  CAS  Google Scholar 

  326. Cuendet M, Oteham CP, Moon RC, Keller WJ, Peaden PA, Pezzuto JM (2008) Dietary administration of Asimina triloba (paw paw) extract increases tumor latency in N-methyl-N-nitrosourea-treated rats. Pharm Biol 46:3

    Article  CAS  Google Scholar 

  327. Chen Y, Chen JW, Xu SS, Wang Y, Li X, Cai BC, Fan NB (2012) Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice. Bioorg Med Chem Lett 22:2717

    Article  CAS  Google Scholar 

  328. Chen Y, Chen JW, Liu SI, Xu CL, Xu HQ, Cai BC, Li X, Ju WZ (2012) Determination of bullatacin in rat plasma by liquid chromatography–mass spectrometry. J Chromatogr B 897:94

    Article  CAS  Google Scholar 

  329. Escobar-Khondiker M, Hoellerhage M, Muriel MP, Champy P, Bach A, Depienne C, Respondek G, Yamada ES, Lannuzel A, Yagi T, Hirsch EC, Oertel WH, Jacob R, Michel PP, Ruberg M, Hoeglinger GU (2007) Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons. J Neurosci 27:7827

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by grants from the Ministry of Science and Technology (National Science Council) of Taiwan NSC100-2320-B-110-001-MY2 awarded to C.C.L., MOST 103-2320-B-037-005-MY2 & 102-2628-B-037-003-MY3 awarded to F.R.C., and NSC 103-2911-I-002-303, NSC101-2632-B039-001-MY3, NSC100-2320-B-110-001-MY2 National Health Research Institutes NHRI-EX102-10241BI, and CMU under the Aim for Top University Plan of the Ministry of Education, Taiwan award to Y.C.W. as well as the Excellence for Cancer Research Center Grant, the Ministry of Health and Welfare, Executive Yuan, Taipei, Taiwan (MOHW104-TDU-B-212-124-003) and the grant for Health and Welfare Surcharge of Tobacco Products.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yang-Chang Wu .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2016 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Liaw, CC., Liou, JR., Wu, TY., Chang, FR., Wu, YC. (2016). Acetogenins from Annonaceae. In: Kinghorn, A., Falk, H., Gibbons, S., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products 101. Progress in the Chemistry of Organic Natural Products, vol 101. Springer, Cham. https://doi.org/10.1007/978-3-319-22692-7_2

Download citation

Publish with us

Policies and ethics