Skip to main content
SpringerLink
Log in

Cytotoxic Cembrane Diterpenoids

  • Chapter
  • First Online:
Handbook of Anticancer Drugs from Marine Origin

Abstract

Cembrane-type diterpenoids are a large and structurally varied group of natural products isolated from both terrestrial and marine organisms. From a biomedical perspective, cytotoxicity is the most remarkable property of this class of diterpenoids, respresented by sarcophytol A. The present paper reviews all the cytotoxic metabolites of cembrane diterpenes, reported up to 2013. The natural products discussed in this review can be divided into several different structural families featuring a variety of ring sizes and oxidation patterns. The currently hypothetical biosynthesis and total syntheses of some representative cembrane diterpenoids will be presented as well.

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

Access this chapter

Log in via an institution
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. Bhatnagar I, Kim SK (2010) Marine antitumor drugs: status, shortfalls and strategies. Mar Drugs 8:2702–2720

    CAS  Google Scholar 

  2. Russo P, Nastrucci C, Cesario A (2011) From the sea to anticancer therapy. Curr Med Chem 18:3551–3562

    CAS  Google Scholar 

  3. Blunt JW, Copp BR, Keyzers RA et al (2012) Marine natural products. Nat Prod Rep 29:144–222

    CAS  Google Scholar 

  4. Cooper EL, Yao D (2012) Diving for drugs: tunicate anticancer compounds. Drug Discov Today 17:636–648

    CAS  Google Scholar 

  5. Nastrucci C, Cesario A, Russo P (2012) Anticancer drug discovery from the marine environment. Recent Pat Anti-Canc 7:218–232

    CAS  Google Scholar 

  6. Yang B, Zhou XF, Lin XP et al (2012) Cembrane diterpenes chemistry and biological properties. Curr Org Chem 16:1512–1539

    CAS  Google Scholar 

  7. Dauben WG, Thiessen WE, Resnick PR (1965) Cembrene, a fourteen-membered ring diterpene hydrocarbon. J Org Chem 30:1693–1698

    CAS  Google Scholar 

  8. Kobayashi M, Nakagawa T, Mitsuhashi H (1979) Marine terpenes and terpenoids. 1. Structures of 4 cembrane type diterpenes sarcophytol A, sarcophytol A acetate, sarcophytol B, and sarcophytonin A from the soft cora, Sarcphyton glaucum. Chem Pharma Bull 27:2382–2387

    CAS  Google Scholar 

  9. Weinheimer AJ, Chang CWJ, Matson JA (1979) Naturally occurring cembranes. Fortschr Chem Org Naturst 36:285–387

    CAS  Google Scholar 

  10. Yang B, Zhou XF, Huang H et al (2012) New cembrane diterpenoids from a Hainan soft coral Sinularia sp. Mar Drugs 10:2023–2032

    CAS  Google Scholar 

  11. Yen WH, Hu LC, Su JH et al (2012) Norcembranoidal diterpenes from a Formosan soft coral Sinularia sp. Molecules 17:14058–14066

    CAS  Google Scholar 

  12. Hu LC, Yen WH, Su JH et al (2013) Cembrane derivatives from the soft corals, Sinularia gaweli and Sinularia flexibilis. Mar Drugs 11:2154–2167

    Google Scholar 

  13. Jia R, Kurtan T, Mandi A et al (2013) Biscembranoids formed from an alpha, beta-Unsaturated gamma-lactone ring as a dienophile: structure revision and establishment of their absolute configurations using theoretical calculations of electronic circular dichroism spectra. J Org Chem 78:3113–3119

    CAS  Google Scholar 

  14. Kawakami S, Matsunami K, Otsuka H et al (2013) Two new cembranoids from the leaves of Croton longissimus Airy Shaw. J Nat Med 67:410–414

    CAS  Google Scholar 

  15. Su CC, Wong BS, Chin C et al (2013) Oxygenated cembranoids from the soft coral Sinularia flexibilis. Int J Mol Sci 14:4317–4325

    CAS  Google Scholar 

  16. Yang EG, Sekar K, Lear MJ (2013) A macrolactonisation approach to the cembrane carbocycle of bielschowskysin. Tetrahedron Lett 54:4406–4408

    CAS  Google Scholar 

  17. Yen WH, Su YD, Chang YC et al (2013) Sinulanorcembranolide A, a novel norcembranoidal diterpene from the octocoral Sinularia gaweli. Tetrahedron Lett 54:2267–2270

    CAS  Google Scholar 

  18. Rodriguez AD, Shi JG (1998) The first cembrane-pseudopterane cycloisomerization. J Org Chem 63:420–421

    CAS  Google Scholar 

  19. Qin S, Huang H, Guo YW (2008) A new cembranoid from the Hainan soft coral Sinularia sp. J Asian Nat Prod Res 10:1075–1079

    CAS  Google Scholar 

  20. Sponholtz WR, Bianco MA, Gribble GW (2008) Isolation and structure determination of the cembranoid eunicin from a new genus of octocoral, Pseudoplexaura. Nat Prod Rep 22:441–448

    Google Scholar 

  21. Sawant SS, Sylvester PW, Avery MA et al (2004) Bioactive rearranged and halogenated semisynthetic derivatives of the marine natural product sarcophine. J Nat Prod 67:2017–2023

    CAS  Google Scholar 

  22. Zeng LM, Lan WJ, Su JY et al (2004) Two new cytotoxic tetracyclic tetraterpenoids from the soft coral Sarcophyton tortuosum. J Nat Prod 67:1915–1918

    CAS  Google Scholar 

  23. Feller M, Rudi A, Berer N et al (2004) Isoprenoids of the soft coral Sarcophyton glaucum: nyalolide, a new biscembranoid, and other terpenoids. J Nat Prod 67:1303–1308

    CAS  Google Scholar 

  24. Fujiki H, Suganuma M, Suguri H et al (1989) Sarcophytol A and satcophytol B inhibit tumor promotion by teleocidin in 2 stage carcinogenesis in mouse skin. J Cancer Res Clin 115:25–28

    CAS  Google Scholar 

  25. Kobayashi M, Kobayashi K, Nomura M et al (1990) Conformational study of the cembranoid sarcophytol A, a pothent antitumor promoter. Chem Pharma Bull 38:815–817

    CAS  Google Scholar 

  26. Nakagane T, Ishitani R (1990) Presence of specific binding-sites for H-3 sarcophytol A in culturedhuman skin fibroblasts. Experientia 46:490–492

    CAS  Google Scholar 

  27. Fujiki H (1991) Sarcophytol A, a new cancer chemopreventive agent. Abstr Pap Am Chem S 202:87–AGFD

    Google Scholar 

  28. Wei HC, Frenkel K (1992) Suppression of tumor promoter-induced oxidative events and DNA damage invivo by sarcophytol A apossible mechanism of antipomotion. Cancer Res 52:2298–2303

    CAS  Google Scholar 

  29. Yokomatsu H, Satake K, Fujiki H (1993) Inhibitory effect of sarcophytol A(SAA) on tumor growth of transplanted Human pancreatic cancer cell (MIA PACA-2) in mude-mice. Gastroenterol Jpn 28:136–136

    Google Scholar 

  30. Yokomatsu H, Satake K, Hiura A et al (1994) Sarcophytol A, a new chemotherapeutic and chemopreventive agent for pancreatic cancer. Pancreas 9:526–530

    CAS  Google Scholar 

  31. Yokomatsu H, Hiura A, Tsutsumi M et al (1996) Inhibitory effect of sarcophytol A on pancreatic carcinogenesis after initiation by N-nitrosobis(2-oxypropyl)amine in Syrian hamsters. Pancreas 13:154–159

    CAS  Google Scholar 

  32. Kobayashi M, Osabe K (1989) Marine terpenes and terpenoids. â«. Minor cembranoid derivatives, structurally related to the potent anti-tumor-promoter Sarcophytol A, from the soft coral Sarcophyton glaucum. Chem Pharm Bull 37:631–636

    CAS  Google Scholar 

  33. Zhang CX, Li J, Su JY et al (2006) Cytotoxic diterpenoids from the soft coral Sarcophyton crassocaule. J Nat Prod 69:1476–1480

    CAS  Google Scholar 

  34. Fontana A, Ciavatta ML, Amodeo P et al (1999) Single solution phase conformation of new antiproliferative cembranes. Tetrahedron 55:1143–1152

    CAS  Google Scholar 

  35. Reyes F, Arda A, Martin R et al (2004) New cytotoxic cembranes from the sea pen Gyrophyllum sibogae. J Nat Prod 67:1190–1192

    CAS  Google Scholar 

  36. Roengsumran S, Achayindee S, Petsom A et al (1998) Two new cembranoids from Croton oblongifolius. J Nat Prod 61:652–654

    CAS  Google Scholar 

  37. Roengsumran S, Singtothong P, Pudhom K et al (1999) Neocrotocembranal from Croton oblongifolius. J Nat Prod 62:1163–1164

    CAS  Google Scholar 

  38. Ortega MJ, Zubia E, Sanchez MC et al (2008) Cembrane diterpenes from the gorgonian Leptogorgia laxa. J Nat Prod 71:1637–1639

    CAS  Google Scholar 

  39. Ma AY, Deng ZW, van Ofwegen LP et al (2008) Dendronpholides A-R, cembranoid diterpenes from the Chinese soft coral Dendronephthya sp. J Nat Prod 71:1152–1160

    CAS  Google Scholar 

  40. Ma AY, Deng ZW, van Ofwegen LP et al (2010) Dendronpholides A-R, cembranoid diterpenes from the Chinese soft coral Dendronephthya sp. J Nat Prod 73:1026–1026. (71:1133, 2008)

    CAS  Google Scholar 

  41. Wen T, Ding Y, Deng ZW et al (2008) Sinulaflexiolides A-K, cembrane-type diterpenoids from the Chinese soft coral Sinularia flexibilis. J Nat Prod 71:1133–1140

    CAS  Google Scholar 

  42. Kashman Y, Carmely S, Groweiss A (1981) Further cembranoid derivatives from the red sea soft corals Alcyonium flaccidum and Lobophytum crassum. J Org Chem 46:3592–3596

    CAS  Google Scholar 

  43. Li GQ, Zhang YL, Deng ZW et al (2005) Cytotoxic cembranoid diterpenes from a soft coral Sinularia gibberosa. J Nat Prod 68:649–652

    CAS  Google Scholar 

  44. Zhang W, Krohn K, Ding J et al (2008) Structural and stereochemical studies of α-methylene-γ-lactone-bearing cembrane diterpenoids from a South China Sea soft coral Lobophytum crassum. J Nat Prod 71:961–966

    CAS  Google Scholar 

  45. Chao CH, Wen ZH, Wu YC et al (2008) Cytotoxic and anti-inflammatory cembranoids from the soft coral Lobophytum crassum. J Nat Prod 71:1819–1824

    CAS  Google Scholar 

  46. Yin SW, Shi YP, Li XM et al (2006) A new cembranoid diterpene and other related metabolites from the south-China-sea soft coral Lobophytum crassum. HeIv Chim Acta 89:567–572

    CAS  Google Scholar 

  47. Duh CY, Wang SK, Huang BT et al (2000) Cytotoxic cembrenolide diterpenes from the Formosan soft coral Lobophytum crassum. J Nat Prod 63:884–885

    CAS  Google Scholar 

  48. Wanzola M, Furuta T, Kohno Y et al (2010) Four new cembrane diterpenes isolated from an Okinawan soft coral Lobophytum crassum with inhibitory effects on nitric oxide production. Chem Pharm Bull 58:1203–1209

    CAS  Google Scholar 

  49. Wang LT, Wang SK, Soong K et al (2007) New cytotoxic cembranolides from the soft coral Lobophytum michaelae. Chem Pharm Bull 55:766–770

    CAS  Google Scholar 

  50. Wang SK, Duh CY, Wu YC et al (1992) Studies on formosan soft corals, â. Cytotoxic cembranolides from the soft cioral Lobophytum michaelae. J Nat Prod 55:1430–1435

    CAS  Google Scholar 

  51. Cheng SY, Wang SK, Chiou SF et al (2010) Cembranoids from the octocoral Sarcophyton ehrenbergi. J Nat Prod 73:197–203

    CAS  Google Scholar 

  52. Su JH, Lu Y, Lin WY et al (2010) A cembranoid, trocheliophorol, from the cultured soft coral Sarcophyton trocheliophorum. Chem Lett 39:172–173

    CAS  Google Scholar 

  53. Yao LG, Liu HL, Guo YW et al (2009) New cembranoids from the Hainan soft coral Sarcophyton glaucum. HeIv Chim Acta 92:1085–1091

    CAS  Google Scholar 

  54. Lin WY, Su JH, Lu Y et al (2010) Cytotoxic and anti-inflammatory cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule. Bioorg Med Chem 18:1936–1941

    CAS  Google Scholar 

  55. Huang HC, Ahmed AF, Su JH et al (2006) Crassocolides A-F, cembranoids with a trans-fused lactone from the soft coral Sarcophyton crassocaule. J Nat Prod 69:1554–1559

    CAS  Google Scholar 

  56. Grote D, Soliman HSM, Shaker KH et al (2006) Cembranoid diterpenes and a briarane diterpene from corals. Nat Prod Rep 20:285–291

    CAS  Google Scholar 

  57. Gross H, Kehraus S, Nett M et al (2003) New cytotoxic cembrane based diterpenes from the soft corals Sarcophyton cherbonnieri and Nephthea sp. Org Biomol Chem 1:944–949

    CAS  Google Scholar 

  58. Iwashima M, Matsumoto Y, Takahashi H et al (2000) New marine cembrane-type diterpenoids from the Okinawan soft coral Clavularia koellikeri. J Nat Prod 63:1647–1652

    CAS  Google Scholar 

  59. Kobayashi M (1988) Marine terpenes and terpenoids. â£. Isolateion of new cembranoid and secocembranoid lactones from the soft coral Sinularia mayi. Chem Pharm Bull 36:488–494

    CAS  Google Scholar 

  60. Chang YC, Huang IC, Chiang MYN et al (2010) Briaviodiol A, a new cembranoid from a soft coral Briareum violacea. Chem Pharm Bull 58:1666–1668

    CAS  Google Scholar 

  61. Duh CY, El-Gamal AAH, Chu CJ et al (2002) New cytotoxic constituents from the Formosan soft corals Clavularia viridis and Clavularia violacea. J Nat Prod 65:1535–1539

    CAS  Google Scholar 

  62. Xu L, Patrick BO, Roberge M et al (2000) New diterpenoids from the octocoral Pachyclavularia violacea collected in Papua New Guinea. Tetrahedron 56:9031–9037

    CAS  Google Scholar 

  63. Sheu JH, Wang GH, Sung PJ et al (2001) Pachyclavulariolides G-L and secopachyclavulariaenone A, seven novel diterpenoids from the soft coral Pachyclavularia violacea. Tetrahedron 57:7639–7648

    CAS  Google Scholar 

  64. Sheu JH, Wang GH, Duh CY et al (2003) Pachyclavulariolides M-R, six novel diterpenoids from a Taiwanese soft coral Pachyclavularia violacea. J Nat Prod 66:662–666

    CAS  Google Scholar 

  65. Shi YP, Rodriguez AD, Barnes CL et al (2002) New terpenoid constituents from Eunicea pinta. J Nat Prod 65:1232–1241

    CAS  Google Scholar 

  66. Manchand PS, Blount JF (1977) Sterostructures of macrocyclic diterpenoids ovatodiolide and iso-ovtodiolide. J Org Chem 42:3824–3828

    CAS  Google Scholar 

  67. Arisawa M, Nimura M, Fujita A et al (1986) Biolgical active macrocyclic diterpenoids from chinese drug Fang Feng Cao.2. derivatives of ovatodiolids and their cytotoxity. Planta Med 4:297–299

    Google Scholar 

  68. Chen YL, Lan YH, Hsieh PW et al (2008) Bioactive cembrane diterpenoids of Anisomeles indica. J Nat Prod 71:1207–1212

    CAS  Google Scholar 

  69. Kao CY, Su JH, Lu MC et al (2011) Lobocrassins A-E: new cembrane-type diterpenoids from the soft coral Lobophytum crassum. Mar Drugs 9:1319–1331

    CAS  Google Scholar 

  70. Lin CY, Lu MC, Su JH et al (2013) Immunomodulatory effect of marine cembrane-type diterpenoids on dendritic cells. Mar Drugs 11:1336–1350

    CAS  Google Scholar 

  71. Su JH, Ahmed AF, Sung PJ et al (2006) Manaarenolides A-I, diterpenoids from the soft coral Sinularia manaarensis. J Nat Prod 69:1134–1139

    CAS  Google Scholar 

  72. Duh CY, Wang SK, Tseng HK et al (1998) Novel cytotoxic cembranoids from the soft coral Sinularia flexibilis. J Nat Prod 61:844–847

    CAS  Google Scholar 

  73. Zou GA, Ding G, Su ZH et al (2010) Lactonecembranoids from Croton laevigatus. J Nat Prod 73:792–795

    CAS  Google Scholar 

  74. Lo KL, Khalil AT, Kuo YH et al (2009) Sinuladiterpenes A-F, new cembrane diterpenes from Sinularia flexibilis. Chem Biodivers 6:2227–2235

    CAS  Google Scholar 

  75. Lo KL, Khalil AT, Chen MH et al (2010) New cembrane diterpenes from Taiwanese soft coral Sinularia flexibilis. HeIv Chim Acta 93:1329–1335

    CAS  Google Scholar 

  76. Lin YS, Chen CH, Liaw CC et al (2009) Cembrane diterpenoids from the Taiwanese soft coral Sinularia flexibilis. Tetrahedron 65:9157–9164

    CAS  Google Scholar 

  77. Guerrero PP, Read RW, Batley M et al (1995) The structure of a novel cembranoid diterpene from a Philippine collection of the soft coral Sinularia flexibilis. J Nat Prod 58:1185–1191

    CAS  Google Scholar 

  78. Anjaneyulu ASR, Sagar KS, Rao GV (1997) New cembranoid lactones from the Indian ocean soft coral Sinularia flexibilis. J Nat Prod 60:9–12

    CAS  Google Scholar 

  79. Tursch B, Braekman JC, Daloze D et al (1975) Chemical studies of marine invertebrates.11. Sinulariolide, a new cembranilide diterpene from soft coral Sinularia flexibilis (Coelenterata, Octocorallia, Alcyonacea). Tetrahedron 31:129–133

    CAS  Google Scholar 

  80. Toth JA, Burreson BJ, Scheuer PJ et al (1980) Emblde, a new polyfunctional cembranilide from the soft coral Sarcophyton glaucum. Tetrahedron 36:1307–1309

    CAS  Google Scholar 

  81. Gross H, Wright AD, Beil W et al (2004) Two new bicyclic cembranolides from a new Sarcophyton species and determination of the absolute configuration of sarcoglaucol-16-one. Org Biomol Chem 2:1133–1138

    CAS  Google Scholar 

  82. Roethle PA, Trauner D (2008) The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products. Nat Prod Rep 25:298–317

    CAS  Google Scholar 

  83. Shoji N, Umeyama A, Arihara S (1993) A novel norditerpenoid from the okinawan soft coral Sinularia sp. J Nat Prod 56:1651–1653

    CAS  Google Scholar 

  84. Sheu JH, Ahmed AF, Shiue RT et al (2002) Scabrolides A-D, four new norditerpenoids isolated from the soft coral Sinularia scabra. J Nat Prod 65:1904–1908

    CAS  Google Scholar 

  85. Ahmed AF, Su JH, Kuo YH et al (2004) Scabrolides E-G, three new norditerpenoids from the soft coral Sinularia scabra. J Nat Prod 67:2079–2082

    CAS  Google Scholar 

  86. Kamel HN, Ferreira D, Garcia-Fernandez LF et al (2007) Cytotoxic diterpenoids from the hybrid soft coral Sinularia maxima x Sinularia polydactyla. J Nat Prod 70:1223–1227

    CAS  Google Scholar 

  87. Pudhom K, Vilaivan T, Ngamrojanavanich N et al (2007) Furanocembranoids from the stem bark of Croton oblongifolius. J Nat Prod 70:659–661

    CAS  Google Scholar 

  88. Leclercq S, de Biseau JC, Braekman JC et al (2000) Furanocembranoid diterpenes as defensive compounds in the Dufour gland of the ant Crematogaster brevispinosa rochai. Tetrahedron 56:2037–2042

    CAS  Google Scholar 

  89. Yan PC, Deng ZW, van Ofwegen L et al (2010) Lobophytones H-N, biscembranoids from the chinese aoft coral Lobophytum pauciflorum. Chem Pharm Bull 58:1591–1595

    CAS  Google Scholar 

  90. Yan PC, Deng ZW, van Ofwegen L et al (2010) Lobophytones O-T, new biscembranoids and cembranoid from soft coral Lobophytum pauciflorum. Mar Drugs 8:2837–2848

    CAS  Google Scholar 

  91. Yan PC, Lv Y, van Ofwegen LP et al (2010) Lobophytones A-G, new isobiscembranoids from the soft coral Lobophytum pauciflorum. Org Lett 12:2484–2487

    CAS  Google Scholar 

  92. Jia R, Guo YW, Chen P et al (2007) Biscembranoids and their probable biogenetic precursor from the hainan soft coral Sarcophyton tortuosum. J Nat Prod 70:1158–1166

    CAS  Google Scholar 

  93. Jia R, Guo YW, Mollo E et al (2008) Further new bis-cembranoids from the Hainan soft coral Sarcophyton tortuosum. HeIv Chim Acta 91:2069–2074

    CAS  Google Scholar 

  94. Leone PA, Bowden BF, Carroll AR et al (1993) Studies of Australian soft coral, a new biscembranoid and its probable biosynthetic precursors from the soft coral Sarcophyton tortuosum. J Nat Prod 56:521–526

    CAS  Google Scholar 

  95. Iwagawa T, Hashimoto K, Okamura H et al (2006) Biscembranes from the soft coral Sarcophyton glaucum. J Nat Prod 69:1130–1133

    CAS  Google Scholar 

  96. Iwagawa T, Hashimoto K, Yokogawa Y et al (2009) Cytotoxic biscembranes from the soft coral Sarcophyton glaucum. J Nat Prod 72:946–949

    CAS  Google Scholar 

  97. Yan XH, Gavagnin M, Cimino G et al (2007) Two new biscembranes with unprecedented carbon skeleton and their probable biogenetic precursor from the Hainan soft coral Sarcophyton latum. Tetrahedron Lett 48:5313–5316

    CAS  Google Scholar 

  98. ElSayed KA, Hamann MT (1996) A new norcembranoid dimer from the Red Sea soft coral Sinularia gardineri. J Nat Prod 59:687–689

    CAS  Google Scholar 

  99. Li J, Lan J, Liu ZS et al (1996) First total synthesis of three cembrene diterpenoids. Tetrahedron-Asymmetry 7:2851–2861

    CAS  Google Scholar 

  100. Tius MA, Cullingham JM (1989) Marine cembranoid synthesis. Tetrahedron Lett 30:3749–3752

    CAS  Google Scholar 

  101. Li Y, Pattenden G (2011) Novel macrocyclic and polycyclic norcembranoid diterpenes from Sinularia species of soft coral: structural relationships and biosynthetic speculations. Nat Prod Rep 28:429–440

    CAS  Google Scholar 

  102. Dambrosio M, Fabbri D, Guerriero A et al (1987) Coralloidolide A and coralloidolide B, the 1st cembranoids from a mediterranean organism, the alcyonacean Alcyonium coralloides. HeIv Chim Acta 70:63–70

    CAS  Google Scholar 

  103. Williams D, Andersen RJ, Vanduyne GD et al (1987) Cembrane and pseudopterane diterpenes from the soft coral Gersemia rubiformis. J Org Chem 52:332–335

    CAS  Google Scholar 

  104. Kobayashi M, Hirase T (1991) Marine terpenes and terpenoids. â©â¢. Isolation of a new dihydrofuranocembranoid, Sarcophytonin E, from the Sarcophyton sp. soft coral of Okinawa. Chem Pharm Bull 39:3055–3056

    Google Scholar 

  105. Rodriguez AD, Soto JJ (1998) Pseudopterane and norcembrane diterpenoids from the Caribbean sea plume Pseudopterogorgia acerosa. J Nat Prod 61:401–404

    CAS  Google Scholar 

  106. Chen SH, Huang H, Guo YW (2008) A new diterpenoid from the south China sea soft coral Lobophytum sp. J Asian Nat Prod Res 10:965–969

    CAS  Google Scholar 

  107. Wright AE, Burres NS, Schulte GK (1989) Cyto-toxic cembranoids from the gorgonian Pseudopterogorgia bipinnata. Tetrahedron Lett 30:3491–3494

    CAS  Google Scholar 

  108. Rodriguez AD, Shi JG, Huang SD (1999) Highly oxygenated pseudopterane and cembranolide diterpenes from the Caribbean Sea feather Pseudopterogorgia bipinnata. J Nat Prod 62:1228–1237

    CAS  Google Scholar 

  109. Rodriguez AD, Shi JG, Shi YP (2000) Isolation, structural characterization, and synthesis of a naturally occurring bisfuranopseudopterane ether: Biskallolide A. Evidence for a carbocation intermediate during the facile conversion of kallolide A and isokallolide A into various solvolysis products. J Org Chem 65:3192–3199

    CAS  Google Scholar 

  110. Marrero J, Benitez J, Rodriguez AD et al (2008) Bipinnatins K-Q, minor cembrane-type diterpenes from the West Indian gorgonian Pseudopterogorgia kallos: isolation, structure assignment, and evaluation of biological activities. J Nat Prod 71:381–389

    CAS  Google Scholar 

  111. Epifanio RD, Maia LF, Fenical W (2000) Chemical defenses of the endemic Brazilian gorgonian Lophogorgia violacea Pallas (Octocorallia, Gorgonacea). J Brazil Chem Soc 11:584–591

    CAS  Google Scholar 

  112. Li YF, Liang LF, Xiao W et al (2013) Progress in the study of biscembranoides from the soft corals of the genus Sarcophyton. Chin J Org Chem 33:1157–1166

    CAS  Google Scholar 

  113. Ichige T, Okano Y, Kanoh N et al (2007) Total synthesis of methyl sarcophytoate. J Am Chem Soc 129:9862 ±

    CAS  Google Scholar 

  114. Ichige T, Okano Y, Kanoh N et al (2009) Total synthesis of methyl sarcophytoate a marine natural biscembranoid. J Org Chem 74:230–243

    CAS  Google Scholar 

  115. Takayanagi H (1995) Synthetic study of sarcophytol A, an anticarcinogenic cembranoid. J Syn Org Chem Jap 53:724–736

    CAS  Google Scholar 

  116. Peniston M, Rodriguez AD (1991) The isolation of (−)-sarcophytol A and (+)-marasol from the caribbean gorgonian Plexaura flexuosa. J Nat Prod 54:1009–1016

    CAS  Google Scholar 

  117. Takahashi T, Yokoyama H, Haino T et al (1992) Enolate reactions on macrocyclic ring systems total synthesis of (+/−)-sarcophytol A. J Org Chem 57:3521–3523

    CAS  Google Scholar 

  118. Kodama M, Yoshio S, Yamaguchi S et al (1993) Total syntheses of both enantimers of sarcophytol A and sarcophytol T based on streospecific 2,3 wittig rearrangement. Tetrahedron Lett 34:8453–8456

    CAS  Google Scholar 

  119. Li YL, Yue YJ, Xing YC (1993) Total synthesis of (+/−)-sarcophytol M. Tetrahedron Lett 34:2799–2800

    CAS  Google Scholar 

  120. Li WD, Mao JM, Li Y et al (1994) A convergent synthesis of (+/−)-sarcophytol A benzyl ether. Org Prep Proced Int 26:445–457

    CAS  Google Scholar 

  121. Li YL, Yue XJ (1994) Studies on macrocyclic diterpenoids.13. an efficient total synthesis of (+/−)-sarcophytol M. Synthesis-Stuttgart 1994:913–914

    Google Scholar 

  122. Takayanagi H, Kitano Y, Morinaka Y (1994) Total synthesis of sarcophytol A, an anticarcinogenic marine cembraoid. J Org Chem 59:2700–2706

    CAS  Google Scholar 

  123. Li WD, Li YL, Li Y (1995) Convergent and stereoselecitive synthesis of sarcophytol Q precursor- (11s)-3,7,11,15-tetramethyl-11-hydroxy-l4-oxo-3E,7E,12E-hexadecatrienal. J Chin Chem S 42:701–707

    CAS  Google Scholar 

  124. Li WD, Li YL, Li Y (1996) Total syntheses of (+/−)-sarcophytol-A and (+/−)-echinodol, two naturally occurring macrocyclic diterpenoids. Prog Nat Sci 6:757–761

    CAS  Google Scholar 

  125. Yasuda M, Ide M, Matsumoto Y et al (1997) Enantiospecific synthesis of the 14-membered diene unit of methyl sarcophytoate. Synlett 1997:899–902

    Google Scholar 

  126. Yasuda M, Ide M, Matsumoto Y et al (1998) Synthetic studies on biscembranoids: asymmetric total synthesis of the 14-membered diene unit of methyl sarcophytoate. B Chem Soc Jap 71:1417–1429

    CAS  Google Scholar 

  127. Ichige T, Kamimura S, Mayumi K et al (2005) Synthetic studies on biscembranoids: asymmetric total synthesis of methyl sarcoate. Tetrahedron Lett 46:1263–1267

    CAS  Google Scholar 

  128. Yao HQ, Gao Y, Liu P et al (2007) Asymmetric synthesis of the diene unit of methyl sartortuoate via a temperature-sensitive intramolecular Horner-Wadsworth-Emmons (HWE) reaction. Synlett 4:571–574

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 510301, Guangzhou, China

    Bin Yang, Juan Liu, Junfeng Wang, Shengrong Liao & Dr. Yonghong Liu

Authors
  1. Bin Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Juan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Junfeng Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shengrong Liao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dr. Yonghong Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yonghong Liu .

Editor information

Editors and Affiliations

  1. Department of Marine-Bio Convergence Science, Pukyong National University, Busan, Korea, Republic of (South Korea)

    Se-Kwon Kim

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Yang, B., Liu, J., Wang, J., Liao, S., Liu, Y. (2015). Cytotoxic Cembrane Diterpenoids. In: Kim, SK. (eds) Handbook of Anticancer Drugs from Marine Origin. Springer, Cham. https://doi.org/10.1007/978-3-319-07145-9_30

Download citation

Publish with us

Policies and ethics

Search

Navigation