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Some Structural and Stereochemical Aspects of Coumarin Biosynthesis

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The Shikimic Acid Pathway

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 20))

Abstract

Although predictions on the course of chemical progress can be widely off the mark, the main outlines of coumarin chemistry seem to be broadly established if one takes as a criterion, the new coumarin structures reported in the past decade. With the exception of a series of 3-substituted 4-hydroxy-5-methylcoumarins, probably biosynthesized from acetate and largely confined to the tribe Vernonieae (Compositae),1 most of the structures of new coumarins reported in this period are predictable variants of established structural patterns. Methods of coumarin isolation and structure determination are straightforward by modern standards. The literature contains a sizable data base of spectroscopic parameters making structure determination a fairly routine procedure.

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References

  1. BOHLMANN, F., C. ZDERo. 1982. Glaucolides and other constituents from South African Vernonia species. Phytochemistry 21: 2263–2267 and preceding papers in this series.

    Article  CAS  Google Scholar 

  2. SHUKLA, V.S., S.C. DUTTA, R.N. BARUAH, R.P. SHARMA, G. THYAGARAJAN, W. HERZ, N. LUMAR, K. WATANABE, J.G. BLOUNT. 1982. New 5-methylcoumarins from Ethulia conyzoides. Phytochemistry 21: 1725–1731.

    CAS  Google Scholar 

  3. MURRAY, R.D.H., Z.D. JORGE. 1984. Claisen rearrage-ments. XV. Structure revision of the coumarin, celerin, by synthesis. Tetrahedron 40: 5229–5233 and preceding papers in this series.

    Article  CAS  Google Scholar 

  4. MURRAY, R.D.H., J. MENDEZ, S.A. BROWN. 1982. The Natural Coumarins, Wiley and Sons, New York, New York, 702 pp.

    Google Scholar 

  5. GUISE, G.B., E. RITCHIE, R.G. SENIOR, W.C. TAYLOR. 1967. The chemical constituents of Australian Zanthoxylum species. IV. Two new coumarins from Zanthoxylum suberosum C. T. White (Syn. Zanthoxylum dominianum Merr. & Perry; Zanthoxylum ovalifolium Wight). Aust. J. Chem. 20: 2429–2439.

    Article  CAS  Google Scholar 

  6. KUTNEY, J.P., T. INABA, D.L. DREYER. 1968. The structure of thamnosin. A novel dimeric coumarin system. J. Amer. Chem. Soc. 90: 813–814.

    Article  CAS  Google Scholar 

  7. KUTNEY, J.P., T. INABA, D.L. DREYER. 1970. Further studies on the constituents of Thamnosma montana Torr, and Frem. The structure of thamnosin, a novel dimeric coumarin system. Tetrahedron 26: 3171–3184.

    Article  CAS  Google Scholar 

  8. SHARMA, P.N., A. SHOEB, R.S. KAPIL, S.P. POPLI. 1980. Toddasin, a new dimeric coumarin from Toddalia asiatica. Phytochemistry 19: 1258–1260.

    Article  CAS  Google Scholar 

  9. CHAKRABORTY, D.P., S. ROY, A. CHAKRABORTY, A.K. MANDAL, B.K. CHOWDHURY. 1980. Structure and synthesis of mexolide; A new antibiotic dicoumarin from Murraya exotica Linn. [Syn. Murraya paniculata (L.) Jack.]. Tetrahedron 36: 3563–3564.

    Article  CAS  Google Scholar 

  10. BROWN, K., R.C. CAMBIE, D. HALL. 1971. Structure of phebalin: a biscoumarin derivative. Chem. and Ind., 1020.

    Google Scholar 

  11. BROWN, K.L., A.I.R. BURFITT, R.C. CAMBIE, D. HALL, K.P. MATHAI. 1975. Constituents of Phebalium nudum. III. Structures of Phebalin and Phebalarin. Aust. J. Chem. 28: 1327–1337.

    Article  CAS  Google Scholar 

  12. GONZALEZ, A.G., R.J. CARDONA, E. DIAZ CHICO, H. LOPEZ DORTA, F. RODRIGUEZ LUIS. 1977. New sources of natural coumarins. XXXIII. Bicoumarins of Ruta sps. Tene. 29662. An. Quim. 73: 1510–1511;

    CAS  Google Scholar 

  13. GONZALEZ, A.G., R.J. CARDONA, E. DIAZ CHICO, H. LOPEZ DORTA, F. RODRIGUEZ LUIS. 1978. New sources of natural coumarins. XXXIII. Bicoumarins of Ruta sps. Tene. 29662. Chem. Abstr. 89: 160105.

    Google Scholar 

  14. NGADJUI, T.B., J.F. AYAFOR, B.L. SONDENGAM, J.D. CONNOLLY, D.S. RYCROFT, S.A. KHALID, P.G. WATERMAN, N.M.D. BROWN, M.F. GRUNDON, V.N. RAMACHANDRAN. 1982. The structures of vepridimerines A-D, four new dimeric prenylated quinolone alkaloids from Vepris louisii and Oricia renieri (Rutaceae). Tetrahedron Lett., 2041–2044.

    Google Scholar 

  15. JURD, L., R.Y. WONG. 1981. New quinolinone alkaloids from the heartwood of Euxylophora paraensis. Aust. J. Chem. 34: 1625–1632.

    Article  CAS  Google Scholar 

  16. JURD, L., R.Y. WONG, M. BENSON. 1982. The structures of paraensidimerin A and C., two bisquinolinone alkaloids from Euxylophora paraensis. Aust. J. Chem. 35: 2505–2517.

    Article  CAS  Google Scholar 

  17. JURD, L., M. BENSON, R.Y. WONG. 1983. New quinolinone and bis-quinolinone alkaloids from Euxylophora paraensis. Aust. J. Chem. 36: 759–786.

    Article  CAS  Google Scholar 

  18. TILLEQUIN, F., M. KOCH, M. BERT, T. SENENET. 1979. Plantes de Nouvelle Caledonie. LV. Isoborreverine et borreverine, alcaloides bis-indoliques de Flindersia fournieri. J. Nat. Products 42: 92–95.

    Article  CAS  Google Scholar 

  19. POUSSET, J.L., A. CAVE, A. CHIARONI, C. RICHE. 1977. A novel bis-indole alkaloid. X-ray crystal structure determination of borreverine and its rearrangement product on diacetylation. Chem. Comm. 261–262.

    Google Scholar 

  20. TILLEQUIN, F., M. KOCH. 1979. Trois nouveaux alcaloides bis-indoliques de Flindersia fournieri. Phytochemistry 18: 1559–1561.

    Article  CAS  Google Scholar 

  21. TILLEQUIN, F., M. KOCH. 1979. Deux nouveaux alcaloides bis-indoliques de Flindersia fournieri. Phytochemistry 18: 2066–2067.

    Article  Google Scholar 

  22. KONG, Y., K. CHENG, R.C. CAMBIE, P.G. WATERMAN. 1985. Yuehchukene: a novel indole alkaloid with anti-implantation activity. Chem. Comm. 47: 47–48.

    Article  Google Scholar 

  23. CHENG, K., Y. KONG, T. CHAn. 1985. Biometrie synthesis of yeuhchukene. Chem. Comm., 48–49.

    Google Scholar 

  24. SUBBA RAO, G.S.R., B. RAVINDRANATH, V.P. SASHI KUMAR. 1984. Volatile constituents of Clausena willdenovii; Structures of the furanoterpenes a-clausenan, diclausenan A and diclausenan B. Phytochemistry 23: 399–401.

    Article  Google Scholar 

  25. CAOLO, M.A., F.R. STERMITZ. 1979. Anew zanthoxylum alkaloid structurally related to tetrahydrocannabinol. Tetrahedron 35: 1487–1492.

    Article  CAS  Google Scholar 

  26. SWINEHART, J.A., F.R. STERMITZ. 1980. Bishordeninyl terpene alkaloids and other constituents of Zanthoxylum culantrillo and Zanthoxylum coriaceum. Phytochemistry 19: 1219–1223.

    Article  CAS  Google Scholar 

  27. SCHROEDER, D.R., F.R. STERMITZ. 1985. Isolation and synthesis of bishordeninyl terpene alkaloids. Some experiments relating to the natural occurrence of formal Diels-Alder adducts. Tetrahedron 41: 4309–4320.

    Article  CAS  Google Scholar 

  28. MOCK, J.R., R.C. SENIOR, W.C. TAYLOr. 1980. The chemical constituents of Australian Zanthoxylum species. VII. Some transformations of suberosin. Aust. J. Chem. 33: 395–411.

    Article  CAS  Google Scholar 

  29. BARNES, C.S., M.I. STRONG, J.L. OCCOLOWITZ. 1963. The 2,2-dimethylchromen dimer 2,2-diphenylchromen and related compounds. Tetrahedron 19: 839–847.

    Article  CAS  Google Scholar 

  30. BOHLMANN, F., R. MATHUR, J. JAKUPOVIC, R.K. GUPTA, R.M. KING, H. ROBINSON. 1982. Furanoheliangolides and other compounds from Celea hymenolepis. Phytochemistry 21: 2045–2048.

    Article  CAS  Google Scholar 

  31. BOHLMANN, F., H. FRANK, C. ZDERo. 1972. Natuerlich vorkommende cumarin-derivate. An. Quim. 68: 765–767.

    Google Scholar 

  32. ARTHUR, H.C., C.M. LEE. 1960. An examination of the Rutaceae of Hong Kong. Part V. A new coumarin, avicennin from the bark of Zanthoxylum avicennae. J. Chem. Soc., 4654–4657.

    Google Scholar 

  33. ARTHUR, H.C., W.D. OLLIU. 1963. A revised structure for avicennin. J. Chem. Soc., 3910–3912.

    Google Scholar 

  34. BOHLMANN, F., M. GRENZ. 1970. Neue isopentenyl-acetophenon-derivative aus Helianthella uniflora. Chem. Ber. 103: 90–96.

    Article  CAS  Google Scholar 

  35. CUCA SUAREZ, L.E., F. DELLA MONACHE, G.B. MARINI BETTOLO, F. MENICHINI. 1980. Tephrosieae. X. Three new prenylated flavanones from Tephrosia sp. Farmaco Ed. Sci. 35: 796–800;

    CAS  Google Scholar 

  36. CUCA SUAREZ, L.E., F. DELLA MONACHE, G.B. MARINI BETTOLO, F. MENICHINI. 1980. Tephrosieae. X. Three new prenylated flavanones from Tephrosia sp. Chem. Abstr. 93: 182824.

    Google Scholar 

  37. GRUNDON, M.F. 1978. The biosynthesis of aromatic hemiterpenes. Phytochemistry 34: 143–161.

    CAS  Google Scholar 

  38. LEMMICH, J., P.A. PEDERSEN, B.E. NIELSEN. 1971. Coumarins and terpenoids from the fruits of Ligusticum sequieri. Phytochemistry 10: 3333–3334 and references cited therein.

    Article  CAS  Google Scholar 

  39. DREYER, D.L. 1969. Coumarins and alkaloids of the genus Ptelea. Phytochemistry 8: 1013–1020.

    Article  CAS  Google Scholar 

  40. BROOKER, R.M., J.N. EBLE, N.A. STARKOVSKY. 1967. Chalepensin, chalepin, and chalepin acetate, three novel furocoumarins from Ruta chalepensis. Lloydia 30: 73–77.

    CAS  Google Scholar 

  41. POZZI, H., E. SANCHEZ, J. COMIN. 1967. Studies on Argentine plants. XXII. Heliettin, a new furo-coumarin from Helietta longifoliata Britt. Tetrahedron 23: 1129–1137.

    Article  CAS  Google Scholar 

  42. CHOW, P.W., A.M. DUFFIELD, P.R. JEFFERIES. 1966. The chemistry of the Western Australian Rutaceae. V. The isolation of some coumarins and the structure of phebalosin. Aust. J. Chem. 19: 483–488.

    Article  CAS  Google Scholar 

  43. SHARMA, Y.N., A. ZAMAN, A.R. KIDWAI. 1964. Chemical examination of Heraceleum candicans. I. Isolation and structure of a new furocoumarins-heraclenin. Tetrahedron 20: 87–90.

    Article  CAS  Google Scholar 

  44. GRUNDON, M.F., D.M. HARRISON, C.G. SPYROPOULOS. 1975. Biosynthesis of aromatic isoprenoids. Part III. Mechanism of formation of the furan ring and origin of the 4-methoxy group in the biosynthesis of furoquinoline alkaloids. J. Chem. Soc. Perkin I, 302–304.

    Article  Google Scholar 

  45. ISHII, H., T. ISHIKAWA, H. SEKIGUCHI, K. HOSAYA. 1973. Xanthoarnol. New dihydrofuranocoumarin. Chem. Pharm. Bull. 21: 2346–2348;

    Article  CAS  Google Scholar 

  46. ISHII, H., T. ISHIKAWA, H. SEKIGUCHI, K. HOSAYA. 1974. Xanthoarnol. New dihydrofuranocoumarin. Chem. Abstr. 80: 45639.

    Google Scholar 

  47. DONNELLY, W.J., M.F. GRUNDON, V.N. RAMACHANDRAN. 1977. Biosynthesis of aromatic isoprenoids. Part IV. Origin of the 1,1-dimethylallyl group of the coumarin, rutamarin. Proc. Roy. Irish Acad. Sect. B 77B: 443–447;

    Google Scholar 

  48. DONNELLY, W.J., M.F. GRUNDON, V.N. RAMACHANDRAN. 1978. Biosynthesis of aromatic isoprenoids. Part IV. Origin of the 1,1-dimethylallyl group of the coumarin, rutamarin. Chem. Abstr. 89: 103824.

    Google Scholar 

  49. BALBAA, S.I., A.F. HALIM, F.T. HALAWEISH, F. BOHLMANN. 1980. New 5-methylcoumarin derivatives from Ethulia conyzoides. Phytochemistry 19: 1519–1522.

    CAS  Google Scholar 

  50. GRUNDON, M.F. 1979. Quinoline alkaloids related to anthranilic acid. In The Alkaloids. (R.H.F. Manske, R. Rodrigo, Eds.), Vol. XVII, Academic Press, New York, New York, pp. 105–191.

    Chapter  Google Scholar 

  51. GRUNDON, M.F., I.S. MCCOLL. 1975. Stereochemical aspects of the biological oxidation of aryl isoprenoids. The asymmetric synthesis and absolute configuration of meranzin and of meranzin hydrate. Phytochemistry 14: 143–150.

    Article  CAS  Google Scholar 

  52. STECK, W., S.A. BROWN. 1970. Biosynthesis of angular furanocoumarins. Can. J. Biochem. 48: 872–880.

    Article  CAS  Google Scholar 

  53. KATSUKI, T., K.B. SHARPLESS. 1980. The first practical method for asymmetric epoxidation. J. Amer. Chem. Soc. 102: 5974–5976.

    Article  CAS  Google Scholar 

  54. SHARPLESS, K.B., C.H. BEHRENS, T. KATSUKI, A.W.M. LEE, V.S. MARTUB, M. TAKATANI, S.M. VITI, F.J. WALKER, S.S. WOODARD. 1983. Stereo and regioselective openings of chiral 2,3-epoxy alcohols. Versatile route to optically pure natural products and drugs. Unusual kinetic resolutions. Pure and Applied Chem. 55: 589–604.

    Article  CAS  Google Scholar 

  55. LUCKNER, M., B. DIETTRICH, W. LERBS. 1980. Progress in Phytochemistry. (L. Reinhold, J.B. Harborne, T. Swain, Eds.), Vol. 6, Pergamon Press, Oxford, pp. 103–142.

    Google Scholar 

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© 1986 Plenum Press, New York

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Dreyer, D.L. (1986). Some Structural and Stereochemical Aspects of Coumarin Biosynthesis. In: Conn, E.E. (eds) The Shikimic Acid Pathway. Recent Advances in Phytochemistry, vol 20. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-8056-6_12

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  • DOI: https://doi.org/10.1007/978-1-4684-8056-6_12

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