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Total synthesis and full NMR assignment of ourouparine, a yohimbane-type indole alkaloid isolated from Gelsemium sempervirens

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Abstract

A yohimbane-type indole alkaloid, ourouparine, was found in Gelsemium sempervirens, and its structure was elucidated by spectroscopic analysis and total synthesis.

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References

  1. Takayama H, Sakai S (1997) Gelsemium alkaloids. In: Cordell GA (ed) The alkaloids, Vol 49, Chap 1, Academic, San Diego, pp 1–78

  2. Kogure N, Nishiya C, Kitajima M, Takayama H (2005) Six new indole alkaloids from Gelsemium sempervirens Ait. f. Tet Lett 46:5857–5861 DOI 10.1016/j.tetlet.2005.06.136

    Google Scholar 

  3. Kitajima M, Arai Y, Takayama H, Aimi N (1998) A chemical study on ‘Yakatsu’ stored in Shosoin repository isolation and characterization of four new indole alkaloids from a 1250 year-old sample of the Chinese toxic medicine. Proc Jpn Acad 74:159–163

    Google Scholar 

  4. Kitajima M, Kogure N, Yamaguchi K, Takayama H, Aimi N (2003) Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid. Org Lett 5:2075–2078 DOI 10.1021/ol0344725

    Google Scholar 

  5. Kitajima M, Urano A, Kogure N, Takayama H, Aimi N (2003) New oxindole alkaloids and iridoid from Carolina jasmine (Gelsemium sempervirens Ait. f.). Chem Pharm Bull 51:1211–1214 DOI 10.1248/cpb.51.1211

    Google Scholar 

  6. Kitajima M, Nakamura T, Kogure N, Ogawa M, Mitsuno Y, Ono K, Yano S, Aimi N, Takayama H (2006) Isolation of gelsedine-type indole alkaloids from Gelsemium elegans and evaluation of the cytotoxic activity of Gelsemium alkaloids for A431 epidermoid carcinoma cells. J Nat Prod 69:715–718 DOI 10.1021/np060016o

    Google Scholar 

  7. Kogure N, Ishii N, Kitajima M, Wongseripipatana S, Takayama H (2006) Four novel gelsenicine-related oxindole alkaloids from the leaves of Gelsemium elegans Benth. Org Lett 8:3085–3088 DOI 10.1021/0l061062i

    Google Scholar 

  8. Tayler WI, Raymond H (1966) Ourouparine, an alkaloid of Ourouparia gambier. C R Acad Sci Paris 262D:1141–1143

    Google Scholar 

  9. Hoshino T, Shimodaira K (1935) Syntheses in the indole group XIV. Synthesis of bufotenine and 3-methyl-3-β-hydroxyethyl indolenine. Liebig Ann Chem 520:19–25

    CAS  Google Scholar 

  10. Frostell E, Jokela R, Lounasmaa M (1981) Sodium dithionite reduction in the preparation of indole alkaloids of gambirtannine-type. Acta Chem Scand B35:671–672

    Article  CAS  Google Scholar 

  11. Rey M, Vergnani T, Dreiding AS (1985) Synthese einiger 8-substituerter 2-methyl-1,2,3,4-tetrahydroisochinoline. Helv Chim Acta 68:1828–1834

    Article  CAS  Google Scholar 

  12. Elderfield RC, Fischer BA (1958) Alstonia alkaloids. IX. Synthesis of alstonilinol and analogs by reductive ring closure. J Org Chem 23:949–953

    Article  CAS  Google Scholar 

  13. Wenkert E, Dave KG, Gnewuch CT, Sprague PW (1968) General methods of synthesis of indole alkaloids. VII. Syntheses of dl-dihydrogambirtannine and Aspidosperma-strychnos alkaloid models. J Am Chem Soc 90:5251–5256 DOI 10.1021/ja01021a033

    Google Scholar 

  14. Lin LZ, Yeh S, Cordell GA, Ni CZ, Clardy J (1991) Three oxindole alkaloids from Gelsemium species. Phytochem 30:679–683 DOI 10.1016/0031-9422(91)83752-7

    Google Scholar 

  15. Lin LZ, Cordell GA (1989) New humantenine-type alkaloids from Gelsemium elegans. J Nat Prod 52:588-594 DOI 10.1021/np50063a019

    Google Scholar 

  16. Ponglux D, Wongseripipatana S, Subhadhirasakul S, Takayama H, Yokota M, Ogata K, Phisalaphong C, Aimi N, Sakai S (1988) Studies on the indole alkaloids of Gelsemium elegans (Thailand): structure elucidation and proposal of biogenetic route. Tetrahedron 44:5075–5094 DOI 10.1016/S0040-4020(01)86012-9

    Google Scholar 

  17. Kitajima M, Takayama H, Sakai S (1994) Synthesis of a novel Gelsemium alkaloid, gelsemicine. J Chem Soc Perkin Trans 1:1573–1578

    Article  Google Scholar 

  18. Schun Y, Cordell GA (1985) 14β-hydroxygelsedine, a new oxindole alkaloid from Gelsemium sempervirens. J Nat Prod 48:788–791 DOI 10.1021/np50041a012

    Google Scholar 

  19. Oranga M, Khuong-Huu F (1980) Alcaloides de Mostuea brunonis Didr. var. brunonis. C R Acad Sci Paris 291:191

    Google Scholar 

  20. Leclercq JQ, Angenot L, Dupont L, Bisset NG (1987) Isolation and purification of panarine, a alkaloid from a Venezuelan curare. Phytochem 27:4002–4004

    Article  Google Scholar 

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Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research (No. 16510156) from the Japan Society for the Promotion of Science and, in part, by Takeda Science Foundation (to H.T.) and by Astellas Foundation for Research on Medicinal Resorces (to M.K.).

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Correspondence to Hiromitsu Takayama.

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Kogure, N., Someya, A., Urano, A. et al. Total synthesis and full NMR assignment of ourouparine, a yohimbane-type indole alkaloid isolated from Gelsemium sempervirens . J Nat Med 61, 208–212 (2007). https://doi.org/10.1007/s11418-006-0125-4

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