Gluco-indole Alkaloids from Nauclea cadamba in Thailand and Transformation of 3α-Dihydrocadambine into the Indolopyridine Alkaloid, 16-Carbomethoxynaufoline

Hiromitsu Takayama; Shun-ichiro Tsutsumi; Mariko Kitajima; Dammrong Santiarworn; Boonsom Liawruangrath; Norio Aimi

doi:10.1248/cpb.51.232

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Gluco-indole Alkaloids from Nauclea cadamba in Thailand and Transformation of 3α-Dihydrocadambine into the Indolopyridine Alkaloid, 16-Carbomethoxynaufoline

Hiromitsu Takayama, Shun-ichiro Tsutsumi, Mariko Kitajima, Dammrong Santiarworn, Boonsom Liawruangrath, Norio Aimi

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Keywords: Nauclea cadamba, indole alkaloid, gluco alkaloid, structure elucidation, trasformation

JOURNAL FREE ACCESS

2003 Volume 51 Issue 2 Pages 232-233

DOI https://doi.org/10.1248/cpb.51.232

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Abstract

Three monoterpenoid gluco-indole alkaloids, 3β-isodihydrocadambine, cadambine, and 3α-dihydrocadambine, were isolated from Nauclea cadamba ROXB. growing in Thailand. The stereochemistry at C19 in 3β-isodihydrocadambine was elucidated to be R by spectroscopic analysis. Treatment of 3α-dihydrocadambine with β-glucosidase in aqueous ammonium acetate solution gave an indolopyridine alkaloid, 16-carbomethoxynaufoline, and an unusually rearranged compound.

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