Gluco-indole alkaloids from Nauclea cadamba in Thailand and transformation of 3 alpha-dihydrocadambine into the indolopyridine alkaloid, 16-carbomethoxynaufoline

  • Chem Pharm Bull (Tokyo). 2003 Feb;51(2):232-3. doi: 10.1248/cpb.51.232.
Hiromitsu Takayama  1 ,  Shun-Ichiro Tsutsumi ,  Mariko Kitajima ,  Dammrong Santiarworn ,  Boonsom Liawruangrath ,  Norio Aimi
Affiliations
  • 1. Graduate School of Pharmaceutical Sciences, Chiba University, Japan. [email protected]
PMID: 12576667 DOI: 10.1248/cpb.51.232
Abstract

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

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