Gluco-indole alkaloids from Nauclea cadamba in Thailand and transformation of 3 alpha-dihydrocadambine into the indolopyridine alkaloid, 16-carbomethoxynaufoline.
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.
Takayama
Hiromitsu
H
Graduate School of Pharmaceutical Sciences, Chiba University, Japan. htakayam@p.chiba-u.ac.jp
Tsutsumi
Shun-Ichiro
S
Kitajima
Mariko
M
Santiarworn
Dammrong
D
Liawruangrath
Boonsom
B
Aimi
Norio
N
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D005947:Glucose; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D018515:Plant Leaves; D011725:Pyridines / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D019666:Rubiaceae; D046948:Secologanin Tryptamine Alkaloids; D013237:Stereoisomerism; D013785:Thailand
D000470:Alkaloids; D026121:Indole Alkaloids; D010936:Plant Extracts; D011725:Pyridines; D046948:Secologanin Tryptamine Alkaloids; C047702:3-dihydrocadambine; D005947:Glucose