Terpenoid indole alkaloids from Winchia calophylla.
Three new indole alkaloids, N(4)-demethyl-12-methoxyalstogustine (1), 17-carboxyl-N(4)-methylechitamidine chloride (2), and 17-carboxyl-12-methoxy-N(4)-methylechitamidine chloride (3), along with 15 known alkaloids, were isolated from the ethanolic extract of the stem bark of Winchia calophylla. The structures of 1-3 were elucidated on the basis of spectroscopic means and chemical methods. The determination of relative configurations at C-19 and C-20 for 1-3 was aided by 13C NMR spectroscopic data. The absolute configurations of alkaloids 1-3 were determined by direct comparison of their CD spectra with those of known alkaloids. All the alkaloids were tested in cytotoxic assays against P-388 and A-549 tumor cell lines, and only two of them showed weak activity against the A-549 cell line.
Gan
Li-She
LS
State Key Laboratory of Drug Research, Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zuchongzhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, People's Republic of China.
Yang
Sheng-Ping
SP
Wu
Yan
Y
Ding
Jian
J
Yue
Jian-Min
JM
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029062:Apocynaceae / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D026121:Indole Alkaloids; D007941:Leukemia P388; D051379:Mice; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
C508464:17-carboxyl-12-methoxy-N(4)-methylechitamidine chloride; C508462:17-carboxyl-N(4)-methylechitamidine chloride; D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D026121:Indole Alkaloids; C508461:N(4)-demethyl-12-methoxyalstogustine; D046948:Secologanin Tryptamine Alkaloids