Tabercarpamines A-J, apoptosis-inducing indole alkaloids from the leaves of Tabernaemontana corymbosa.
A total of 10 new indole alkaloids, tabercarpamines A-J (1-10), were isolated from the leaves of Tabernaemontana corymbosa. Tabercarpamines C-F (3-6) are rare C-14/C-15-seco-tabersonine-type monoterpenoid indole alkaloids, and 5 and 6 are the first examples with a lactone linkage between C-14 and C-20. The structures of these alkaloids were elucidated using spectroscopic methods, and the absolute configurations of 1 and 2 were determined using the ECD exciton chirality method. In addition, an MTT assay was used to examine the growth-inhibitory effects of all new isolates and of two known isolates on MCF-7, HepG2, and SMMC-7721 cells; 1 exhibited significant inhibitory effects against these three human cancer cell lines with IC50 values of 8.54, 3.31, and 6.76 μM, respectively. Additionally, the results from the annexin-V/PI double-staining assay indicated that 1 might inhibit the proliferation of HepG2 cells by inducing apoptosis.
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.
Ke
K
Ma
Jun-Song
JS
Wang
Jun
J
Luo
Ming-Hua
MH
Yang
Lingyi
L
Kong
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D056945:Hep G2 Cells; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D030014:Tabernaemontana / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D026121:Indole Alkaloids; D011804:Quinolines; C009373:tabersonine