P-27 ゲルセミウム属植物含有新規インドールアルカロイドの探索と腫瘍細胞殺傷作用(ポスター発表の部)
書誌事項
- タイトル別名
-
- P-27 New Indole Alkaloids from Gelsemium Plants and their Cytotoxic Activity on Tumor Cells
抄録
To discover new antitumor natural products, we carried out the chemical investigation of the alkaloids in Gelsemium elegans and G. sempervirens (Loganiaceae), and the evaluation of the cytotoxic effects of Gelsemium alkaloids on some tumor cells. Four new gelsenicine-related alkaloids (7-10) were isolated from G. elegans. Gelsedilam (7) and 14-acetoxygelsedilam (8) are unprecedented 18,19-nor-type monoterpenoid indole alkaloids. Gelsefuranidine (9) is the first example of a monoterpenoid indole alkaloid having a furan residue on the side chain. Gelseiridone (10) is a new type of alkaloid having a nitrogen-carbon linkage between a gelsenicine-type monoterpenoid indole alkaloid that possesses an α,β-unsaturated ketone residue as well as the N_b-C20 seco-form and a monoterpene unit having an iridoid skeleton. Five new sarpagine-type alkaloids, gelsempervine-A (23), -B (24), -C (25), and -D (26), and 19Z-16-epi-voacarpine (27), and one yohimbane-type alkaloid, sempervilam (29) were isolated from G. sempervirens. Spectroscopic data suggest that 23 existed as a C/D ring-opening structure with the keto-amine form (A) in such aprotic solvents as CH_3CN, and as a transannular structure with the zwitterionic form (B) in such protic solvents as CH_3OH. The structure of sempervilam (29) was confirmed by the total synthesis. The gelsedine-type alkaloids, 14-acetoxygelsenicine (18, EC_<50>=250nM), 14,15-dihydroxygelsenicine (19), gelsedine (34), and gelsemicine (35) showed relatively strong cytotoxic effects on the A431 human epidermoid carcinoma cell line (positive control, cisplatin: EC_<50>=3.5μM).
収録刊行物
-
- 天然有機化合物討論会講演要旨集
-
天然有機化合物討論会講演要旨集 48 (0), 319-324, 2006
天然有機化合物討論会実行委員会
- Tweet
詳細情報 詳細情報について
-
- CRID
- 1390001206077372800
-
- NII論文ID
- 110006682674
-
- ISSN
- 24331856
-
- 本文言語コード
- ja
-
- データソース種別
-
- JaLC
- CiNii Articles
-
- 抄録ライセンスフラグ
- 使用不可