Melohenines A and B, Two Unprecedented Alkaloids from Melodinus henryi

被引:79
作者
Feng, Tao [1 ,2 ]
Cai, Xiang-Hai [1 ]
Li, Yan [1 ]
Wang, Yuan-Yuan [1 ]
Liu, Ya-Ping [1 ,2 ]
Xie, Ming-Jin [3 ]
Luo, Xiao-Dong [1 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
[3] Yunnan Univ, Dept Chem, Kunming 650091, Peoples R China
基金
中国国家自然科学基金;
关键词
MONOTERPENOID INDOLE ALKALOIDS; ALSTONIA-SCHOLARIS; NATURAL-PRODUCTS; DES STRYCHNINS; CHEMISTRY; CAMPTOTHECIN; SCANDENS; CORE;
D O I
10.1021/ol9018826
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
A phytochemical study on Melodinus henryi has led to the Isolation of two novel alkaloids, melohenines A (1), a monoterpenoid indole alkaloid with additional skeletal carbons arranged compactly in eight rings, and melohenine B (2), an alkaloid with an unprecedented 6/9/6/6 tetracyclic ring system regarded as a key intermediate from indole to quinoline alkaloids. Their structures were elucidated by means of spectroscopic methods and further confirmed by X-ray diffraction analysis.
引用
收藏
页码:4834 / 4837
页数:4
相关论文
共 39 条
[1]
A NEW ANTIBIOTIC [J].
AU, KS ;
GRAY, DE .
BIOCHEMICAL PHARMACOLOGY, 1969, 18 (11) :2673-&
[2]
(+) MELONINE AND NB-OXY MELONINE, A NEW INDOLINE SKELETON [J].
BAASSOU, S ;
MEHRI, HM ;
RABARON, A ;
PLAT, M .
TETRAHEDRON LETTERS, 1983, 24 (08) :761-762
[3]
Natural, semisynthetic and synthetic microtubule inhibitors for cancer therapy [J].
Beckers, T ;
Mahboobi, S .
DRUGS OF THE FUTURE, 2003, 28 (08) :767-785
[4]
STRUCTURE OF MELODINUS ALKALOIDS, (+)-MELOSCINE,(+)-EPIMELOSCINE AND (+)-SCANDINE .1. ALKALOIDS FROM MELODINUS SCANDENS FORST [J].
BERNAUER, K ;
ENGLERT, G ;
VETTER, W ;
WEISS, E .
HELVETICA CHIMICA ACTA, 1969, 52 (07) :1886-&
[5]
Synthesis of strychnine [J].
Bonjoch, J ;
Solé, D .
CHEMICAL REVIEWS, 2000, 100 (09) :3455-3482
[6]
A cage-monoterpene indole alkaloid from Alstonia scholaris [J].
Cai, Xiang-Hai ;
Tan, Qin-Gang ;
Liu, Ya-Ping ;
Feng, Tao ;
Du, Zhi-Zhi ;
Li, We-Qi ;
Luo, Xiao-Dong .
ORGANIC LETTERS, 2008, 10 (04) :577-580
[7]
Unique monoterpenoid indole alkaloids from Alstonia scholaris [J].
Cai, Xiang-Hai ;
Du, Zhi-Zhi ;
Luo, Xiao-Dong .
ORGANIC LETTERS, 2007, 9 (09) :1817-1820
[8]
RHAZINILAM MIMICS THE CELLULAR EFFECTS OF TAXOL BY DIFFERENT MECHANISMS OF ACTION [J].
DAVID, B ;
SEVENET, T ;
MORGAT, M ;
GUENARD, D ;
MOISAND, A ;
TOLLON, Y ;
THOISON, O ;
WRIGHT, M .
CELL MOTILITY AND THE CYTOSKELETON, 1994, 28 (04) :317-326
[9]
A tandem, nitroalkene conjugate addition/[3+2] cycloaddition approach to the synthesis of the pentacyclic core of (±)-scandine [J].
Denmark, Scott E. ;
Cottell, Jeromy J. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2397-2402
[10]
Recent findings on natural products with erectile-dysfunction activity [J].
Drewes, SE ;
George, J ;
Khan, F .
PHYTOCHEMISTRY, 2003, 62 (07) :1019-1025