Aphanamixoid A, a Potent Defensive Limonoid, with a New Carbon Skeleton from Aphanamixis polystachya

被引：57

作者：

Cai, Jie-Yun ^{[1
,2
]}

Zhang, Yu ^{[1
]}

Luo, Shi-Hong ^{[1
]}

Chen, Duo-Zhi ^{[1
,2
]}

Tang, Gui-Hua ^{[1
,2
]}

Yuan, Chun-Mao ^{[1
]}

Di, Ying-Tong ^{[1
]}

Li, Sheng-Hong ^{[1
]}

Hao, Xiao-Jiang ^{[1
]}

He, Hong-Ping ^{[1
]}

机构：

[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650201, Yunnan, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 10期

基金：

中国国家自然科学基金;

关键词：

MELIACEAE; AZADIRACHTIN; PRIEURIANIN; CHEMISTRY;

D O I：

10.1021/ol3008149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aphanamixoid A (1), a limonoid with a new carbon skeleton, along with its biogenetically related limonoid aphanamixoid B (2), was isolated from the leaves and twigs of Aphanamixis polystachya. Their structures with the absolute stereochemistry were determined by spectroscopic analysis, X-ray crystallography and computational methods. The significant antifeedant activity of 1 against the generalist plant-feeding insect Helicoverpa armigera (EC50 = 0.015 mu mol/cm(2)) suggested it may be a potent defensive component of A. polystachya.

引用

页码：2524 / 2527

页数：4

共 36 条

[1]

Chen S. K., 1997, FLORA REIPUBLICAE PO, V43, P239

[2]

Fang X, 2011, CURR ORG CHEM, V15, P1363

[3] Cipadonoid A, a novel limonoid with an unprecedented skeleton, from Cipadessa cinerasecns [J].

Fang, Xin ;

Di, Ying-Tong ;

He, Hong-Ping ;

Liu, Hai-Yang ;

Zhang, Zhen ;

Ren, Yan-Li ;

Gao, Zhu-Lin ;

Gao, Suo ;

Hao, Xiao-Jiang .

ORGANIC LETTERS, 2008, 10 (10) :1905-1908

[4] ON ENANTIOMORPH-POLARITY ESTIMATION [J].

FLACK, HD .

ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881

[5] Identification of new limonoids from Swietenia and their biological activity against insects [J].

Fowles, Robert ;

Mootoo, Baldwin ;

Ramsewak, Russel ;

Khan, Ayub ;

Ramsubhag, Adesh ;

Reynolds, William ;

Nair, Muraleedharan .

PEST MANAGEMENT SCIENCE, 2010, 66 (12) :1298-1303

[6]

Frisch M.J., 2004, Gaussian 09

[7] Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin [J].

Fukuzaki, T ;

Kobayashi, S ;

Hibi, T ;

Ikuma, Y ;

Ishihara, J ;

Kanoh, N ;

Murai, A .

ORGANIC LETTERS, 2002, 4 (17) :2877-2880

[8] Munronoids A-J, ten new limonoids from Munronia unifoliolata Oliv [J].

Ge, Yong-Hui ;

Zhang, Jian-Xin ;

Mu, Su-Zhen ;

Chen, Yan ;

Yang, Fu-Mei ;

Lu, Yang ;

Hao, Xiao-Jiang .

TETRAHEDRON, 2012, 68 (02) :566-572

[9] Walsucochinoids A and B: New Rearranged Limonoids from Walsura cochinchinensis [J].

Han, Mei-Ling ;

Zhang, Hua ;

Yang, Sheng-Ping ;

Yue, Jian-Min .

ORGANIC LETTERS, 2012, 14 (02) :486-489

[10] Limonoid orthoacetates and antiprotozoal compounds from the roots of Pseudocedrela kotschyi [J].

Hay, Anne-Emmanuelle ;

Ioset, Jean-Robert ;

Ahua, Kouassi Maximin ;

Diallo, Drissa ;

Brun, Reto ;

Hostettmann, Kurt .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (01) :9-13

← 1 2 3 4 →