Limonoids from the Fruits of Aphanamixis polystachya (Meliaceae) and Their Biological Activities

被引：58

作者：

Zhang, Yao ^{[1
]}

Wang, Jun-Song ^{[1
]}

Wang, Xiao-Bing ^{[1
]}

Gu, Yu-Cheng ^{[2
]}

Wei, Dan-Dan ^{[1
]}

Guo, Chao ^{[1
]}

Yang, Ming-Hua ^{[1
]}

Kong, Ling-Yi ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Nat Med Chem, State Key Lab Nat Med, Nanjing 210009, Peoples R China

[2] Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2013年 / 61卷 / 09期

基金：

中国国家自然科学基金;

关键词：

limonoids; fungicidal activity; insecticidal activity; Aphanamixis polystachya; Meliaceae; TRITERPENOIDS; EXTRACTIVES; SEED;

D O I：

10.1021/jf3049774

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

Seven new prieurianin-type limonoids, aphapolynins C-I (1-7), and a new aphanamolide-type limonoid, aphanamolide B (8), along with seventeen known compounds, were isolated from the fruits of Aphanamixis polystachya. The structures of these compounds were established on the basis of spectroscopic studies. The absolute configurations were determined by combination of electronic circular dichroism (ECD) calculation, CD exciton chirality method, and single crystal X-ray diffraction. All these isolates were evaluated for their cytotoxicities against three human cancer cell lines, for their inhibitory effects on lipopolysaccharide (LPS) induced RAW264.7 murine macrophages, and for their fungicidal, herbicidal, and insecticidal activities. Compounds 1, 14, 16, and 17 exhibited significant fungicidal activities; 1 and 25 in particular showed good insecticidal activities. The alpha,beta-unsaturated lactone and 14,15-epoxy ring moieties were essential for the insecticidal activity.

引用

页码：2171 / 2182

页数：12

共 30 条

[1] LIMONOID EXTRACTIVES FROM APHANAMIXIS-POLYSTACHA [J].

BROWN, DA ;

TAYLOR, DAH .

PHYTOCHEMISTRY, 1978, 17 (11) :1995-1999

[2] Impact of botanical pesticides derived from Melia azedarach and Azadirachta indica on the biology of two parasitoid species of the diamondback moth [J].

Charleston, DS ;

Kfir, R ;

Dicke, M ;

Vet, LEM .

BIOLOGICAL CONTROL, 2005, 33 (02) :131-142

[3] Limonoids and sesquiterpenoids from Amoora tsangii [J].

Chen, Hua-Dong ;

Yang, Sheng-Ping ;

Liao, Shang-Gao ;

Zhang, Bo ;

Wu, Yan ;

Yue, Jian-Min .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (01) :93-97

[4]

Chen S.K., 1997, FLORA REIPUBLICAE PO, V43, P79

[5] Tabularisins A-D, phragmalin ortho esters with new skeleton isolated from the seeds of Chukrasia tabularis [J].

Fan, Cheng-Qi ;

Wang, Xiao-Ning ;

Yin, Sheng ;

Zhang, Chuan-Rui ;

Wang, Fang-Dao ;

Yue, Jian-Min .

TETRAHEDRON, 2007, 63 (29) :6741-6747

[6]

Frisch M, 2015, Gaussian 09, revision a 02

[7] Relationship of Chemical Structure to in Vitro Anti-inflammatory Activity of Tirucallane Triterpenoids from the Stem Barks of Aphanamixis grandifolia [J].

Guo, Chao ;

Wang, Jun-Song ;

Zhang, Yao ;

Yang, Lei ;

Wang, Peng-Ran ;

Kong, Ling-Yi .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (08) :1003-1010

[8] LIMONOID EXTRACTIVES FROM APHANAMIXIS-POLYSTACHA .2. THE STRUCTURE OF THE LIMONOID ROHITUKA SUBSTANCE-7 FROM APHANAMIXIS-POLYSTACHA [J].

KING, TJ ;

TAYLOR, DAH .

PHYTOCHEMISTRY, 1983, 22 (01) :307-307

[9] Antifeedant effects of the limonolds from Entandrophragma candolei (Meliaceae) on the Gram Pod Borer, Helicoverpa armigera (Lepidoptera:Noctuidae) [J].

Koul, O ;

Daniewski, WM ;

Multani, JS ;

Gumulka, M ;

Singh, G .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (25) :7271-7275

[10] Mulavanins A-E: Limonoids from Munronia delavayi [J].

Lin, Bing-Dong ;

Chen, Hua-Dong ;

Liu, Jia ;

Zhang, Sheng ;

Wu, Yan ;

Dong, Lei ;

Yue, Jian-Min .

PHYTOCHEMISTRY, 2010, 71 (13) :1596-1601

← 1 2 3 →