Phragmalin-Type Limonoid Orthoesters from Chukrasia tabularis var. velutina

被引：29

作者：

Luo, Jun ^{[1
]}

Wang, Jun-Song ^{[1
]}

Wang, Xiao-Bing ^{[1
]}

Luo, Jian-Guang ^{[1
]}

Kong, Ling-Yi ^{[1
]}

机构：

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

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2011年 / 59卷 / 02期

基金：

中国国家自然科学基金;

关键词：

phragmalin-type limonoid; orthoester; Chukrasia tabularis var. veluinu; 16-NORPHRAGMALIN LIMONOIDS; XYLOCARPUS-GRANATUM;

D O I：

10.1248/cpb.59.225

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Nine new phragmalin-type limonoid orthoesters, tabulalides F-N (1-9), together with three known compounds, tabulalides C and D, and tabularisin N (10-12), were isolated from the stem bark of Chukrasia tabularis var. velutina. Extensive spectroscopic technologies were applied to elucidate the structures of these new compounds, including the application of circular dichroism (CD) exciton chirality method for the determination of the absolute configurations of 1 and 2. Tabulalide F (1) has a rare orthoisobutylate moiety in phragmalin-type limonoid orthoesters. These compounds were evaluated for cytotoxic activity against five human cancer cell lines in vitro. Tabulalide G (2) exhibts moderate cytotoxic activity against MCF-7 with IC50 value of 20.4 mu mol/l, and other compounds have weak inhibitory effects on the growth of tested tumor cells.

引用

页码：225 / 230

页数：6

共 17 条

[1] Gedunin, a Novel Hsp90 inhibitor: Semisynthesis of Derivatives and Preliminary Structure-Activity Relationships [J].

Brandt, Gary E. L. ;

Schmidt, Matthew D. ;

Prisinzano, Thomas E. ;

Blagg, Brian S. J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (20) :6495-6502

[2] TETRANORTRITERPENOIDS AND RELATED SUBSTANCES .20. NEW TETRANORTRITERPENOIDS FROM SEEDS OF CHUKRASIA-TABULARIS (MELIACEAE) - SIMPLE ESTERS OF PHRAGMALIN AND 12-ALPHA-ACETOXYPHRAGMALIN [J].

CONNOLLY, JD ;

LABBE, C ;

RYCROFT, DS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (03) :285-288

[3] Phragmalin-type limonoids from the mangrove plant Xylocarpus granatum [J].

Cui, JX ;

Deng, ZW ;

Li, J ;

Fu, HZ ;

Proksch, P ;

Lin, WH .

PHYTOCHEMISTRY, 2005, 66 (19) :2334-2339

[4]

FAN CB, 2007, TETRAHEDRON, V63, pO4721, DOI DOI 10.1107/S1600536807056899

[5]

Kaur R, 2009, J MED PLANTS RES, V3, P196

[6] Plant Orthoesters [J].

Liao, Shang-Gao ;

Chen, Hua-Dong ;

Yue, Jian-Min .

CHEMICAL REVIEWS, 2009, 109 (03) :1092-1140

[7] Four new steroidal glycosides from Solanum torvum and their cytotoxic activities [J].

Lu, Yuanyuan ;

Luo, Jianguang ;

Huang, Xuefeng ;

Kong, Lingyi .

STEROIDS, 2009, 74 (01) :95-101

[8] Chuktabularins E-T, 16-Norphragmalin Limonoids from Chukrasia tabularis var. velutina [J].

Luo, Jun ;

Wang, Jun-Song ;

Wang, Xiao-Bing ;

Luo, Jian-Guang ;

Kong, Ling-Yi .

JOURNAL OF NATURAL PRODUCTS, 2010, 73 (05) :835-843

[9] Chukvelutins A-C, 16-Norphragmalin Limonoids with Unprecedented Skeletons from Chukrasia tabularis var. velutina [J].

Luo, Jun ;

Wang, Jun-Song ;

Luo, Jian-Guang ;

Wang, Xiao-Bing ;

Kong, Ling-Yi .

ORGANIC LETTERS, 2009, 11 (11) :2281-2284

[10] Chukvelutilides A-F, phragmalin limonoids from the stem barks of Chukrasia tabularis var. velutina [J].

Luo, Jun ;

Wang, Jun-Song ;

Wang, Xiao-Bing ;

Huang, Xue-Feng ;

Luo, Jian-Guang ;

Kong, Ling-Yi .

TETRAHEDRON, 2009, 65 (17) :3425-3431

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