Trigocherrin A, the First Natural Chlorinated Daphnane Diterpene Orthoester from Trigonostemon cherrieri

被引：56

作者：

Allard, Pierre-Marie ^{[1
]}

Martin, Marie-Therese ^{[1
]}

Dau, Marie-Elise Tran Huu ^{[1
]}

Leyssen, Pieter ^{[2
]}

Gueritte, Francoise ^{[1
]}

Litaudon, Marc ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 01期

关键词：

PLANT; HALOGENATION;

D O I：

10.1021/ol2030907

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trigocherrin A, a chlorinated and highly oxygenated daphnane diterpenold orthoester (DDO), was isolated from the bark of Trigonostemon cherrieri Trigocherrin A is the first example of a naturally occurring halogenated DDO. Its structure was elucidated by comprehensive analysis of NMR spectroscopic data, and its absolute configuration was determined by comparison of experimental and theoretically calculated ECD spectra. Trigocherrin A exhibited a potent and selective effect against Chikungunya virus In Vero cells.

引用

页码：342 / 345

页数：4

共 24 条

[1] Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].

Berova, Nina ;

Di Bari, Lorenzo ;

Pescitelli, Gennaro .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931

[2] Structural Perspective on Enzymatic Halogenation [J].

Blasiak, Leah C. ;

Drennan, Catherine L. .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (01) :147-155

[3] Trigochinins D-I: six new daphnane-type diterpenoids from Trigonostemon chinensis [J].

Chen, Hua-Dong ;

Yang, Sheng-Ping ;

He, Xiu-Feng ;

Liu, Hong-Bing ;

Ding, Jian ;

Yue, Jian-Min .

TETRAHEDRON, 2010, 66 (27-28) :5065-5070

[4] Trigochinins A-C: Three New Daphnane-Type Diterpenes from Trigonostemon chinensis [J].

Chen, Hua-Dong ;

Yang, Sheng-Ping ;

He, Xiu-Feng ;

Ai, Jing ;

Liu, Zhen-Kai ;

Liu, Hong-Bing ;

Geng, Mei-Yu ;

Yue, Jian-Min .

ORGANIC LETTERS, 2010, 12 (06) :1168-1171

[5] Trigochilides A and B, Two Highly Modified Daphnane-Type Diterpenoids from Trigonostemon chinensis [J].

Chen, Hua-Dong ;

He, Xiu-Feng ;

Ai, Jing ;

Geng, Mei-Yu ;

Yue, Jian-Min .

ORGANIC LETTERS, 2009, 11 (18) :4080-4083

[6] Daphnane-Type Diterpenoids from Trigonostemon howii [J].

Dong, Shi-Hui ;

Zhang, Chuan-Rui ;

Xu, Cheng-Hui ;

Ding, Jian ;

Yue, Jian-Min .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (05) :1255-1261

[7]

Fan D., 2010, KEW B, V65, P111

[8] Halogenation of unactivated carbon centers in natural product biosynthesis: Trichlorination of leucine during barbamide biosynthesis [J].

Galonic, DP ;

Vaillancourt, FH ;

Walsh, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3900-3901

[9]

Gribble G W., 2010, Naturally Occurring Organohalogen Compounds - A Comprehensive Update, V1st edn, DOI DOI 10.1007/978-3-211-99323-1

[10]

Hu X.-J., 2010, ORG LETT, V12, P2370

← 1 2 3 →