Isolation and characterization of biogenetically related highly oxygenated nortriterpenoids from Schisandra chinensis

被引：95

作者：

Huang, Sheng-Xiong ^{[1
]}

Li, Rong-Tao

Liu, Jing-Ping

Lu, Yang

Chang, Ying

Lei, Chun

Xiao, Wei-Lie

Yang, Li-Bin

Zheng, Qi-Tai

Sun, Han-Dong

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 Med Sci, Inst Mat Med, Beijing 100050, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 11期

关键词：

D O I：

10.1021/ol070510z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pre-schisanartanin ( 1) and schindilactones A-C (2-4) were isolated from Schisandra chinensis. Among them, compound 1 had an unprecedented carbon skeleton. More importantly, the structure features of this compound provided new insight into the biosynthesis of triterpenoids with schisanartane skeleton. Their structures were determined by extensive spectroscopic analysis, single-crystal X-ray diffraction, and on the basis of the absolute structure of one related nortriterpenoid (5), which was determined for the first time by a modified Mosher method.

引用

页码：2079 / 2082

页数：4

共 19 条

[1] Progress on the chemistry of dibenzocyclooctadiene lignans [J].

Chang, JB ;

Reiner, J ;

Xie, JX .

CHEMICAL REVIEWS, 2005, 105 (12) :4581-4609

[2] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[3] Structure characterization and possible bioggenesis of three new families of nortriterpenoids: Schisanartane, schiartane, and 18-norschiartane [J].

Li, RT ;

Xiao, WL ;

Shen, YH ;

Zhao, QS ;

Sun, HD .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (10) :2989-2996

[4] Structure and anti-HIV activity of micrandilactones B and C, new nortriterpenoids possessing a unique skeleton from Schisandra micrantha [J].

Li, RT ;

Han, QB ;

Zheng, YT ;

Wang, RR ;

Yang, LM ;

Lu, Y ;

Sang, SQ ;

Zheng, QT ;

Zhao, QS ;

Sun, HD .

CHEMICAL COMMUNICATIONS, 2005, (23) :2936-2938

[5] Four novel nortriterpenoids isolated from Schisandra henryi var. yunnanensis [J].

Li, RT ;

Shen, YH ;

Xiang, W ;

Sun, H .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :807-811

[6] Lancifodilactones B-E, new nortriterpenes from Schisandra lancifolia [J].

Li, RT ;

Xiang, W ;

Li, SH ;

Lin, ZW ;

Sun, HD .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (01) :94-97

[7] Lancifodilactone A, a novel bisnortriterpenoid from Schisandra lancifolia [J].

Li, RT ;

Li, SH ;

Zhao, QS ;

Lin, ZW ;

Sun, HD ;

Lu, Y ;

Wang, C ;

Zheng, QT .

TETRAHEDRON LETTERS, 2003, 44 (17) :3531-3534

[8] Micrandilactone A:: A novel triterpene from Schisandra micrantha [J].

Li, RT ;

Zhao, QS ;

Li, SH ;

Han, QB ;

Sun, HD ;

Lu, Y ;

Zhang, LL ;

Zheng, QT .

ORGANIC LETTERS, 2003, 5 (07) :1023-1026

[9] Cytotoxic ent-kaurane diterpenoids from Isodon eriocalyx var. laxiflora [J].

Niu, XM ;

Li, SH ;

Li, ML ;

Zhao, QS ;

Mei, SX ;

Na, Z ;

Wang, SJ ;

Lin, ZW ;

Sun, HD .

PLANTA MEDICA, 2002, 68 (06) :528-533

[10] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

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