24-Hydroxyoleanane-Type Triterpenes from the Aerial Parts and Roots of Oxytropis falcata

被引:19
作者
Chen, Wen-Hao [1 ]
Qi, Huan-Yang [2 ]
Shi, Yan-Ping [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, Key Lab Nat Med Gansu Prov, Lanzhou 730000, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2009年 / 72卷 / 08期
基金
中国国家自然科学基金;
关键词
LEGUMINOUS PLANTS; WISTARIA-BRACHYBOTRYS; CONSTITUENTS; SAPOGENOLS; CHEMISTRY; SAPONIN; SPECTRA;
D O I
10.1021/np900199x
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Phytochemical investigation of the aerial parts of Oxytropis falcata led to the isolation of three new 24-hydroxyoleanane-type triterpenes (1-3), seven known analogues (4-10), and two rare sesquiterpenoids (12, 13). Compounds 6 and 12 were isolated as new natural products. Triterpenes (5, 6, 8, 11) were isolated from the roots of O. falcata. The structures and relative configurations of these compounds were elucidated by spectroscopic analyses, including 1D and 2D NMR spectroscopy and mass spectrometry, and by comparison of their NMR data with those of related compounds. Single-crystal X-ray diffraction analyses confirmed the structures of 1-4, and the absolute configuration of 3 was evidenced by the incorporation of DMSO (crystallization solvent) in the crystal lattice.
引用
收藏
页码:1410 / 1413
页数:4
相关论文
共 22 条
[1]   C-13 NMR-SPECTROSCOPY OF OLEANANE TRITERPENOIDS [J].
AGRAWAL, PK ;
JAIN, DC .
PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 1992, 24 :1-90
[2]   Synthesis of natural oxygenated monocarbocyclic sesquiterpenoids from 6,7-epoxygeranyl acetate [J].
Barrero, AF ;
Alvarez-Manzaneda, EJ ;
Chahboun, R ;
Rivas, AR ;
Palomino, PL .
TETRAHEDRON, 2000, 56 (33) :6099-6113
[3]   SAPOGENIN STRUCTURE - ANALYSIS OF THE C-13-NMR AND H-1-NMR SPECTRA OF SOYASAPOGENOL-B [J].
BAXTER, RL ;
PRICE, KR ;
FENWICK, GR .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (02) :298-302
[4]  
BIEMANN K, 1962, MASS SPECTROMETRY OR, P347
[5]  
BUDZICIEWICZ H, 1964, STRUCTURE ELUCIDATIO, V2
[6]  
CHEN WH, 2008, ANAL SCI XRAY STRUCT, V24, pX209
[7]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[8]   Biomedical applications of poisonous plant research [J].
James, LF ;
Panter, KE ;
Gaffield, W ;
Molyneux, RJ .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (11) :3211-3230
[9]   Titanocene-catalyzed cascade cyclization of epoxypolyprenes:: Straightforward synthesis of terpenoids by free-radical chemistry [J].
Justicia, J ;
Rosales, A ;
Buñuel, E ;
Oller-López, JL ;
Valdivia, N ;
Haïdour, A ;
Oltra, JE ;
Barrero, AF ;
Cárdenas, DJ ;
Cuerva, JM .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (07) :1778-1788
[10]  
KITAGAWA I, 1993, CHEM PHARM BULL, V41, P1567, DOI 10.1248/cpb.41.1567