On the origins of triterpenoid skeletal diversity

被引:456
作者
Xu, R
Fazio, GC
Matsuda, SPT
机构
[1] Rice Univ, Dept Chem, Houston, TX 77005 USA
[2] Rice Univ, Dept Biochem & Cell Biol, Houston, TX 77005 USA
关键词
triterpene; triterpenoid; oxidosqualene cyclization; squalene; cyclization; isoprene rule;
D O I
10.1016/j.phytochem.2003.11.014
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The triterpenoids are a large group of natural products derived from C-30 precursors. Nearly 200 different triterpene skeletons are known from natural sources or enzymatic reactions that are structurally consistent with being cyclization products of squalene, oxidosqualene, or, bis-oxidosqualene. This review categorizes each of these structures and provides mechanisms for their formation. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:261 / 291
页数:31
相关论文
共 264 条
  • [1] DAMMARANE TRITERPENOIDS FROM DYSOXYLUM-RICHII
    AALBERSBERG, W
    SINGH, Y
    [J]. PHYTOCHEMISTRY, 1991, 30 (03) : 921 - 926
  • [2] INHIBITORS OF SQUALENE BIOSYNTHESIS AND METABOLISM
    ABE, I
    TOMESCH, JC
    WATTANASIN, S
    PRESTWICH, GD
    [J]. NATURAL PRODUCT REPORTS, 1994, 11 (03) : 279 - 302
  • [3] Molecular cloning, expression, and site-directed mutations of oxidosqualene cyclase from Cephalosporium caerulens
    Abe, I
    Naito, K
    Takagi, Y
    Noguchi, H
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 2001, 1522 (02): : 67 - 73
  • [4] PURIFICATION OF SQUALENE-2,3-EPOXIDE CYCLASES FROM CELL-SUSPENSION CULTURES OF RABDOSIA-JAPONICA HARA
    ABE, I
    EBIZUKA, Y
    SEO, S
    SANKAWA, U
    [J]. FEBS LETTERS, 1989, 249 (01) : 100 - 104
  • [5] MOLECULAR-CLONING, CHARACTERIZATION, AND FUNCTIONAL EXPRESSION OF RAT OXIDOSQUALENE CYCLASE CDNA
    ABE, I
    PRESTWICH, GD
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (20) : 9274 - 9278
  • [6] ENZYMATIC CYCLIZATION OF SQUALENE AND OXIDOSQUALENE TO STEROLS AND TRITERPENES
    ABE, I
    ROHMER, M
    PRESTWICH, GD
    [J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2189 - 2206
  • [7] ACHARI B, 1975, TETRAHEDRON LETT, P4275
  • [8] STEROLS AND TRITERPENES OF PELARGONIUM-HORTORUM
    AEXEL, RT
    RAMSEY, RB
    NICHOLAS, HJ
    [J]. PHYTOCHEMISTRY, 1972, 11 (07) : 2353 - &
  • [9] AGETA H, 1994, CHEM PHARM BULL, V42, P39
  • [10] COMPARISON OF ADIPEDATOL WITH HYDROXYHOPANE AND HYDROXYISOHOPANE
    AGETA, H
    SHIOJIMA, K
    [J]. CHEMICAL COMMUNICATIONS, 1968, (22) : 1372 - &