An Arabidopsis oxidosqualene cyclase catalyzes iridal skeleton formation by Grob fragmentation

被引：62

作者：

Xiong, QB

Wilson, WK

Matsuda, SPT ^{[1
]}

机构：

[1] Rice Univ, Dept Chem, Houston, TX 77005 USA

[2] Rice Univ, Dept Biochem & Cell Biol, Houston, TX 77005 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 08期

关键词：

cyclization; fragmentation; iridals; oxidosqualene; terpenoids;

D O I：

10.1002/anie.200503420

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Mechanistic and phylogenetic surprises: A triterpene synthase (MRN1) from Arabidopsis invokes a Grob fragmentation in the cyclization of oxidosqualene. The enzymatic product is the elusive carbocyclic precursor of iridals, unusual triterpenoids known only in the distant Iris family. The results demonstrate the power of genome mining and exemplify the facile evolution of cyclases to generate diverse triterpene skeletons. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1285 / 1288

页数：4

共 55 条

[1] Camelliols A-C, three novel incompletely cyclized triterpene alcohols from sasanqua oil (Camellia sasanqua)
Akihisa, T
Arai, K
Kimura, Y
Koike, K
Kokke, WCMC
Shibata, T
Nikaido, T
[J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (02): : 265 - 268
[2] Isohelianol:: A 3,4-seco-triterpene alcohol from sasanqua oil
Akihisa, T
Kimura, Y
Koike, K
Shibata, T
Yoshida, Z
Nikaido, T
Tamura, T
[J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (03): : 409 - 412
[3] Acyclic and incompletely cyclized triterpene alcohols in the seed oils of Theaceae and Gramineae
Akihisa, T
Koike, K
Kimura, Y
Sashida, N
Matsumoto, T
Ukiya, M
Nikaido, T
[J]. LIPIDS, 1999, 34 (11) : 1151 - 1157
[4] Sasanquol, a 3,4-seco-triterpene alcohol from sasanqua oil, and its anti-inflammatory effect
Akihisa, T
Yasukawa, K
Kimura, Y
Yamanouchi, S
Tamura, T
[J]. PHYTOCHEMISTRY, 1998, 48 (02) : 301 - 305
[5] NATURALLY-OCCURRING SECO-RING-A-TRITERPENOIDS AND THEIR POSSIBLE BIOLOGICAL SIGNIFICANCE
BAAS, WJ
[J]. PHYTOCHEMISTRY, 1985, 24 (09) : 1875 - 1889
[6] MOLECULAR-CLONING OF THE HUMAN GENE ENCODING LANOSTEROL SYNTHASE FROM A LIVER CDNA LIBRARY
BAKER, CH
MATSUDA, SPT
LIU, DR
COREY, EJ
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1995, 213 (01) : 154 - 160
[7] ACHILLEOL-A - A NEW MONOCYCLIC TRITERPENE SKELETON FROM ACHILLEA-ODORATA L
BARRERO, AF
ALVAREZMANZANEDA, EJ
ALVAREZMANZANEDA, R
[J]. TETRAHEDRON LETTERS, 1989, 30 (25) : 3351 - 3352
[8] Antiplasmodial and antifungal activities of iridal, a plant triterpenoid
Benoit-Vical, F
Imbert, C
Bonfils, JP
Sauvaire, Y
[J]. PHYTOCHEMISTRY, 2003, 62 (05) : 747 - 751
[9] Cytotoxicity of iridals, triterpenoids from Iris, on human tumor cell lines A2780 and K562
Bonfils, JP
Pinguet, F
Culine, S
Sauvaire, Y
[J]. PLANTA MEDICA, 2001, 67 (01) : 79 - 81
[10] Triterpenoids
Connolly, JD
Hill, RA
[J]. NATURAL PRODUCT REPORTS, 2003, 20 (06) : 640 - 659

← 1 2 3 4 5 6 →