Hydroxynitrile glucosides

被引:50
作者
Bjarnholt, Nanna
Moller, Birger Lindberg [1 ]
机构
[1] Univ Copenhagen, Fac Life Sci, Dept Plant Biol & Biotechnol, Plant Biochem Lab, DK-1871 Copenhagen, Denmark
关键词
cyanogenic glucosides; hydroxynitrile glucosides; CYP71; nitrogen metabolism; bioactive compounds;
D O I
10.1016/j.phytochem.2008.04.018
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
beta- and gamma-Hydroxynitrile glucosides are structurally related to cyanogenic glucosides (Phi-hydroxynitrile glucosides) but do not give rise to hydrogen cyanide release upon hydrolysis. Structural similarities and frequent co-occurrence suggest that the biosynthetic pathways for these compounds share common features. Based on available literature data we propose that oximes produced by CYP79 orthologs are common intermediates and that their conversion into beta- and gamma-hydroxynitrile glucosides is mediated by evolutionary diversified multifunctional orthologs to CYP71E1. We designate these as CYP71(beta gamma) and CYP71(alpha beta gamma); in combination with the classical CYP71(alpha) (CYP71E1 and orthologs) these are able to hydroxylate any of the carbon atoms present in the amino acid and oxime derived nitriles. Subsequent dehydration reactions and hydroxylations and a final glycosylation step afford the unsaturated beta- and gamma-hydroxynitrile glucosides. This scheme would explain the distribution patterns of alpha-, beta- and gamma-hydroxynitrile glucosides found in plants. The possible biological functions of these hydroxynitriles are discussed. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1947 / 1961
页数:15
相关论文
共 159 条
[31]  
Fan WZ, 1999, BIOL PHARM BULL, V22, P157, DOI 10.1248/bpb.22.157
[32]   Prolyl endopeptidase inhibitors from the underground part of Rhodiola sachalinensis [J].
Fan, WZ ;
Tezuka, Y ;
Ni, KM ;
Kadota, S .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (04) :396-401
[33]   ENZYMATIC FORMATION OF BETA-CYANOALANINE FROM CYANIDE [J].
FLOSS, HG ;
HADWIGER, L ;
CONN, EE .
NATURE, 1965, 208 (5016) :1207-&
[34]   Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus [J].
Forslund, K ;
Morant, M ;
Jorgensen, B ;
Olsen, CE ;
Asamizu, E ;
Sato, S ;
Tabata, S ;
Bak, S .
PLANT PHYSIOLOGY, 2004, 135 (01) :71-84
[35]   Analysis of a chemical plant defense mechanism in grasses [J].
Frey, M ;
Chomet, P ;
Glawischnig, E ;
Stettner, C ;
Grun, S ;
Winklmair, A ;
Eisenreich, W ;
Bacher, A ;
Meeley, RB ;
Briggs, SP ;
Simcox, K ;
Gierl, A .
SCIENCE, 1997, 277 (5326) :696-699
[36]   Antifungal activities of nine traditional Mexican medicinal plants [J].
García, VMN ;
Gonzalez, A ;
Fuentes, M ;
Aviles, M ;
Rios, MY ;
Zepeda, G ;
Rojas, MG .
JOURNAL OF ETHNOPHARMACOLOGY, 2003, 87 (01) :85-88
[37]   Evolution of benzoxazinone biosynthesis and indole production in maize [J].
Gierl, A ;
Frey, M .
PLANTA, 2001, 213 (04) :493-498
[38]   Cytochrome P450 monooxygenases of DIBOA biosynthesis:: Specificity and conservation among grasses [J].
Glawischnig, E ;
Grün, S ;
Frey, M ;
Gierl, A .
PHYTOCHEMISTRY, 1999, 50 (06) :925-930
[39]   Constraints on effectiveness of cyanogenic glycosides in herbivore defense [J].
Gleadow, RM ;
Woodrow, IE .
JOURNAL OF CHEMICAL ECOLOGY, 2002, 28 (07) :1301-1313
[40]   Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases [J].
Greenhagen, BT ;
Griggs, P ;
Takahashi, S ;
Ralston, L ;
Chappell, J .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2003, 409 (02) :385-394