Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

被引：26

作者：

Hakki, Zalihe ^{[2
,3
]}

Cao, Benjamin ^{[2
,3
]}

Heskes, Allison M. ^{[1
]}

Goodger, Jason Q. D. ^{[1
]}

Woodrow, Ian E. ^{[1
]}

Williams, Spencer J. ^{[2
,3
]}

机构：

[1] Univ Melbourne, Sch Bot, Melbourne, Vic 3010, Australia

[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

[3] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

来源：

CARBOHYDRATE RESEARCH | 2010年 / 345卷 / 14期

基金：

澳大利亚研究理事会;

关键词：

Eucalyptus; Total synthesis; Monoterpenoids; Oleuropeic acid; Noreugenin; Essential oils; GLYCOSIDES; LEAVES; YIELD; ACID;

D O I：

10.1016/j.carres.2010.07.029

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：

Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K-1 and K-2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2079 / 2084

页数：6

共 33 条

[1]

AIMI N, 1980, SHOYAKUGAKU ZASSHI, V34, P151

[2] PYRIDINIUM DICHROMATE ACETIC-ANHYDRIDE - A NEW AND HIGHLY EFFICIENT REAGENT FOR THE OXIDATION OF ALCOHOLS [J].

ANDERSSON, F ;

SAMUELSSON, B .

CARBOHYDRATE RESEARCH, 1984, 129 (JUL) :C1-C3

[3]

[Anonymous], 2006, FIELD GUIDE EUCALYPT

[4] LARGE-SCALE PREPARATION OF D-ALLOSE - OBSERVATIONS ON STEREOSELECTIVITY OF REDUCTION OF 1,2-5,6-DI-0-ISOPROPYLIDENE-ALPHA-D-RIBO-HEXOFURANOS-3-ULOSE HYDRATE [J].

BAKER, DC ;

TINDALL, CG ;

HORTON, D .

CARBOHYDRATE RESEARCH, 1972, 24 (01) :192-&

[5] HYDROBORATION OF TERPENES .10. AN IMPROVED PROCEDURE FOR THE CONVERSION OF ALPHA-PINENE INTO BETA-PINENE IN HIGH CHEMICAL AND OPTICAL YIELD USING A COMBINATION OF THE SCHLOSSER ALLYLIC METALATION OF ALPHA-PINENE AND ALLYLBORANE CHEMISTRY [J].

BROWN, HC ;

ZAIDLEWICZ, M ;

BHAT, KS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1764-1766

[6] ISOLATION OF 5,7-DIHYDROXY-2-METHYLCHROMONE AND ITS 7-0-GLYCOSIDES FROM ADINA-RUBESCENS [J].

BROWN, RT ;

BLACKSTOCK, WP ;

CHAPPLE, CL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (18) :1776-1778

[7] SYNTHESIS OF QUERCETIN-3-0-BETA-D-GLUCOPYRANOSYL-(1-]2)-BETA-D-XYLOPYRANOSIDE VIA ORTHOESTER METHODOLOGY [J].

DEMETZOS, C ;

SKALTSOUNIS, AL ;

RAZANAMAHEFA, B ;

TILLEQUIN, F .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1234-1238

[8] PHASE-TRANSFER-CATALYZED SYNTHESIS OF FLAVONOID GLYCOSIDES [J].

DEMETZOS, C ;

SKALTSOUNIS, AL ;

TILLEQUIN, F ;

KOCH, M .

CARBOHYDRATE RESEARCH, 1990, 207 (01) :131-137

[9] Total synthesis of quercetin 3-sophorotrioside [J].

Du, YG ;

Wei, GH ;

Linhardt, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :2206-2209

[10] Examination of the consistency of plant traits driving oil yield and quality in short-rotation coppice cultivation of Eucalyptus polybractea [J].

Goodger, Jason Q. D. ;

Connelly, Christine A. ;

Woodrow, Ian E. .

FOREST ECOLOGY AND MANAGEMENT, 2007, 250 (03) :196-205

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