CONFIRMATION OF STRUCTURE AND ABSOLUTE STEREOCHEMISTRY OF 9-EPI-BETA-CARYOPHYLLENE FROM DACRYDIUM-CUPRESSINUM

被引：37

作者：

HINKLEY, SFR ^{[1
]}

PERRY, NB ^{[1
]}

WEAVERS, RT ^{[1
]}

机构：

[1] UNIV OTAGO,DEPT CHEM,PLANT EXTRACTS RES UNIT,OTAGO,NEW ZEALAND

来源：

PHYTOCHEMISTRY | 1994年 / 35卷 / 06期

关键词：

DACRYDIUM CUPRESSINUM; PODOCARPACEAE; RIMU; ABSOLUTE STEREOCHEMISTRY; MOLECULAR MODELING; SESQUITERPENE; 9-EPI-BETA-CARYOPHYLLENE; BETA-CARYOPHYLLENE;

D O I：

10.1016/S0031-9422(00)86882-X

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 structure of the rare sesquiterpene 9-epi-beta-caryophyllene, isolated from the foliage of the New Zealand rimu tree, Dacrydium cupressinum was verified by 2D NMR techniques and the relative stereochemistry determined by NOE studies. The absolute stereochemistry was determined by conversion of both beta-caryophyllene and 9-epi-beta-caryophyllene into the same known [7,2,0(1,6),0(1,9)] tricyclic compound. Molecular modelling results on the lowest energy conformations of beta-caryophyllene and 9-epi-beta-caryophyllene were in agreement with experimental results.

引用

页码：1489 / 1494

页数：6

共 20 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[2]

ANDERSEN NH, 1978, BIOORGANIC CHEM TREA, V2, P1

[3] CONFORMATIONAL ISOMERS OF 14-HYDROXY-9-EPI-BETA-CARYOPHYLLENE ISOLATED FROM THE WOOD OF JUNIPERUS-OXYCEDRUS [J].

BARRERO, AF ;

SANCHEZ, JF ;

FERROL, N ;

SANFELICIANO, A .

TETRAHEDRON LETTERS, 1989, 30 (02) :247-250

[4] EVIDENCES ABOUT THE STEREOCHEMISTRY OF 14-HYDROXY-9-EPI-BETA-CARYOPHYLLENE [J].

BARRERO, AF ;

OLTRA, JE ;

BARRAGAN, A .

TETRAHEDRON LETTERS, 1990, 31 (28) :4069-4072

[5] FOLIAGE SESQUITERPENES OF DACRYDIUM-CUPRESSINUM - IDENTIFICATION, VARIATION AND BIOSYNTHESIS [J].

BERRY, KM ;

PERRY, NB ;

WEAVERS, RT .

PHYTOCHEMISTRY, 1985, 24 (12) :2893-2898

[6] NATURALLY-OCCURRING TERPENE DERIVATIVES .299. SESQUITERPENES FROM 3 SENECIO SPECIES [J].

BOHLMANN, F ;

ZIESCHE, J .

PHYTOCHEMISTRY, 1981, 20 (03) :469-472

[7] NATURALLY OCCURRING TERPENE DERIVATIVES .138. NEW FURANOEREMOPHILANES AND OTHER SESQUITERPENES FROM SPECIES EURYOPS [J].

BOHLMANN, F ;

ZDERO, C .

PHYTOCHEMISTRY, 1978, 17 (07) :1135-1153

[8] TOTAL SYNTHESIS OF D,L-CARYOPHYLLENE + D,L-ISOCARYOPHYLLENE [J].

COREY, EJ ;

MITRA, RB ;

UDA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (03) :485-&

[9]

HIKINO H, 1969, CHEM PHARM BULL, V17, P1390

[10]

KLYNE W, 1978, ATLAS STEREOCHEMISTR, V2, P54

← 1 2 →