SESQUITERPENE CONSTITUENTS IN AGARWOOD .4. FRAGRANT SESQUITERPENES FROM AGARWOOD

被引：90

作者：

ISHIHARA, M ^{[1
]}

TSUNEYA, T ^{[1
]}

UNEYAMA, K ^{[1
]}

机构：

[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN

来源：

PHYTOCHEMISTRY | 1993年 / 33卷 / 05期

关键词：

AQUILARIA-AGALLOCHA; THYMELAEACEAE; AGARWOOD; SESQUITERPENES; (-)-SELINA-3,11-DIEN-14-AL; (+)-SELINA-4,11-DIEN-14-AL; SELINA-3,11-DIEN-14-OIC ACID; SELINA-4,11-DIEN-14-OIC ACID; 9-HYDROXYSELINA-4,11-DIEN-14-OIC ACID; (+)-1,5-EPOXY-NOR-KETOGUAIENE; DEHYDROJINKOH-EREMOL; NEOPETASANE;

D O I：

10.1016/0031-9422(93)85039-T

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：

Two new sesquiterpene aldehydes (-)-selina-3,11-dien-14-al and (+)-selina-4,11-dien-14-al, methyl ester derivatives of three new sesquiterpene carboxylic acids, (-)-methyl selina- 3,11-dien-14-oate, (+)-methyl selina-4,11-dien-14-oate, and (+)-methyl 9-hydroxyselina-4,11-dien-14-oate, and a new nor-sesquiterpene ketone, (+)-1,5-epoxy nor-ketoguaiene, have been isolated from Aquilaria agallocha (agarwood). Their structures have been established on the bases of detailed spectroscopic analyses and. synthesis. The occurrences of dehydrojinkoh-eremol and neopetasane in agarwood were also confirmed by comparison of their mass spectral data and R(t) on capillary GC with those of synthesized samples. The odoriferous properties of some natural and synthesized sesquiterpenes are also described.

引用

页码：1147 / 1155

页数：9

共 19 条

[1]

ANDERSEN NH, 1970, TETRAHEDRON LETT, P1759

[2]

BATES RB, 1966, CHEM IND-LONDON, P2170

[3] NATURALLY OCCURRING TERPENE DERIVATIVES .109. NEW EUDESMANE DERIVATIVES AND OTHER SESQUITERPENES FROM VERBESINA SPECIES [J].

BOHLMANN, F ;

LONITZ, M .

CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (01) :254-263

[4] SOLVOMERCURATION-DEMERCURATION .1. OXYMERCURATION-DEMERCURATION OF REPRESENTATIVE OLEFINS IN AN AQUEOUS SYSTEM - A CONVENIENT MILD PROCEDURE FOR MARKOVNIKOV HYDRATION OF CARBON-CARBON DOUBLE BOND [J].

BROWN, HC ;

GEOGHEGA.PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :1844-&

[5] PREPARATION OF (-)-ARISTOLOCHENE FROM (+)-VALENCENE - ABSOLUTE-CONFIGURATION OF (+)-ARISTOLOCHENE FROM ASPERGILLUS-TERREUS [J].

CANE, DE ;

SALASKI, EJ ;

PRABHAKARAN, PC .

TETRAHEDRON LETTERS, 1990, 31 (14) :1943-1944

[6] ULTRASOUND IN ORGANIC-SYNTHESIS .18. SELECTIVE OXYMERCURATION VIA SONOCHEMICALLY INSITU GENERATED MERCURY SALTS [J].

EINHORN, J ;

EINHORN, C ;

LUCHE, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4479-4481

[7] SYNTHETIC STUDY ON SEVERAL EREMOPHILANE SESQUITERPENES USING A COMMON INTERMEDIATE [J].

HAGIWARA, H ;

UDA, H ;

KODAMA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (04) :963-977

[8]

HASHIMOTO K, 1985, CHEM PHARM BULL, V33, P5088

[9] PREPARATION OF (-)-GUAIA-1(10),11-DIEN-15,2-OLIDE AND (-)-2-ALPHA-HYDROXYGUAIA-1(10),11-DIEN-15-OIC ACID, FRAGRANT SESQUITERPENES IN AGARWOOD (AQUILARIA-AGALLOCHA ROXB) [J].

ISHIHARA, M ;

MASATSUGU, Y ;

UNEYAMA, K .

TETRAHEDRON, 1992, 48 (47) :10265-10276

[10] SESQUITERPENE CONSTITUENTS IN AGARWOOD .2. GUAIANE SESQUITERPENES FROM AGARWOOD [J].

ISHIHARA, M ;

TSUNEYA, T ;

UNEYAMA, K .

PHYTOCHEMISTRY, 1991, 30 (10) :3343-3347

← 1 2 →