MICROBIAL TRANSFORMATIONS OF THE SESQUITERPENE LACTONE COSTUNOLIDE

被引：29

作者：

CLARK, AM ^{[1
]}

HUFFORD, CD ^{[1
]}

机构：

[1] UNIV MISSISSIPPI,SCH PHARM,DEPT PHARMACOGNOSY,UNIVERSITY,MS 38677

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 12期

关键词：

D O I：

10.1039/p19790003022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The microbial transformation of the sesquiterpene lactone costunolide has been studied. Preliminary screening experiments indicated a large number of fungi were capable of biotransforming costunolide. In preparative-scale fermentations, Aspergillus niger converted costunolide into dihydrocostunolide (5) and into four eudesmanolide derivatives, colartin (2), 11,13- dihydrosantamarine (6), 11,13-dihydroreynosin (7), and tetrahydrovulgarin (8) formed by a sequence in which costunolide was reduced, epoxidized, and then cyclized. Cunninghamella echinulata produced 1β-hydroxyarbusculin A (10) and Fusarium oxysporum produced dihydrocostunolide (5). A proposal of the sequence of events in the conversion of costunolide to the eudesmanolide metabolites is discussed.

引用

页码：3022 / 3028

页数：7

共 25 条

[11]

HIKINO H, 1977, CHEM PHARM BULL, V25, P6

[12]

IIZUKA H, 1967, MICROBIAL TRANSFORMA

[13] SESQUITERPENE LACTONES OF ARTEMISIA SPECIES . NEW LACTONES FROM A-ARBUSCULA SSP ARBUSCULA AND A-TRIPARTITA SSP RUPICOLA [J].

IRWIN, MA ;

GEISSMAN, TA .

PHYTOCHEMISTRY, 1969, 8 (12) :2411-&

[14] TERPENOIDS .49. TRANSFORMATION PRODUCTS OF COSTUNOLIDE . STEREOCHEMISTRY OF (-) SANTONIN ANDSOLID DIHYDROCOSTUNOLIDE AT C11 [J].

JOSHI, RS ;

KULKARNI, GH ;

KELKAR, GR ;

BHATTACH.SC .

TETRAHEDRON, 1966, 22 (07) :2331-&

[15]

Kieslich K., 1976, MICROBIAL TRANSFORMA

[16] TUMOR INHIBITORS .69. STRUCTURE-CYTOTOXICITY RELATIONSHIPS AMONG SESQUITERPENE LACTONES [J].

KUPCHAN, SM ;

EAKIN, MA ;

THOMAS, AM .

JOURNAL OF MEDICINAL CHEMISTRY, 1971, 14 (12) :1147-&

[17] STRUCTURE-ACTIVITY-RELATIONSHIPS AMONG INVIVO ACTIVE GERMACRANOLIDES [J].

KUPCHAN, SM ;

ASHMORE, JW ;

SNEDEN, AT .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1978, 67 (06) :865-867

[18] SIMPLE METHODS TO FIND STEREOCHEMISTRY OF SIDE CHAIN OF GAMMA-LACTONES [J].

NARAYANAN, CR ;

VENKATAS.NK .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (08) :3156-+

[19] ANTI-CANCER SESQUITERPENE LACTONES OF MICHELIA-COMPRESSA (MAGNOLIACEAE) [J].

OGURA, M ;

CORDELL, GA ;

FARNSWORTH, NR .

PHYTOCHEMISTRY, 1978, 17 (05) :957-961

[20] TERPENOIDS .11. THE STRUCTURE OF COSTUNOLIDE, A NEW SESQUITERPENE LACTONE FROM COSTUS ROOT OIL [J].

RAO, AS ;

KELKAR, GR ;

BHATTACHARYYA, SC .

TETRAHEDRON, 1960, 9 (3-4) :275-283

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