Biotransformation of ent-Atisenes and ent-Beyerenes by Rhizopus nigricans and Fusarium moniliforme Cultures
Microbial transformations of ent-atisene and ent-beyerene compounds were carried out using cultures of R. nigricans and F. moniliforme. Rhizopus nigricans metabolized all of the substrates, at higher yields than F. moniliforme, to give an ent-3β hydroxylation (60−65% for ent-atisenes and 80−85% for...
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| Published in | Journal of natural products (Washington, D.C.) Vol. 60; no. 2; pp. 86 - 92 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.02.1997
Amer Chemical Soc American Society of Pharmacognosy |
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| Abstract | Microbial transformations of ent-atisene and ent-beyerene compounds were carried out using cultures of R. nigricans and F. moniliforme. Rhizopus nigricans metabolized all of the substrates, at higher yields than F. moniliforme, to give an ent-3β hydroxylation (60−65% for ent-atisenes and 80−85% for ent-beyerenes). Moreover, the double bond of the ent-beyerene skeleton was epoxidized by both fungi at lower yields (3−6%). Fusarium moniliforme produced a number of additional minor products by hydroxylation at other positions. |
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| AbstractList | Microbial transformations of ent-atisene and ent-beyerene compounds were carried out using cultures of R. nigricans and F. moniliforme. Rhizopus nigricans metabolized all of the substrates, at higher yields than F. moniliforme, to give an ent-3 beta hydroxylation (60-65% for ent-atisenes and 80-85% for ent-beyerenes). Moreover, the double bond of the ent-beyerene skeleton was epoxidized by both fungi at lower yields (3-6%). Fusarium moniliforme produced a number of additional minor products by hydroxylation at other positions. Microbial transformations of ent-atisene and ent-beyerene compounds were carried out using cultures of R. nigricans and F. moniliforme. Rhizopus nigricans metabolized all of the substrates, at higher yields than F. moniliforme, to give an ent-3β hydroxylation (60−65% for ent-atisenes and 80−85% for ent-beyerenes). Moreover, the double bond of the ent-beyerene skeleton was epoxidized by both fungi at lower yields (3−6%). Fusarium moniliforme produced a number of additional minor products by hydroxylation at other positions. |
| Author | García-Granados, Andrés Parra, Andrés Arias, José María |
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| Keywords | MICROBIOLOGICAL TRANSFORMATION DITERPENOIDS GIBBERELLA-FUJIKUROI Hydroxylation Rhizopus stolonifer Phycomycetes Metabolism Fungi Terpene Enantiomer Diterpene Epoxidation Fungi Imperfecti Fusarium moniliforme Ethylenic compound Thallophyta |
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| References | FRAGA, BM (WOS:A1992HC57100023) 1992; 31 BEILBY J P (BCI:BCI197309099986) 1973; 28 GARCIAGRANADOS, A (WOS:A1994NT71200023) 1994; 36 GARCIAGRANADOS, A (WOS:A1981MY61000001) 1981; 77 BEARDER, JR (WOS:A1976BE48900015) 1976 GARCIAGRANADOS, A (WOS:A1985AMV7100004) 1985; 48 HANSON, JR (WOS:A1992HP46700002) 1992; 9 ALI, MS (WOS:A1992HC57100024) 1992; 31 GARCIAGRANADOS, A (WOS:A1981LU45700010) 1981; 77 GARCIAGRANADOS, A (WOS:A1980KJ36900027) 1980; 21 DIAZ, CE (WOS:A1985ALT2900016) 1985; 24 HANSON, JR (WOS:A1979HS65400026) 1979; 18 García-Granados A. (np960426kb00004/np960426kb00004_1) 1985; 48 Fraga B. M. (np960426kb00009/np960426kb00009_1) 1992; 31 Beilby J. P. (np960426kb00002/np960426kb00002_1) 1973; 28 García-Granados A. (np960426kb00007/np960426kb00007_1) 1994; 36 Díaz C. E. (np960426kb00005/np960426kb00005_1) 1985; 24 Ali M. S. (np960426kb00006/np960426kb00006_1) 1992; 31 García-Granados A. (np960426kb00012/np960426kb00012_1) 1981; 77 Hanson J. R. (np960426kb00008/np960426kb00008_1) 1979; 18 García-Granados A. (np960426kb00011/np960426kb00011_1) 1981; 77 García-Granados A. (np960426kb00010/np960426kb00010_1) 1980; 21 Hanson J. R. (np960426kb00001/np960426kb00001_1) 1992; 9 Bearder J. R. (np960426kb00003/np960426kb00003_1) 1976; 173 |
| References_xml | – volume: 48 start-page: 371 year: 1985 ident: WOS:A1985AMV7100004 article-title: MICROBIAL TRANSFORMATION OF TETRACYCLIC DITERPENES - CONVERSION OF ENT-BEYERENES BY RHIZOPUS-NIGRICANS CULTURES publication-title: JOURNAL OF NATURAL PRODUCTS contributor: fullname: GARCIAGRANADOS, A – volume: 9 start-page: 139 year: 1992 ident: WOS:A1992HP46700002 article-title: THE MICROBIOLOGICAL TRANSFORMATION OF DITERPENOIDS publication-title: NATURAL PRODUCT REPORTS contributor: fullname: HANSON, JR – volume: 28 start-page: 2589 year: 1973 ident: BCI:BCI197309099986 article-title: MICROBIOLOGICAL TRANSFORMATIONS OF TETRA CYCLIC DI TERPENES publication-title: Tetrahedron Letters contributor: fullname: BEILBY J P – volume: 77 start-page: 239 year: 1981 ident: WOS:A1981MY61000001 article-title: TERPENE COMPONENTS OF SPANISH LABIATES .5. STRUCTURE DETERMINATION BY HIGH-RESOLUTION (360MHZ) H-1-NMR OF A-11, 18-DIHYDROXIKAUR-16-ENE, A NEW DITERPENIC DERIVATIVE FROM SIDERITIS-ARBORESCENS SALZM publication-title: ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA contributor: fullname: GARCIAGRANADOS, A – volume: 36 start-page: 657 year: 1994 ident: WOS:A1994NT71200023 article-title: BIOTRANSFORMATION OF ENT-BEYERENONES BY RHIZOPUS NIGRICANS AND CURVULARIA-LUNATA CULTURES publication-title: PHYTOCHEMISTRY contributor: fullname: GARCIAGRANADOS, A – volume: 24 start-page: 1489 year: 1985 ident: WOS:A1985ALT2900016 article-title: THE MICROBIOLOGICAL TRANSFORMATION OF SOME ENT-BEYERENE DITERPENOIDS BY GIBBERELLA-FUJIKUROI TO BEYERGIBBERELLINS AND BEYERENOLIDES publication-title: PHYTOCHEMISTRY contributor: fullname: DIAZ, CE – volume: 21 start-page: 3611 year: 1980 ident: WOS:A1980KJ36900027 article-title: TERPENIC COMPONENTS OF SPANISH LABIATAE .5. ATISIDERITOL, A NEW ENT-ATIS-13-ENE FROM A SIDERITIS-PUSILLA (LAG) PAU SSP publication-title: TETRAHEDRON LETTERS contributor: fullname: GARCIAGRANADOS, A – volume: 31 start-page: 503 year: 1992 ident: WOS:A1992HC57100023 article-title: MICROBIOLOGICAL PREPARATION OF ATISENOLIDES BY GIBBERELLA-FUJIKUROI publication-title: PHYTOCHEMISTRY contributor: fullname: FRAGA, BM – start-page: 173 year: 1976 ident: WOS:A1976BE48900015 article-title: FUNGAL PRODUCTS .16. CONVERSION OF ISOSTEVIOL AND STEVIOL ACETATE INTO GIBBERELLIN ANALOGS BY MUTANT B1-41A OF GIBBERELLA-FUJIKUROI AND PREPARATION OF [H-3]GIBBERELLIN A20 publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: BEARDER, JR – volume: 31 start-page: 507 year: 1992 ident: WOS:A1992HC57100024 article-title: THE BIOTRANSFORMATION OF SOME ENT-BEYERAN-19-OIC ACIDS BY GIBBERELLA-FUJIKUROI publication-title: PHYTOCHEMISTRY contributor: fullname: ALI, MS – volume: 77 start-page: 48 year: 1981 ident: WOS:A1981LU45700010 article-title: TERPENIC COMPONENTS OF SPANISH LABIATAE .7. 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S. – volume: 21 start-page: 3612 year: 1980 ident: np960426kb00010/np960426kb00010_1 publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(80)80249-8 contributor: fullname: García-Granados A. – volume: 36 start-page: 663 year: 1994 ident: np960426kb00007/np960426kb00007_1 publication-title: Phytochemistry doi: 10.1016/S0031-9422(00)89792-7 contributor: fullname: García-Granados A. |
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| SubjectTerms | Biological and medical sciences CELL CULTURE CHEMICAL STRUCTURE Chemistry, Medicinal CULTIVO DE CELULAS CULTURE DE CELLULE DERIVATIVES DITERPENOIDE DITERPENOIDS DITERPENOS ESPECTROMETRIA ESTRUCTURA QUIMICA Fundamental and applied biological sciences. Psychology Fusarium moniliforme GIBBERELLA FUJIKUROI Growth, nutrition, metabolism, transports, enzymes. Molecular biology Life Sciences & Biomedicine METABOLISM METABOLISME METABOLISMO METABOLITE METABOLITES METABOLITOS Microbiology Mycology Pharmacology & Pharmacy Plant Sciences Rhizopus nigricans RHIZOPUS STOLONIFER Science & Technology SPECTRAL ANALYSIS SPECTROMETRIE SPECTROMETRY STRUCTURE CHIMIQUE |
| Title | Biotransformation of ent-Atisenes and ent-Beyerenes by Rhizopus nigricans and Fusarium moniliforme Cultures |
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