Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene

Jair Mafezoli; Maria C.F. Oliveira; José R. Paiva; Antônio H. Sousa; Mary A.S. Lima; José N. Silva; Francisco G. Barbosa; E. M.Kithsiri Wijeratne; A. A.Leslie Gunatilaka

doi:10.1177/1934578x1400900607

Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene

Jair Mafezoli, Maria C.F. Oliveira, José R. Paiva, Antônio H. Sousa, Mary A.S. Lima, José N. Silva, Francisco G. Barbosa, E. M.Kithsiri Wijeratne, A. A.Leslie Gunatilaka

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

The biotransformation of the clerodane diterpene, 3,12-dioxo-15,16-epoxy-4- hydroxy-cleroda-13(16),14-diene (1), obtained from Croton micans var. argyroglossum (Baill.) Müll., was investigated for the first time. Whole cells of Cunninghamella echinulata and Rhizopus stolonifer were used as enzymatic systems, and with both fungi the only biotransformation product obtained was the new ent-neo-clerodane diterpene (3R,4S,5S,8S,9R,10S)-3,4- dihydroxy-15,16-epoxy-12-oxo-cleroda-13(16),14-diene (2a). The absolute stereochemistry of 2a was inferred by comparison of its optical rotation with those of the chemical reduction product of 1 and its quasienantiomer 2c.

Original language	English (US)
Pages (from-to)	759-762
Number of pages	4
Journal	Natural Product Communications
Volume	9
Issue number	6
DOIs	https://doi.org/10.1177/1934578x1400900607
State	Published - Jun 2014

Keywords

3α,4α-Dihydroxy-15,16-epoxy-12-oxo- cleroda-13(16),14-diene
Biotransformation
Cunninghamella echinulata
Rhizopus stolonifer
ent-neo-Clerodane diterpene

ASJC Scopus subject areas

Pharmacology
Plant Science
Drug Discovery
Complementary and alternative medicine

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10.1177/1934578x1400900607

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Mafezoli, J., Oliveira, M. C. F., Paiva, J. R., Sousa, A. H., Lima, M. A. S., Silva, J. N., Barbosa, F. G., Wijeratne, E. M. K., & Gunatilaka, A. A. L. (2014). Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene. Natural Product Communications, 9(6), 759-762. https://doi.org/10.1177/1934578x1400900607

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title = "Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene",

abstract = "The biotransformation of the clerodane diterpene, 3,12-dioxo-15,16-epoxy-4- hydroxy-cleroda-13(16),14-diene (1), obtained from Croton micans var. argyroglossum (Baill.) M{\"u}ll., was investigated for the first time. Whole cells of Cunninghamella echinulata and Rhizopus stolonifer were used as enzymatic systems, and with both fungi the only biotransformation product obtained was the new ent-neo-clerodane diterpene (3R,4S,5S,8S,9R,10S)-3,4- dihydroxy-15,16-epoxy-12-oxo-cleroda-13(16),14-diene (2a). The absolute stereochemistry of 2a was inferred by comparison of its optical rotation with those of the chemical reduction product of 1 and its quasienantiomer 2c.",

keywords = "3α,4α-Dihydroxy-15,16-epoxy-12-oxo- cleroda-13(16),14-diene, Biotransformation, Cunninghamella echinulata, Rhizopus stolonifer, ent-neo-Clerodane diterpene",

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year = "2014",

month = jun,

doi = "10.1177/1934578x1400900607",

language = "English (US)",

volume = "9",

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AU - Oliveira, Maria C.F.

AU - Paiva, José R.

AU - Sousa, Antônio H.

AU - Lima, Mary A.S.

AU - Silva, José N.

AU - Barbosa, Francisco G.

AU - Wijeratne, E. M.Kithsiri

AU - Gunatilaka, A. A.Leslie

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AB - The biotransformation of the clerodane diterpene, 3,12-dioxo-15,16-epoxy-4- hydroxy-cleroda-13(16),14-diene (1), obtained from Croton micans var. argyroglossum (Baill.) Müll., was investigated for the first time. Whole cells of Cunninghamella echinulata and Rhizopus stolonifer were used as enzymatic systems, and with both fungi the only biotransformation product obtained was the new ent-neo-clerodane diterpene (3R,4S,5S,8S,9R,10S)-3,4- dihydroxy-15,16-epoxy-12-oxo-cleroda-13(16),14-diene (2a). The absolute stereochemistry of 2a was inferred by comparison of its optical rotation with those of the chemical reduction product of 1 and its quasienantiomer 2c.

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Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene

Abstract

Keywords

ASJC Scopus subject areas

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