volume 22 issue 6 pages 2279-2282

Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity

Publication typeJournal Article
Publication date2012-03-01
scimago Q2
wos Q2
SJR0.472
CiteScore5.1
Impact factor2.2
ISSN0960894X, 14643405
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
Penicillium digitatum, as well as five other citrus pathogenic species, ( Penicillium ulaiense Link, Geotrichum citri Link, Botrytis cinerea P. Micheli ex Pers., Lasiodiplodia theobromae (Pat.) Griffon & Maubl., and Phomopsis citri (teleomorph Diaporthe citri )) were observed to convert 6′,7′-epoxybergamottin ( 1 ) into 6′,7′-dihydroxybergamottin ( 2 ), bergaptol ( 3 ), and an opened lactone ring metabolite 6,7-furano-5-(6′,7′-dihydroxy geranyloxy)-2-hydroxy-hydrocoumaric acid ( 4 ). Metabolism of 2 by these fungi also proceeded to 4 . The structure of 4 was established by high resolution mass spectrometry and 1 H and 13 C NMR techniques. The inhibitory activity of 4 towards human intestinal cytochrome P450 3A4 (CYP3A4) was greatly decreased (IC 50 >172.0 μM) compared to 2 (IC 50 = 0.81 μM).
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Myung K., Manthey J. A., Narciso J. A. Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity // Bioorganic and Medicinal Chemistry Letters. 2012. Vol. 22. No. 6. pp. 2279-2282.
GOST all authors (up to 50) Copy
Myung K., Manthey J. A., Narciso J. A. Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity // Bioorganic and Medicinal Chemistry Letters. 2012. Vol. 22. No. 6. pp. 2279-2282.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.bmcl.2012.01.081
UR - https://doi.org/10.1016/j.bmcl.2012.01.081
TI - Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Myung, Kyung
AU - Manthey, John A.
AU - Narciso, Jan A.
PY - 2012
DA - 2012/03/01
PB - Elsevier
SP - 2279-2282
IS - 6
VL - 22
PMID - 22342630
SN - 0960-894X
SN - 1464-3405
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Myung,
author = {Kyung Myung and John A. Manthey and Jan A. Narciso},
title = {Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2012},
volume = {22},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.bmcl.2012.01.081},
number = {6},
pages = {2279--2282},
doi = {10.1016/j.bmcl.2012.01.081}
}
MLA
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MLA Copy
Myung, Kyung, et al. “Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity.” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 6, Mar. 2012, pp. 2279-2282. https://doi.org/10.1016/j.bmcl.2012.01.081.