Biotransformations of 6′,7′-dihydroxybergamottin and 6′,7′-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity
Publication type: Journal Article
Publication date: 2012-03-01
scimago Q2
wos Q2
SJR: 0.472
CiteScore: 5.1
Impact factor: 2.2
ISSN: 0960894X, 14643405
PubMed ID:
22342630
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.
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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.
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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 -
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BibTex (up to 50 authors)
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@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}
}
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MLA
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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.