Stereoselective oxidation at C-4 of flavans by the endophytic fungus Diaporthe sp. isolated from a tea plant.

Szczegóły
Abstrakt

Tytuł:: Stereoselective oxidation at C-4 of flavans by the endophytic fungus Diaporthe sp. isolated from a tea plant.
Autorzy:: Agusta A; Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Sanzo, Hiroshima, Japan.
Maehara S
Ohashi K
Simanjuntak P
Shibuya H
Źródło:: Chemical & pharmaceutical bulletin [Chem Pharm Bull (Tokyo)] 2005 Dec; Vol. 53 (12), pp. 1565-9.
Typ publikacji:: Journal Article; Research Support, Non-U.S. Gov't
Język:: English
Imprint Name(s):: Original Publication: Tokyo, Pharmaceutical Society of Japan.
MeSH Terms:: Ascomycota/*chemistry
Camellia/*microbiology
Flavins/*chemistry
Catechin/analogs & derivatives ; Catechin/chemistry ; Chromatography, High Pressure Liquid ; DNA, Fungal/biosynthesis ; DNA, Fungal/genetics ; Methylation ; Oxidation-Reduction ; Oxygen/chemistry ; Reverse Transcriptase Polymerase Chain Reaction ; Spectrophotometry, Ultraviolet ; Spectroscopy, Fourier Transform Infrared ; Stereoisomerism
Substance Nomenclature:: 0 (DNA, Fungal)
0 (Flavins)
8R1V1STN48 (Catechin)
92587OVD8Z (epicatechin gallate)
S88TT14065 (Oxygen)
Entry Date(s):: Date Created: 20051206 Date Completed: 20060222 Latest Revision: 20190706
Update Code:: 20240104
DOI:: 10.1248/cpb.53.1565
PMID:: 16327190
: Czasopismo naukowe

The microbial transformation of five flavans (1-5) by endophytic fungi isolated from the tea plant Camellia sinensis was investigated. It was found that the endophytic filamentous fungus Diaporthe sp. oxidized stereoselectively at C-4 position of (+)-catechin (1) and (-)-epicatechin (2) to give the correspondent 3,4-cis-dihydroxyflavan derivatives (6, 10), respectively. (-)-Epicatechin 3-O-gallate (3) and (-)-epigallocatechin 3-O-gallate (4) were also oxidized by the fungus into 3,4-dihydroxyflavan derivatives (10, 12) via (-)-epicatechin (2) and (-)-epigallocatechin (11), respectively. Meanwhile, (-)-gallocatechin 3-O-gallate (5), (-)-catechin (ent-1) and (+)-epicatechin (ent-2), which possess a 2S-phenyl substitution, resisted the biotransformation.

Informacja