（±）-黄烷酮和（±）-异黄烷酮的微生物转化

Microbiological transformation of (+/-)-flavanone and (+/-)-isoflavanone.

作者信息

Ibrahim A R, Abul-Hajj Y J

机构信息

Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis 55455.

出版信息

J Nat Prod. 1990 May-Jun;53(3):644-56. doi: 10.1021/np50069a017.

DOI:10.1021/np50069a017

PMID:2213034

Abstract

The microbiological transformation of flavanone and isoflavanone was explored using a group of 80 microorganisms in the initial screening. Ten metabolites of flavanone were isolated and identified as 4'-hydroxyflavanone [3], 3',4'-dihydroxyflavanone [4], 3-hydroxyflavone [2], flavone [5], 2'-hydroxydihydrochalcone [7], 2',4-dihydroxydihydrochalcone [6], 2',3,4-trihydroxydihydrochalcone [8], 2',5'-dihydroxydihydrochalcone [9], 4'-hydroxyflavan-4 alpha-ol [11], and 2'-hydroxydibenzoylmethane [10]. The isoflavanone metabolites were identified as isoflavone [15], 2-hydroxyisoflavanone [16], 4'-hydroxyisoflavanone [13], 6,4'-dihydroxyisoflavanone [17], and 3',4'-dihydroxyisoflavone [14]. The structures of the metabolites were established using spectroscopic techniques including ir, ms, uv, 1H-nmr, and 13C-nmr spectroscopy. Production of 4'-hydroxyflavanone, 3',4'-dihydroxyflavanone, and 2',4-dihydroxydihydrochalcone by 13 microorganisms was assayed using reversed-phase hplc.

摘要

在初步筛选中，使用一组80种微生物探索了黄烷酮和异黄烷酮的微生物转化。分离并鉴定出10种黄烷酮代谢产物，分别为4'-羟基黄烷酮[3]、3',4'-二羟基黄烷酮[4]、3-羟基黄酮[2]、黄酮[5]、2'-羟基二氢查耳酮[7]、2',4-二羟基二氢查耳酮[6]、2',3,4-三羟基二氢查耳酮[8]、2',5'-二羟基二氢查耳酮[9]、4'-羟基黄烷-4α-醇[11]和2'-羟基二苯甲酰甲烷[10]。异黄烷酮代谢产物被鉴定为异黄酮[15]、2-羟基异黄烷酮[16]、4'-羟基异黄烷酮[13]、6,4'-二羟基异黄烷酮[17]和3',4'-二羟基异黄酮[14]。代谢产物的结构通过红外光谱、质谱、紫外光谱、1H-核磁共振光谱和13C-核磁共振光谱等光谱技术确定。使用反相高效液相色谱法测定了13种微生物产生4'-羟基黄烷酮、3',4'-二羟基黄烷酮和2',4-二羟基二氢查耳酮的情况。