微生物代谢。第12部分。4'-羟基黄烷酮的18种微生物代谢产物的分离、表征及生物活性评价。

Microbial metabolism. Part 12. Isolation, characterization and bioactivity evaluation of eighteen microbial metabolites of 4'-hydroxyflavanone.

作者信息

Mikell Julie Rakel, Herath Wimal, Khan Ikhlas Ahmad

机构信息

National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA.

出版信息

Chem Pharm Bull (Tokyo). 2011;59(6):692-7. doi: 10.1248/cpb.59.692.

DOI:10.1248/cpb.59.692

PMID:21628902

Abstract

Fermentation of 4'-hydroxyflavanone (1) with fungal cultures, Beauveria bassiana (ATCC 13144 and ATCC 7159) yielded 6,3',4'-trihydroxyflavanone (2), 3',4'-dihydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (3), 4'-hydroxyflavanone 3'-sulfate (4), 6,4'-dihydroxyflavanone 3'-sulfate (5) and 4'-hydroxyflavanone 6-O-β-D-4-methoxyglucopyranoside (7). B. bassiana (ATCC 13144) and B. bassiana (ATCC 7159) in addition, gave one more metabolite each, namely, flavanone 4'-O-β-D-4-methoxyglucopyranoside (6) and 6,4'-dihydroxyflavanone (8) respectively. Cunninghamella echinulata (ATCC 9244) transformed 1 to 6,4'-dihydroxyflavanone (8), flavanone-4'-O-β-D-glucopyranoside (9), 3'-hydroxyflavanone 4'-sulfate (10), 3',4'-dihydroxyflavanone (11) and 4'-hydroxyflavanone-3'-O-β-D-glucopyranoside (12). Mucor ramannianus (ATCC 9628) metabolized 1 to 2,4-trans-4'-hydroxyflavan-4-ol (13), 2,4-cis-4'-hydroxyflavan-4-ol (14), 2,4-trans-3',4'-dihydroxyflavan-4-ol (15), 2,4-cis-3',4'-dihydroxyflavan-4-ol (16), 2,4-trans-3'-hydroxy-4'-methoxyflavan-4-ol (17), flavanone 4'-O-α-D-6-deoxyallopyranoside (18) and 2,4-cis-4-hydroxyflavanone 4'-O-α-D-6-deoxyallopyranoside (19). Metabolites 13 and 14 were also produced by Ramichloridium anceps (ATCC 15672). The former was also produced by C. echinulata. Structures of the metabolic products were elucidated by means of spectroscopic data. None of the metabolites tested showed antibacterial, antifungal and antiprotozoal activities against selected organisms.

摘要

用球孢白僵菌（ATCC 13144和ATCC 7159）真菌培养物发酵4'-羟基黄烷酮（1），得到6,3',4'-三羟基黄烷酮（2）、3',4'-二羟基黄烷酮6-O-β-D-4-甲氧基葡萄糖苷（3）、4'-羟基黄烷酮3'-硫酸盐（4）、6,4'-二羟基黄烷酮3'-硫酸盐（5）和4'-羟基黄烷酮6-O-β-D-4-甲氧基葡萄糖苷（7）。此外，球孢白僵菌（ATCC 13144）和球孢白僵菌（ATCC 7159）分别还产生了一种代谢产物，即黄烷酮4'-O-β-D-4-甲氧基葡萄糖苷（6）和6,4'-二羟基黄烷酮（8）。刺孢小克银汉霉（ATCC 9244）将1转化为6,4'-二羟基黄烷酮（8）、黄烷酮-4'-O-β-D-葡萄糖苷（9）、3'-羟基黄烷酮4'-硫酸盐（10）、3',4'-二羟基黄烷酮（11）和4'-羟基黄烷酮-3'-O-β-D-葡萄糖苷（12）。总状毛霉（ATCC 9628）将1代谢为2,4-反式-4'-羟基黄烷-4-醇（13）、2,4-顺式-4'-羟基黄烷-4-醇（14）、2,4-反式-3',4'-二羟基黄烷-4-醇（15）、2,4-顺式-3',4'-二羟基黄烷-4-醇（16）、2,4-反式-3'-羟基-4'-甲氧基黄烷-4-醇（17）、黄烷酮4'-O-α-D-6-脱氧阿洛吡喃糖苷（18）和2,4-顺式-4-羟基黄烷酮4'-O-α-D-6-脱氧阿洛吡喃糖苷（19）。代谢产物13和14也由枝顶孢霉（ATCC 15672）产生。前者也由刺孢小克银汉霉产生。通过光谱数据阐明了代谢产物的结构。所测试的代谢产物均未对选定的生物体表现出抗菌、抗真菌和抗原生动物活性。