Mikell Julie Rakel, Khan Ikhlas Ahmad
National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
Chem Pharm Bull (Tokyo). 2012;60(9):1139-45. doi: 10.1248/cpb.c12-00296.
Microbial metabolism of 7-hydroxyflavanone (1) with fungal culture Cunninghamella blakesleeana (ATCC 8688a), yielded flavanone 7-sulfate (2), 7,4'-dihydroxyflavanone (3), 6,7-dihydroxyflavanone (4), 6-hydroxyflavanone 7-sulfate (5), and 7-hydroxyflavanone 6-sulfate (6). Mortierella zonata (ATCC 13309) also transformed 1 to metabolites 2 and 3 as well as 4'-hydroxyflavanone 7-sulfate (7), flavan-4-cis-ol 7-sulfate (8), 2',4'-dihydroxychalcone (9), 7,8-dihydroxyflavanone (10), 8-hydroxyflavanone 7-sulfate (11), and 8-methoxy-7-hydroxyflavanone (12). Beauveria bassiana (ATCC 7159) metabolized 1 to 2, 3, and 8, flavanone 7-O-β-D-O-4-methoxyglucopyranoside (13), and 8-hydroxyflavanone 7-O-β-D-O-4-methoxyglucopyranoside (14). Chaetomium cochlioides (ATCC 10195) also transformed 1 to 2, 3, 9, together with 7-hydroxy-4-cis-ol (15). Mucor ramannianus (ATCC 9628) metabolized 1 in addition to 7, to also 4,2',4'-trihydroxychalcone (16), 7,3',4'-trihydroxyflavanone (17), 4'-hydroxyflavanone 7-O-α-L-rhamnopyranoside (18), and 7,3',4'-trihydroxy-6-methoxyflavanone (19). The organism Aspergillus alliaceus (ATCC 10060) transformed 1 to metabolites 3, 16, 7,8,4'-trihydroxyflavanone (20), and 7-hydroxyflavanone 4'-sulfate (21). A metabolite of 1, flavanone 7-O-β-D-O-glucopyranoside (22) was produced by Rhizopus oryzae (ATCC 11145). Structures of the metabolic products were elucidated by means of spectroscopic data. None of the metabolites tested showed antibacterial, antifungal and antimalarial activities against selected organisms. Metabolites 4 and 16 showed weak antileishmanial activity.
7-羟基黄烷酮（1）经真菌菌株布氏小克银汉霉（ATCC 8688a）进行微生物代谢后，产生了黄烷酮7-硫酸盐（2）、7,4'-二羟基黄烷酮（3）、6,7-二羟基黄烷酮（4）、6-羟基黄烷酮7-硫酸盐（5）和7-羟基黄烷酮6-硫酸盐（6）。带状被孢霉（ATCC 13309）也将1转化为代谢产物2和3以及4'-羟基黄烷酮7-硫酸盐（7）、黄烷-4-顺式醇7-硫酸盐（8）、2',4'-二羟基查耳酮（9）、7,8-二羟基黄烷酮（10）、8-羟基黄烷酮7-硫酸盐（11）和8-甲氧基-7-羟基黄烷酮（12）。球孢白僵菌（ATCC 7159）将1代谢为2、3和8、黄烷酮7-O-β-D-O-4-甲氧基吡喃葡萄糖苷（13）以及8-羟基黄烷酮7-O-β-D-O-4-甲氧基吡喃葡萄糖苷（14）。耳蜗毛壳菌（ATCC 10195）也将1转化为2、3、9以及7-羟基-4-顺式醇（15）。拉曼被孢霉（ATCC 9628）除了将1代谢为7外，还代谢生成4,2',4'-三羟基查耳酮（16）、7,3',4'-三羟基黄烷酮（17）、4'-羟基黄烷酮7-O-α-L-鼠李吡喃糖苷（18）和7,3',4'-三羟基-6-甲氧基黄烷酮（19）。蒜曲霉（ATCC 10060）将1转化为代谢产物3、16、7,8,4'-三羟基黄烷酮（20）和7-羟基黄烷酮4'-硫酸盐（21）。米根霉（ATCC 11145）产生了1的一种代谢产物，即黄烷酮7-O-β-D-O-吡喃葡萄糖苷（22）。代谢产物的结构通过光谱数据得以阐明。所测试的代谢产物中，没有一种对选定的生物体表现出抗菌、抗真菌和抗疟活性。代谢产物4和16表现出较弱的抗利什曼原虫活性。
