Abstract

Eight fungal strains (Penicillium raistrickii CBMAI 931, Cladosporium sp. CBMAI 1237, Aspergillus sydowii CBMAI 935, Penicillium oxalicum CBMAI 1996, Penicillium citrinum CBMAI 1186, Mucor racemosus CBMAI 847, Westerdykella sp. CBMAI 1679, and Aspergillus sclerotiorum CBMAI 849) mediated the biotransformation of the 2′-hydroxychalcone 1a. The main products obtained were from hydrogenation, hydroxylation, and cyclization reactions. Penicillium raistrickii CBMAI 931 catalyzed the chemoselective reduction of 1a to produce 2′-hydroxydihydrochalcone 2a (72%) in 7 days of incubation in phosphate buffer (pH 7). Aspergillus sydowii CBMAI 935 promoted the hydroxylation of 1a to yield 2′,4-dihydroxy-dihydrochalcone 5a (c = 42%) in 7 days of incubation in phosphate buffer (pH 8). The reaction using P. citrinum CBMAI 1186 and M. racemosus CBMAI 847 presented main cyclization products in phosphate buffer (pH 8), but the reactions with these fungi did not present enantioselectivity. Marine-derived fungi were effective and versatile biocatalysts for biotransformation of the 2′-hydroxychalcones yielding different products according to the conditions and microorganism used.

摘要

八种真菌菌株（Penicillium raistrickii CBMAI 931、Cladosporium sp. CBMAI 1237、Aspergillus sydowii CBMAI 935、Penicillium oxalicum CBMAI 1996、Penicillium citrinum CBMAI 1186、Mucor racemosus CBMAI 847、Westerdykella sp. CBMAI 1679 和 Asperdykella sp. CBMAI 1679 和Aspergillus biorottransformation9 BMAI） 2'-羟基查尔酮1a。获得的主要产物来自氢化、羟基化和环化反应。雷氏青霉CBMAI 931 催化1a化学选择性还原生成 2'-羟基二氢查尔酮2a (72%) 在磷酸盐缓冲液 (pH 7) 中孵育 7 天。Aspergillus sydowii CBMAI 935 在磷酸盐缓冲液 (pH 8) 中孵育 7 天后，促进1a的羟基化产生 2',4-二羟基-二氢查耳酮5a (c = 42%)。使用P. citrinum CBMAI 1186 和M. racemosus CBMAI 847 的反应在磷酸盐缓冲液 (pH 8) 中呈现主要环化产物，但与这些真菌的反应不呈现对映选择性。海洋来源的真菌是 2'-羟基查尔酮生物转化的有效且通用的生物催化剂，根据使用的条件和微生物产生不同的产物。