Cassemiro Nadla Soares, Sanches Luana Bonifácio, Kato Natalia Naomi, Ruller Roberto, Carollo Carlos Alexandre, de Mello João Carlos Palazzo, Dos Santos Dos Anjos Edson, Silva Denise Brentan
Laboratório de Produtos Naturais E Espectrometria de Massas (LaPNEM), Faculdade de Ciências Farmacêuticas, Alimentos E Nutrição (FACFAN), Universidade Federal Do Mato Grosso Do Sul, Av. Costa e Silva, s/nº, Campo Grande, MS, 79070-900, Brazil.
Laboratório de Bioquímica, Instituto de Biociências (INBIO), Universidade Federal de Mato Grosso Do Sul (UFMS), Campo Grande, MS, Brazil.
Appl Microbiol Biotechnol. 2021 Oct;105(20):7731-7741. doi: 10.1007/s00253-021-11504-7. Epub 2021 Sep 27.
Iridoids are widely found from species of Bignoniaceae family and exhibit several biological activities, such as anti-inflammatory, antimicrobial, antioxidant, and antitumor. Specioside is an iridoid found from Tabebuia species, mainly in Tabebuia aurea. Thus, here fungus-mediated biotransformation of the iridoid specioside was investigated by seven fungi. The fungus-mediated biotransformation reactions resulted in a total of nineteen different analogs by fungus Aspergillus niger, Aspergillus flavus, Aspergillus japonicus, Aspergillus terreus, Aspergillus niveus, Penicillium crustosum, and Thermoascus aurantiacus. Non-glycosylated specioside was the main metabolite observed. The other analogs were yielded from ester hydrolysis, hydroxylation, methylation, and hydrogenation reactions. The non-glycosylated specioside and coumaric acid were yielded by all fungi-mediated biotransformation. Thus, fungus applied in this study showed the ability to perform hydroxylation and glycosidic, as well as ester hydrolysis reactions from glycosylated iridoid. KEY POINTS: • The biotransformation of specioside by seven fungi yielded nineteen analogs. • The non-glycosylated specioside was the main analog obtained. • Ester hydrolysis, hydroxylation, methylation, and hydrogenation reactions were observe.
环烯醚萜类化合物在紫葳科植物中广泛存在，并具有多种生物活性，如抗炎、抗菌、抗氧化和抗肿瘤活性。梓苷是从 Tabebuia 属植物中发现的一种环烯醚萜类化合物，主要存在于金黄风铃木中。因此，本文研究了七种真菌对环烯醚萜类化合物梓苷的真菌介导生物转化。真菌介导的生物转化反应共产生了 19 种不同的类似物，这些类似物由黑曲霉、黄曲霉、日本曲霉、土曲霉、雪白曲霉、 crustosum 青霉和橙黄嗜热子囊菌产生。非糖基化梓苷是观察到的主要代谢产物。其他类似物则通过酯水解、羟基化、甲基化和氢化反应产生。所有真菌介导的生物转化均产生了非糖基化梓苷和香豆酸。因此，本研究中使用的真菌显示出能够对糖基化环烯醚萜进行羟基化、糖苷化以及酯水解反应的能力。要点：• 七种真菌对梓苷的生物转化产生了 19 种类似物。• 获得的主要类似物是非糖基化梓苷。• 观察到酯水解、羟基化、甲基化和氢化反应。
