Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi

Abstract

Incubation of salpichrolide A (1) with Rhizomucor miehei produced hydroxylation in rings B and C (C-7 and C-12) and led to C-5-C-6 epoxide opening, while incubation of salpichrolides C (2) and G (3) with R. miehei led to epoxide opening at the C-24-C-25 and C-5-C-6 positions, respectively. Biotransformation of salpichrolide A (1) with Cunninghamella elegans produced stereoselective hydroxylated, oxidized, and reduced derivatives in different positions of the A, B, and C rings and C-5-C-6 epoxide opening. In addition, selective epoxide opening at the C-5-C-6 or C-24-C-25 positions was obtained from the incubation of salpichrolide A (1) with Curvularia lunata.

Biotransformation of α-terpineol by Alternaria alternata

“…Biotransformation is superior to chemical synthesis due to superior regio-and stereo-selectivities, 1 environmentally friendly procedures, 2 and mild reaction conditions. 3 Biocatalysts play an important role in regio-and stereo-selective reactions, 4,5 including acetylation, 6 hydroxylation, 7 and epoxidation of steroids. 8 Our previous studies have shown that many transformations have been achieved by microorganisms.…”

Phytochemical Study of the Genus Salpichroa (Solanaceae), Chemotaxonomic Considerations, and Biological Evaluation in Prostate and Breast Cancer Cells

“…The salpichrolide derivatives tested ( 2 – 11 ) were obtained by biotransformation of salpichrolides A, C, and G with filamentous fungi Rhizomucor miehei (CECT 2749) and Cunninghamella elegans (CECT 2113) ( Fig. ) . The results, expressed as half maximal inhibitory concentration ( IC 50 ), are summarized in Table .…”

“…Salpichrolide derivatives obtained by biotransformation assayed against human prostate and breast cancer cell lines.…”

“…4). [29] The results, expressed as half maximal inhibitory concentration (IC 50 ), are summarized in Table 1. Cell lines were exposure for 48 h with the compounds at a range 10 -65 lM.…”

Biotransformation of labdane and halimane diterpenoids by two filamentous fungi strains

“…Biotransformation mediated by filamentous fungi consists of a powerful method to perform chemical modifications of a variety of starting materials such as bioactive natural products, to obtain derivatives with improved biological properties or even new biological activities [ 8 ]. This approach stands out as a promising alternative to conventional chemical methods since fungi contain multi-enzymatic systems with broad specificities and are, therefore, able to catalyse chemo, regio and stereoselective reactions on non-activated molecular sites that are normally unreactive or difficult to reach chemically [ 9 ]. Furthermore, microbial transformation is a fast, efficient, cost-effective and ecologically friendly technique because it requires only mild reaction conditions [ 10 ].…”