Enhancement of steroid hydroxylation yield from dehydroepiandrosterone by cyclodextrin complexation technique

• An inclusion complex between CDs and dehydroepiandrosterone (DHEA) could be formed at a 1:1 molar ratio.
• Hydroxylation yield from DHEA by Colletotrichum lini ST-1 was increased significantly by cyclodextrin complexation technique.
• The mechanisms of CD complexation technique for enhancing the hydroxylation yield of DHEA were analyzed systematic.

The cyclodextrins (CDs) complexation technique was performed for the enhancement of hydroxylation yield from dehydroepiandrosterone (DHEA) by Colletotrichum lini ST-1. Using DHEA/methyl-β-cyclodextrin (M-β-CD) or DHEA/hydroxypropyl-β-cyclodextrin (HP-β-CD) inclusion complexes as substrate (10 g/L), the hydroxylation yields were increased by 14.98% and 20.54% respectively, and the biotransformation course was shortened by 12 h. X-ray diffractometry, differential scanning calorimetry, and phase solubility analyses showed an inclusion complex was formed between CDs and DHEA at a molar ratio of 1:1, which remarkably increased the solubility of DHEA, and then improved substrate biotransformation efficiency and hydroxylation yield. Meanwhile, results of thermodynamic parameters (ΔG, ΔH, ΔS and Ks) analysis revealed the complexation process was spontaneous and DHEA/CDs inclusion complex was stable. Scanning electron microscopy and transmission electron microscopy showed that the enhancement of DHEA hydroxylation yield also depended on the improvement of cell permeability through interaction between cytomembrane and CDs. These results suggested that the CDs complexation technique was a promising method to enhance steroids hydroxylation yield by increasing steroids solubility and decreasing membrane resistance of substrate and product during biotransformation process.

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