Cordyceps sinensis-mediated biotransformation of notoginsenoside R1 into 25-OH-20(S/R)-R2 with elevated cardioprotective effect against DOX-induced cell injury
2022
Liu, Jishuang | Xin, Yu | Qiu, Zhidong | Zhang, Qi | He, Tianzhu | Qiu, Ye | Wang, Weinan
Notoginsenoside R1 is a dammarane saponin in Panax notoginseng with promising cardioprotective effects. The bioactivity–structure relationship of such saponins suggested that the presence of a hydroxyl group at C25 could elevate its performance. To fulfill that goal, bioconversion of notoginsenoside R1 was mediated by a biocatalytic system of Cordyceps sinensis that had successfully produced multiple 25-OH derivatives from ginsenoside Re and Rg1. The major metabolic products of notoginsenoside R1 were identified as 25-OH-20(S/R)-R2 via the techniques of HRMS, ¹³C-NMR, ¹H-NMR, HSQC and HMBC. Time-course experiments were designed to monitor the reaction process, establishing a biocatalytic pathway of “R1→20(S/R)-R2→25-OH-20(S/R)-R2”. The bioconversion rate of these 25-OH derivatives added up to 69.87% which greatly precedes the previous report. Afterwards, the effect of these biocatalytic products against doxorubicin-induced cardiotoxicity was evaluated, indicating a significant increase in efficacy after the hydration of the C24–C25 double bond on the dammarane skeleton. In conclusion, the biocatalytic system employed in this paper is able to harvest 25-OH-20(S/R)-R2 in high yield from notoginsenoside R1, which will provide lead compounds or drug candidates to alleviate myocardial injury caused by doxorubicin.
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