Hyperkouytones A—O, New Polyprenylated Acylphloroglucinols from Hypericum kouytchense with Multidrug Resistance Reversal Activity
Hua-Yong Lou , Mei-Jun Chen , Ping Yi , Jun Jin , Yan-Rong Zeng , Wei Gu , Zhan-Xing Hu , Jue Yang , Xiao-Jiang Hao , Chun-Mao Yuan
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3293 -3307.
Hyperkouytones A—O, New Polyprenylated Acylphloroglucinols from Hypericum kouytchense with Multidrug Resistance Reversal Activity
Comprehensive Summary:Given the lack of systematic polyprenylated acylphloroglucinols (PPAPs) research on traditional Chinese medicine of Hypericum kouytchense, this plant was applied for the phytochemical study, which led to fifteen new PPAPs ( 1— 15, PPAPs), along with 36 known PPAP derivatives. Their structures and absolute configurations were established by comprehensive spectral analysis and theoretical ECD and NMR calculations. Structurally, compound 1 possesses a rare fused 6/6/6/5/5 pentacyclic ring system. Eleven compounds exhibited good multidrug resistance reversal activity (RF ranging from 5 to 53) in HepG2/ADR cells. Importantly, compound 34, the most potential MDR modulator, showed better reversal effect (RF: 53) than positive control, verapamil. The primary mechanistic study of compound 34, implied that this compound could prohibit the function of P-gp transport rather than its expression. The possible recognition mechanism between compound 34 and P-gp was predicted by molecular docking.
Natural products / Hypericum kouytchense / Phytochemistry / Structure elucidation / Multidrug resistance reversal activity
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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