Volume 42, Issue 24 pp. 3293-3307
Concise Report

Hyperkouytones A—O, New Polyprenylated Acylphloroglucinols from Hypericum kouytchense with Multidrug Resistance Reversal Activity

Hua-Yong Lou

Hua-Yong Lou

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

Those authors contribute equally.

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Mei-Jun Chen

Mei-Jun Chen

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

Those authors contribute equally.

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Ping Yi

Ping Yi

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

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Jun Jin

Jun Jin

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

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Yan-Rong Zeng

Yan-Rong Zeng

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Chinese Ethnic Medicine, Guizhou Minzu University, Guiyang, Guizhou, 550025 China

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Wei Gu

Wei Gu

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

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Zhan-Xing Hu

Zhan-Xing Hu

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

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Jue Yang

Corresponding Author

Jue Yang

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
Xiao-Jiang Hao

Corresponding Author

Xiao-Jiang Hao

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Kunming, Yunnan, 650201 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
Chun-Mao Yuan

Corresponding Author

Chun-Mao Yuan

State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, Guizhou, 550014 China

Natural Products Research Center, Guiyang, Guizhou, 550014 China

School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang, Guizhou, 561113 China

E-mail: [email protected]; [email protected]; [email protected]Search for more papers by this author
First published: 30 August 2024
Citations: 2

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 (115, 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.

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