Hyparillums A and B: polycyclic polyprenylated acylphloroglucinols from Hypericum patulum

Yulin DUAN; Zhengyi SHI; Fei SONG; Zhangrong HOU; Xiaosheng TAN; Yeting ZHANG; Xincai HAO; Gang CHEN; Changxing QI; Yonghui ZHANG

doi:10.1016/S1875-5364(24)60599-6

Chinese Journal of Natural Medicines ›› 2024, Vol. 22 ›› Issue (3) :273 -279. DOI: 10.1016/S1875-5364(24)60599-6

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Hyparillums A and B: polycyclic polyprenylated acylphloroglucinols from Hypericum patulum

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¹ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China

² Department of Pharmacy, Wuhan No. 1 Hospital, 215 Zhongshan Road, Wuhan 430022, China

³ Key Laboratory of Organ Transplantation, Ministry of Education; NHC Key Laboratory of Organ Transplantation; Key Laboratory of Organ Transplantation, Chinese Academy of Medical Sciences, Wuhan 430030, China

⁴ Hubei Key Laboratory of Wudang Local Chinese Medicine Research, Hubei Engineering Technology Center for Comprehensive Utilization of Medicinal Plants, College of Pharmacy Hubei University of Medicine, Shiyan 442000, China

^* E-mails: qichangxing@hust.edu.cn (QI Changxing);

zhangyh@mails.tjmu.edu.cn (ZHANG Yonghui)

Dr. QI Changxing is presently a vice professor at the School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, China. Dr. Qi majored in the medicinal chemistry of natural products and innovative drug research. In recent years, QI has isolated and elucidated more than 1500 bioactive natural products and over 826 were undescribed compounds including polycyclic polyprenylated acylphloroglucinols, terpenoids, and polyketides. Among them, 4 compounds with potential for medicinal development were discovered. Remarkably, he has published nearly 60 SCI papers as the first or corresponding author.

Prof. ZHANG Yonghui is currently dean of the School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, China. He focused on the medicinal chemistry of natural products and innovative drug research. To date, his team has isolated and elucidated more than 8000 bioactive natural products and over 4000 were undescribed. In particular, 13 compounds have the potential to develop clinical drugs. Remarkably, kinsenoside has received a Notification of Approval for Clinical Trials of National Class I New Drugs. Furthermore, Prof. ZHANG has published nearly 350 SCI papers as a corresponding author with the total impact factor of the article being 1832.

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Abstract

Hyparillums A (1) and B (2), two previously unidentified polycyclic polyprenylated acylphloroglucinols (PPAPs) with intricate architectures, were isolated from Hypericum patulum Thunb. Hyparillum A was the first PPAP with eight-carbon rings based on an unprecedented 6/6/5/6/6/5/6/4 octocyclic system featuring a rare heptacyclo[10.8.1.1^1,10.0^3,8.0^8,21.0^12,19.0^14,17]docosane core. In contrast, hyparillum B featured a novel heptacyclic architecture (6/6/5/6/6/5/5) based on a hexacyclo[9.6.1.1^1,9.0^3,7.0^7,18.0^11,16]nonadecane motif. Furthermore, hyparillums A and B demonstrated promising inhibitory effects on the proliferation of murine splenocytes stimulated by anti-CD3/anti-CD28 monoclonal antibodies and lipopolysaccharide, exhibiting half-maximal inhibitory concentration (IC₅₀) values ranging from 6.13 ± 0.86 to 12.69 ± 1.31 μmol·L⁻¹.

Keywords

Polycyclic polyprenylated acylphloroglucinols / Hypericum patulum Thunb. / Immunosuppressive activities / Structure elucidation.

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Yulin DUAN, Zhengyi SHI, Fei SONG, Zhangrong HOU, Xiaosheng TAN, Yeting ZHANG, Xincai HAO, Gang CHEN, Changxing QI, Yonghui ZHANG. Hyparillums A and B: polycyclic polyprenylated acylphloroglucinols from Hypericum patulum. Chinese Journal of Natural Medicines, 2024, 22(3): 273-279 DOI:10.1016/S1875-5364(24)60599-6

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