A polycyclic polyisoprenyl cyclopentanone compound, a preparation method and application thereof

By extracting polycyclic isopentenylcyclopentanone compounds from the berry St. John's wort, the problem of protecting against myocardial cold ischemia injury in heart transplantation was solved, achieving significant cell protection effects, reducing apoptosis rate and ROS generation, and providing a novel cardioprotective agent.

CN121085879BActive Publication Date: 2026-07-03CHANGZHI MEDICAL COLLEGE
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
CHANGZHI MEDICAL COLLEGE
Filing Date
2025-09-01
Publication Date
2026-07-03

AI Technical Summary

Technical Problem

Existing strategies for protecting against myocardial cold ischemia injury in heart transplantation are limited. In particular, when the cold ischemia time exceeds 4 to 6 hours, the incidence of primary graft dysfunction is significantly increased, leading to high early post-transplant mortality. There is a lack of effective new cardioprotective agents.

Method used

Polycyclic isopentenylcyclopentanone compounds were extracted from the berry St. John's wort. Compound (±)-1 was obtained by multi-step chromatographic separation and purification. As a lead compound for the prevention and treatment of myocardial cold ischemia injury, it can be used to prepare cardioprotective drugs.

Benefits of technology

Compound (±)-1 significantly alleviates cold ischemia injury to cardiomyocytes, reduces apoptosis rate, inhibits excessive ROS production, inhibits Ser9 dephosphorylation of GSK3β, and provides protection for cardiomyocytes.

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Abstract

This invention relates to the field of biomedical technology, and more particularly to a polycyclic isopentenylcyclopentanone compound, its preparation method, and its application. The polycyclic isopentenylcyclopentanone compound provided by this invention has the structural formula shown in Formula 1. Using dried fruit of *Hypericum perforatum* as raw material, the extract is obtained through percolation extraction and concentration, and then suspended in water to obtain a suspension. This suspension is then extracted with petroleum ether and concentrated to obtain a crude extract. The crude extract is then separated by normal- and reverse-phase silica gel column chromatography, MCI medium-pressure column chromatography, Sephadex LH-20 gel column chromatography, high-performance liquid chromatography, and chiral column resolution using a Chiral PAK IG to obtain the polycyclic isopentenylcyclopentanone compound. Evaluation of the protective activity of these compounds against cold ischemia-induced AC16 cardiomyocyte injury demonstrates that these compounds can serve as lead compounds for the development of drugs to prevent and treat myocardial cold ischemia injury.
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