Kiiacylphnols A−H, eight undescribed polycyclic polyprenylated acylphloroglucinols with anticancer activities from Hypericum przewalskii Maxim

• Published in: Phytochemistry (Oxford) Vol. 199; p. 113166
• Main Authors: Duan, Yulin, Hu, Ping, Guo, Yi, Bu, Pengfei, Shi, Zhengyi, Cao, Yunfang, Zhang, Yeting, Hu, Hong, Tong, Qingyi, Qi, Changxing, Zhang, Yonghui
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.07.2022; Elsevier
• Subjects: Biochemistry & Molecular Biology; Cytotoxic activity; Hypericaceae; Hypericum przewalskii Maxim; Life Sciences & Biomedicine; Plant Sciences; Polycyclic polyprenylated acylphloroglucinols; Science & Technology; Hypericum przewalskii Maxim; Hypericaceae; Polycyclic polyprenylated acylphloroglucinols; Cytotoxic activity
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2022.113166

Kiiacylphnols A−H, eight previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs), along with two known congeners (hyperforcinol F and oxepahyperforin), were obtained from Hypericum przewalskii Maxim. The structures of these metabolites were confirmed by spectroscopic analyses, quantum-chemical 1H and 13C NMR calculations with DP4+ analyses, electronic circular dichroism (ECD) comparisons and calculations. Kiiacylphnols A and B were the first [3.3.1]-type PPAPs with an unusual octahydrooxireno[2,3-i]chromene scaffold bearing a rare 6/6/6/3 ring system. More significantly, kiiacylphnol A and oxepahyperforin displayed cytotoxicity against acute myeloid leukemia and diffuse large B-cell lymphoma cell lines by inducing cell apoptosis. Eight previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) and two known congeners were isolated from Hypericum przewalskii Maxim., and their cytotoxic activities were evaluated. [Display omitted] •Eight undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) were obtained.•Kiiacylphnols A and B possessed an unusual octahydrooxireno[2,3-i]chromene scaffold.•Kiiacylphnol A and oxepahyperforin displayed cytotoxicity by inducing cell apoptosis.