Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

• Published in: Phytochemistry (Oxford) Vol. 198; p. 113173
• Main Authors: Shi, Zhengyi, Tan, Xiaosheng, Hu, Hong, Zhang, Na, Duan, Yulin, Guo, Yi, Feng, Hao, Sun, Lingjuan, Chen, Gang, Qi, Changxing, Zhang, Yonghui
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.06.2022; Elsevier
• Subjects: Animals; Biochemistry & Molecular Biology; Chemical calculation; Clusiaceae; Hypericum; Hypericum longistylum; Immunosuppressive activity; Immunosuppressive Agents - pharmacology; Life Sciences & Biomedicine; Mice; Molecular Structure; Monoterpenes - pharmacology; Monoterpenoid polyprenylated acylphloroglucinols; Phloroglucinol - pharmacology; Plant Sciences; Science & Technology; Structural elucidation; Hypericum longistylum; Structural elucidation; Clusiaceae; Chemical calculation; Immunosuppressive activity; Monoterpenoid polyprenylated acylphloroglucinols; A-C; Monoterpenoid polyprenylated; acylphloroglucinols
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2022.113173

Acylphlorostylums A–G (1–7), seven undescribed monoterpenoid polyprenylated acylphloroglucinols, were isolated and identified from Hypericum longistylum. Significantly, acylphlorostylums A and B were the first monoterpenoid polyprenylated acylphloroglucinols possessing a dodecahydro-1H-benzo [b]cyclopenta [e]oxepine moiety bearing a 6/7/5 fused tricyclic ring system that assembled by the attack from 4-OH to C-13. In addition, acylphlorostylums A–G exhibited moderate in vitro immunosuppressive activity in anti-CD3/anti-CD28 monoclonal antibodies, lipopolysaccharide and concanavalin A-induced murine splenocyte proliferation, with IC50 values ranging from 1.51 ± 0.12 to 18.49 ± 1.67 μM, underscoring those isolates as novel chemical templates in the development of novel immunosuppressors. Seven undescribed monoterpenoid polyprenylated acylphloroglucinols with in vitro immunosuppressive activity. [Display omitted] •Seven undescribed monoterpenoid polyprenylated acylphloroglucinols were isolated.•Acylphlorostylums A and B bear a notable 6/7/5 tricyclic ring system.•Acylphlorostylums A–G exhibited in vitro immunosuppressive activity.