Citation: Jiwu Huang, Chuangjun Li, Jie Ma, Yingda Zang, Xingyan Sun, Xiaoguang Chen, Dongming Zhang. Psiguamers A–C, three cytotoxic meroterpenoids bearing a methylated benzoylphloroglucinol framework from Psidium guajava and total synthesis of 1 and 2[J]. Chinese Chemical Letters, ;2021, 32(5): 1721-1725. doi: 10.1016/j.cclet.2020.11.028 shu

Psiguamers A–C, three cytotoxic meroterpenoids bearing a methylated benzoylphloroglucinol framework from Psidium guajava and total synthesis of 1 and 2

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

zhangdm@imm.ac.cn

Received Date: 27 August 2020
Revised Date: 27 September 2020
Accepted Date: 12 November 2020
Available Online: 22 November 2020

Figures(4)

Three sesquiterpene-based meroterpenoids psiguamers A–C (1–3) with new skeletons were isolated from Psidium guajava leaves. Compounds (±)-1 and (±)-2 were two pairs of humulene-derived meroterpenoids bearing a rare methylated benzoylphloroglucinol unit, while 3 was an unprecedented adduct of bicyclogermacrene and methylated benzoylphloroglucinol. Their structures were determined based on comprehensive analyses of spectroscopic data, calculated electronic circular dichroism (ECD) spectra, total synthesis, and X-ray crystallographic data. The biomimetic synthesis of (±)-1 and (±)-2 was achieved. Compound (+)-1 exhibited cytotoxic activities against five human tumor cell lines (HCT-116, HepG2, BGC-823, A549, and U251), with IC₅₀ values of 2.94, 9.01, 6.45, 5.42, and 5.33 μmol/L, respectively.
- Psidium guajava,
- Methylated benzoylphloroglucinol,
- Meroterpenoids,
- Biomimetic synthesis,
- Cytotoxic activities
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