Details

Autor(en) / Beteiligte

• Qin, Xu-Jie
• Jin, Ling-Yu
• Yu, Qian
• Liu, Hui
• Khan, Afsar
• Yan, Huan
• Hao, Xiao-Jiang
• An, Lin-Kun
• Liu, Hai-Yang

Titel

Eucalypglobulusals A–J, Formyl-Phloroglucinol–Terpene Meroterpenoids from Eucalyptus globulus Fruits

Ist Teil von

• Journal of natural products (Washington, D.C.), 2018-12, Vol.81 (12), p.2638-2646

Ort / Verlag

United States: American Chemical Society and American Society of Pharmacognosy

Erscheinungsjahr

2018

Quelle

MEDLINE

Beschreibungen/Notizen

• Ten new formyl-phloroglucinol–terpene meroterpenoids, eucalypglobulusals A–J (1–10), and ten known analogues were isolated from Eucalyptus globulus fruits. The structures of 1–10 were determined by spectroscopic analysis, while their absolute configurations were established using calculated and experimental electronic circular dichroism (ECD) spectra. Eucalypglobulusal A was assigned as a new formyl-phloroglucinol–terpene meroterpenoid with a rearranged sesquiterpene skeleton, and an aldol condensation between C-3 and C-5 of the germacrene C moiety was proposed to be a key step in its putative biosynthetic pathway. Eucalypglobulusal F exhibited cytotoxicity against the human acute lymphoblastic cell line (CCRF-CEM) with an IC50 value of 3.3 μM, while eucalypglobulusal A, eucarobustol C, macrocarpal A, macrocarpal B, and macrocarpal D exhibited DNA topoisomerase I (Top1) inhibition. The compounds eucalypglobulusal A and macrocarpal A act as Top1 catalytic inhibitors and delay Top1 poison-mediated DNA double-strand damage.