2. Academic Validation
  3. Eucalypglobulusals A-J, Formyl-Phloroglucinol-Terpene Meroterpenoids from Eucalyptus globulus Fruits

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

  • J Nat Prod. 2018 Dec 28;81(12):2638-2646. doi: 10.1021/acs.jnatprod.8b00430.
Xu-Jie Qin 1,  Ling-Yu Jin 1 2,  Qian Yu 3,  Hui Liu 1,  Afsar Khan 4,  Huan Yan 1,  Xiao-Jiang Hao 1,  Lin-Kun An 3,  Hai-Yang Liu 1
Affiliations

Affiliations

  • 1 State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , People's Republic of China.
  • 2 School of Traditional Dai-Thai Medicine , West Yunnan University of Applied Sciences , Jinghong 666100 , People's Republic of China.
  • 3 Institute of Medicinal Chemistry and Chemical Biology, School of Pharmaceutical Sciences , Sun Yat-sen University , Guangzhou 510006 , People's Republic of China.
  • 4 Department of Chemistry , COMSATS University Islamabad, Abbottabad Campus , Abbottabad - 22060 , Pakistan.
PMID: 30543429 DOI: 10.1021/acs.jnatprod.8b00430
Abstract

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.

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