Inubritantrimers A-D: Trimerized Sesquiterpenoid [4 + 2] Adducts Featuring a Distinctive Spiro-Polycyclic Scaffold from Inula britannica .

Autor: Guo C; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, No. 3 Taicheng Road, Yangling, Shaanxi, 712100, China., Qi RY; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, No. 3 Taicheng Road, Yangling, Shaanxi, 712100, China., Ren JY; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, No. 3 Taicheng Road, Yangling, Shaanxi, 712100, China., Xu DD; School of Foundational Education, Xizang Agricultural and Animal Husbandry University, No. 100 Yucai West Road, Nyingchi, Xizang, 860000, China., Zhang Q; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, No. 3 Taicheng Road, Yangling, Shaanxi, 712100, China., Gao JM; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, No. 3 Taicheng Road, Yangling, Shaanxi, 712100, China., Tang JJ; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, No. 3 Taicheng Road, Yangling, Shaanxi, 712100, China.; Shenzhen Research Institute, Northwest A&F University, Shenzhen Virtual University Park Building, High-Tech Industrial Park, Shenzhen, Guangdong, 518000, China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Apr 05; Vol. 89 (7), pp. 5029-5037. Date of Electronic Publication: 2024 Mar 26.
DOI: 10.1021/acs.joc.4c00248
Abstrakt: Inubritantrimer A ( 1 ), a trace trimerized sesquiterpenoid [4 + 2] adduct featuring an unusual exo - exo type spiro-polycyclic scaffold, together with three new endo - exo [4 + 2] adducts, inubritantrimers B-D ( 2 - 4 ), were discovered from the flowers of Inula britannica . Their structures were elucidated using 1D/2D NMR, X-ray diffraction, and ECD approaches. 1 is characterized as a novel exo - exo trimer, synthesized biogenetically from three sesquiterpenoid monomers, featuring a unique linkage of C-11/C-1', C-13/C-3' and C-13'/C-3″, C-11'/C-1″ through a two-step exo [4 + 2] cycloaddition process. Compounds 1 - 4 exhibited modest cytotoxicity against breast cancer cells with IC 50 values in the range of 5.84-12.01 μM.
Databáze: MEDLINE