Structure revision and absolute configuration of 5,7- diepi-2α -hydroxyoplopanone and anti-osteoporotic activities of sesquiterpenoids from the rhizomes of Homalomena pendula .

Autor: Nguyen LTK; Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, Hue City, Vietnam.; Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh City, Ho Chi Minh, Vietnam., Vo HQ; Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, Hue City, Vietnam., Hoang HNT; Faculty of Engineering and Food Technology, Hue University of Agriculture and Forestry, Hue University, Hue City, Vietnam., Tran TVA; Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh City, Ho Chi Minh, Vietnam., Minh Nguyen H; Faculty of Pharmacy, Ton Duc Thang University, Ho Chi Minh City, Vietnam., Pham TV; Faculty of Chemistry, Hue University of Education, Hue University, Hue City, Vietnam., Ngo HPT; Faculty of Biology, Hue University of Education, Hue University, Hue City, Vietnam., Pham T; Faculty of Biology, Hue University of Education, Hue University, Hue City, Vietnam., Ho DV; Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, Hue City, Vietnam.
Jazyk: angličtina
Zdroj: Natural product research [Nat Prod Res] 2024 Jul; Vol. 38 (14), pp. 2453-2462. Date of Electronic Publication: 2023 Feb 20.
DOI: 10.1080/14786419.2023.2180505
Abstrakt: Five sesquiterpenoids including 2 α -hydroxyoplopanone (1) , oplopanone ( 2 ), 1 β ,4 β ,6 α -trihydroxy-eudesmane ( 3 ), 1 β ,4 β ,7 α -trihydroxy-eudesmane ( 4 ) and bullatantriol ( 5 ) were isolated from Homalomena pendula . The structure of the previously reported compound, 5,7- diepi -2 α -hydroxyoplopanone ( 1a ), has been revised to 1 by the spectroscopic evidences (1D-/2D-NMR, IR, UV and HRESIMS) and by comparison between experimental and theoretical NMR data using DP4+ protocol. Furthermore, the absolute configuration of 1 was unambiguously assigned by ECD experiments. Compounds 2 and 4 displayed a potent ability to stimulate osteogenic differentiation of MC3T3-E1 cells at 4 µg/mL (by 123.74% and 131.07%, respectively) and 20 µg/mL (by 112.45% and 126.41%, respectively) whilst 3 and 5 did not show any activities. At 20 µg/mL, 4 and 5 significantly promoted the mineralization of MC3T3-E1 cells with values of 112.95% and 116.37%, respectively, whereas 2 and 3 were inactive. The results indicated that 4 could be an excellent component for anti-osteoporosis studies from the rhizomes of H. pendula .
Databáze: MEDLINE