Twelve new diterpenoids, isoresbins A-L (1-12), together with twenty-eight known ones, were isolated from the aerial parts of Isodon oresbius. Their diverse structures included 6,7-seco-ent-kaurane, 7,20-epoxy-ent-kaurane, 6,7:8,15-diseco-ent-kaurane, and abietanes skeletons, which were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction, and quantum chemical calculation. Isoresbins A (1) and B (2) possessed a new rearranged 15(8 → 11)-abeo-6,7-seco-ent-kaurane skeleton. 1 and 5 promoted lysosomal function, which was evaluated by LysoTracker Red staining and DQ-ovalbumin dequenching assay. 1 showed cytotoxicity against six human tumor cell lines with IC values in 2.07-4.04 μM range. Moreover, 1 induced damage of mitochondrial membrane potential, G2/M cell cycle arrest and apoptosis in SW480 cells.
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Structurally diverse diterpenoids from Isodon oresbius and their bioactivity.
Bioorg Chem
July 2022
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, Yunnan, China. Electronic address:
Twelve new diterpenoids, isoresbins A-L (1-12), together with twenty-eight known ones, were isolated from the aerial parts of Isodon oresbius. Their diverse structures included 6,7-seco-ent-kaurane, 7,20-epoxy-ent-kaurane, 6,7:8,15-diseco-ent-kaurane, and abietanes skeletons, which were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction, and quantum chemical calculation. Isoresbins A (1) and B (2) possessed a new rearranged 15(8 → 11)-abeo-6,7-seco-ent-kaurane skeleton.
View Article and Find Full Text PDFA New Rosmarinic Acid Derivative from Isodon oresbius.
Planta Med
February 1999
Department of Biological Science & Technology, Nanjing University, Nanjing, P.R. China (Present address: Institute of Organic Chemistry, Academia Sinica, Shanghai, China).
Phytochemical reinvestigation of ISODON ORESBIUS afforded, in addition to oleanolic acid, ursolic acid, sodoponin, astragalin, and quercetin-3- O-glucoside, three known (oresbiusin A, rosmarinic acid and methyl rosmarinate) and a new rosmarinic acid derivative as well as an ENT-kaurene diterpenoid, neo-angustifolin, characterized as a separated component for the first time. By a combination of 1D- and 2D-NMR techniques the structure of the new compound was established as butyl rosmarinate. The IN VITRO antifungal assay showed that neoangustifolin was active against CANDIDA ALBICANS with the MIC being 50 microg/ml.
View Article and Find Full Text PDFent-Kaurene diterpenoids from Isodon oresbius.
Phytochemistry
April 2004
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, PR China.
Three new ent-kaurene diterpenoids, oreskaurins A-C (1-3), together with ten known ent-kaurene diterpenoids, enmenin monoacetate (4), effusanin E (5), adenolin B (6), maoecrystal G (7), enmelol (8), trichokaurin (9), sodoponin (10), trichorabdal A (11), nodosin (12), enmein (13), and a flavonoid, vitexin (14), were isolated from Isodon oresbius. Their structures were determined by spectroscopic means. Compound 12 showed inhibitory activity toward K562 cells with IC(50)=1.
View Article and Find Full Text PDF[Chemical constituents in the stem and leaf of Isodon oresbius].
Zhongguo Zhong Yao Za Zhi
January 1998
Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009. Kunming Institute of Botany, Academia Sinica, Kunming 650204.
Five triterpenoids were isolated from Isodon oresbius. Their structures were identified as ursolic acid, 2 alpha, 19 alpha-dihydroxy ursolic acid, 2 alpha, 3 alpha, 19 alpha-trihydroxy-12-ursen-28-oic acid, 2 alpha-hydroxy oleanolic acid and 2 alpha, 23-dihydroxy oleanolic acid by physico-chemical constants and spectral analysis.
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