Two strobane diterpenoids, strobols A (1) and B (2), 15 new pimarane diterpenoids (3-6 and 8-18), and the known compounds kirenol (19), darutigenol (20), and ent-2β,15,16,19-tetrahydroxypimar-8(14)-ene (7) were isolated from the aerial parts of Siegesbeckia pubescens Makino. The structures of the new compounds were established based on the interpretation of HRESIMS and NMR analysis. The configurations of 1, 6, and 17 were confirmed by X-ray crystallographic data. Compounds 3, 5, and 11 inhibited the migration of MB-MDA-231 breast cancer cells induced by the chemokine epithelial growth factor, with IC values of 4.26, 3.45, and 9.70 μM, respectively.
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http://dx.doi.org/10.1021/acs.jnatprod.6b00150 | DOI Listing |
Nat Prod Res
December 2023
Maternal and Child Health Hospital of Hubei Province, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, China.
Two new fungal polyketides with unusual skeleton, collecapsins A and B (-), along with two known macrolactins A and B (-), were isolated from the rice cultures of an endophytic fungus obtained from the fresh Makino. Their structures were established by a combination of NMR, HRESIMS, and IR analysis. The absolute configurations of and were determined on the detailed analysis of the modified Mosher's derivatives' spectra and its key NOEs correlations.
View Article and Find Full Text PDFNat Prod Res
November 2023
Institute of Translational Medicine, School of Medicine, Yangzhou University, Yangzhou, China.
-kaurane diterpenoids were studied as a biologically active ingredient group of (Makino) Makino. Here, five known -kaurane diterpenoids were isolated and identified, named -16,17-dihydroxy-kauran-19-oic acid (, -16,17-dihydroxy-kauran-19-oate (, -18-acetoxy-17-hydroxykauran-19-oic acid (), -16,17,18-trihydroxy-kauran-19 -oic acid (), and -17-hydroxy-kauran-16H-19-oic acid (). Their inhibitory effects of these compounds on MDA-MB-231 breast cancer migration were firstly tested in a chemotaxis invasion assay.
View Article and Find Full Text PDFMolecules
July 2023
Department of Pharmaceutical Engineering, Institute of Agricultural and Life Science (IALS), Anti-Aging Bio Cell Factory Regional Leading Research Center (ABC-RLRC), Gyeongsang National University, Jinju 52725, Republic of Korea.
This study aimed to isolate bacterial neuraminidase (BNA) inhibitory O-methylated quercetin derivatives from the aerial parts of . All the isolated compounds were identified as O-methylated quercetin (-), which were exhibited to be noncompetitive inhibitors against BNA, with IC ranging from 14.0 to 84.
View Article and Find Full Text PDFJ Sep Sci
August 2023
School of Pharmacy, Hangzhou Medical College, Hangzhou, Zhejiang, P. R. China.
Siegesbeckiae Herba, a traditional Chinese medicine, originates from Siegesbeckia orientalis, S. glabrescens, and S. pubescens in the Pharmacopoeia of the People's Republic of China.
View Article and Find Full Text PDFChem Biodivers
March 2023
School of Biological Science and Technology, University of Jinan, Jinan, 250022, P. R. China.
Five new ent-pimarane diterpenes (1-5) and five known analogs (6-10) were isolated from the aerial parts of Siegesbeckia pubescens. Their structures, including absolute configurations, were determined by comprehensive spectroscopic methods especially 1D and 2D NMR and quantum chemical electronic circular dichroism calculations. All the isolated compounds were evaluated for their cytotoxicity against human BT549, A549 and H157 cancer cell lines.
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