Five pregnane C21-steroids, including three 5,6-epoxy steroids (1-3) and two 8,14-seco-steroids (4 and 5), were isolated from the acid hydrolysate of Cynanchum bungei roots. Cynbungenins L-O (1-4) are previously undescribed compounds. Compound 3 with a 5a,6a-epoxy group represents the first example found in the Cynanchum plants. Their structures and absolute configurations were elucidated by a variety of spectroscopic analysis and theoretical ECD calculations. All compounds (1-5) were evaluated for their anti-inflammatory activity by inhibiting the lipopolysaccharide (LPS)-induced nitric oxide (NO) released in RAW264.7 cells. The results showed that they all possessed NO inhibitory activity at 50 μM, and compounds 3 and 4 exhibited stronger NO inhibitory activity than indomethacin.
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http://dx.doi.org/10.1002/cbdv.202403412 | DOI Listing |
Chem Biodivers
January 2025
Guangdong Medical University School of Pharmacy, School of Pharmacy, Xincheng Road, 523808, Dongguan, CHINA.
J Agric Food Chem
October 2024
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
-pregnane C steroids exhibit high antiviral activity against the tobacco mosaic virus (TMV). However, the structural modification of -pregnane C steroids and the structure-activity relationship (SAR) of the modified compounds remain unevaluated. Hence, the present study investigated how variations in the original skeletons of natural -pregnane C steroids affect their antiviral activity.
View Article and Find Full Text PDFChem Biodivers
December 2024
The MOE Key Laboratory of Standardization of Chinese Medicines and SATCM Key Laboratory of New Resources and Quality Evaluation of Chinese Medicines, Institute of Chinese Materia Medica (ICMM), Shanghai University of Traditional Chinese Medicine (SHUTCM), Shanghai, 201203, PR China.
Three undescribed pregnane steroids, 12β-O-4-hydroxybenzoyl tenacigenin D (1), 12β-O-4-hydroxybenzoyl tenacigenin A (2), and 11α-nicotinoyl-17β-marsdenin (3), along with two known analogues (4 and 5), were isolated from the roots of Marsdenia tenacissima. Their structures were elucidated using one- and two-dimensional NMR, high-resolution electron ionization-mass spectrometry, single-crystal X-ray diffraction data, and experimental and density-functional-theory-calculated electronic circular dichroism measurements. All isolated compounds were evaluated for their cytotoxic activities against human lung cancer cells (A549), ovarian carcinoma cells (SKOV-3), gastric cancer cells (MGC 803) and breast cancer cells (MCF-7).
View Article and Find Full Text PDFJ Steroid Biochem Mol Biol
April 2024
Graduate School of Fisheries Sciences, Hokkaido University, Minato-cho 3-1-1, Hakodate, Hokkaido 041-8611, Japan. Electronic address:
Although 17α, 20β-dihydroxy-4-pregnen-3-one (DHP) and 17α, 20β, 21-trihydroxy-4-pregnen-3-one (20β-S) have been identified as maturation-inducing steroids (MIS) in several teleosts, to date, no MISs have been identified in sturgeons. As it remains possible that an unidentified steroid is an MIS in sturgeons, this study aimed to identify a sturgeon MIS via comprehensive analyses and maturation-inducing (MI) assay of C21 steroids. In vivo and in vitro comprehensive analyses of C21 steroids revealed that serum DHP concentrations were rapidly elevated in the oocyte maturation phase and the DHP production level was notably high among C21 steroids.
View Article and Find Full Text PDFNat Prod Res
December 2023
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, P.R. China.
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