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Six new prenylated flavonoid glycosides, including four new furan-flavonoid glycosides wushepimedoside A–D (1 – 4) and two new prenyl flavonoid derivatives wushepimedoside E–F (5 – 6), and one know analog epimedkoreside B (7) were isolated from biotransformation products of the aerial parts of Epimedium wushanense. Their structures were elucidated according to comprehensive analysis of HR-MS and NMR spectroscopic data, and the absolute configurations were assigned using experimental and calculated electronic circular dichroism (ECD) data. The regulatory activity of compounds 1 – 7 on the production of testosterone in primary rat Leydig cells were investigated, and 4 and 5 exhibited testosterone production-promoting activities. Molecular docking analysis suggested that bioactive compounds 4 and 5 showed the stable binding with 3 β -HSD and 4 also had good affinity with Cyp17A1, which suggested that these compounds may regulate testosterone production through stimulating the expression of the above two key proteins. [ABSTRACT FROM AUTHOR]

[Display omitted] • Two new alkaloidal flavonoids were isolated from H. littoralis. • Glycosidic narciclasine derivative was obtained from H. littoralis for the first time. • The chemical composition of H. littoralis was further understand. A chemical study focusing on the N-containing constituents of Hymenocallis littoralis was carried out, leading to the isolation of two new alkaloidal flavonoids (1 – 2) and five known alkaloids (3 - 7). Structures of the isolated compounds were established mainly by spectroscopic techniques, including NMR spectroscopy and mass spectrometry as well as the CD experiment. These compounds were subjected to the in vitro cytotoxicity assays using Hep3B cells, and among them only the known pancratistatine (3) and lycorine (5) could significantly inhibit the Hep3B cell proliferation. [ABSTRACT FROM AUTHOR]

A method coupling ultra-performance liquid chromatography (UPLC) with quadrupole time-of-flight mass spectrometer (Qtof MS) using the electrospray ionization (ESI) source was developed for the identification of the major saponins from Panax notoginseng powder (PNP). Ten different PNP samples were analyzed and evaluated for their quality by similarity evaluation and principle component analysis (PCA). Based on the accurate mass, summarized characteristic fragmentation behaviors, retention times of different types of saponins, related botanical biogenesis, and reported chromatographic behavior of saponins, fifty-one common peaks were effectively separated and identified, including 28 protopanaxadiol saponins and 18 protopanaxatriol saponins. Simultaneously, 15 significant discrepancy compounds were identified from the disqualified PNP samples. The established UPLC/Qtof MS fingerprint method was successfully applied for profiling and identifying the major saponins of PNP, providing a fast quality evaluation tool for distinguishing the authentic PNP and the adulterated products. [ABSTRACT FROM AUTHOR]

Abstract: Twelve flavonoid glycosides were involved in the biotransformation of the glycosyl moieties by Curvularia lunata 3.4381, and the products were analyzed by UPLC/PDA-Q-TOF-MSE. Curvularia lunata displayed hydrolyzing activities on the terminal Rha or Glc units of some flavonoid glycosides. Terminal Rha with a 1→2 linkage of isorhamnetin-3-O-neohesperidoside and typhaneoside could be hydrolyzed by Curvularia lunata, but terminal Rha with a 1→6 linkage of rutin, typhaneoside, and quercetin-3-O-apiosyl-(1→2)-[rhamnosyl-(1→6)]-glucoside could not be hydrolyzed. Curvularia lunata could also hydrolyze the Glc of icariin, floramanoside B, and naringin. This is the first report of the hydrolysis of glycosyl units of flavonoid glycosides by Curvularia lunata. A new way to convert naringin to naringenin was found in this research. [Copyright &y& Elsevier]

Abstract: Aim: To investigate the chemical constituents from the fresh fruits of Momordica charantia L. Methods: Chemical constituents were isolated and purified by chromatography on silica gel and octadecylsilanized (ODS) silica gel, and the structures were determined by spectral data and chemical evidence. Results: A new C30 sterol glycoside, named 25ξ-isopropenylchole-5, (6)-ene-3-O-β-D-glucopyranoside (1), was isolated from the fresh fruits of M. charantia L. Conclusion: Compound 1 is a new C30 sterol glycoside. [Copyright &y& Elsevier]

Abstract: Aim: To study the hydroxylation in glycyrrhetinic acid (GA) by biocatalysis, and evaluate the antibacterial activities of the derivatives. Methods: The hydroxylation was performed via incubating GA with a fungus, Cunninghamella blakesleeana (C. blakesleeana) AS 3.970 at 30 °C for 5 days. Results: GA was converted into two major derivatives and four minor derivatives. The two major derivatives were isolated and elucidated as 3-oxo-7β-hydroxy-glycyrrhetinic acid (GA-1) and 7β-hydroxy-glycyrrhetinic acid (GA-2) based on their spectral data, and other derivatives (GA-3–GA-6) were identified by HR-ESI-MS. The antibacterial activities of substrate and two major derivatives were evaluated on four bacteria strains and one yeast strain. Conclusion: Cunninghamella blakesleeana AS 3.970 has the capability of hydroxylation for GA. The two major derivatives and GA were found to have considerable activities against drug-resistant Enterococcus faecalis. [ABSTRACT FROM AUTHOR]

Abstract: Aim: To study of structural modification in steroidal saponin by biotransformation technology. Methods: Structural modification was carried out of glycosyl residues of dichotomin at C-3 position by Pectinex BE XXL (PBX). Cytotoxicity against HL-60 cells of all products was investigated. Results: The PBX could hydrolyze the glycosyl residues of dichotomin one-by-one to produce nine transformed compounds. The transformed product (mixture) and four secondary spirostanosides among them exhibited cytotoxicity. Compounds P5, P6 and P7 with α-1, 2 end-rhamnosyl residues showed a potential cytotoxic effect on HL-60 cells; P8 with α-1, 4 end-rhamnosyl residue had a weak effect on HL-60 cells. Dichotomin, secondary furostanosides and aglycone were not cytotoxic. Conclusion: PBX has various hydrolyzation to the glycosidic bonds of dichotomin. Nine obtained transformed compounds widen steroidal saponin library. Meanwhile, screening activity affords data for further pharmacological study. [Copyright &y& Elsevier]