Zheng Xiang

A pair of new isocoumarin epimers from soil fungus Hypoxylon sp.

Abstract In our research on novel secondary metabolites from micro-organisms, two new (1–2) and four known dihydroisocoumarins (3–6) were derived from soil fungus Hypoxylon sp. Their structures were determined with extensive NMR data analysis and ECD calculation comparing with those of experimental CD spectra. Interestingly, compounds 1 and 2 possessed the same planar structure and very similar NMR data, suggesting 1 and 2 were a pair of epimers at either C-3 or at C-4, confirmed by the totally opposite cotton effect around 250 nm in the CD spectra of 1 and 2. Moreover, for the first time, we revealed that the CD absorption peak at 250 nm was dominated by C-3 orientation, rather than the orientation of C-3 substituents, by intensive ECD investigations.

New flavonoid from Patrinia villosa

Abstract Context: Patrinia villosa (Thunb.) Juss (Valerianaceae) is an important ancient herbal medicine widely used for inflammation, wound healing, and abdominal pain. But little is known of the phytochemical constituents of this herbal plant. Objective: The objective of this study is to isolate and identify the bioactive components from P. villosa. Materials and methods: A 70% EtOH extract of P. villosa was subjected to normal-phase silica, ODS silica gel column chromatography, and semi-preparative HPLC chromatography after partitioned successively with light petroleum, dichloromethane and n-BuOH. Chemical structures of the compounds were elucidated by spectroscopic methods including UV, 1D-NMR, 2D-NMR, HR-ESI-MS, and CD spectra. The cytotoxic activity of the new component was determined with the SMMC-7721 cell line using the MTT method after incubation for 48 h. Results: A new flavonoid named patriniaflavanone A (1) along with four known compounds was isolated from P. villosa. The four known compounds were identified as luteolin 7-O-glucuronide-6″-methyl ester (2), p-hydroxyphenylacetic acid methyl ester (3), trans-caffeic acid (4), and trans-caffeic acid methylate (5) by comparison of their spectral data with the reported data. The IC50 value of patriniaflavanone A (1) on SMMC-7721 was 61.27 μM. Discussion and conclusion: This is the first report on the isolation and identification of patriniaflavanone A (1), and compounds 2–5 were isolated for the first time from the title plant. Patriniaflavanone A (1) exhibited moderate cytotoxic activity.

Study of the estrogenic-like mechanism of glycosides of cistanche using metabolomics

Cistanche deserticola, known as Rou Cong-Rong in China, has been used as a tonic for more than 1800 years, with previous studies demonstrating that glycosides of cistanche (GCs) are a main active component. In this study, a uterotrophic assay and histological analysis were utilized to confirm the estrogenic activity of GCs, and UPLC-MS/MS-based metabolomics was used to explore the estrogenic-like mechanism of GCs in serum and urine. Seven altered differential metabolites, including citric acid, taurine, proline, betaine, ornithine, pyroglutamic acid, and α-ketoglutaric acid, were of particular interest due to being present in both serum and urine. Moreover, the differential metabolites were categorized into several major pathways, including the citrate cycle (TCA cycle), glutathione metabolism, arginine and proline metabolism, D-glutamine and D-glutamate metabolism, phenylalanine, tyrosine, and tryptophan biosynthesis, and phenylalanine metabolism. The estrogenic-like mechanism of GCs could be concluded as closely related to the TCA cycle and glutathione metabolism due to these pathways being present in both serum and urine. Our results shed light on the estrogenic-like mechanism of GCs, which will be helpful for GC development and utilization.

Identification of Estrogenic Constituents in Serum after Oral Administration of Tu-Si-Zi Extract Using HPLC–ESI/Q–TOF MS/MS

To identify the estrogenic constituents in Tu-Si-Zi extracts. Estrogen activity of Tu-Si-Zi extracts was assayed by the method of uterotrophic assay and MTT. Chemical ingredients in the serum were confirmed by HPLC/MS-Q-TOF. Ethanol (95%, v/v) extract of Tu-Si-Zi could significantly increase the uterine coefficient of minor mice and the proliferation of MCF-7 cell lines at the dosage of 24 g · kg−1 · d−1(p < 0.05). Nine constituents in the serum, including five prototype ingredients (kaempferol-3-O-coffeeacyl glucoside, apigenin, hyperin, quercetin, and Kaempferol) and four metabolic ingredients (Shikimic acid, Chlorogenic acid Metabolite I, Isorhamnetin glucuronide, and 4-caffeoyl-5-coumaroyl quinic acid Metabolite I) were identified or tentatively characterized based on their MS data, respectively. It is for the first time to identify the estrogenic constituents in Tu-Si-Zi by HPLC/MS. And this finding could be valuable for the further research of Tu-Si-Zi.

The Cyclodipeptides Compounds from Pinellia Ternate (Thunb.) Breit

Chemical investigation on Pinellia ternate (Thunb.) Breit led to the isolation and identification of 12 cyclodipeptides alkaloids. Compounds 1-3, 7 and 10-12 were isolated from P. ternate for the first time. Compounds 4-6 and 8-9 were isolated from the family Araceae for the first time. The presences of cyclodipeptides alkaloids might be employed as the common characteristic constituents of the genus Panax (Araliaceae), Portulaca (Portulacaceae) and Pinellia (Araceae). The found of compounds 1-3, 8 and 11 indicated a close relationship between the both Araceae and Caryophyllaceae families.