Five new compounds from Zingiberis Rhizoma Recens and their anti-apoptotic activity.

Five new compounds, named gingerol A (1a and 1b), gingerol B (2), diphenylheptane glycoside A (3) and diphenylheptane glycoside B (4), were isolated from the acetone extract of Zingiberis Rhizoma Recens. The structures of new compounds were elucidated on the basis of spectroscopic methods including UV, IR, 1D NMR, 2D NMR and HR-ESI-MS. Compounds 2-4 could significantly decrease the apoptosis rate and increase the survival rate of human normal lung epithelial cells (BEAS-2B) at the concentration of 10 µM.

Seven diterpenoids from the resin of Pinus yunnanensis Franch and their anti-inflammatory activity.

Phytochemical investigation of the 95% ethanol extract from Pinus yunnanensis Franch resin induced the isolation of six previously unreported diterpenoids pinuyunnanacids K - N, P - Q, a nor-diterpenoid with a novel skeleton pinuyunnanacid O and six known analogues. Their structures were elucidated by spectroscopic analysis and computational methods, including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, calculated NMR chemical shifts method and electronic circular dichroic (ECD) spectra. All the compounds were analyzed for anti-inflammatory activity through western blotting and cell viability, compounds 2, 10 and 12 significantly downregulated the protein expression of iNOS at the concentration of 40 µM. At the same time, compounds 10 and 12 decreased the expression of COX-2 in LPS-treated RAW264.7 (leukemia cells in mouse macrophage) cells at the concentration of 40 µM.

Diarylheptanoid glycosides from Zingiber officinale peel and their anti-apoptotic activity.

Four new diarylheptanoid glycosides (1-4), (1S,3R,5S)-2-(4-hydroxy-3- methoxyphenyl)-6-[2-(4-hydroxyphenyl)ethyl]-tetrahydropyran-4-ol-4'-O-ß-D-glucopyranoside (1), (1S,3R,5S)-2-(4,5-dihydroxy-3-methoxyphenyl)-6-[2-(4-hydroxyphenyl) ethyl]-tetrahydropyran-4-ol-4'-O-ß-D-glucopyranoside (2), (1S,3R,5S)-2-(4-hydroxy- 3,5-dimethoxyphenyl)-6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-tetrahydropyran-4-ol-4'-O-ß-D-glucopyranoside (3), and (1R,3R,5R)-2-(4-hydroxy-3,5-dimethoxyphenyl)- 6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-tetrahydropyran-4-ol-3-O-ß-D-glucopyranoside (4) were isolated from the 50% ethanol extract of Zingiber officinale peel. The structures of the isolated compounds were determined by HR-ESI-MS and extensive spectroscopic techniques (UV, IR, 1D-NMR, and 2D-NMR). Compounds 1-4 significantly increased the survival rate of human normal lung bronchial epithelial cells (BEAS-2B) induced by lipopolysaccharide (LPS) at the concentration of 10 µM.

[A new monoterpene ester from Zingiberis Rhizoma Recens].

Five monoterpenoid compounds(1-5) were isolated and purified from the acetone fraction of the aqueous extract of Zingiberis Rhizoma Recens by MCI, Sephadex LH-20, silica gel, semi-preparative HPLC, and TLC. Their structures were identified with multiple spectroscopical methods including 1 D-NMR, 2 D-NMR, and MS. The five compounds were identified as(2E,6Z)-8-hydroxy-2,6-dimethylocta-2,6-dien-1-yl-(E)-3-(4-hydroxy-3-methoxyphenyl) acrylate(1),(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-die-noic acid(2),(E)-1,8-dihydroxy-3,7-dimethyl-2-octenoic acid(3), linalyl-ß-D-glucopyranoside(4), and ß-D-glucopyranoside-(2E)-3,7-dimethyl-2,6-octadien-1-yl(5), respectively.Compound 1 was a new monoterpene ester, and compounds 4-5 were isolated from this plant for the first time.

Qualitative analysis on chemical constituents from different polarity extracted fractions of the pulp and peel of ginger rhizomes by ultra-high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry.

RATIONALE: Ginger pulp is the dried rhizome scraped off the skin which originates from Zingiber officinale Rosc., a Zingiberaceae plant. Ginger peel is the dried rhizome skin of Zingiber officinale Rosc. (Zingiberaceae). The present work aims to investigate the different chemical constituents that are related to the medicinal properties of the ginger pulp and ginger peel. METHODS: A rapid ultra-high-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC/ESI-QTOF/MS) method was developed for qualitative analysis of the constituents in different polarity extracted fractions of the pulp and peel of ginger rhizomes. RESULTS: A total of 83 compounds were identified from the pulp and peel of ginger rhizomes, including 36 diarylheptanoids, 25 gingerols and 22 other compounds. Nine of these were new compounds. In total, 46, 27, 65 and 51 compounds were identified from the crude extract, petroleum ether, ethyl acetate, and n-butanol fractions of the ginger pulp, respectively, and 60, 30, 70 and 62 compounds were identified from the crude extract, petroleum ether, ethyl acetate, n-butanol fractions of the ginger peel, respectively. Each identified compound is marked on the corresponding chromatogram. CONCLUSIONS: The integrated method is sensitive and reliable for searching the different chemical constituents from different polarity extracted fractions of the ginger pulp and ginger peel. This work may provide a significant contribution to research into the medicinal properties of the ginger pulp and ginger peel.