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Koji Kato – One of the best experts on this subject based on the ideXlab platform.

  • Antioxidative compounds isolated from the rhizomes of smaller galanga (Alpinia officinarum Hance)
    BioFactors (Oxford England), 2004
    Co-Authors: Makoto Shimoyamada, Koji Kato, Ryo Yamauchi
    Abstract:

    Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1-7) were obtained and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol gamma-O-methyl ether (1) and (E)-p-coumaryl alcohol (6); and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxy-phenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxy-phenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1-7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bulk phase.

  • Isolation and characterization of some antioxidative compounds from the rhizomes of smaller galanga (Alpinia officinarum Hance).
    Journal of agricultural and food chemistry, 2003
    Co-Authors: Makoto Shimoyamada, Koji Kato, Ryo Yamauchi
    Abstract:

    Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1−7) were finally obtained by reversed-phase HPLC, and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol γ-O-methyl ether (1) and (E)-p-coumaryl alcohol (6), and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxyphenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1−7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bu…

  • Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance).
    Journal of agricultural and food chemistry, 2002
    Co-Authors: Ryo Yamauchi, Makoto Shimoyamada, Koji Kato
    Abstract:

    Glycosidically bound compounds were isolated from the methanol extract of fresh rhizomes of smaller galanga (Alpinia officinarum Hance). Nine glycosides (1-9) were finally obtained by reversed-phase HPLC and their structures were elucidated by MS and NMR analyses. They were the three known glycosides, (1R,3S,4S)-trans-3-hydroxy-1,8-cineole beta-D-glucopyranoside (1), benzyl beta-D-glucopyranoside (3), and 1-O-beta-D-glucopyranosyl-4-allylbenzene (chavicol beta-D-glucopyranoside, 4); and the six novel glycosides, 3-methyl-but-2-en-1-yl beta-D-glucopyranoside (2), 1-hydroxy-2-O-beta-D-glucopyranosyl-4-allylbenzene (5), 1-O-beta-D-glucopyranosyl-2-hydroxy-4-allylbenzene (demethyleugenol beta-D-glucopyranoside, 6), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-2-hydroxy-4-allylbenzene (demethyleugenol beta-rutinoside, 7), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-4-allylbenzene (chavicol beta-rutinoside, 8), and 1,2-di-O-beta-D-glucopyranosyl-4-allylbenzene (9). Compounds 2-9 were detected for the first time as constituents of galanga rhizomes.

Ryo Yamauchi – One of the best experts on this subject based on the ideXlab platform.

  • Antioxidative compounds isolated from the rhizomes of smaller galanga (Alpinia officinarum Hance)
    BioFactors (Oxford England), 2004
    Co-Authors: Makoto Shimoyamada, Koji Kato, Ryo Yamauchi
    Abstract:

    Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1-7) were obtained and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol gamma-O-methyl ether (1) and (E)-p-coumaryl alcohol (6); and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxy-phenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxy-phenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1-7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bulk phase.

  • Isolation and characterization of some antioxidative compounds from the rhizomes of smaller galanga (Alpinia officinarum Hance).
    Journal of agricultural and food chemistry, 2003
    Co-Authors: Makoto Shimoyamada, Koji Kato, Ryo Yamauchi
    Abstract:

    Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1−7) were finally obtained by reversed-phase HPLC, and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol γ-O-methyl ether (1) and (E)-p-coumaryl alcohol (6), and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxyphenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1−7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bu…

  • Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance).
    Journal of agricultural and food chemistry, 2002
    Co-Authors: Ryo Yamauchi, Makoto Shimoyamada, Koji Kato
    Abstract:

    Glycosidically bound compounds were isolated from the methanol extract of fresh rhizomes of smaller galanga (Alpinia officinarum Hance). Nine glycosides (1-9) were finally obtained by reversed-phase HPLC and their structures were elucidated by MS and NMR analyses. They were the three known glycosides, (1R,3S,4S)-trans-3-hydroxy-1,8-cineole beta-D-glucopyranoside (1), benzyl beta-D-glucopyranoside (3), and 1-O-beta-D-glucopyranosyl-4-allylbenzene (chavicol beta-D-glucopyranoside, 4); and the six novel glycosides, 3-methyl-but-2-en-1-yl beta-D-glucopyranoside (2), 1-hydroxy-2-O-beta-D-glucopyranosyl-4-allylbenzene (5), 1-O-beta-D-glucopyranosyl-2-hydroxy-4-allylbenzene (demethyleugenol beta-D-glucopyranoside, 6), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-2-hydroxy-4-allylbenzene (demethyleugenol beta-rutinoside, 7), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-4-allylbenzene (chavicol beta-rutinoside, 8), and 1,2-di-O-beta-D-glucopyranosyl-4-allylbenzene (9). Compounds 2-9 were detected for the first time as constituents of galanga rhizomes.

Makoto Shimoyamada – One of the best experts on this subject based on the ideXlab platform.

  • Antioxidative compounds isolated from the rhizomes of smaller galanga (Alpinia officinarum Hance)
    BioFactors (Oxford England), 2004
    Co-Authors: Makoto Shimoyamada, Koji Kato, Ryo Yamauchi
    Abstract:

    Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1-7) were obtained and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol gamma-O-methyl ether (1) and (E)-p-coumaryl alcohol (6); and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxy-phenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxy-phenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1-7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bulk phase.

  • Isolation and characterization of some antioxidative compounds from the rhizomes of smaller galanga (Alpinia officinarum Hance).
    Journal of agricultural and food chemistry, 2003
    Co-Authors: Makoto Shimoyamada, Koji Kato, Ryo Yamauchi
    Abstract:

    Antioxidative compounds were isolated from the methanol extract of fresh rhizome of smaller galanga (Alpinia officinarum Hance). Seven phenylpropanoids (1−7) were finally obtained by reversed-phase HPLC, and their structures were elucidated by MS and NMR analyses. They comprised the two known compounds, (E)-p-coumaryl alcohol γ-O-methyl ether (1) and (E)-p-coumaryl alcohol (6), and the five novel compounds, stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-methoxy-2-(methoxymethyl)-4-pentene (2a and 2b), stereoisomers of (4E)-1,5-bis(4-hydroxyphenyl)-1-ethoxy-2-(methoxymethyl)-4-pentene (3a and 3b), (4E)-1,5-bis(4-hydroxyphenyl)-1-[(2E)-3-(4-acetoxyphenyl)-2-propenoxy]-2-(methoxymethyl)-4-pentene (4), (4E)-1,5-bis(4-hydroxyphenyl)-2-(methoxymethyl)-4-penten-1-ol (5), and (4E)-1,5-bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (7). Compounds 1−7 were detected for the first time as constituents of galanga rhizomes and exhibited antioxidative activities against the autoxidation of methyl linoleate in bu…

  • Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance).
    Journal of agricultural and food chemistry, 2002
    Co-Authors: Ryo Yamauchi, Makoto Shimoyamada, Koji Kato
    Abstract:

    Glycosidically bound compounds were isolated from the methanol extract of fresh rhizomes of smaller galanga (Alpinia officinarum Hance). Nine glycosides (1-9) were finally obtained by reversed-phase HPLC and their structures were elucidated by MS and NMR analyses. They were the three known glycosides, (1R,3S,4S)-trans-3-hydroxy-1,8-cineole beta-D-glucopyranoside (1), benzyl beta-D-glucopyranoside (3), and 1-O-beta-D-glucopyranosyl-4-allylbenzene (chavicol beta-D-glucopyranoside, 4); and the six novel glycosides, 3-methyl-but-2-en-1-yl beta-D-glucopyranoside (2), 1-hydroxy-2-O-beta-D-glucopyranosyl-4-allylbenzene (5), 1-O-beta-D-glucopyranosyl-2-hydroxy-4-allylbenzene (demethyleugenol beta-D-glucopyranoside, 6), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-2-hydroxy-4-allylbenzene (demethyleugenol beta-rutinoside, 7), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-4-allylbenzene (chavicol beta-rutinoside, 8), and 1,2-di-O-beta-D-glucopyranosyl-4-allylbenzene (9). Compounds 2-9 were detected for the first time as constituents of galanga rhizomes.

Ying Wang – One of the best experts on this subject based on the ideXlab platform.

  • Dimeric Diarylheptanoids with Neuroprotective Activities from Rhizomes of Alpinia officinarum.
    ACS omega, 2020
    Co-Authors: Hui Liu, Xiao-jun Huang, Xiaojun Wang, Qiaoyun Shi, Qinghua Zhang, Qing-wen Zhang, Ying Wang
    Abstract:

    Two novel dimeric diarylheptanoids, alpinidinoids A [(±)-1] and B (2), with two unusual coupling patterns, together with a new naturally occurring diarylheptanoid dimer possessing a rare pyridine ring linkage (alpinidinoid C, 3), were isolated from the rhizomes of Alpinia officinarum. Their structures including absolute configurations were determined by extensive spectroscopic methods and theoretical calculations. All isolates were examined for their neuroprotective activities against oxygen-glucose deprivation and reoxygenation (OGD/R) damage in primary cortical neurons. Remarkably, the dextrorotatory enantiomer of alpinidinoid A [(+)-1] significantly ameliorated OGD/R-induced neuronal apoptosis, which was dependent on the activation of the AKT/mTOR signaling pathway.

  • PHMH, a diarylheptanoid from Alpinia officinarum attenuates VEGF-induced angiogenesis via inhibition of the VEGFR-2 signaling pathway
    Food & function, 2019
    Co-Authors: Weihuan Huang, Ying Wang, Yong Ding, Min Liu, Mei Wang, Wei Zhang
    Abstract:

    The rhizome of Alpinia officinarum Hance, a popular spice used as a condiment in China and Europe, has various reported bioactivities, including anticancer, anti-inflammatory and antioxidant effects. However, its anti-angiogenic activity has not previously been reported. In this study, a diarylheptanoid was isolated from Alpinia officinarum and identified as 1-phenyl-7-(4-hydroxy-3-methoxyphenyl)-4E-en-3-heptanone (PHMH). We demonstrated that PHMH exerts anti-angiogenic activity both in vitro and in vivo. PHMH inhibited vascular endothelial growth factor (VEGF)-induced viability, migration, invasion and tube formation in human umbilical vein endothelial cells (HUVECs) in vitro, and also suppressed VEGF-induced sprout formation of rat aorta ex vivo. Furthermore, PHMH was found to block VEGF-induced vessel formation in mice and suppress angiogenesis in both zebrafish and chorioallantoic membrane models. Mechanistic studies indicated that PHMH inhibited VEGF-induced VEGF receptor-2 (VEGFR-2) auto-phosphorylation and resulted in the blockage of VEGFR-2-mediated signaling cascades in HUVECs, including the Akt/mTOR, ERK1/2, and FAK pathways. Our findings provide new insights into the potential application of PHMH as a therapeutic agent for anti-angiogenesis.

  • Evaluation of Diarylheptanoid-Terpene Adduct Enantiomers from Alpinia officinarum for Neuroprotective Activities.
    Journal of natural products, 2018
    Co-Authors: Hui Liu, Xiao-jun Huang, Yinghui Peng, Xiaojie Huang, Lei Shi, Ying Wang
    Abstract:

    Two pairs of new diarylheptanoid-monoterpene adduct enantiomers, (±)-alpininoids A and B [(±)-1 and (±)-2], as well as three pairs of new diarylheptanoid-sesquiterpene adduct enantiomers, (±)-alpininoids C-E [(±)-3-(±)-5], together with four known diarylheptanoids (6-9) were isolated from the rhizomes of Alpinia officinarum. Their structures with absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses and computational calculation methods. The skeletons of these cyclohexene-containing hybrid natural products were hypothesized to be generated via a crucial Diels-Alder cyclcycloaddition between the diarylheptanoids (7 and 8) and terpenes, of which 1 represents a new carbon skeleton. All isolated compounds were evaluated for their neuroprotective effects against MPP+ (1-methyl-4-phenylpyridinium)-induced cortical neurneuron injury. At a concentration of 16 μM, (+)-1 significantly increased cell viability when compared with MPP+ treatment alone.

Yong Wang – One of the best experts on this subject based on the ideXlab platform.

  • Protective effects of total flavonoids from Alpinia officinarum rhizoma against ethanol-induced gastric ulcer in vivo and in vitro
    Pharmaceutical biology, 2020
    Co-Authors: Kaiwen Lin, Yong Wang, Yinfeng Tan, Jingwen Gong, Tang Deng, Na Wei
    Abstract:

    Alpinia officinarum Hance (Zingiberaceae) is traditionally used to treat inflammation, pain, colds and digestive diseases. To investigate the potential protective mechanism of total flavonoids from…

  • A new diarylheptanoid from Alpinia officinarum promotes the differentiation of 3T3-L1 preadipocytes.
    Natural product research, 2017
    Co-Authors: Zhang Xuguang, Yong Wang, Xiaopo Zhang, Feng Chen, Li Yonghui, Yinfeng Tan, Jingwen Gong, Xia Zhong
    Abstract:

    A new diarylheptanoid, namely trans-(4R,5S)-epoxy-1,7-diphenyl-3-heptanone (1), and a new natural product, 7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-hepta-4E,6E-dien-3-one (2), were obtained from the aqueous extract of Alpinia officinarum Hance, together with three other diarylheptanoids, 5-hydroxy-1,7-diphenyl-3-heptanone (3), 1,7-diphenyl-4E-en-3-heptanone (4) and 5-methoxy-1,7-diphenyl-3-heptanone (5). The structures were characterised mainly by analysing their physical data including IR, NMR and HRMS. This study highlights that the 4,5-epoxy moiety in 1 is rarely seen in diarylheptanoids. In addition, the five isolates were tested for their differentiation activity of 3T3-L1 preadipocytes. The results showed that these compounds could dose-dependently promote adipocyte differentiation without cytotoxicity (IC50 > 100 μM).

  • A novel diarylheptanoid-bearing sesquiterpene moiety from the rhizomes of Alpinia officinarum
    Natural Product Research, 2016
    Co-Authors: Zhonglin Zhou, Yong Wang, Jun Jiang, Junqing Zhang, Lixiang Wu, Youbin Li
    Abstract:

    AbstractA new diarylheptanoid analogue-bearing sesquiterpene moiety, named Alpinisin A, was isolated from the rhizomes of Alpinia officinarum Hance. The new structure was determined by various spectroscopic techniques 1H-nuclear magnetic resonance (1H NMR), 13C-attached proton test (13C-APT), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), 1H-1H correlation spectroscopy (1H–1HCOSY), nuclear overhauser effect spectroscopy (NOESY) and high resolution electrospray ioniionization mass spectrometry (HR–ESI–MS). The compound was tested for cytotoxic activity in vitro against human tumour cell lines (gastric carcinoma cell -7901 (SGC-7901), Michigan Cancer Foundation-7 (MCF-7) and Caski), which showed significant inhibitory effects with IC50 levels of 11.42, 15.14 and 14.78 μM, respectively. The novel chemical structure characterised with a diarylheptanoid linked to a chain-like sesquiterpenoid should be highlighted.