• Korean Journal of Food Science and Technology
• /
• v.45 no.4
• /
• pp.508-514
• /
• 2013

2Department of Marine Molecular Biotechnology, College of Life Science, Gangneung-Wonju National University Recently, we reported that diarylheptanoid hirsutenone (HST) effectively inactivated T lymphocytes. However, it has not been evaluated whether HST is involved in calcineurin or calmodulin inactivation. In the present study, cells were treated with T-cell inhibitors with or without HST. Our results revealed that HST successfully inhibited expression of T-helper type I (Th1) and Th2 cytokines. Co-treatment with HST and nuclear factor-activated T cell (NFAT) activation inhibitor III (INCA-6) showed a more sensitive effect than that with other inhibitors, suggesting that HST contributes to inhibition of dephosphorylation of NFAT in the cytosol. HST up-regulated cell cycle arrest genes and inhibited the growth of Staphylococcus aureus. These effects were confirmed in an NFAT electrophoretic-mobility shift assay via successful inhibition of NFAT translocation and in the histological recovery in a 2,4-dinitrochloro benzene-induced in vivo model. Taken together, HST was shown to effectively inhibit T-cell activation via inhibition of cytosolic NFAT dephosphorylation, similar to INCA-6.

• Archives of Pharmacal Research
• /
• v.15 no.3
• /
• pp.211-214
• /
• 1992

Chemical examination of Betula platyphylla var. latifolia afforded a novel diarylheptanoid named betulateraol, together with a phenylpropanoid (3, 4'-dihydroxypropio-phenone), flavan-3-ol [(+)-catechin] and its glycosides [(+)-catechin 5-O-$\beta$-glucopyranoside, (+)-catechin 7-0-$\beta$-D-glucopyranoside] and two proanthocyanidins (procyanidins B-1 and B-3).

• Bulletin of the Korean Chemical Society
• /
• v.25 no.3
• /
• pp.397-399
• /
• 2004

• Korean Journal of Pharmacognosy
• /
• v.39 no.4
• /
• pp.347-351
• /
• 2008

The methanol (MeOH) extract of the rhizome of Alpinia officinarum Hance (Zingiberaceae) demonstrated a potent inhibition on the proliferation of cultured human tumor cell lines such as MES-SA (human uterine carcinoma cell line), MESSA/DX5 (multidrug resistant subline of MES-SA), HCT-15 (human colorectal adenocarcinoma cell line), HCT15/CL02 (multidrug resistant subline of HCT15). The MeOH extract was fractionated into four portions by serial solvent partition, ie., methylene chloride (CH2Cl2) soluble part, ethylacetate (EtOAc) soluble part, n-butanol (BuOH) soluble part and remaining water layer. Among them, the $CH_2Cl_2$ soluble part of the extract exhibited a most potent inhibition on the proliferation of tested tumor cell lines. Bioassay-guided fractionation of the $CH_2Cl_2$ soluble part led to the isolation of five diarylheptanoid and two flavonoid constituents, i. e., galangin (1), 7-(4"-hydroxy-3"-methoxyphenyl)-1-phenylhept-4-en-3-one (2), 1,7-diphenyl-5-hydroxy-3-heptanone (3), trans,trans-1-(3'-methoxy-4'-hydroxyphenyl)-7-phenyl-5-ol-4,6-dien-3-heptanone (4), 5-methoxy-7-(4"-hydroxy-3"-methoxyphenyl)-1-phenyl-3-heptanone (5), kaempferide (6), 5-hydroxy-7-(4"-hydroxy-3"-methoxyphenyl)-1-phenyl-3-heptanone (7). Structures of the isolated active components (1 - 7) were established by chemical and spectroscopic means.

• Archives of Pharmacal Research
• /
• v.23 no.1
• /
• pp.50-53
• /
• 2000

Diarylheptanoids, (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-one (1, hirsutanonol), $(5S)-1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-{\beta}-D-xylopyranoside (2, oregonin)$, $(5R)-1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-{\beta}-D-xylopyranoside (3)$, and $(5R)-1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-{\beta}$-D-glucopyranoisde$ (4) were isolated from the leaves of Alnus hirsuta Trucz. The structures of these compounds were identified based on the spectral and physicochemical data.

• Bulletin of the Korean Chemical Society
• /
• v.26 no.11
• /
• pp.1878-1880
• /
• 2005

• Archives of Pharmacal Research
• /
• v.25 no.4
• /
• pp.457-462
• /
• 2002

Oregonin, a diarylheptanoid derivative from Alnus hirsuta Turcz, Betulaceae, was evaluated for its antitumor activity. Oregonin, known to have an antitumor function, and is a novel immunomodulator, which may augment macrophage activity. MTT assays and NO production tests were performed in order to investigate the cytotoxicity of oregonin in tumor cells and to examine its influence on macrophage in detail. In this study, the tumoricidal activity was also evaluated by a MTT assay. The cytotoxicity measurements in the oregon in-treated group both in vitro and in vivo showed a significant difference from that of the control group. In vivo, oregonin significantly increased NO production in a dose-dependent manner, and in vitro, the thioglycolate-induced inflammatory macrophages increased NO production in a dose-dependent manner after incubation. These results suggest that oregonin reacts with both the inflammatory and non-inflammatory macrophages in a similar way.

• Proceedings of the PSK Conference
• /
• 2002.10a
• /
• pp.379.1-379.1
• /
• 2002

As described previously. we reported twenty two compounds including one naphthoquinone. eight diarylheptanoids, two tetralone. one sesquiterpenoid. one diarylheptanoid glucoside, two tetralone glucosides. one naphthalene carboxylic acid glucoside and six naphthalenyl glycosides were isolated from the roots of Juglans mandshurica (17-22). Here we report that al of these compounds and a known triterpene are tested for the inhibitory effects against DNA topoisomerases I and II activities. (omitted)

• Korean Journal of Pharmacognosy
• /
• v.31 no.1
• /
• pp.28-33
• /
• 2000

Chemical investigation of the stem bark of Alnus hirsuta Turcz var. sibirica (Betulaceae), one of the indigenous Alnus species growing in Korea has led to the isolation of five diarylheptanoids. Structures of these compounds were identified as hirsutenone (1), hirsutanonol (2), oregonin (3), (5S)-1,$7-bis-(3,4-dihydroxyphenyl)-heptan-3-one-5-0-{\beta}-D-glucopyranoside$ (4) and (5R)-1,$7-bis-(3,4-dihydroxyphenyl)-heptane-5-0-{\beta}-D-glucopyranoside$ (5) by the analysis of spectroscopic evidences and comparison with the data of authentic samples.

• Natural Product Sciences
• /
• v.18 no.2
• /
• pp.106-110
• /
• 2012

Diarylheptanoids, (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-one-5-O-${\beta}$-D-xylopyranoside (1, Oregonin), 1,7-bis-(3,4-dihydroxyphenyl)-4-heptene-3-one (2, Hirsutenone), (5S)-7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxyphenyl)-3-heptanone-5-O-${\beta}$-D-xylopyranoside (3, Alnuside A), (5S)-1-(3,4-dihydroxyphenyl)-5-hydroxy-7-(4-hydroxyphenyl)-3-heptanone-5-O-${\beta}$-D-xylopyranoside (4, Alnuside B), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-on-5-O-${\beta}$-D-glucopyranoside (5) and 1,7-bis-(4-hydroxyphenyl)-5-hydroxyheptane-3-on-5-O-${\beta}$-D-glucopyranoside (6, Platyphylloside) were isolated from the bark of Alnus pendula Matsumura. The structures of these compounds were identified based on the spectral and physicochemical data.