• Journal of the Korean Wood Science and Technology
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• v.37 no.1
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• pp.73-77
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• 2009

This study was carried out to investigate the valuable antioxidative compound from extracts of Alnus hirsuta Turcz. which has a nationwide distribution. The bark (2 kg) was extracted with 70% aqueous acetone and fractionated, and the ethyl acetate and $H_2O$ fractions, separately, were chromatographed on a Sephadex LH-20 column to purify the mixture and to give two diarylheptanoid compounds. The isolated compounds were analyzed by NMR spectroscopy, including $^1H$, $^{13}C$ and two-dimensional NMR, and identified as oregonin (1) and 1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-${\beta}$-D-xylopyranoside (2). The antioxidative activity was evaluated by DPPH method using two diarylheptanoids and acid-hydrolyzed oregonin derivative which indicated higher activity potential. Of those the acid-hydrolyzed oregonin derivative showed highly active potential with the value of 2.6 of $IC_{50}$.

• Bulletin of the Korean Chemical Society
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• v.26 no.3
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• pp.447-450
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• 2005

The crude methanol extract of the fruits of Amomum tsao-ko (Zingiberaceae) showed cytotoxic activity. Bioactivity-guided separation led to the isolation of a diarylheptanoid, tsaokoarylone [7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hepta-4E,6E-dien-3-one] (2). 2 showed cytotoxicity at 4.9 and 11.4 $\mu$g/mL ($IC_{50}$) against human nonsmall cell lung cancer A549 and human melanoma SK-Mel-2, respectively, determined by SRB colorimetric method. During purification-(4-hydroxyphenyl)-4-hydroxyhexan-2-one (4) together with three known diarylheptanoids was also isolated. Their structures were determined from interpretation of spectroscopic data (IR, UV, MS, and NMR) and synthesis confirmed the structure of 2.

• Korean Journal of Pharmacognosy
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• v.35 no.4 s.139
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• pp.384-387
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• 2004

Genus Alnus are deciduous board-leaved trees or shrubs found in the damp place and mountain and more than 17 species are growing in Korea. The bark of Alnus japonica has been used for the treatment of fever, hemorrhage and diarrehea in oriental traditional medicine. Quantitative analysis of diarylheptanoids which were characteristic components of Alnus species (A. japonica, A. hirsuta, and A. hirsuta var. sibirica), has been conducted by HPLC. The results showed that these plants were rich source of diarylheptanoids and the amount of oregonin and hirsutanonol which were major diarylheptanoids showed seasonal variation.

• Korean Journal of Pharmacognosy
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• v.34 no.2 s.133
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• pp.190-192
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• 2003

Anitioxidative activities againt 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were evaluated for ten diarylheptanoids, $1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-{\beta}-D-glucopyranosyl(1{\rightarrow}3)-{\beta}-D-xylopyranoside(1)$, $1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-{\beta}-D-apiofuranosyl(1{\rightarrow}6)-{\beta}-D-glucopyranoside(2)$, $1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-{\beta}-D-glucopyranoside(3)$, 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane(4), $1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-{\beta}-D-glucopyranoside(5)$, oregonin(6), hirsutanonol(7), hirsutenone(8), $1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-{\beta}-D-xylopyranoside(9)$ and platyphylloside(10), which were isolated from Alnus japonica. Aglycones (4,7 and 8) and mono glycosides (3,6 and 9) showed more strong antioxidative activities than diglycosides (1 and 2) against the DPPH radical. Especially, hirsutenone(8) showed superior activity among ten diarylheptanoid.

• Natural Product Sciences
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• v.23 no.2
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• pp.146-150
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• 2017

Alnus sibirica (AS) geographically distributes in Korea, Japan, Northeast China and Russia. The bark of this plant had been used for antipyretic, expectorant, anti-phlogistic, antitussive, anti-asthmatic and as a health tea for alcoholism. Recently, we studied various biological activities of AS and the isolated diarylheptanoid. In present study, we conducted fermentation of AS (FAS) and isolated two diarylheptanoid (hirsutenone and muricarpone B). Moreover, we established the validation and contents determinations of the two compounds by HPLC on FAS.

• YAKHAK HOEJI
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• v.44 no.2
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• pp.193-196
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• 2000

Four diarylheptanoids oregonin, hirsutanonol, 1,7-bis- (3,4-dihydroxyphenyl)-heptane-5-O-$\beta$-D-xylopyanoside and 1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-0-$\beta$-D-glucopyranoside isolated from Alnus hirsuta were evaluated for their antioxidative effects with 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and lipid peroxidation generation system mediated by addition of $H_2O$$_2$and/or Fe$^{2+}$ to rat liver homogenate. All these diarylheptanoids showed significant inhibitory activities against the DPPH radical and demonstrated strong activities in preventing the lipid peroxidation induced by $H_2O$$_2$.>.

• Korean Journal of Pharmacognosy
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• v.49 no.4
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• pp.336-340
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• 2018

Alnus sibirica Fisch. ex Turcz.(AS) geographically distributes in Korea, Japan, Northeast China and Russia. The bark of Alnus species have been used as traditional medicine for the treatment of allergic skin diseases. The content evaluation of compounds which were isolated from the barks of A. sibirica processed enzymatic hydrolysis(EAS); hirsutanonol(1), 5-O-methylhirsutanonol(2), rubranol(3), hirsutenone(4) and muricarpone B(5) was conducted using HPLC. Consequently, in EAS, the content of glycoside was decreased considerably. But the aglycones(1, 3 and 4) were increased highly and 2, 5 were formed newly.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.226.1-226.1
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• 2003

Pancreatic lipase-inhibitory activity of the rhizome of Alpinia officinarum (AO) and its antihyperlipidemic activity were measured. When water extract of AO was stepwise fractionated with organic solvents, ethylacetate fraction exhibited the most potent inhibition. From it, Diarylheptanoid was isolated as an inhibitor of pancreatic lipase and we investigated its in vitro inhibitory effect of lipase activity and in vivo antihyperlipidemic effect. (omitted)

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.264.2-264.2
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• 2003

The bark of Alnus japonica has been used of fever, hemorrhage and diarrehea in oriental traditional medicine. This research was focused on the anti-inflammatory activities of diarylheptanoid from the bark of A. japonica on RAW 264.7 cell line. Phytochemical examination of the bark of Alnus japonica Steudel had led to the isolation of ten diarylheptanoids. To investigate the anti-inflammatory activities of these compounds, nitric oxide and PGE2 production inhibitory in IFN-${\gamma}$, LPS stimulated RAW 264.7 cell were examined. (omitted)

• Preventive Nutrition and Food Science
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• v.11 no.2
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• pp.171-175
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• 2006

Alnus japonica Steud (Betulaceae) has long been used as a Korean traditional medicine for gastric disorders, hepatitis, and fatty liver. As a part of our study on the identification of secondary metabolites of naturally occurring bioactive compounds, we isolated 1,7-bis(4-hydroxyphenyl)-3,5-heptanediol(1), 5-hydroxy-1,7bis(4-hydroxyphenyl)-3-heptanone(2), 5,3'-dihydroxy-7,4'-dimethoxyflavone(3) and 3,5,7,3',4'-pentahydroxyflavone(4) from the dichloromethane and ethylacetate-soluble fractions of Alnus japonica Steud. These compounds showed significant antioxidant activity in a concentration-dependent manner. The $IC_{50}$ values of compounds 1, 2, 3 and 4 were 30.1, 37.4, 20.2 and 13.7 ${\mu}g/mL$, respectively, through the scavenging capacity of 1,1-diphenyl-2-picrylhydrazyl radical assay.