• 생약학회지
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• 제34권2호통권133호
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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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• 제23권2호
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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.

• 생약학회지
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• 제49권4호
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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.

• Journal of Pharmaceutical Investigation
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• 제41권6호
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• pp.331-336
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• 2011

The instability of hirsutenone (HST), a potential therapeutic candidate for the treatment of atopic dermatitis (AD) and ovarian carcinoma, is one of the main concerns for the development of drug product. In the present study, aqueous stability of HST was investigated by kinetic analysis, and the effect of several factors covering temperature, nitrogen gas ($N_2$) flushing, and selection of proper antioxidant was compared. Cosolvent system composed of distilled water and methanol (9:1 v/v) was used as a vehicle to dissolve HST at the concentration of $200{\mu}g/mL$. Samples of aqueous solution were prepared under the absence or presence of antioxidants, such as ascorbic acid (AA), sodium edetate (EDTA), and ascorbyl palmitate (AP), and subjected for stability test. The degradation of HST in aqueous solution was followed by the first order kinetics with an extremely short half life of less than a week at room temperature, and was accelerated as the temperature increased. $N_2$ flushing brought a little enhancement in stability compared to control solution, but the effect was insufficient. The addition of AA and EDTA (0.1%) significantly enhanced the stability of HST at $40^{\circ}C$, but the addition of AP (0.01%) was limited due to its water insolubility and revealed no promising result. The stability of HST was increased proportionally by the amount of AA added, showing the difference in degree of stabilization as an order of magnitude. Finally, we conclude that HST was stabilized by the addition of a suitable antioxidant, suggesting AA as the most effective stabilizer.

• 한국식품과학회지
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• 제45권4호
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• pp.508-514
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• 2013

본 연구에서는 오리나무유래 HST의 T 세포 비활성화 효능을 확인하고 그 기전을 탐색하여 새로운 항아토피 천연소재로의 개발 가능성을 제시하고자 하였다. HST는 T 세포 mitogen으로서 anti-CD3 mAb가 처리 된 마우스 비장에서 Th 사이토카인(IL-2, IFN-${\gamma}$, IL-4, IL-5, IL-10)의 발현을 효과적으로 억제하였으며, T 세포 early activation marker인 CD25 유전자 발현이 INCA-6에서 매우 효과적으로 억제되는 것으로 보아, NFAT inactivator-유사 NFAT 탈인산화 억제 기전을 가지는 것으로 예측되었다. 또한 세포주기조절 단백질인 p21과 p27의 유전자도 HST에 의해 upregulation이 되어 효과적인 T 세포 증식 및 분화를 억제할 것으로 생각되었다. 이러한 세포주기조절 효과는 AD를 악화시키는 세균인 S. aureus 성장억제 실험에서 확인되어 향후 항박테리아 효능을 갖는 우수한 항아토피피부염 천연소재로서 HST의 활용 가치가 높을 것으로 판단된다.

• 생약학회지
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• 제31권1호
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• pp.28-33
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• 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
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• 제18권2호
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• pp.106-110
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• 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.

• 한국약용작물학회지
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• 제13권2호
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• pp.85-90
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• 2005

Phytochemical study on the EtOAc fraction from a MeOH extract of the leaves of Alnus hirsuta Rupr. led to the isolation of nine compounds betulin (1), betulinic acid (2), hirsutanonol (3), hirsutenone (4), quercetin (5), avicularin (6), gallic acid (7), hyperin (8), and daucosterol (9). Among them, six compounds 1, 2, 57, and 9 are report from this plant for the first time. All isolated compounds were evaluated for their antioxidant activity using DPPH radical scavenging capacity and inhibition effect on mitochondrial lipid peroxidation. Six phenolic compounds 3-8 were found to have potent antioxidant activity. Of which, compounds 3, 4 and 5 showed significant free radical scavenging activity with the $IC_{50}$ values of $18.3\;{\pm}\;2.5,\;15.7\;{\pm}\;3.8\;and\;23.5\;{\pm}\;3.1\;{\mu}m$, respectively. In addition, the compounds 3-8 exhibited inhibition effect on the mitochondrial lipid peroxidation with the $IC_{50}$ values of $88.0\;{\pm}\;6.5,\;12.6\;{\pm}\;1.2,\;8.0 \;{\pm}\;1.1,\;58.5\;{\pm}\;4.3,\;173.6\;{\pm}\;15.2,\;and\;75.0\; {\pm}\; 6.7\;{\mu}m$, respectively.