• Biomolecules & Therapeutics
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• v.16 no.3
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• pp.226-230
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• 2008

Monoolein-based cubic liquid crystalline systems were formulated for the local delivery of oregonin and hirsutanonol for the treatment of atopic dermatitis. The liquid crystalline phase and its nanodispersion containing drugs were prepared. The skin permeation and deposition properties of the drugs were examined in normal and delipidized rat skin. The proportion of oregonin (%) deposited in normal skin after topical administration of the drugs in the form of aqueous solution, cubic phase or cubic nanodispersions were $1.53\;{\pm}\;0.46$, $3.62\;{\pm}\;0.17$ and $5.13\;{\pm}\;0.73$, and those of hirsutanonol were $2.46\;{\pm}\;0.02$, $5.44\;{\pm}\;0.27$ and $17.28\;{\pm}\;2.19$, respectively. The greater lipophilicity and thus greater skin affinity of hirsutanonol than oregonin contributed the greater amount of skin deposition. The monoolein-based liquid crystalline phases significantly increased the amount of both drugs permeated and deposited. Approximately 3.2, 2.1 and 3.0 times greater amount of oregonin, and 3.4, 2.1 and 2.2 times greater amount of hirsutanonol were deposited in delipidized skin after administration of each drug in the form of aqueous solution, cubic phase and cubic nanodispersions system, respectively, because of lowered barrier function of the delipidized skin. In this study, the effects of drug property, vehicles type and skin condition on skin deposition and permeation properties of drug were examined and concluded that monoolein-based liquid crystalline systems would be a promising formulation for the local delivery of drugs.

• 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.

• 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.

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

• Archives of Pharmacal Research
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• v.25 no.6
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• pp.885-888
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• 2002

Four diarylheptanoids, (5R)-1,7-bis (3,4-dihydroxyphenyl)-heptane-5-O-$\beta$-D-glucoside (1), (5R)-1,7-bis (3,4-dihydroxyphenyl)-heptane-5-ol (2), oregonin (3), hirsutanonol (4), were isolated from the bark of Alnus hirsuta Turcz and its inhibitory effects on melanogenesis by measuring the melanin level and tyrosinase activity in B16 melanoma cell were examined. Melanin level and tyrosinase activity were reduced to 75 to 85% by addition of diarylheptanoids to incubation medium of the melanoma cell. On the other hand, melanin level and tyrosinase activity were reduced to 13 to 43% by the addition of diarylheptanoids to incubation medium of the melanoma cell treated with melanogenesis stimulator, $\alpha$-MSH and forskolin. These melanogenesis inhibitory effects were significantly different compared with control.

• 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.31 no.1
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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.

• 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.

• Korean Journal of Medicinal Crop Science
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• v.13 no.2
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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.