• 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$.>.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.265.2-265.2
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• 2003

Diarylheptanoids [curcumin (1), demethoxycurcumin (2), bisdemethoxycurcumin (3), bisdimethoxymethylcurcumin (4), and 1,2-dihydrobis(de-O-methyl)curcumin (5)] were isolated from the methanolic extract of Curcuma longa L. and A new cyclic diarylheptanoiid (6) and a known compound 7 were isolated from fruits of Alnus japonica S. Diarylheptanoids (1-3) inhibited farnesyl protein transferase (FTPase) with an IC50 of 29-50 $\mu\textrm{m}$. (omitted)

• 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.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.

• Natural Product Sciences
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• v.24 no.4
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• pp.219-224
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• 2018

During the screening for cytotoxic compounds from plants grown in Korea, Betula platyphylla (BP) showed potent activity against the adenocarcinomic human alveolar basal epithelial A549 cell line. To identify the cytotoxic components from BP, the $CH_2Cl_2$ fraction with the most significant cytotoxic effect was applied to the column chromatographies. Seven compounds were isolated: lupeol (1), betulinic acid (2), (-)-rhododendrol (3), platyphyllenone (4), platyphyllone (5), (-)-centrolobol (6), and oleanolic acid (7). Among them, three diarylheptanoids (4 - 6) exhibited cytotoxicity toward A549 cells. Especially, $50{\mu}M$ of 4 reduced A549 cell viability to $18.93{\pm}0.82%$ compared to control ($100.00{\pm}21.48%$). Lactate dehydrogenase (LDH) leakage and intracellular reactive oxygen species (ROS) production were also induced by $50{\mu}M$ 4. This is the first report on the cytotoxic effect of BP-derived diarylheptanoids 4-6 against A549 cells. The compound 4 may be useful for the development of early hit compounds for non-small cell lung carcinoma, but the consideration about selectivity of 4 is required since 4 also showed the cytotoxicity in the human normal lung epithelial BEAS-2B cell line.

• 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.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.370.4-371
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• 2002

The roots of Juglans mandshurica Maximowicz (Juglandaceae) have been used as a folk medicine for treatment of cancer in Korea. Several naphthoquinones and naphthalenyl glucosides from Juglans species have been reported (1-7). In the course of isolating cytotoxic compounds from the roots of this plant. we have isolated six naphthalene glycosides. four tetralone, one naphthalene carboxylic acid glucoside and nine diarylheptanoids (8-13). (omitted)

• Proceedings of the PSK Conference
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• 2001.10a
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• pp.255.2-255.2
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• 2001

• Archives of Pharmacal Research
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• v.28 no.2
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• pp.177-179
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• 2005

Nine known diarylheptanoids (1-9) isolated from the barks of Alnus japonica were evaluated for their inhibitory activities on nitric oxide (NO) and prostagrandin $E_2$ (COX-2) production in interferon-${\gamma}$ (INF-${\gamma}$) and lipopolysaccharide (LPS)-activated RAW 264.7 cells in vitro. The NO and COX-2 levels were moderately reduced by the addition of compounds (1-9). Among these compounds, compounds 6 and 8 inhibited NO production in a dose dependent manner with an $IC_{50}$ of 16.7 and $27.2\;{\mu}g/mL$, respectively (positive control, L-NMMA; $22.8\;{\mu}g/mL$), and compounds 6, 7, 8, and 9 reduced the COX-2 level in a dose dependent manner with an $IC_{50}$ of 20.7, 25.7, 25.0, and $27.3\;{\mu}g/mL$, respectively (positive control, indomethacin; $26.2\;{\mu}g/mL$). An analysis of the structural activity relationship among these diarylheptanoids suggests that the presence of a keto-enol group in the heptane moiety or a caffeoyl group in the aromatic ring were important for the efficacy on the inhibitory activities of NO and COX-2 production.