• Journal of the Korean Wood Science and Technology
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• v.37 no.1
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• pp.78-86
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• 2009

In this study 2 cadalene homologues - 3,7-dimethoxycadalene and 7-hydroxycadalene-5,8-quinone (keyakinone A)-were further identified from ethanol extracts of Zelkova serrata wood, except 7-hydroxy-3-methoxycadalene. Two biological activities-scavenging activity of hydroxy radical and cell toxicity by MTT assay-were measured with 7-hydroxy-3-methoxycadalene. The scavenging activity of hydroxyl radical of the compound was excellent and increased with its concentration. At 100 ppm hydroxyl radicals were removed completely. However, MTT assay revealed that 7-hydroxy-3-methoxycadalene showed critical toxicity to the cells. When 1 ppm of the compound was treated to the cells, cell viability was reached up to 90%, while it was reduced to 22% after treatment of 9 ppm. In 4 different Ulmaceae species, such as Ulmus davidiana, Ulmus parvifolia, Ulmus macrocarpa, Ulmus macrophylla, 7-hydroxy-3-methoxycadalene was not found at all. Instead, 7-hydroxycadalene (Mw 214), in which methoxyl group is omitted from 7-hydroxy-3-methoxycadalene, was distributed in the heartwood of 4 Ulmaceae species as major cadalene compound.

• Journal of the Korean Wood Science and Technology
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• v.37 no.3
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• pp.239-244
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• 2009

In order to alleviate the cyto-toxicity and improve the poor water solubility of 7-hydroxy-3-methoxycadalene, it was substituted with glucose, a strong hydrophilic and non cyto-toxiccompound, in the C-7 position. The yield of final product was ca. 55.4%. The $IC_{50}$ values of 7-O-${\beta}$-D-glucopyranosyl-3-methoxycadalene against normal lung cell (WI-38 cell line) and human lung cancer cell (A-549 cell line), which is a parameter for determination of cell viability, were measured to $298.2{\mu}m$ and $88.6{\mu}m$, respectively. This result indicates that the pharmaceutical efficiency of the cadalene-glucose derivative targeted to lung cancer cell could be improved more than three times compared to the non derivatized cadalene. In addition, glycosylation of 7-hydroxy-3-methoxycadalene turned its hydrophobic property to more soluble in water.

• Journal of the Korean Wood Science and Technology
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• v.36 no.6
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• pp.130-137
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• 2008

In this study cadalene, which is classified into sesquiterpenes constructed with 15 carbons of naphthalene skeleton, was isolated from ethanol extracts of Zelkova wood (Zelkova serrata) using successive silica gel column chromatography. The purified cadalene compound was subjected to structural analysis using HPLC, EI-MS and $^1H$, $^{13}C-NMR$. Its molecular weight was measured to 244 (m/z) and methyl and isopropyl group were attached at C1 and C4 position, as well as hydroxyl group at C7 and methoxyl group at C3 in the naphthalene skeleton, respectively. Yield of 7-hydroxy-3-methoxycadalene amounts to 0.03% based on air dried Zelkova wood powder. It was distributed only in xylem tissues(only in heartwood) of Zelkova wood, not in leaves and bark.

• Journal of the Korean Wood Science and Technology
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• v.28 no.2
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• pp.32-41
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• 2000

Antimicrobial and antioxidative activities on heartwood extractives from Zelkova serrata were investigated to develop a natural fungicide or preservative. The ethanol extract from Z. serrata was fractionated in the order of petroleum ether, diethylether and ethylacetate to determine antimicrobial activity. The highest antimicrobial activity against the tested microorganisms was found in the petroleum ether soluble fraction. An active antimicrobial compound was isolated from petroleum ether soluble fraction, and identified as 7-hydroxy-3-methoxycadalene by $^1H$-, $^{13}C$-NMR and EI-MS spectrometry. This compound showed higher antifungal activity, but lower antibacterial activity than hinokitiol(${\beta}$-thujaplicin), strong antimicrobial compound isolated from Thujopsis dolabrata. Antioxidative activity was also higher than ${\alpha}$-tocopherol and similar to BHT(butylated hydroxytoluene), one of the strongest synthetic antioxidant. As a result, it was concluded that 7-hydroxy-3-methoxycadalene isolated from Z. serrata had strong antifungal and antioxidative activities.