• Journal of Microbiology and Biotechnology
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• 제2권2호
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• pp.92-97
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• 1992

Microbial transformation of (-)kaur-l6-en-19-oic acid and (-)pimara-9(1l), 15-dien-19-oic acid from A. koreanum was investigated. Throughout the screening of the capability of metabolizing these bioactive diterpenoids, two microorganisms have chosen among various fungi and streptomycetes tested. Scale-up fermentation with Fusarium oxysporum KCTC 6051 produced two metabolites related to the precursor diterpenoids. The two metabolites were isolated by column chromatography and identified by chemical and spectroscopic methods as $2\beta$, $16\alpha$-dihydroxy kauran-19-oic acid and $16\alpha$-hydroxy kauran-19-oic acid. However any microorganisms capable to transform (-) pimara-9(11), 15-dien-19-oic acid was not screened in this condition.

• Archives of Pharmacal Research
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• 제8권2호
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• pp.59-65
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• 1985

Besides (-) pimara-8(14), 15-dien-19-oic acid [I] which had already been isolated as an active anti-inflammtory principle of Aralia continentalis, (-) kaur-16-en-19-oic acid [II] was separated as another active component of the plant, by tracing albumin stabilizing activity. $IC_{50}$ of [II] for the protein stabilizing activity was 0.026mg/3ml, when those of [I] and phenylbutazone were 0.032 and 0.32 mg/3ml, respectively. Being investigated employing carrageenin-induced edema test in rat hind paw, the anti-inflammatory activity of [II] administered s. c. was slightly lower than that of phenylbutazone, whereas the activity of [II] administered p. p. was three times greater than that of phenylbutazone. These results of [II] were contrary to those of [I] in the aspect of administration routes.

• Archives of Pharmacal Research
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• 제28권1호
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• pp.28-33
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• 2005

Seven diterpenes, four polyacetylenes, a lipid glycerol, and two sterols were isolated from the methylene chloride fraction of the root of Aralia cordata. Their chemical structures were determined as (-)-pimara-8(14), 15-dien-19-oic acid (2), pimaric acid (3), (-)-kaur-16-en-19-oic acid (4), 17-hydroxy-ent-kaur-15-en-19-oic acid (9), $7{\alpha}$-hydroxy-(-)-pimara-8(14), 15-dien-19-oic acid (10), $16\alpha$, 17 -dihydroxy-(-)-kauran-19-oic acid (11), 16-hydroxy-17-isovaleroyloxy-ent-kauran-19­oic acid (12), falcarindiol (5), dehydrofalcarindiol (6), dehydrofalcarindiol-8-acetate (7), falcarin­diol-8-acetate (8), alpha-mono palmitin (13), stigmasterol (1), and daucosterol (14) by the spectral evidences. These compounds were tested with COX-1 and COX-2 inhibition assays. This study found that compounds 2, 4, 5, 6, 7, 8, and 10 inhibited COX-1 dependent conversion of the exogenous arachidonic acid to $PGE_2$ in a dose-dependent manner with $IC_{50}$ values of $134.2{\mu}M$, $121.6{\mu}M$, $170{\mu}M$, $50.4{\mu}M$, $11.7{\mu}M$, $99.6{\mu}M$, and $69.6{\mu}M$, respectively. But, most of these compounds weakly inhibited COX-2 dependent $PGE_2$ generation. Among them, only compound 4 showed relatively significant inhibitory activity $(IC_{50}\;:\;127.6{\mu}M)$.

• Applied Biological Chemistry
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• 제40권6호
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• pp.501-507
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• 1997

파라과이 원산의 국화과 식물 Stevia rebaudiana Bertoni는 steviol (ent-13-hydroxy kaur-16-en-19-oic acid)을 기본 골격으로 하는 stevia 감미료를 건물 중량의 5-10%를 생합성하여 축적을 한다. 감미성분은 Gibberellin 생합성의 전구체로 알려진 ent-kaurenoic acid (ent-kaur-16-en-19-oic acid; ent-KA)의 7번과 13번의 어느 탄소에 hydroxylation을 시키느냐에 따라 gibberellin 대사와 steviol 대사로 나뉘어진다. ent-KA 13-hydroxylase를 stevia 엽록체의 stroma에 존재하는 것을 확인했다. Stroma 분획 단백질 $100\;{\mu}g$으로 효소 반응의 cofactor 요구성을 조사해 본 결과, 반응 혼합액에 NADPH를 첨가하지 않았을 때는 85%의 효소활성의 감소를 보였고, NADPH 대신 NADH를 첨가해도 34%의 감소를 보였다. anaerobic 조건에서는 2.1%의 활성을 뛰었다. 이 결과로 ent-KA 13-hydroxylase는 NADPH와 $O_2$ 요구성임을 밝혔다. FAD, FMN, riboflavin을 첨가함으로써 FAD는 1.5배, riboflavin은 1.7배의 효소활성 증가 효과가 나타났다. 효소의 기질 특이성을 조사한 결과, t-cinnamic acid, 4-hydroxyphenyl acetic acid, choline과 resorcinol에는 전혀 활성이 검출되지 않았으며, $[^(14)C]-methyl-KA$를 ent-KA 대신에 기질로 사용했을 때는 16.7% 의 활성이 검출되어 ent-KA 13-hydroxylase는 기질특이성이 높은것으로 확인되었다.

• Archives of Pharmacal Research
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• 제19권1호
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• pp.77-78
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• 1996

• Archives of Pharmacal Research
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• 제26권9호
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• pp.731-734
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• 2003

Five known kaurane type diterpenoids, 16$\alpha$H, 17-isovaleryloxy-ent-kauran-19-oic acid (1), 16$\alpha$-hydroxy-17-isovaleryloxy-ent-kauran-19-oic acid (2), paniculoside-IV (3), 16$\alpha$-hydroxy-ent-kauran-19-oic acid (4), and ent-kaur-16-en-19-oic acid (5) were isolated from the root of Acanthopanax koreanum by repeated column chromatography and reversed phase preparative HPLC. The structures of these compounds were established from physicochemical and spectral data. Among the isolated compounds 16$\alpha$H, 17-isovaleryloxy-ent-kauran-19-oic acid (1) showed potent inhibitory activity ($IC_50$ value, 16.2 $\mu$ M) on TNF-$\alpha$ secretion from HMC-1, a trypsin-stimulated human leukemic mast cell line.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.222.2-222.2
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• 2003

The Araliae continental is Radix is the root of Aralia continentalis Kitagawa, which belongs to the Araliaceae and is distributed in Korea, Japan, Manchuria, China and Sahalane. It is generally used as a folk medicine for its excellent medical action and efficacy in various symptoms such as headache, edema, inflammation, rheumatism and neuralgia. (-)-Pimara-8(14)-15-dien-19-oic acid (1) and l-kaur-16-en-19-oic acid have been reported as the major constituent of A. continental is Radix. Essential oils such as limonene, sabinene, myrcene, humulene and sesamin, ${\beta}$-sitosterol are also reported as constituent elements. (omitted)