• 제목/요약/키워드: $\alpha$-hydroxy kauran-19-oic acid

검색결과 5건 처리시간 0.024초

Microbial Transformation of Bioactive Diterpenoids from Acanthopanax koreanum by Fusarium oxysporum

  • Kim, Young-Ho;Hyun, Seoung-Hae;Kim, Hang-Sub;Lee, Sung-Woo;Kim, Dong-Hyun
    • 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.

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Inhibitory Effect of Kaurane Type Diterpenoids from Acanthopanax koreanum on TNF-$\alpha$ Secretion from Trypsin-Stimulated HMC-1 Cells

  • Cai, Xing-Fu;Shen, Guanghai;Dat, Nguyen-Tien;Kang, Ok-Hwa;Lee, Young-Mi;Lee, Jung-Joon;Kim, Young-Ho
    • 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.

Inhibitory Constituents against Cyclooxygenases from Aralia cordata Thunb

  • Dang Nguyen Hai;Zhang XinFeng;Zheng MingShan;Son Kun Ho;Chang Hyeun Wook;Kim Hyun Pyo;Bae KiHwan;Kang Sam Sik
    • 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 $(IC_{50}\;:\;127.6{\mu}M)$.

ent-Kaurane- and ent-Pimarane-Type Diterpenoids from Siegesbeckia pubescens and Their Cytotoxicity in Caki Cells

  • Lee Sanghyun;Noh Eun Jung;Kim Jung Sook;Son Eun Mi;Pan Xu;Kim Yeong Shik;Kim Bak-Kwang;Lee Burm-Jong
    • 한국작물학회지
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    • 제50권2호
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    • pp.147-150
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    • 2005
  • ent-Kaurane- and ent-pimarane-type diterpenoids were isolated from the methanol extract of Siegesbeckia pubescens by column chromatography. Their structures were elucidated as ent-16$\alpha$H,17-hydroxy-kau­ran-19-oic acid (1), ent-4,17-dihydroxy-16$\alpha$-methyl-kau­ran-19-oic acid (2), ent-16$\beta$,17-dihydroxy-kauran-19-oic acid (3), kirenol (4) and ent-16$\beta$,17,18-trihydroxy-kauran­19-oic acid (5) by spectral analysis. The cytotoxicity of these compounds in Caki cells was assayed by a cell counting kit. Only one group treated with kirenol (4), an entpimarane-type diterpenoid, showed the inhibition of the cell growth in Caki cells.

섬오갈피나무 줄기 유래 테르펜 화합물의 멜라닌 생성 저해 활성 (Anti-melanogenesis Activities for the Terpenes from the Acantophanax koreanum Stems)

  • 문승리;현주미;조연정;정은영;이남호
    • 대한화장품학회지
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    • 제43권4호
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    • pp.289-295
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    • 2017
  • 본 연구에서는 섬오갈피 줄기 추출물 및 용매 분획물의 미백 활성을 검색하고 유효성분을 분리하여 화학구조를 규명하였다. 섬오갈피 줄기 에탄올 추출물 및 용매 분획물의 멜라닌 생성 억제활성을 측정한 결과, 헥산 및 에틸아세테이트 분획물에서 우수한 멜라닌 생성 억제 효과가 있음을 확인하였다. 비교적 세포독성이 적은 헥산 분획물에서 유효성분을 찾고자 크로마토크래피를 실시하여 3개의 화합물을 분리하였으며 $^1H$$^{13}C$ NMR 데이터 분석 및 문헌 비교를 통하여 화학구조를 동정하였다; kaurenoic acid (1), $16{\alpha}$-hydro-17-isovaleroyloxy-ent-kauran-19-oic acid (2), $16{\alpha}$-hydroxy-17-isovaleroyloxy-ent-kauran-19-oic acid (3). 분리된 화합물에 대한 미백 활성 실험 결과, 화합물 1-3 모두 농도의존적으로 멜라닌 생성을 억제하였다. 또한 세포 내 티로시나제 효소의 활성을 감소시킴을 확인하였으며 이러한 연구 결과를 바탕으로 섬오갈피 줄기 추출물은 기능성 미백 화장품 소재로써 활용 가능할 것이라 사료된다.