• Title/Summary/Keyword: stigmast-4-en-3-one

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Deveolopment of Biologically Active Compounds from Edible Plant Sources-VI - Isolation of Sterol Compounds from the Aerial Parts of Garland (Chrysanthemum coronarium L.) - (식용식물자원으로부터 활성물질의 탐색-VI - 쑥갓(Chrysanthemum coronarium L.)으로부터 sterol의 분리 -)

  • Song, Myoung-Chong;Hong, Yoon-Hee;Kim, Dong-Hyun;Kim, Dae-Keun;Chung, In-Sik;Lee, Youn-Hyung;Kim, Sung-Hoon;Park, Mi-Hyun;Kim, In-Ho;Kwon, Byoung-Mog;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.46 no.4
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    • pp.376-379
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    • 2003
  • The aerial parts of tile Garland (Chrysanthemum comnarium L.) were extracted in MeOH and solvent fractionated with EtOAc, n-BuOH and water, successively. EtOAc fractions gave three steroid compounds through application of silica gel column chromatographies. The chemical structures of the steroids were determined by the interpretation of several spectral data, including NMR and MS as $stigmast-5-en-3{\beta}-ol\;(1,\;{\beta}-sitosterol),\;stigmast-4-en-6{\beta}-ol-3-one$ (2), $stigmast-4-en-6{\alpha}-ol-3-one$ (3). Compounds 2 and 3 have been so far reported only in the aquatic plants, were isolated for the first time from the land plants.

A Study on the Constituents from the roots of Astragalus membranaceus(Bunge) (III) (황기(Astragalus membranaceus Bunge) 뿌리의 성분연구 (III))

  • Kim, Chung-Sook;Kim, Jin-Sook
    • Korean Journal of Pharmacognosy
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    • v.31 no.1
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    • pp.109-111
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    • 2000
  • Two compounds were isolated from the root of Astragalus membranaceus(Bunge). On the basis of spectroscopic data their structures were identified as stigmast-4-en-3-one and a mixture of 2'-angeloyloxy-1',2'-dihydroxanthyletin and 2'-senecioyloxy-1',2'-dihydroxanthyletin. They were first isolated from the genus of Astragalus.

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Studies on Biological Activity of Wood Extractives (IX) - Antionxidative Compounds from Heartwood of Robinia pseudo-acacia - (수목추출물의 생리활성에 관한 연구(IX) - 아까시나무 심재의 항산화활성 물질 -)

  • Choi, Don-Ha;Lee, Hak-Ju;Lee, Sung-Suk;Kim, Yun-Geun;Kang, Ha-Young
    • Journal of the Korean Wood Science and Technology
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    • v.30 no.4
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    • pp.51-57
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    • 2002
  • Antimicrobial and antioxidative activites on heartwood extractives of domestic species were investigated to develop a natural fungicide or preservative. One steroid, stilbene derivatives and two flavonoids were isolated from heartwood of Robinia pseudo-acacia which has been selected due to its high antioxidative activity among the tested species. The structures were determinded as: 3-𝛽-stigmast-5-en-3-ol(daucosterol), 3,3'4,5-tetrahydroxystilbene, 3,3'4'5,7-pentahydroxyflavone(robinetin) and 3,3'4'7-tetrahydroxyflavanone(fustin) respectively on the basis of spectroscopic data and chemical correlations. According to the results of free radical scavenging activity, 3,3'4'5,7-pentahydroxyflavone was evaluated as the highest antioxidative compound among the four compounds and showed higher radical scavenging activity than those of 𝛼-tocopherol and butylated hydroxytoluene(BHT), one of the strongest synthetic antioxidants. 3,3'4'5-Tetrahydroxystilbene and 3,3'4'7-tetrahydroxyflavanone showed higher antioxidative activities than that of 𝛼-tocopherol. However, 3-𝛽-stigmast-5-en-3-ol did not show free radical scavenging activity. In this regard, it could inferred that high antioxidative activity of extractives of R. pseudo-acacia was derived from 3,3'4'5'7-pentahydroxyflavone, 3,3'4'5-tetrahydroxystilbene and 3,3'4'7-tetrahydroxyflavanone.

Antimicrobial Constituents from Fruits of Ailanthus Altissima SWINGLE

  • Zhao Chun-Chao;Shao Jian-Hua;Li Xian;Xu Jing;Zhang Peng
    • Archives of Pharmacal Research
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    • v.28 no.10
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    • pp.1147-1151
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    • 2005
  • A new naturally occurring sterol, compound 5, and six known stigmasterols were isolated from fruits of Ailanthus altissima Swingle by repeated column chromatography and RP-HPLC. Their structures were identified as, 5${\alpha}$-stigmastane-3,6-dione (1), 3${\beta}$-hydroxystigmast-5-en-7-one (2), stigmast-5-ene-3${\beta}$, 7${\alpha}$-diol (3), 6${\alpha}$-hydroxystigmast-4-en-3-one (4), 5${\alpha}$-stigmastane-3${\beta}$, 6${\beta}$-diol (5), stigmast-4-ene-3${\beta}$, 6${\alpha}$-diol (6), stigmast-5-ene-3${\beta}$, 7${\alpha}$, 20$\xi$-triol (7) by spectral analysis and comparison with the published data. These compounds have not been reported from genus Ailanthus, whereas compound 7 was identified by NMR for the first time. In addition, the $95\%$ ethanol extract and compounds from the fruits of Ailanthus altissima SWINGLE were assayed for in vitro antimicrobial activity. The extract was potent active against the assayed bacteria while compounds 3 and 7 exhibited moderate activity.

Potentially Bioactive Two New Natural Sesquiterpenoids from the Rhizomes of Zingiber zerumbet

  • Jang Dae Sik;Seol Eun Kyoung
    • Archives of Pharmacal Research
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    • v.28 no.3
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    • pp.294-296
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    • 2005
  • Repeated chromatography of the n-hexane-soluble fraction of the MeOH extract of the rhizomes of Zingiber zerumbet led to the isolation of two isomers of 6-methoxy-2E,9E-humula-dien-8-one (1 and 2) and stigmast-4-en-3-one. The structures of 1 and 2 were determined by spectroscopic methods including 10 and 2D-NMR elucidated by analysis of spectroscopic data as well as by comparison with published values. This is the first report on the isolation of compounds 1 and 2 from the nature. Stigmast-4-en-3-one was first isolated from this plant.

A Study on the Constituents from the Roots of Astragalus membranaceus (I) (황기(黃芪) (Astragalus membranaceus Bunge.) 뿌리의 성분연구(I))

  • Kim, Jin-Sook;Kim, Yun-Tai;Kim, Chung-Sook
    • Korean Journal of Pharmacognosy
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    • v.27 no.4
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    • pp.336-341
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    • 1996
  • The roots of Korean Astragalus membranaceus Bunge. (Leguminosae), Astragali Radix, were extracted following general methods. During these extractions, first of all, 1,2-benzendicarboxylic acid diisononylester(compound A), ${\beta}-sitosterol(compound\;B)$, $3-0-{\beta}-D-galactopyranosyl-{\beta}-sitosterol(compound\;C)$ and $stigmast-4-en-6{\beta}-ol-3-one(compound\;D)$ were isolated. Three of these compounds were identified the first time isolation from the genus of Astragalus.

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Development of Biologically Active Compounds from Edible Plant Sources-XVII. Isolation of Sterols from the Fruits of Cornus kousa Burg (식용식물자원으로부터 활성물질의 탐색-XVII. 산딸나무(Cornus kousa Burg.)의 열매로부터 sterol 화합물의 분리)

  • Lee, Dae-Young;Song, Myoung-Chong;Yoo, Jong-Su;Kim, Sung-Hoon;Chung, In-Sik;Kim, Dae-Keun;Park, Mi-Hyun;Kwon, Byoung-Mog;Kim, Se-Young;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.49 no.1
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    • pp.82-85
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    • 2006
  • The fruits of Cornus kousa Burg. were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. From the EtOAc fraction, three sterols were isolated through the repeated silica gel and ODS column chromatographies. According to the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as ${\beta}-sitosterol$ (1), $stigmast-4-en-6{\beta}-ol-3-one$ (2) and daucosterol (3). They were the first to be isolated from Cornus kousa Burg.

New Components from the Thorns of Gleditsia sinensis and Their Antimutagenic Activities

  • Lim, Jae-Chul;Park, Jong-Hee;Lee, Dong-Ung
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.204.3-205
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    • 2003
  • Antimutagenic activity-guided fractionation of an extract prepared from the thorns of Gleditsia sinensis Lam. (Leguminosae), which is a perennial shrub widely distributed throughout China (called "Zao Jiao Ci" ) and in Gyeongju city area in Korea (called "Jo Gak Ja" ) and has been used in traditional medicine for the treatment of swelling, suppuration, carbuncle and skin diseases, led to the isolation of one triterpenoid and four steroids, which were identified as D:C-friedours-7-en-3-one (1), stigmastane-3,6-dione (2), ${\beta}$-sitosterol (3), sigmasterol (4), and stigmast-4-en-3,6-dione (5). (omitted)

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Phytochemical Constituents from Aconitum pseudolaeve Var. erectum (진범의 식물화학적 성분)

  • Kim, Dae-Keun;Kwak, Jong-Hwan;Song, Ki-Won;Kwon, Hack-Cheol;Zee, Ok-Pyo;Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.27 no.1
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    • pp.75-79
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    • 1996
  • Four steroids and one flavonol glycoside were isolated from the ethanol extract of the whole plant of Aconitum pseudolaeve var. erectum. Their structures were identified as ${\beta}-sitost-4-en-3-one$, 22-dihydro-stigmast-4-en-3,6-dione, ${\beta}-sitosterol$, ${\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside$ and $kaempferol-3-O-{\beta}-D-glucopyranoside(astragalin)$ on the basis of spectral data.

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Norsesquiterpene and Steroid Constituents of Humulus japonicus

  • Yu, Byung-Chul;Yang, Min-Cheol;Lee, Kyu-Ha;Kim, Ki-Hyun;Lee, Kang-Ro
    • Natural Product Sciences
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    • v.13 no.4
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    • pp.332-336
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    • 2007
  • Five steroids and two norsesquiterpene glycosides were isolated from the methanol extract of H. japonicus. Their structures were determined by means of physio-chemical and spectral data to be friedelin (1), stigmast-5-en-3-${\beta}$-ol (${\beta}$-sitosterol) (2), 7-keto-${\beta}$-sitosterol (3), 6${\beta}$-hydroxy-4-stigmasten-3-one (4), 7${\alpha}$-hydroxy-${\beta}$-sitosterol (5), 3-hydroxy-4,4-dimethyl-4-butyrolactone (6), daucosterol (7), (6S, 9S)-roseoside (8), and (9S)-drummondol-9-O-${\beta}$-D-glucopyranoside (spinoside B) (9). The compounds 1, 3, 4, and 6 - 9 were first isolated from this plant source.