• Title/Summary/Keyword: $stigmast-5-en-3{\beta}-ol\

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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.

Correlation of Lipid Soluble Compounds of Colored Rices and its Mutagenicity, Antimutagenicity and Antioxidativity (유색미 지용성 성분들의 변이원성.항변이원성.항산화 효과에 대한 상관관계)

  • Shin, Su-Young;Kang, Mi-Young;Nam, Seok-Hyun
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.214-219
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    • 2003
  • The fractions extracted with methylene chloride from colored rice seeds of 19 cultivars were prepared to examine the correlationties of both antimutagenicity and antioxidiativity with physiological functionalities. The data revealed a positive correlation of the antimutagenicity with the content of $(3.{\beta},22Z)-Acetate-stigmasta-5,22-dien-3-ol$, 24-Oxocholesterol acetate, 6(E),8(E)-Heptadiene, and Eicosane. For antioxidativity, electron donating ability to DPPH radicals exhibited a positive correlation with the content of (24R,25S)-Aplysterylacetate, however, negative correlations were found between scavenging activity toward hydroxyl radicals and the content of either Tetradecanoic acid or Methyl ester-hexadecanoic acid, $(3.{\beta},24S)-Stigmast-5-en-3-ol$, respectively. In addition, a positive correlation was detected between the inhibitory effect of the fractions and the content of $(3.{\beta},24S)-Stigmast-5-en-3-ol$, however, a negative correlation with the content of 3',3'-Dimethylspiro [acridane-9,1'-indane], $(3.{\beta})-24-Methylene-9,19-cyclolanostan-3-ol$, and some other compounds was observed, respectively.

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.

Isolation of Two Steroids and a Triterpenoid from the Roots of Potentilla discolor (솜양지꽃 뿌리로부터 스테로이드와 트리테르페노이드 성분의 분리)

  • Park, Hee-Juhn;Lee, Kyung-Tae;Park, Jong-Hee
    • Korean Journal of Pharmacognosy
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    • v.38 no.4
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    • pp.354-357
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    • 2007
  • Three compounds (1-3) were isolated from the roots of Potentilla discolor (Rosaceae). The structure of compounds 1-3 were elucidated as stigmast-5-en-3-ol $({\beta}-sitosterol,\;1),\;2,19{\alpha}-dihydroxy$-2-oxo-urs-1,12-dien-28-oic acid (fupenjic acid, 2), 3-O-${\beta}$-D-glucopyranosylstigmast-5-en-3-ol (${\beta}-sitosterol\;{\beta}-D-glucopyranoside, 3) based on physical and spectroscopic data. $^{13}C-NMR$ assignments were completed by 2D-NMR technique. The three compounds were firstly isolated from Potentilla discolor.

Effects of the Constituents of Melonis Pedicellus in the Animal Models of Hepatic Diseases (과체 성분의 간질환 모델에서의 효과)

  • 최선희;이석용;조태순
    • YAKHAK HOEJI
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    • v.44 no.1
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    • pp.87-94
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    • 2000
  • In order to investigate the hepatoprotective constituents, Melonis Pedicellus was systematically extracted and fractionated with n-hexane, ethyl acetate, butanol and water Treatment of rats with ethyl acetate fraction reduced hepatic injuries induced by $\alpha$-naphthylisothiocyanate or D-galactosamine, whereas the components in water fraction showed protective effect only against D-galactosamine-induced hepatitis in rats. Two cucurbitacins and three sterols were isolated from ethylacetate fraction and their chemical structures were identified as cucurbitacin B, isocucurbitacin B, $\alpha$-spinasterol, stigmast-7-en-3-ol and stigmast-7-en-3-ol-0-$\beta$-D-glucopyranoside. Cucurbitacin B at the dose of 1 mg/kg (p.o.) signifcantly increased in bile flow in rats with ANIT-induced cholestasis. Isocucurbitacin B at 5 mg/hg (p.o.) showed signilicant protective effects against ANIT-induced cholestasis. These results showed that cucurbitacin B and isocucurbitacin B from Melonis Pedicellus may have hepatoprotective effect in rats with experimental cholestasis.

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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.

Active Compounds and Antimicrobial Effects from Castanea crenata Leaf (밤나무 잎의 항미생물 효과 및 활성물질)

  • Choi Ok-Beom
    • The Korean Journal of Food And Nutrition
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    • v.18 no.4
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    • pp.367-372
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    • 2005
  • Antimicrobial effects of the extracts from Castanea crenata leaf were investigated. The antimicrobial effects of methanol extract (8 mg, 20 mg) of 0.2 g and 0.5 g. eq. of Castanea crenata leaf was stronger than that of 0.65 mg of benzoic acid against Gram(+) bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, Micrococcus luteus, Leuconostoc mesenteroides and Bacillus subtilig and Gram(-) bacteria such as Escherichia coli, Salmonella typhimurium, and Pseudomonas aeruginosa. Growth inhibition of various microorganisms was observed in Castanea crenata leaf, therefor the Castanea crenata leaf were solvent fractionated. The ethyl acetate-soluble acidic and phenolic fraction were showed remarkable antimicrobial activity against microorganisms tested. The acidic fraction was purified with silica gel adsorption column chromatography, Sephadex LH-20 column chromatography and HPLC, subsequantly. The antimicrobial active substance isolated from the acid fraction of Castanea crenata leaf was characterized as stigmast-5-en-3-ol($\beta$-sitosterol) by MS and NMR analysis.

Phytochemical Constituents of Schizonepeta tenuifolia Briquet

  • Lee, Il-Kyun;Kim, Min-Ah;Lee, Seung-Young;Hong, Jong-Ki;Lee, Jei-Hyun;Lee, Kang-Ro
    • Natural Product Sciences
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    • v.14 no.2
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    • pp.100-106
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    • 2008
  • Column chromatographic separation of the MeOH extract from the aerial parts of Schizonepeta tenuifolia Briquet led to the isolation of twelve terpenes (1 - 11 and 17), four phenolics (13 - 16) and a hexenyl glucoside (12). Their structures were determined by spectroscopic means to be (-)-pulegone (1), piperitenone (2), p-cymene-3,8-diol (3), schizonepetoside A (4), schizonepetoside C (5), (+)-spatulenol (6), ursolic acid (7), $2{\alpha}$,$3{\alpha}$,$24{\alpha}$,-trihydroxyolean-12en-28oic acid (8), $5{\alpha}$,$8{\alpha}$-epidioxyergosta-6,22-diol-$3{\beta}$-ol (9), stigmast-4-en-3-one (10), ${\beta}-sitosterol$ (11), (Z)-3-hexenyl-1-O-${\beta}$-D-glucopyranoside (12), rosmarinic acid (13), apigenin-7-O-${\beta}$-D-glucopyranoside (14), luteolin-7-O-${\beta}$-D-glucuronopyranoside (15), hesperidin (16) and trans-phytol (17). Compounds 2, 3, 8, 9 and 12 were for the first time isolated from S. tenuifolia Briq.

Steroids from the Aerial Parts of Artemisia princeps Pampanini

  • Yoo, Jong-Su;Ahn, Eun-Mi;Bang, Myun-Ho;Song, Myoung-Chong;Yang, Hye-Joung;Kim, Dong-Hyun;Lee, Dae-Young;Chung, Hae-Gon;Jeong, Tae-Sook;Lee, Kyung-Tae;Choi, Myung-Sook;Baek, Nam-In
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.5
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    • pp.273-277
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    • 2006
  • Three stigmastane-type sterols and one ergostane-type sterol were isolated from the ethyl acetate soluble fraction of the aerial parts of Artemisia princeps Pampanini (Sajuarissuk). From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as $stigmasta-5,22-dien-3,{\beta}-ol (stigmasterol, 1),stigmast-5-en-3{\beta}-ol({\beta}-sitosterol,2), 5{\beta},8{\beta}-epidioxy-5{\beta},8{\beta}-ergosta-6,22-dien-3{\beta}-ol(ergosterol peroxide, 3),\;and\;{\beta}-sitosterol\;3-O-{\beta}D-glucopyranoside(daucosterol,4)$.

Sterol Composition and Phytoestrogen Activity of Safflower(Carthamus tinctorius L.) Seed (홍화(Carthamus tinctorius L.)씨의 sterol 및 Phytoestrogen 분석)

  • 최영주;최상욱
    • Journal of Life Science
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    • v.13 no.4
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    • pp.529-534
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    • 2003
  • This study was done to investigated the phytosterol compositions of safflower (Carthamus tinctorius L.) seed. The phytoestrogen activity was also determined using CAT-ELISA Kit in ethanol extract of safflower seed. The phytosterol of safflower seeds was identified using gas chromatography-mass spectrometry after saponification of the oils. The phytosterol content and composition of safflower seed oils were 4% and identified stigmast-5-en-3-ol (3$\beta$, 24S)-form, ${\gamma}$-sitosterol (clionasterol) with Wiley MS spectrum library. The synergistic effect of human estrogen receptor (hER) has been investigated using a minimal chimeric promoters composed of the TATA region of the adenovirus-2 major late promoter (A22MLP) and two consensus perfectly polindromic Xenopus vitellogenin A2 gene estrogen responsive elements (XVEREl19). Transient transfection experiments in tile human breast adenocarcinoma cell line MCF-7, which is known to express the estrogen receptor endogenously, revealed that phytoestrogen from Carthamus tinctorius L. acts as estrogen. We have observed the transcriptional activities stimulated methanol and ethanol extract of safflower seed in MCF-7, were 0.43 and 0.37 respectively, compared to that by $\beta$-estradiol as 1.0. Our data showed that safflower seeds have estrogenic activity methanol and ethanol extracts and ethanol lower than that of $\beta$-estradiol. This result provides the first evidence that the beneficial effect of safflower seeds may be mediated, at least in part, by the stimulating effect of phytoestrogen ell bone-protecting.