• 제목/요약/키워드: 15-diol

검색결과 53건 처리시간 0.028초

Monoterpenoid계의 새로운 항암제 합성 및 In vitro 세포독성 평가 (Synthesis and in vitro Cytotoxicity Monoterpenoid as New Antitumor Agents)

  • 이민정;김대근;백형근;이강노;정규혁
    • Biomolecules & Therapeutics
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    • 제9권3호
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    • pp.143-155
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    • 2001
  • Many attention has been focused on developing new chemotherapeutic agents for a treatment of cancer from natural products. From Carpesium divaricatum S. et Z. (Compositae), various monoterpenoid compounds were isolated and exhibited mild antitumor activity against human tumor cell lines. These facts prompted us to explore the structure-activity relationship of these compounds. The synthesis of monoterpenoid compound was accomplished by Fries rearrangement, Grignard reaction, elimination, allylic oxidation, esterification and epoxidation as key steps. The results of in vitro cytotoxicity (A549, SK-OV-3, SK-MEL-2, XF498, HCT15) of the synthesised compounds are as follows: First of all, epoxide moiety is prerequisite for cytotoxic activity in diester compound. Any kind of compounds with olefin or diol moiety instead of epoxide ring exhibited poor or mild cytotoxic activity respectively. Of o-acetoxy and isobutoxy epoxy esters, p-sub-stituted phenylacetate compounds exhibited high cytotoxic activities against SK-MEL-2 and HCT15.

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13(E)-Labd-13-ene-8$\alpha$, 15-diol isolated from Brachyglottis monroi Induces Apoptosis on Human Breast Cancer MDA-MB231 cell line

  • Lim, Jin-A;Lee, Jeong-Ho;Lee, In-A;Nigel, B;Baek, Seung-Hwa
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.141.1-141.1
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    • 2003
  • The inhibitory effect of 13(E)-Labd-13-ene-8$\alpha$ 15-diol(1), isolated from the ethanol extract of Brachyglottis monroi, on the proliferation of human breast cancer MDA-MB231 cells was examined. Compound (1) at concentration as high as 16$\mu$/$m\ell$ has inhibited the proliferation of MDA-MB231 and this cytotoxic effect was increased in a time and dose-dependent manners. (omitted)

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The Cytotoxic Activity of 13(E)-Labd-13-ene-8$\alpha$, 15-diol from Brachyglottis monroi

  • Lim, Jin-A;Kwag, Jung-Sook;Nigel, B.Perry;Baek, Seung-Hwa
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.179.2-179.2
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    • 2003
  • The cytotoxic activity of 13(E)-Labd-13-ene-8$\alpha$, 15-diol(1), isolated from the ethanol extract of Brachyglottis monroi was evaluated against tumor cell lines such as P388, SNU-C4 MDA-MB231, B 16 melanoma and A549 in vitro. By mean of spectral analysis particularly by the aid of various two dimensional NMR experiments, 1H-NMR and 13C-NMR signals of (1) was completely assigned, and thus the structure of (1) was established unambiguously. (omitted)

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A New Chemical Constituent from the Hairy Root Cultures of Catharanthus roseus

  • Chung, Ill-Min;Park, Han-Young;Ali, Mohd;San, Ka Yiu;Peebles, Christie A. M.;Hong, Seung-Beom;Ahmad, Ateeque
    • Bulletin of the Korean Chemical Society
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    • 제28권2호
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    • pp.229-234
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    • 2007
  • One new compound, 3,7,11,19,23,27-hexamethyl-15-hydroxymethylene-n-octacos-5,8,20-triene-10β,18α- diol-10β-D-glucopyranoside (1), along with the three known compounds, 3-epibetulinic acid (2), n-pentadecanyl octa-dec-19-en-oate (3) and β-sitosterol (4) were isolated from the methanolic extract of the cultured Catharanthus roseus hairy roots. The structures of the one new and three known compounds were elucidated using one- and two-dimensional NMR in combination with IR, EI/MS, FAB/MS. To the best of our knowledge, 3,7,11,19,23,27-hexamethyl-15-hydroxymethylene-n-octacos-5,8,20-triene-10β,18α-diol-10β-D-glucopyranoside, 3-epibetulinic acid and n-pentadecanyl octa-dec-19-en-oate were identified for the first time from the hairy roots of C. roseus.

New Stigmastane Steroids Constituents from Rice Hulls of Oryza sativa and Inhibitory Activity on Radish seed

  • Jeong, Il-Min;Ali, Mohd;Khanh, Tran Dang;Choung, Myoung-Gun;Park, Hong-Jae;Ahmad, Ateeque
    • Bulletin of the Korean Chemical Society
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    • 제27권1호
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    • pp.93-98
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    • 2006
  • Two new compounds 1'-(stigmast-11,20(21),25-trien 3$\alpha$,9$\alpha$-diolyl)-3'-(pimara-11,15-dien-3$\alpha$-olyl) glycerol (1) and stigmast-5-en-3$\alpha$,26-diol (2) along with known fatty acids n-hexacosanoic acid (3) and hexadecanoic acid (4), have been isolated from the methanol extract of rice hulls of Oryza sativa. The structures of the compounds were elucidated using 1D and 2D NMR spectral methods, viz; $^1H, ^{13}C, ^{13}C$-DEPT, $^1H-^1H$ COSY, $^1H-^{13}C$ HETCOR, HSQC and HMBC aided by IR, EIMS, FABMS and HRFABMS. Compound (1) showed inhibition to radish germination, growth of shoot and root length.

Di- and Sesqui-Terpenoids Isolated from the Pods of Sindora sumatrana and Their Potential to Inhibit Lipopolysaccharide-Induced Nitric Oxide Production

  • Jang, Dae-Sik;Min, Hye-Young;Jeong, Yeon-Hee;Lee, Sang-Kook;Seo, Eun-Kyoung
    • Archives of Pharmacal Research
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    • 제27권3호
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    • pp.291-294
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    • 2004
  • Activity-guided fractionation of the n-hexane and ${CHCl_3}-soluble$ fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, $(+)-7{\beta}-acetoxy-15,16-epoxy-3$, 13(16), 14-clero-datriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3, 13-clerodadiene-16,15-olide-18-oic acid (3), $(+)-7{\beta}-acetoxy-3$,13-clerodadiene-16,15-olide-18-oic acid (4), $(+)-7{\beta}-acetoxy-16-hydroxy-3$,13-clerodadiene-16, 15-olide-18-oic acid (5), ${\beta}-caryophyllene$ oxide (6), $clovane-2{\beta},9{\beta}-diol (7),{\;}and{\;}caryolane-1,9{\beta}-diol$ (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with $IC_{50}$/ value of $51.6{\;}\mu\textrm{m}M$.

측백엽의 Diterpenes 성분 (Diterpenes of Biota orientalis Leaves)

  • 성상현;구경아;임혜경;이흠숙;조정희;김혜수;김영중
    • 생약학회지
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    • 제29권4호
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    • pp.347-352
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    • 1998
  • Six minor diterpenes were isolated from Biota orientalis (Cupressa-ceae) leaves. On the basis of comparison with reported spectral data, they were identified as 7,15-isopimaradien-18-oic acid (isopimaric acid), 8(14),15-isopimaradien-18-oic acid (sandaracopimaric acid), 7,15-isopimaradien-3-ol, 7,15-isopimaradien-3,19-diol, 8(17),13-labdadien-16,15-olid-19-oic acid (demethylpinusolide), and 15-hydroxy-8(17),13-labdadien-19-oic acid (isocupric acid). They were first reported in the genus of Biota.

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Indomethacin이 백서의 4-nitroquinoline 1-oxide (4NQO) 유도 구개암 발암과정에서 미세구조에 미치는 영향에 관한 연구 (ULTRASTRUCTURAL STUDY ON THE EFFECTS OF INDOMETHACIN ON 4-NITROQUINOLINE 1-OXIDE (4NQO) INDUCED PALATAL CARCINOMA OF ALBINO RAT.)

  • 김해근
    • Maxillofacial Plastic and Reconstructive Surgery
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    • 제11권1호
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    • pp.171-186
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    • 1989
  • This study was undertaken to investigate the effects of indomethacin on 4-nitroquinoline 1-oxide (4NQO) induced palatal carcinoma of albino rats. Sixty albino rats about 100 gms of body weight, 6 weeks old-were used classifying as 1) six albino rats of normal group received no treatment, 2) six albino rats of control group treated with propane 1, 2-diol 3 times a week, 3) twenty four albino rats of experimental group I treated with 0.5% 4NQO in propane 1, 2-diol 3 times a week, 4) twenty four albino rats of experimental group II treated with 0.5% of 4NQO in propane 1, 2-diol 3 times a week and administrated 20${\mu}g/ml$ indomethacin in drinking water ad lib. The animals of normal and control groups were sacrificed 7th, 11th, 15th, 19th, 23rd and 27th week, while those of experimental group I and II were sacrificed 7th, 9th, 11th, 13th, 15th, 17th, 19th, 21st, 23rd, 25th, 27th and 29th week after the experiment. The palatal mucosa was excised and examined grossly, light-microscopically and electron-microscopically. Following results were obtained. 1. In control group, there was no specific difference from normal tissue histopathologically. 2. In group I, hyperkeratosis mild acantosis and dyskeratosis in in 7th week, dysplasia in 11th week and severe acantosis in 19th week were observed, but squamous cell carcinoma not observed until 29th week on light-microscope. 3. In group II, hyperkeratosis, mild acantosis in 9th week, dyskeratosis and dysplasia in 21st week, severe acantosis in 27th week and squamous cell carcinoma in 29th week were observed on light-microscope. 4. In group I, widening of intercellular space in 7th week, increasing of desmosome, giant desmosome and tonofilament in cytoplasm in 9th week, severe widening of intercellular space, increasing of mitochondria and vascular degeneration in 11th week, irregular pattern of cell feature and nucleus and prominent nucleoli in 19th week, and continuity of basal lamina in 29th week were observed on electron-microscope. 5. In group II, mild widening of intercellular space in 9th week, increasing of mitochondria, vascular degeneration and tonofilament in cytoplasm in 13th week, increasing of desmosome and giant desmosome in 15th week, irregular pattern of cell surface and nucleus and prominent nucleoli, and in 21st week continuity of basal lamina were observed on electron-microscope which phenomenon occurred little later than group I. After 21st week, however, severe widening of intercellular space, vascular degeneration and continuity of basal lamina were observed as in group I.

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