• 제목/요약/키워드: betulinic acid

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상기생의 트라이테르펜 및 페놀성 성분의 면역조절 작용 (Immunodulatory Activity of Triterpenes and Phenolic Compounds from Viscum Album L.)

  • 박대섭;최상진;김경란;이선미;이강노;표석능
    • Biomolecules & Therapeutics
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    • 제11권1호
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    • pp.1-4
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    • 2003
  • Plants are known as important source in the search for new drugs. The twelve compounds from Viscum album (Loranthaceae), lupeol (1), betulonic acid (2), betulinic acid (3), terminic acid (4), ursolic acid (5), $\beta$-sitosterol (6), $\alpha$-spinasterol (7), oleanolic acid (8), 5-hydroxy-1-(4′-hydoxyphenyl)-7-(4"-hydroxyphenyl)-hepta-1-en-3-on (9), 2′-hydroxy-4′,6′-dimethoxychalcone-4-O-glucoside (10), 2′-hydroxy-4′,6′-dimethoxychalcone-4-O-[apiosyl(l$\longrightarrow$2)]glucoside (11) and syringin (12) were evaluated for their immunomodulatory properties. Compounds 6 and 11 induced the macrophage tumoricidal activity and the lymphocyte blastogenesis. In addition, these compounds stimulated the macrophages to induce the production of TNF-$\alpha$ and NO. These findings suggest that compounds 6 and 11 are modulating various elements of the host immune response.

작약(芍藥)의 성분연구(成分硏究) (3);Triterpenoid의 분리 (Phytocheical Studies on Paeoniae Radix (3);Triterpenoids)

  • 김주선;김윤정;이소영;강삼식
    • 생약학회지
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    • 제39권1호
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    • pp.37-42
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    • 2008
  • From the 70% EtOH extract from the roots of Paeonia lactiflora (Paeoniaceae), nine triterpenoids were isolated and identified as ${\beta}-amyrin$ (1), 24-methylenecycloartanol (2), betulinic acid (3), oleanolic acid (4), hederagenin (5), 30-norhederagenin (6), 30-norarjunolic acid (7), arjunolic acid (8), and $3{\beta},4{\beta},23-trihydroxy-24,30-dinorolean-12,20(29)-dien-28-oic$ acid (9) by spectroscopic methods. Among these compounds, 1, 2, 7, 8 and 9 were isolated for the first time from this plant.

Secondary Metabolites from Anthonotha cladantha (Harms) J.Léonard

  • Laurent Voufack Lefack Bongmo;Achille Nouga Bissoue;Samuel Magloire Bissim;Georges Bellier Tabekoueng;Willifred Dongmo Tekapi Tsopgni;Mehreen Lateef;Felicien Mushagalusa Kasali;Muhammad Shaiq Ali;Alain Francois Kamdem Waffo;Jean Duplex Wansi
    • Natural Product Sciences
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    • 제29권1호
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    • pp.50-58
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    • 2023
  • The phytochemical investigation of the crude methanolic extracts roots and stem bark of Anthonotha cladantha (Harms) J.Léonard led to the isolation and identification of twelve secondary metabolites: 2,3-dihydroxypropyl hexacosanoate (1), hederagenine (2), cycloeucalenol (3), 2α-hydroxylupeol (4), betulinic acid (5), lupeol (6), heptacosan-2-one (7), triacontanoic acid (8), stigmast-4-en-3-one (9), β-sitosterol (10), stigmasterol (11), and stigmasterol-3-O-β-D-glucopyranoside (12). Their structures were elucidated with the help of their spectroscopic and physical data and by comparison with those reported in the literature. To the best of our knowledge, from all those compounds, 2,3-dihydroxypropyl hexacosanoate (1), hederagenine (2), cycloeucalenol (3), 2α-hydroxylupeol (4), and betulinic acid (5) are being reported for the first time from this genus. In addition, the acetylation of compound 1 afforded a new derivative 3-(hexacosanoyloxy)propane-1,2-diyl diacetate (1a). Compound 1 possessed a moderate α-glucosidase inhibitory activity with an IC50 value of 39.2 ± 0.22 μM; it neither showed antioxidant activity nor inhibition against the enzyme urease. Compound 1a exhibited weak antioxidant activity in the DPPH assay with an IC50 value of 80.3 ± 0.83 μM but was inactive against α-glucosidase and urease. Furthermore, both compounds 1 and 1a were inactive against seven pathogenic bacterial strains.

Triterpenoids from Acanthopanax koreanum Root and Their Inhibitory Activities on NFAT Transcription

  • Cai, Xing-Fu;Lee, Im-Seon;Shen, Guanghai;Dat, Nguyen-Tien;Lee, Jung-Joon;Kim, Young-Ho
    • Archives of Pharmacal Research
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    • 제27권8호
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    • pp.825-828
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    • 2004
  • Two triterpenoids (1,4) and two triterpenoid glycosides (2,3) were isolated from the root of Acanthopanax koreanum (Araliaceae). Their structures were identified as impressic acid (1), acankoreoside A (2), 3-epi-betulinic acid 28-O-[(${\alpha}-L-rhamnopyranosyl(1{\rightarrow}4)-{\beta}-D-glucopyrano-syl(1{\rightarrow}6)]-{\beta}-D-glucopyranosyl]$ ester (3), and ursolic acid (4) by physicochemical and spectro-scopic methods. Of these compounds, impressic acid (1) exhibited a potent inhibitory activity against NFAT transcription factor ($IC_{50}:{\;}12.65{\;}{\mu\textrm{m}}$).

Antitumor activity of organic compounds isolated from Korean mistletoe

  • Yoo, Yung-Choon;Song, Kyung-Sik;Lee, Kyung-Bok;Lee, Hoi-Young;Kim, Jong-Bae
    • 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.215.2-216
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    • 2003
  • Velutin and betulinic acid were isolated as a cytotoxic principle from the dichloromethane extract of Korean mistletoe (Viscum album var. coloratum) by repeated silicagel chromatography and recrystallization. In in vitro analysis of cytotoxic activity using NIH-3T3 cells, dichloromethane extract of Korean mistletoe was shown to be highly cytotoxic against tumor cells. And we obtained active compound (reffered to VD-2 and VD-6) from the dichloromethane extract. (omitted)

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루판 유도체의 합성 및 세포독성-II: 아미노아세칠 유도체 (Synthesis and Cytotoxic Activity-II, Aminoacetyl Derivatives)

  • 유영제;김용;뉘엥남하이;안병준
    • 약학회지
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    • 제46권5호
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    • pp.301-306
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    • 2002
  • To increase the water solubility, sixteen lupane derivatives bearing aminoacetyl moiety at C3 were synthesized. Their cytotoxic activities against three cancer cell lines, SK-MEL-2, A549, and B16, were tested. Among them, six derivatives showed significant cytotoxic activity.

상백피(Morus alba root bark)로부터 triterpenoid의 분리 및 동정 (Isolation and Identification of Triterpenoids from the Mulberry (Morus alba) Root Bark)

  • 정재우;박지해;정예진;이창호;한대석;백남인
    • Journal of Applied Biological Chemistry
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    • 제57권4호
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    • pp.295-299
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    • 2014
  • 뽕나무(Morus alba L.) 뿌리껍질을 실온에서 80% MeOH 수용액으로 추출하고 이 추출물을 EtOAC 분획, n-BuOH 분획, $H_2O$ 분획으로 나누었다. EtOAc 분획에 대하여 silica gel과 ODS column chromatography를 반복 실시하여 5종의 triterpenoid를 분리, 정제하였다. NMR, IR, 및 EI/MS 등을 해석하여, ${\alpha}$-amyrin (1), ${\alpha}$-acetyl amyrin (2), lupeol (3), betulinic acid (4) 그리고 glutinol (5)로 구조동정 하였다. 화합물 중 a-amyrin (1), lupeol (3) 그리고 glutinol (5)은 상백피로부터는 이번 실험에서 처음으로 분리되었다.

Chemicals Constituents from Leaves of Diospyros iturensis (Gürke) Letouzey & F. White and their Biological Activities

  • Feusso, Hermann Marius Feumo;Dongmo, Jean de dieu;Djomkam, Hermine Laure Maza;Akak, Carine Mvot;Lateef, Mehreen;Ahmed, Ayaz;Azebaze, Anatole Guy Blaise;Waffo, Alain Francois Kamdem;Ali, Muhammad Shaiq;Vardamides, Juliette Catherine
    • Natural Product Sciences
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    • 제26권4호
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    • pp.311-316
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    • 2020
  • The chemical investigation of the methanolic crude extract of leaves of Diospyros iturensis gave us 15 known secondary metabolites identified as mixture of α-amyrenone (1) and β-amyrenone (2), β-amyrin (3), mixture of β-sitosterol (4) and stigmasterol (5), betulin (6), uvaol (7), betulinic acid (8), ursolic acid (9), corosolic acid (10), actinidic acid (11),11-O-p-hydroxybenzoylbergenin (12), bergenin (13) and mixture of stigmasterol glucoside (14) and β-sitosterol glucoside (15) respectively. The structures of secondary metabolites were elucidated with the help of NMR and mass spectral data and by comparison of their spectral data with literature. Among the fifteen isolated compounds, four compounds were identified for the first time in Diospyros genus. These included uvaol (7), corosolic acid (10), actinidic acid (11) and 11-O-p-hydroxybenzoylbergenin (12). Crude methanolic extract of leaves and four isolated compounds including betulin (6), betulinic acid (8), 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) were evaluated for their antiproliferative activity against two cancer cell lines CAL-27 and NCI-H460 by the MTT assay, antioxidant potential and inhibitory activity against the lipoxygenase and urease enzymes, respectively. The results indicated that the methanolic crude extract of leaves exhibited moderate antioxidant activity and was inactive against the two cancer cell lines. Betulin (6), 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate antioxidant and lipoxygenase inhibition with IC50 = 65.8, 85.6, 82.5 μM and IC50 = 58.5, 95.2, 76.2 μM, respectively. Furthermore, 11-O-p-hydroxybenzoylbergenin (12) and bergenin (13) exhibited moderate urease inhibition activity with IC50 values of 45.6 μM and 49.8 μM, respectively.

Cytotoxic Terpenes and Lignans from the Roots of Ainsliaea acerifolia

  • Choi Sang-Zin;Yang Min-Cheol;Choi Sang-Un;Lee Kang-Ro
    • Archives of Pharmacal Research
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    • 제29권3호
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    • pp.203-208
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    • 2006
  • The chromatographic separation of the MeOH extract of the roots of Ainsliaea acerifolia (Compositae) led to the isolation of six known terpenes and two known lignans. Their structures were identified by spectroscopic methods as mokko lactone (1), betulonic acid (2), betulinic acid (3), zaluzanin C (4), $1{\beta}-hydroperoxygermacra-4(15)$, 5, 10(14)-triene (5), pluviatilol (6), (+)-syringaresinol (7), and glucozaluzanin C (8). Compounds $1{\sim}4$ and 8 showed non-specific significant cytotoxicity against five human tumor cell lines with $ED_{50}$ values ranging from $0.36{\sim}5.54{\mu}g/mL$.

Tectona grandis Callus Produces Antibacterial Triterpene Acids Not Detected in the Intact Plant

  • Marwani, Erly;Kobayashi, Akio;Kajiyama, Shin-ichiro;Fukusaki, Eiichiro;Nitoda, Teruhiko;Kanzaki, Hiroshi;Kawazu, Kazuyoshi
    • Natural Product Sciences
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    • 제3권1호
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    • pp.75-80
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    • 1997
  • Preliminary antibacterial assay data that the Tectona grandis callus extract showed more antibacterial activity against E. coli and B. subtilis than the leaf extract led the authors to isolate the following antibacterial compounds from the callus. A mixture (3) of $2{\alpha},3{\beta}-dihydroxy-olean-12-en-28-oic$ acid (3a) and $2{\alpha},3{\beta}-dihydroxy-urs-12-en-28-oic$ acid (3b) exhibited the most potent antibacterial activity against both bacteria. The other 3 compounds, in the decreasing order of the activity, were identified as $2{\alpha},3{\beta}-dihydroxy-urs-12-en-28-oic$ acid (2), betulinic acid (1), and $2{\alpha},3{\alpha}$,23-trihydroxy-urs-12-en-28-oic acid (4). The antibacterial compounds (2, 3a, 3b and 4) were not detected or occurring in small quantities in the intact tissue, while they were observed in the callus. Only the less active compound 1 was present more abundantly in intact tissues than the callus.

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