CAS: 472-15-1; (1R,3As,5Ar,5Br,7Ar,9S,11Ar,11Br,13Ar,13Br)-9-Hydroxy-5A,5B,8,8,11A-Pentamethyl-1-(Prop-1-En-2-yl)Icosahydro-1H-Cyclopenta[a]Chrysene-3A-Carboxylic Acid

该化合物是来自某些树皮的三叶类化合物,表现出强效抗炎和抗氧化特性. 其主要优势包括有效抑制梅氏发芽,强抗微生物活性以及作为抗癌剂的潜在用途,为进一步研究药物应用提供了有希望的渠道.

结构式图片

相似化合物

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CAS号13159-28-9 白桦脂醛 | CAS号473-98-3 白桦脂醇; 桦木醇 | CAS号4481-62-3 路路通酸 | CAS号10376-50-8 3Beta-乙酰氧基白桦酸 | CAS号135757-66-3 lup-20(29)-en-2... | CAS号22333-85-3 28-O-β-D-glucop... | CAS号27570-20-3 Betulin-3-acetate | CAS号1125546-06-6 28-O-β-glucuron... | CAS号80832-44-6 圆齿火棘酸 | CAS号473-98-3 白桦脂醇; 桦木醇 | CAS号13159-28-9 白桦脂醛 | CAS号4481-62-3 路路通酸 | CAS号85999-40-2 23-羟基白桦酸 | CAS号174022-42-5 贝韦立马 | CAS号174740-41-1 3-[[(1R,3aS,5aR... | CAS号2131-43-3 1,2,5,6-四甲基萘

合成工艺路线路线简述

    β-D-Glucopyranosyl 3β-Hydroxylup-20(29)-En-28-Oate置于enzyme β-Glucosidase体系中,用 N,N-二甲基甲酰胺 作为反应溶剂,化学反应 72.0H,反应生成 白桦脂酸
    参考文献:Glucosidation Of Betulinic Acid By Cunninghamella Species
    标题:Glucosidation Of Betulinic Acid By Cunninghamella Species
    摘要:Microbial Transformation Of The Antimelanoma Agent Betulinic Acid (1) Was Studied. Preparative Scale Biotransformation With Resting-Cell Suspensions Of Cunninghamella Species Nrrl 5695 Resulted In The Production Of A Fungal Metabolite Of 1,Which Has Been Characterized As 28-O-Beta-D-Glucopyranosyl 3 Beta-Hydroxy-Lup-20(29)-En-28-Oate (2) Based On Spectral And Enzymic Data. The In Vitro Cytotoxicity Assay Of Metabolite 2 Revealed No Activity Against Several Human Melanoma Cell Lines.
    DOI:10.1021/np980432B

    专利信息


    专利号:US-8865935-B2
    优先权日:2011-06-30
    标题:Purification methods for betulonic acid and Boc-lysinated betulonic acid, and organic synthesis of betulonic acid amides with piperazine derivatives
    发明人:CHUE KUCK-TACK; KIM TAE-HWAN; TEN LEONID
    权利人:CHUE KUCK-TACK; KIM TAE-HWAN; TEN LEONID; KOREA ENERGY RESEARCH INST
    摘要:The present invention provides a method of purifying betulonic acid contained the reaction product of organic synthesis of a Jones oxidation reagent and betulin extracted from the bark of a birch, a method of preparing a piperazine betulonic acid amide derivative, which is used as a chemical having an antibacterial function, using the high-purity betulonic acid obtained by the purification method and a derivative prepared by this method, a method of purifying a Boc-lysinated betulonic acid monomer ester contained in the reaction product of organic synthesis of lysine and the high-purity betulonic acid (starting material) obtained by the purification method, and a method of purifying Boc-lysinated betulonic acid contained in the reaction product of hydrolysis of the high-purity Boc-lysinated betulonic acid monomer ester.

    专利号:WO-2017100796-A1
    优先权日:2015-12-11
    标 题 :Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
    发明人:WONG CHI-HUEY; HSU TSUI-LING; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI
    权利人:SINACA ACAD; WONG CHI-HUEY; HSU TSUI-LING
    摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta- 4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for disgnostic and therapeutic uses.

    专利号:US-2014206842-A1
    优先权日:2013-01-22
    标题:Peptides Modified with Triterpenoids and Small Organic Molecules: Synthesis and use in Cosmeceutical
    发明人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; CHANDRAMOULI RENUKESHWAR H; SOOD RATTAN; PRAKASH SUBBALAKSHMI; ANAND SUSMITHA
    权利人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; CHANDRAMOULI RENUKESHWAR H; SOOD RATTAN; PRAKASH SUBBALAKSHMI; ANAND SUSMITHA
    摘要:The present invention relates to the Synthesis of Triterpenoid peptides and mechanism of action for Anti ageing and skin care. The present invention is directed towards anti-aging skin care compositions comprising peptides which are made by linking herbal actives to a pentapeptide for enhanced anti ageing activity by regenerating the dermal matrix. In detail, the present invention relates to the Synthesis of Triterpenoid peptides, providing an enhanced and synergistic activity for reducing the consequences of ageing such as appearance of fine expression lines and wrinkles on the skin by cosmetic modes of application. The Triterpenoid peptides of the present invention with its novel dual action mode can be used for skin ageing & collagen insufficiency. Its Triterpenoid group acts by preventing oxidation and excess activity of serine proteases like elastase and collagenase that result in wrinkling of skin. With added peptides which boost the collagen and other matrix protein, Triterpenoid peptides provide a complete protection against pre mature ageing and functions as a best anti ageing ingredient.

    专利号:US-2017283878-A1
    优先权日:2015-12-11
    标题:Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
    发明人:WONG CHI-HUEY; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI; HSU TSUI-LING
    权利人:ACADEMIA SINICA
    摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta-4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for diagnostic and therapeutic uses.

    专利号:US-8383594-B2
    优先权日:2007-08-07
    标题:Peptides modified with triterpenoids and small organic molecules: synthesis and use in cosmeceuticals
    发明人:MAJEED MUHAMMED; CHANDRAMOULI RENUKESHWAR H; NAGABHUSHANAM KALYANAM; SOOD RATTAN; PRAKASH SUBBALAKSHMI; ANAND SUSMITHA
    权利人:SAMI LABS LTD; MAJEED MUHAMMED; CHANDRAMOULI RENUKESHWAR H; NAGABHUSHANAM KALYANAM; SOOD RATTAN; PRAKASH SUBBALAKSHMI; ANAND SUSMITHA
    摘要:The present invention relates to the Synthesis of Triterpenoid peptides and mechanism of action for Anti ageing and skin care. The present invention is directed towards anti-aging skin care compositions comprising peptides which are made by linking herbal actives to a pentapeptide for enhanced anti ageing activity by regenerating the dermal matrix. In detail, the present invention relates to the synthesis of Triterpenoid peptides, providing an enhanced and synergistic activity for reducing the consequences of ageing such as appearance of fine expression lines and wrinkles on the skin by cosmetic modes of application. The Triterpenoid peptides of the present invention with its novel dual action mode can be used for skin ageing & collagen insufficiency. Its Triterpenoid group acts by preventing oxidation and excess activity of serine proteases like elastase and collagenase that result in wrinkling of skin. With added peptides which boost the collagen and other matrix protein, Triterpenoid peptides provide a complete protection against pre mature ageing and functions as a best anti ageing ingredient.

    专利号:US-10342858-B2
    优先权日:2015-01-24
    标题 :Glycan conjugates and methods of use thereof
    发明人:WONG CHI-HUEY; WU CHUNG-YI
    权利人:ACADEMIA SINICA
    摘要:The present disclosure is directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA3/SSEA4/GloboH associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globo-series glycosphingolipid synthesis. The present disclosure relates to methods and compositions which can modulate the globo-series glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globo-series glycosphingolipid SSEA3/SSEA4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta-4GalNAcT-I; or beta-3GalT-V enzymes in the globo-series synthetic pathway. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions.
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    主要参考文献


    1: Chaouki W, Leger DY, Eljastimi J, Beneytout JL, Hmamouchi M. Antiproliferative effect of extracts from Aristolochia baetica and Origanum compactum on human breast cancer cell line MCF-7. Pharm Biol. 2010 Mar;48(3):269-74. Epub 2010 Jun 1.
    5: Cheng MJ, Chen JJ, Wu MD, Yang PS, Yuan GF. Isolation and structure determination of one new metabolite isolated from the red fermented rice of Monascus purpureus. Nat Prod Res. 2010 Jun;24(10):979-88. Epub 2010 May 7. Epub 2010 Apr 18. Epub 2010 Apr 20.
    9: da Silveira CV, Trevisan MT, Rios JB, Erben G, Haubner R, Pfundstein B, Owen RW. Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart. Food Chem Toxicol. 2010 Jun;48(6):1597-606. Epub 2010 Mar 27. Betulinic Acid a Radiosensitizer in Head and Neck Squamous Cell Carcinoma Cell Lines. Strahlenther Onkol. 2010 Feb 22. [Epub ahead of print]

    合成参考文献


    参考文献:10.3390/molecules16076010
    摘要:Yang ZG, Matsuzaki K, Takamatsu S, Kitanaka S. Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells. Molecules. 2011 Jul 19;16(7):6010–22.
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