CAS: 6754-13-8; Helenalin

该化合物是一种自然产生的松树脂内酯,主要产自植物物种 *Arnica montana* 和阿斯特雷莎家族其他成员,其特征为黄色晶状外观,分子分子配方为C15H18O3. 海伦娜林展示了一系列生物活动,包括抗炎,止痛和抗微生物特性,使其对药理研究感兴趣.人们认为,其行动机制包括抑制亲炎细胞细胞和各种信号路径.此外,还研究了helenalin的潜在抗癌作用,因为它在某些癌症细胞线上可诱发流行.但是,必须指出, helenalin在高浓度时也表现出细胞毒性,这需要在治疗应用中加以仔细考虑.由于其生物活性,Helenalin经常在草药和天然产品化学中被探索.

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上下游产品

-furan-2(3H)-one(3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-°Ctahydro-4,5-dihydroxy-3-methylene-4a,8-dimethylazuleno6,5-b-furan-2(3H)-one -azylenofuran-2(3H)-one(3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-°Ctahydro-8-hydroxy-4a,8-dimethyl-4-(tetrahydro-2H-pyran-2-yl)oxy-azyleno6,5-bfuran-2(3H)-one (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-°Ctahydro-azuleno[6,5-b]furan-2,4-dione (3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-°Ctahydro-3H-azuleno[6,5-b]furan-2-one2,3-epoxyhelenalin bis(helenalinyl) glutarate helenalin acetate bis(helenalinyl) malonate

合成工艺路线路线简述

    📜(3Aα,4α,4Aβ,5β,7Aα,8α,9Aα)-3A,4,4A,5,7A,8,9,9A-octahydro-3-(Hydroxymethyl)-4A,8-Dimethyl-4,5-Bis<(Tetrahydro-2H-Pyran-2-yl)Oxy>Azuleno<6,5-B>Furan-2(3H)-One置于manganese(Iv) Oxide,1,8-二氮杂双环[5.4.0]十一碳-7-烯体系中,用 吡啶,二氯甲烷,水,溶剂黄146,苯 作为反应溶剂,化学反应 10.0H,反应生成 心菊内酯
    参考文献:Pseudoguaianolides. 2. Stereocontrolled Total Synthesis Of The Helenanolide Dl-Helenalin
    标题:Pseudoguaianolides. 2. Stereocontrolled Total Synthesis Of The Helenanolide Dl-Helenalin
    摘要:
    DOI:10.1021/ja00379A030

    海关参考信息

    专利信息


    专利号:US-12098115-B2
    优先权日:2016-09-15
    标 题:Methods and compositions for terpenoid synthesis
    发明人:GRENNING ALEXANDER JAMES
    权利人:UNIV FLORIDA
    摘要:In one aspect, the disclosure relates to methods for preparation of terpene and terpene-like molecules. In a further aspect, the disclosure relates to the products of the disclosed methods, i.e., terpene and terpene-like molecules prepared using the disclosed methods. Intermediates for the synthesis of a wide variety of terpenoids are γ-allyl Knoevenagel adducts or quasi γ-allyl Knoevenagel adducts are disclosed. In various aspects, methods of preparing terpenoids through these intermediates are disclosed. The methods can comprise α-alkylation of an allylic electrophile followed by ring-closure metathesis to a polycyclic terpenoid structure. In a further aspect, the disclosure pertains to terpenoid frameworks, and compounds prepared via disclosed oxidation and substitution reactions on the disclosed terpenoid frameworks. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

    专利号:US-12435055-B2
    优先权日:2019-08-06
    标 题 :3-methylideneoxan-4-one compounds and substituted derivates thereof as inhibitors of telomerase
    发明人:SCHEIDT KARL A; BETORI RICK C
    权利人:UNIV NORTHWESTERN
    摘要:Disclosed are 3-methylideneoxan-4-one compounds, derivatives thereof, and methods of their synthesis and methods of their use in treating a disease or disorder in a subject in need thereof, such as diseases and disorders that are associated with telomerase activity such as cancer. The disclosed compounds may be formulated in a pharmaceutical composition for treating diseases and disorders that are associated with telomerase activity such as cancer.

    专利号:CN-114957174-A
    优先权日:2022-05-26
    标 题:A kind of alkyl-substituted α-methylene-γ-butyrolactone derivative and synthesis method thereof

    专利号:WO-9411382-A1
    优先权日:1992-11-09
    标题 :Antineoplastic heteronaphthoquinones
    发明人:ATTARDO GIORGIO; BREINING TIBOR; COURCHESNE MARC; KRAUS JEAN-LOUIS; LAMOTHE SERGE; LAVALLEE JEAN-FRANCOIS; LEBEAU ELAINE; NGUYEN DIEU; REJ RABINDRA; ST-DENIS YVES; WANG WUYI; XU YAO-CHANG; BARBEAU FRANCE
    权利人:IAF BIOCHEM INT; ATTARDO GIORGIO; BREINING TIBOR; COURCHESNE MARC; KRAUS JEAN LOUIS; LAMOTHE SERGE; LAVALLEE JEAN FRANCOIS; LEBEAU ELAINE; NGUYEN DIEU; REJ RABINDRA; ST DENIS YVES; WANG WUYI; XU YAO CHANG; BARBEAU FRANCE
    摘要:Tricyclic heteronaphthoquinone derivatives, that have antineoplastic activity, are disclosed, together with processes for their synthesis. Some of these anti-neoplastics compounds have a saccharide moiety. Some members of this structurally distinct group exhibit activity against multiple drug resistant cancer cells.

    专利号:US-7544375-B1
    优先权日:2006-06-12
    标 题:Composition
    发明人:BELLIN HOWARD T; DE BORG BEATRICE
    权利人:SWISS SKIN REPAIR INC
    摘要:A topically applied composition or cream for treatment of the skin. A preferred composition includes a) a skin plumper; b) a tetrapeptide; c) a soya plant extract; d) Centella Asiatica extract; e) a cosmetic soothing or anti-inflammatory component; f) a component that acts on fibronectin synthesis; g) a moisturizing component; h) a structured conditioning component; i) an emulsifier component; and j) a transdermal delivery agent.

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Li Y, Zeng Y, Huang Q, Wen S, Wei Y, Chen Y, Zhang X, Bai F, Lu Z, Wei J, Lin X. Retraction notice to "Helenalin from Centipeda minima ameliorates acute hepatic injury by protecting mitochondria function, activating Nrf2 pathway and inhibiting NF-κB activation" [Biomed. Pharmacother. 119 (2019) 109435]. Biomed Pharmacother. 2024 Dec;181:117697. doi: 10.1016/j.biopha.2024.117697. Epub 2024 Dec 9.
    178:106195. doi: 10.1016/j.fitote.2024.106195. Epub 2024 Aug 31. 398(2):1597-1612. doi: 10.1007/s00210-024-03353-8. Epub 2024 Aug 12.
    4: Petrova M, Miladinova-Georgieva K, Geneva M. Influence of Abiotic and Biotic Elicitors on Organogenesis, Biomass Accumulation, and Production of Key Secondary Metabolites in Asteraceae Plants. Int J Mol Sci. 2024 Apr 10;25(8):4197. doi: 10.3390/ijms25084197.

    合成参考文献


    摘要:American Journal of Veterinary Research., 37(859), 1976 []
    摘要:Pharmazie in Unserer Zeit., 10(1), 1981 []
    摘要:HALL IH ET AL; ANTIHYPERLIPIDEMIC ACTIVITY OF SESQUITERPENE LACTONES AND RELATED COMPOUNDS; J PHARM SCI 69(6) 694 (1980)
    摘要:WITZEL DA ET AL; MAMMALIAN TOXICITY OF HELENALIN, THE TOXIC PRINCIPLE OF HELENIUM MICROCEPHALUM DC (SMALLHEAD SNEEZEWEED); AM J VET RES 37(7) 859 (1976)
    参考文献:10.1016/j.reprotox.2006.04.011
    摘要:Supornsilchai V, Söder O, Svechnikov K. Sesquiterpene lactone helenalin suppresses Leydig and adrenocortical cell steroidogenesis by inhibiting expression of the steroidogenic acute regulatory protein. Reprod Toxicol. 2006 Nov;22(4):631–5. doi: 10.1016/j.reprotox.2006.04.011.
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