CAS: 105471-98-5; ((2R,3S,4S,5R,6R)-6-(3,4-Dihydroxyphenethoxy)-3,4,5-Trihydroxytetrahydro-2H-Pyran-2-yl)Methyl (E)-3-(3,4-Dihydroxyphenyl)Acrylate

该化合物是自然形成的化学化合物,被归类为苯球甘蓝,主要来自Calceolaria genus的植物,这些植物以其观赏花和潜在的药用特性著称.该化合物具有复杂的结构,包括一种与苯球甘蓝相连的糖浆,有助于其生物活动.Calceolarioside B 已经研究过其潜在的抗氧化剂和抗炎效应,这可能是由于它能够对自由基和各种生物化学途径进行调控.此外,它可能表现出抗微生物特性,使其在药理研究中引起兴趣.该化合物的溶性性和稳定性可因环境条件而变化,影响其生物利用性和生物系统的效率.总的来说, Calceolarioside B是天然产品化学中的一个重要研究领域,对治疗应用和了解植物二次代谢物都具有影响.

结构式图片

物理性质

MSDS等安全信息

上下游产品

p-tolyl 6-O-[(E)-3,4-bis-(O-tert-butyldimethylsilyl)-caffeoyl]-3-O-allyl-2,4-di-O-(2-naphthyl)methyl-1-thio-β-D-glucopyranoside 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl-6-O-[(E)-3,4-bis-(O-tert-butyldimethylsilyl)caffeoyl]-3-O-allyl-2,4-di-O-(2-naphthyl)methyl-β-D-glucopyranose p-tolyl 3-O-allyl-2,4-di-O-(2-napthyl)methyl-1-thio-β-D-glucopyranoside (E)-3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)acrylic acidD-Glucose caffeic acid Methyl caffeate β-(3,4-dihydroxyphenyl)-ethyl-O-β-D-glucopyranoside

合成工艺路线路线简述

    📜(E)-3-(3,4-Bis((Tert-Butyldimethylsilyl)Oxy)Phenyl)Acrylic Acid置于氯化亚砜,四丁基氟化铵,二甲基二氯化锡,N,N-二异丙基乙胺体系中,用 四氢呋喃,二氯甲烷 用作溶剂,化学反应 32.0H,反应生成木通苯乙醇苷b
    参考文献:苯丙烷类糖苷calceolarioside-B和eutigoside-A的短合成
    标题:苯丙烷类糖苷calceolarioside-B和eutigoside-A的短合成
    摘要:描述了以高的总收率方便地进行四步合成钙黄绿藻糖苷-B 1和洋红甙-A 2的方法.关键步骤涉及使用未反应的2-苯基乙基-β-D-葡萄糖苷5A-B与肉桂酰氯6A-B的区域选择性,Me 2 Sncl 2催化的o-6酰化,产率极高.在o-6的酰化作用对所用的酰氯是选择性的.这项工作为方便合成在o-6上酰化的苯丙烷类糖苷提供了模型.
    Doi:10.1016/j.Tetlet.2016.11.116

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    专利信息


    专利号:CN-110215517-A
    优先权日:2019-04-12
    标 题 :Application of signal pathway signal inhibitor or protein synthesis inhibitor or madecassoside in preparation of medicine for treating osteoporosis

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    主要参考文献

    参考标题:A General Synthetic Strategy And The Anti-Proliferation Properties On Prostate Cancer Cell Lines For Natural Phenylethanoid Glycosides
    作者:Shaheen K. Mulani,Jih-Hwa Guh,Kwok-Kong Tony Mong
    摘要:A General Strategy For The Synthesis Of Phenylethanoid Glycosides (Phg) Including Echinacoside 1, Acteoside 2, Calceolarioside-A 3 And Calceolarioside-B 4 Is Reported. The Strategy Features The Application Of Low Substrate Concentration Glycosylation And N-Formyl Morpholine Modulated Glycosylation Methods For The Construction Of 1,2-Trans β- And α-Glycosidic Bonds. The Reported Strategy Does Not Invoke The Use Of The Participatory Acyl Protecting Function, Which Is Incompatible With The Ester Function Present In Target Phg Compounds. A Preliminary Study Of The Anti-Proliferation Properties Of The Phg Compounds 1-4 Was Performed; The Acteoside 2 Exhibited The Best Inhibition On The Prostatic Cancer Cell Proliferation.

    合成参考文献


    参考文献:10.1248/cpb.41.1649
    摘要:TANAHASHI T, SHIMADA A, NAGAKURA N, INOUE K, KUWAJIMA H, TAKAISHI K, CHEN C, HE Z, YANG C. Isolation of Oleayunnanoside from Fraxinus insularis and Revision of Its Structure to Insularoside-6'''-O-.BETA.-D-glucoside. Chem. Pharm. Bull. 1993;41(9):1649–51. doi: 10.1248/cpb.41.1649.
    参考文献:10.1016/s0031-9422(00)84720-2
    摘要:Shimomura H, Sashida Y, Adachi T. Cyanogenic and phenylpropanoid glucosides from Prunus grayana. Phytochemistry. 1987 Jan;26(8):2363–6. doi: 10.1016/s0031-9422(00)84720-2.
    参考文献:10.1016/0305-1978(94)00088-x
    摘要:Di Fabio A, Bruni A, Poli F, Garbarino JA, Chamy MC, Piovano M, Nicoletti M. The distribution of phenylpropanoid glycosides in Chilean calceolaria Spp. Biochemical Systematics and Ecology. 1995 Mar;23(2):179–82. doi: 10.1016/0305-1978(94)00088-x.
    参考文献:10.1016/s0031-9422(00)82474-7
    摘要:Matsumoto M, Koga S, Shoyama Y, Nishioka I. Phenolic glycoside composition of leaves and callus cultures of Digitalis purpurea. Phytochemistry. 1987 Jan;26(12):3225–7. doi: 10.1016/s0031-9422(00)82474-7.
    参考文献:10.1101/2023.02.14.528433
    摘要:Balcke GU, Vahabi K, Giese J, Finkemeier I, Tissier A. The Arabidopsis Concert of Metabolic Acclimation to High Light Stress. (). doi: 10.1101/2023.02.14.528433.
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