CAS: 465-99-6; Hederagenin

该化合物是一种与若干植物物种隔离的三叶虫状沙邦宁化合物,其主要优势包括表现出各种临床前期研究所证明的强效抗炎和抗氧化性特性. 这种化合物在治疗炎症和氧化性压力相关条件方面可能提供治疗用途.

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合成工艺路线路线简述

    Hederagenin-Methylester-3-Acetat置于lithium Bromide体系中,用 N,N-二甲基甲酰胺 作为反应溶剂,化学反应 48.0H,以90%的收率获得产物常春藤皂苷元
    参考文献:Remote Hydroxylation Of Methyl Groups By Regioselective Cyclopalladation. Partial Synthesis Of Hyptatic Acid-A
    标题:Remote Hydroxylation Of Methyl Groups By Regioselective Cyclopalladation. Partial Synthesis Of Hyptatic Acid-A
    摘要:Hyptatic Acid-A (32),A 2 Alpha,3 Beta,24-Trihydroxyolean-12-En-28-Oic Acid,Previously Isolated From Hyptis Capitata,Was Obtained From Maslinic Acid (2). The Regioselective Cyclopalladation Of The Axial Methyl Group On C-4 Of Maslinic Acid Afforded The C-24 Hydroxymethylene Group Due To The Presence Of A C-2-Or Substituent. Nevertheless,Hederagenin (7) (23-Hydroxy Derivative) Was Formed When This Oxygenated Group Was Not Present.
    DOI:10.1021/jo070116E

    海关参考信息

    专利信息


    专利号:US-2022162188-A1
    优先权日:2019-01-15
    标 题:Isoprenoids and methods of making thereof
    发明人:WILLIAMS GAVIN; LUND SEAN; HALL RACHAEL
    权利人:UNIV NORTH CAROLINA STATE
    摘要:Disclosed are methods for preparing isoprenoid subunits, as well as methods of employing these isoprenoid subunits for the synthesis of isoprenoids. Also provided are isoprenoids prepared using the methods described herein.

    专利号:US-12187755-B2
    优先权日:2014-05-30
    标题 :Minimal saponin analogues, synthesis and use thereof
    发明人:GIN DAVID Y; CHEA ERIC K; FERNANDEZ-TEJADA ALBERTO; TAN DEREK S; LEWIS JASON S; GARDNER JEFFREY R; PILLARSETTY NAGAVARAKISHORE
    权利人:MEMORIAL SLOAN KETTERING CANCER CENTER
    摘要:Truncated triterpene saponin analogues containing a trisaccharide or tetrasaccharide ester are disclosed. Also disclosed are pharmaceutical compositions comprising truncated saponin analogues and synthetic methods of producing the truncated saponin analogues. Another aspect of the present application relates to a method for immunizing a subject, comprising administering to the subject the pharmaceutical composition comprising a minimal saponin analogue and an antigen.

    专利号:CN-116445442-A
    优先权日:2023-01-07
    标题:UDP-glycosyltransferase and application thereof in synthesis of alpha-hederacoside glycoside compound
    南京春秋生物工程有限公司
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    主要参考文献


    1: Han JY, Chun JH, O SA, Park SB, Hwang HS, Lee H, Choi YE. Transcriptomic analysis of Kalopanax septemlobus and characterization of KsBAS, CYP716A94, and CYP72A397 genes involved in hederagenin saponin biosynthesis. Plant Cell Physiol. 2017 Nov 24. doi: 10.1093/pcp/pcx188. [Epub ahead of print] doi: 10.1016/j.ejmech.2017.09.016. Epub 2017 Oct 7. doi: 10.1016/j.ejmech.2017.09.045. Epub 2017 Sep 22. pii: E41. doi: 10.3390/nu9010041.
    5: Wu AG, Zeng W, Wong VK, Zhu YZ, Lo AC, Liu L, Law BY. Hederagenin and α-hederin promote degradation of proteins in neurodegenerative diseases and improve motor deficits in MPTP-mice. Pharmacol Res. 2017 Jan;115:25-44. doi: 10.1016/j.phrs.2016.11.002. Epub 2016 Nov 9. doi: 10.1080/10286020.2016.1232252. Epub 2016 Sep 26. doi: 10.1016/j.ejmech.2016.08.030. Epub 2016 Aug 17. doi: 10.1002/bmc.3801. Epub 2016 Aug 21. doi: 10.1002/open.201500149. eCollection 2015 Dec.
    10: Rodríguez-Hernández D, Demuner AJ, Barbosa LC, Heller L, Csuk R. Novel hederagenin-triazolyl derivatives as potential anti-cancer agents. Eur J Med Chem. 2016 Jun 10;115:257-67. doi: 10.1016/j.ejmech.2016.03.018. Epub 2016 Mar 9. doi: 10.1016/j.phytochem.2015.12.016. Epub 2016 Jan 19. doi: 10.1155/2015/456354. Epub 2015 Oct 19.

    合成参考文献


    摘要:Indian Journal of Medical Research., 58(724), 1970
    参考文献:10.1007/bf02976370
    摘要:Kim SY, Son KH, Chang HW, Kang SS, Kim HP. Inhibition of mouse ear edema by steroidal and triterpenoid saponins. Arch Pharm Res. 1999 Jun;22(3):313–6. doi: 10.1007/bf02976370.
    参考文献:10.1007/bf02976371
    摘要:Oh SR, Jung KY, Son KH, Park SH, Lee IS, Ahn KS, Lee HK. In vitro anticomplementary activity of hederagenin saponins isolated from roots of Dipsacus asper. Arch Pharm Res. 1999 Jun;22(3):317–9. doi: 10.1007/bf02976371.
    参考文献:10.1016/s0031-9422(01)00180-7
    摘要:Gu JQ, Park EJ, Luyengi L, Hawthorne ME, Mehta RG, Farnsworth NR, Pezzuto JM, Kinghorn AD. Constituents of Eugenia sandwicensis with potential cancer chemopreventive activity. Phytochemistry. 2001 Sep;58(1):121–7. doi: 10.1016/s0031-9422(01)00180-7.
    参考文献:10.1007/bf02975104
    摘要:Park HJ, Kwon SH, Han YN, Choi JW, Miyamoto K, Lee SH, Lee KT. Apoptosis-Inducing costunolide and a novel acyclic monoterpene from the stem bark of Magnolia sieboldii. Arch Pharm Res. 2001 Aug;24(4):342–8. doi: 10.1007/bf02975104.
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