CAS: 19121-58-5; Solasonine

该化合物是主要在索拉纳塞亚家族某些物种,特别是苦薯等植物和一些茄子品种中发现的甘蓝碱,其特点是结构复杂,包括典型与氮原子有关的血清脊柱和甘蔗味;Solasonine展示了一系列生物活动,包括潜在的抗风素和杀虫性能,有助于植物的防御机制;然而,它也有其毒性,因为高浓度可对人类和动物造成有害健康影响,包括胃肠扰动和...

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合成工艺路线路线简述

    在 水,Sodium Hydroxide体系中,用 甲醇,二氯甲烷 用作溶剂,化学反应 10.0H,以45%的收率获得澳洲茄碱
    参考文献:螺甾碱烷型糖苷生物碱的合成方法
    标题:螺甾碱烷型糖苷生物碱的合成方法
    摘要:本发明公开了一种螺甾碱烷型糖苷生物碱汇聚式化学合成方法,该方法包括如下步骤:(A)将3位羟基用硅基或酰基保护的螺甾皂苷元(II)转化为相应的16乙酰氧基22羰基26羟基胆甾烷(III);(B)3位羟基用硅基或酰基保护的16乙酰氧基22羰基26磺酸酯胆甾烷的制备(Iv);(C)3位羟基用硅基或酰基保护的16乙酰氧基22羰基26叠氮基胆甾烷的制备(V);(D)螺甾碱烷型皂苷元(Vi)的制备;(E)酰基保护螺甾碱烷型糖苷生物碱的制备(Vii);(F)螺甾碱烷型糖苷生物碱(I)的制备.本发明的制备方法工艺简单,收率高,具有较强的实用价值.

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    专利信息


    专利号:US-7435816-B2
    优先权日:2003-04-30
    标 题 :Synthesis of solanum glycosides
    发明人:SHAHID MOHAMMED
    权利人:SHAHID MOHAMMED
    摘要:The present invention relates to the chemical synthesis of solanum glycosides, in particular to the synthesis of solasonine as well as to novel β-monosaccharide intermediate compounds, of Formula (2), where R 1 is a benzylidene, 4-nitrobenzylidene or 4-methoxybenzylidine group, and each R 2 independently is a benzoyl, acetyl or pivaloyl group:

    专利号:EP-1421100-B1
    优先权日:2001-08-21
    标 题 :Chemical synthesis of solamargine
    发明人:SHAHID MOHAMMED
    权利人:GLYCOMED SCIENCES LTD
    摘要:The present invention relates to the chemical synthesis of solanum glycosides, in particular to the synthesis of solamargine as well as to novel beta-monosaccharide Intermediate compounds.

    专利号:US-2009012013-A9
    优先权日:2003-07-08
    标题 :Steroid modified solatrioses
    发明人:LAWSON CHRISTOPHER J; WEYMOUTH-WILSON ALEXANDER C
    权利人:LAWSON CHRISTOPHER J; WEYMOUTH-WILSON ALEXANDER C
    摘要:The invention pertains to steroid modified solatrioses and the synthesis thereof as well as to intermediate compounds useful for the synthesis of the steroid modified solatrioses.

    专利号:EP-1654271-B1
    优先权日:2003-07-08
    标题:Steroid modified solatrioses
    发明人:LAWSON CHRISTOPHER JOHN; WEYMOUTH-WILSON ALEXANDER CHARLES
    权利人:GLYCOMED SCIENCES LTD
    摘要:The present invention relates to steroid modified chacotrioses and the synthesis thereof as well as to intermediate compounds useful for the synthesis of the steroid modified chacotrioses and solatrioses. Moreover, the present inventions relates to a method for the preparation of steroid-modified solatrioses.

    专利号:US-2004024230-A1
    优先权日:2002-04-29
    标 题:Synthesis of cyproterone acetate

    专利号:US-2006211873-A1
    优先权日:2002-04-29
    标 题 :Synthesis of cyproterone acetate
    发明人:MANOSROI ARANYA; MANOSROI JIRADEJ; BUDDHASUKH DUANG; SRIPALAKIT PATTANA; MAIER ROLAND; WERNER ROLF G
    权利人:BOEHRINGER INGELHEIM INT
    摘要:The present invention relates to improved methods for synthesising cyproterone acetate (17α-Acetoxy-6-chloro-1α, 2(α-methylene-4,6-pregnadiene-3,20-dione) from solasodine.
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    主要参考文献


    1: Huang W, Wang Y, Zhu H, Wu Y, Xie X, Wang D. [Solasonine-induced Apoptosis in Lung Cancer Cell Line H446 and Its Mechanism]. Zhongguo Fei Ai Za Zhi. 2015 Jul;18(7):416-21. doi: 10.3779/j.issn.1009-3419.2015.07.05. Chinese.
    2: Chen Y, Zhang S, Chen D, Zhou M, Zheng J, Xiang Z. An UPLC-MS/MS method for determination of solasonine in rat plasma and its application of a pharmacokinetic and bioavailability study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 15;985:1-5. doi: 10.1016/j.jchromb.2015.01.017. Epub 2015 Jan 23. pii: E1364. doi: 10.1007/s11418-013-0757-0. Epub 2013 Mar 10. doi: 10.1021/jf100709g. doi: 10.1128/AAC.02804-15. Print 2016 May.
    8: Fewell AM, Roddick JG, Weissenberg M. Interactions between the glycoalkaloids solasonine and solamargine in relation to inhibition of fungal growth. Phytochemistry. 1994 Nov;37(4):1007-11. doi: 10.1021/acs.jafc.5b00818. Epub 2015 Mar 30. Review. German. doi: 10.1002/cbdv.201200063. doi: 10.1016/j.ejpb.2014.01.010. Epub 2014 Feb 6. eCollection 2017.

    合成参考文献


    参考文献:10.1055/s-2006-961733
    摘要:Schulz D, Eilert U, Willker W, Leibfritz D, Ehmke A. Steroidal Glycoalkaloids fromSolanum triflorum. Planta Med. 1992 Dec;58(S 1):707. doi: 10.1055/s-2006-961733.
    参考文献:10.1021/jf00120a019
    摘要:Eldridge AC, Hockridge ME. High-performance liquid chromatographic separation of Eastern black nightshade (Solanum ptycanthum) glycoalkaloids. J. Agric. Food Chem. 1983 Nov;31(6):1218–20. doi: 10.1021/jf00120a019.
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