CAS: 50932-20-2; (1As,1Bs,2S,5Ar,6S,6As)-1A-(Hydroxymethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-yl)Oxy)-1A,1B,2,5A,6,6A-Hexahydrooxireno[2',3':4,5]Cyclopenta[1,2-C]Pyran-6-Yl 3,4-Dihydroxybenzoate
- 英文名称(1As,1Bs,2S,5Ar,6S,6As)-1A-(Hydroxymethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-2-yl)Oxy)-1A,1B,2,5A,6,6A-Hexahydrooxireno[2',3':4,5]Cyclopenta[1,2-C]Pyran-6-Yl 3,4-Dihydroxybenzoate
- 中文名称毛蕊花糖苷
- IUPAC名称(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-6-yl 3,4-dihydroxybenzoate
- 其它别名Verproside - ; Verproside, >= (Lc/ms-Elsd); Protocatechuoyl Catalpol; Beta-D-Glucopyranoside, 6-((3,4-Dihydroxybenzoyl)Oxy)-1A,1B,2,5A,6,6A-Hexahydro-1A-(Hydroxymethyl)Oxireno(4,5)Cyclopenta(1,2-C)Pyran-2-Yl, (1As-(1Aalpha,1Bbeta,2Bet
- CAS编号50932-20-2
- MFCD编号:MFCD02259447
- EINECS号:803-857-6
- FDA UNII编号:96K9991JMW
- 分子式:C22H26O13分子量:498.44
- 产品CID: 1498074
- 产品分类生物化工 → 中草药成分
MSDS等安全信息
欧盟法规
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longifolioside A合成工艺路线路线简述
📜Longifolioside A置于sodium Hydroxide体系中,用 Water-D2 作为反应溶剂,化学反应 24.0H,反应生成 毛蕊花糖苷
参考文献:Chlorinated Iridoid Glucosides From Veronica Longifolia And Their Antioxidant Activity
标题:Chlorinated Iridoid Glucosides From Veronica Longifolia And Their Antioxidant Activity
摘要:From Veronica Longifolia Were Isolated Three Chlorinated Iridoid Glucosides,Namely,Asystasioside E (6) And Its 6-O-Esters 6A And 6B,Named Longifoliosides A And B,Respectively. The Structures Of 6A And 6B Were Proved By Analysis Of Their Spectroscopic Data And By Conversion To The Catalpol Ester Verproside (5A) Or To Catalpol (5),Respectively. The Configuration Of The Previously Known Vanilloyl Analogue,Urphoside B,Was Shown To Be The 6 Beta-Epimer (6C) Of The Structure Originally Reported. Longifoliosides A (6A) And B (6B) Were Found To Exhibit Radical-Scavenging Activity Against Nitric Oxide,Superoxide,And 2,2-Diphenyl-1-Picrylhydrazyl Radicals.
DOI:10.1021/np100366K
海关参考信息
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主要参考文献
1: Oh ES, Ryu HW, Kim MO, Lee JW, Song YN, Park JY, Kim DY, Ro H, Lee J, Kim TD, Hong ST, Lee SU, Oh SR. Verproside, the Most Active Ingredient in YPL-001 Isolated from Pseudolysimachion rotundum var. subintegrum, Decreases Inflammatory Response by Inhibiting PKCδ Activation in Human Lung Epithelial Cells. Int J Mol Sci. 2023 Apr 13;24(8):7229. doi: 10.3390/ijms24087229.
2: Lee SU, Sung MH, Ryu HW, Lee J, Kim HS, In HJ, Ahn KS, Lee HJ, Lee HK, Shin DH, Lee Y, Hong ST, Oh SR. Verproside inhibits TNF-α-induced MUC5AC expression through suppression of the TNF-α/NF-κB pathway in human airway epithelial cells. Cytokine. 2016 Jan;77:168-75. doi: 10.1016/j.cyto.2015.08.262. Epub 2015 Aug 28. 17(10):11990-2002. doi: 10.3390/molecules171011990.
4: Park EJ, Lee HS, Oh SR, Lee HK, Lee HS. Pharmacokinetics of verproside after intravenous and oral administration in rats. Arch Pharm Res. 2009 Apr;32(4):559-64. doi: 10.1007/s12272-009-1412-x. Epub 2009 Apr 29. 38(1):2252198. doi: 10.1080/14756366.2023.2252198.
合成参考文献
参考文献:10.1016/s0031-9422(98)00090-9
摘要:Taskova R, Handjieva N, Peev D, Popov S. Iridoid glucosides from three veronica species. Phytochemistry. 1998 Nov;49(5):1323–7. doi: 10.1016/s0031-9422(98)00090-9.
参考文献:10.1002/hlca.19800630716
摘要:Afifi‐Yazar FÜ, Sticher O. Verproside, a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae). Helvetica Chimica Acta. 1980 Oct 29;63(7):1905–7. doi: 10.1002/hlca.19800630716.
参考文献:10.1016/s0021-9673(01)86878-3
摘要:Dallenback-Toelke K, Nyiredy S, Sticher O. Application of various planar chromatographic techniques for the separation of iridoid glycosides from Veronica officinalis. Journal of Chromatography A. 1987 Jan;404():365–71. doi: 10.1016/s0021-9673(01)86878-3.
参考文献:10.3390/molecules22040670
摘要:Kim JH, Hwang DK, Moon JY, Lee Y, Yoo JS, Shin DH, Lee HS. Multiple UDP-Glucuronosyltransferase and Sulfotransferase Enzymes are Responsible for the Metabolism of Verproside in Human Liver Preparations. Molecules. 2017 Apr 22;22(4).
参考文献:10.1124/mol.119.115964
摘要:Lee TD, Lee OW, Brimacombe KR, Chen L, Guha R, Lusvarghi S, Tebase BG, Klumpp-Thomas C, Robey RW, Ambudkar SV, Shen M, Gottesman MM, Hall MD. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular Pharmacology. 2019 Nov;96(5):629–40. doi: 10.1124/mol.119.115964.
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