Harpagoside 哈巴俄苷
CAS 19210-12-9 MFCD00017415
化学结构图
SMILES: C[C@]1(OC(=O)/C=C/c2ccccc2)C[C@@H](O)[C@]2(O)C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12
化学属性
| Mol. Formula | C24H30O11 |
|---|---|
| Mol. Weight | 494.49 |
| Density | 1.52 |
| Melting Point | 129-132 |
| Appearance | Solid powder |
| Solubility | Soluble in DMSO. |
别名和识别编码
| Chemical Name | Harpagoside |
|---|---|
| MDL Number | MFCD00017415 |
| CAS Number | 19210-12-9 |
| EC Number | 242-881-6 |
| Beilstein Registry Number | 2384789 |
| Synonym | 7,7a-hexahydro-4a,5-dihydroxy-7-methyl-7-[[(2E)-1-oxo-3-phenyl-2-propen-1-yl]oxy]cyclopenta[c]pyran-1-yl 8'-CINNAMOYLHARPAGIDE HARPAGOSIDE HARPAGOSIDE WITH HPLC HARPAGOSIDE hplc Harpagosid Harpogoside SMR001233395; Eharpagoside; AC1NQYLY; Prestwick3000988 [(1S)-1,4a,5,6,7,7aα-Hexahydro-4aα,5α-dihydroxy-7-methyl-7α-[[(E)-1-oxo-3-phenyl-2-propenyl]oxy]cyclopenta[c]pyran-1α-yl]β-D-glucopyranoside [(1S,4aS,5R,7S,7aS)-4a,5-Dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate [1S-[1alpha,4aalpha,5alpha,7alpha(E),7aalpha]]-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methyl-7-[(allyl-1-oxo-3-phenyl)oxy]cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside {} { β-D-Glucopyranoside, (1S,4aS,5R,7S,7aS)-1,4a,5,6 哈 |
| Chemical Name Translation | 哈巴俄苷 |
| Formula | C24H30O11 |
| IUPAC Name | [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate |
| InChIKey | KVRQGMOSZKPBNS-FMHLWDFHSA-N |
| InChI | InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/b8-7+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1 |
| Canonical SMILES | O=C(O[C@@]1(C)C[C@@H](O)[C@@]2(O)[C@]1([H])[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2)/C=C/C4=CC=CC=C4 |
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分类
- Alphabetical, Analytical Standards, Analytical/Chromatography, Chromatography, E - H, Harpagophytum, Isoprenoids, Life Sciences Standards, Natural Compounds, Phytopharma Primary Standards, Phytopharma Standards, Scrophularia, Standards by Plant Genus, Substance Classification, Verbascum
- {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, H, HA -HT
产品应用
- Harpagoside is an anti-inflammatory small molecule natural product originally isolated from the Harpagophytum procumbens (DevilÂ’s Claw) root, but can be isolated from other plants such as Crophularia ningpoensis Hemsl (Figwort). Treatment of HepG2 cells with Harpagoside demonstrated suppression of NF-κB nuclear translocation and degradation of IκB-α, blocking NF-κB activation. Multiple anti-inflammatory cellular effects were correlated with this blockade, as Harpagoside was observed to inhibit the expression of inflammation-mediating enzymes cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS), and to reduce lipopolysaccharide-induced mRNA levels. The suppression of NF-κB activation is indicated as the mechanism beneath the anti-inflammatory effects of Harpagoside. (Source: http://www.scbt.com/datasheet-203073-harpagoside.html)
安全信息
GHS Symbol
- H302 Harmful if swallowed 吞食有害
- S22 Do not breathe dust 不要吸入粉尘；
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
- R22 Harmful if swallowed 吞咽有害
其他信息
- MOL 文件:19210-12-9.mol
- Sigma Aldrich:19210-12-9(sigmaaldrich)
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