| Identification | Back Directory | [Name]
PICROSIDE I | [CAS]
27409-30-9 | [Synonyms]
PICROSIDE I
Picroside-Ⅰ
AMphicoside I
Amphicoside Ⅰ
PICOLINIC ACID(P)
Other Cas No, 76248-14-1
β-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-
Picroside I, 98%, from Picrorhiza scrophulariiflora Pennel
6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl,6-(3-phenyl-2-propenoate), [1aS-[1aα,1bβ,2β(E),5aβ,6β,6aα]]-
(1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-β-D-glucopyranoside 6-[(2E)-3-phenyl-2-propenoate]
β-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl, 6-[(2E)-3-phenyl-2-propenoate]
(1aS,1bS,2S,5aR,6S,6aS)-6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-2-yl 6-O-[(2E)-3-phenyl-2-propenoyl]-beta-D-glucopyranoside
β-d-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl, 6-(3-phenyl-2-propenoate), [1aS-[1aα,1bβ,2β(E),5aβ,6β,6aα]]-
[1aS-[1aalpha,1bbeta,2beta(E),5abeta,6beta,6aalpha]]-1a,1b,2,5a,6,6a-Hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl 6-(3-phenyl-2-propenoate) beta-D-glucopyranoside
beta-d-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl, 6-(3-phenyl-2-propenoate), [1aS-[1aalpha,1bbeta,2beta(E),5abeta,6beta,6aalpha]]- | [EINECS(EC#)]
248-445-1 | [Molecular Formula]
C24H28O11 | [MDL Number]
MFCD00017720 | [MOL File]
27409-30-9.mol | [Molecular Weight]
492.47 |
| Chemical Properties | Back Directory | [Boiling point ]
778.6±60.0 °C(Predicted) | [density ]
1.56±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
ethanol: soluble1mg/mL, clear, colorless | [form ]
powder | [pka]
12.70±0.70(Predicted) | [color ]
White | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChIKey]
BSYHSWKTXMTFNF-NTLZGZQOSA-N | [SMILES]
[C@]12(CO)O[C@H]1[C@H]([C@]1([H])C=CO[C@@H](O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@]21[H])OC(=O)/C=C/C1=CC=CC=C1 |&1:0,4,5,6,11,13,14,16,17,19,24,r| |
| Safety Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
3 | [HS Code ]
29389090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Description]
Picroliv is a hepatoprotective mixture of compounds that is isolated from an herb native to the Himalayas.1 Picroside I is an iridoid glycoside found in picroliv.1 By itself, picroside I blocks changes in acid phosphatase activity, phospholipid levels, and lipid peroxide production induced by D-galactosamine in rat liver.2 Picroside I also enhances neurite outgrowth in PC12D cells induced by basic fibroblast growth factor and 7S nerve growth factor when given at 60 μM.3,4 At concentrations as low as 5 μM, picroside I enhances the ATPase activity of the efflux transporter P-glycoprotein.5 | [Chemical Properties]
Yellow needle-shaped crystals, soluble in methanol, derived from Picrorhizoma Coptidis. | [Uses]
Picroside I acts as an oxygen free radical scavenger and thus promotes anti-inflammatory activity and may be used in the treatment of arthritis. | [in vivo]
Picroside I (20 mg/kg, o.p, 12 d) reduces AHR in the experimental asthma model and reduces OVA-associated IgE levels[2].
| Animal Model: | Ovalbumin (OVA) systematic sensitization BALB/c mice model[2] | | Dosage: | 0.2, 2.0 and 20 mg/kg
| | Administration: | Orally, once daily, from day 20 to day 32
| | Result: | Inhibited allergen-triggered inflammatory cell infiltration. |
| [IC 50]
STAT6 | [References]
[1] C. GIRISH Suresh C P. Drug development for liver diseases: focus on picroliv, ellagic acid and curcumin[J]. Fundamental & Clinical Pharmacology, 2008, 22 6: 623-632. DOI: 10.1111/j.1472-8206.2008.00618.x
[2] YOGESH DWIVEDI. Picroliv and its Components Kutkoside and Picroside I Protect Liver Against Galactosamine-Induced Damage in Rats[J]. Basic & Clinical Pharmacology & Toxicology, 1992, 71 5: 383-387. DOI: 10.1111/j.1600-0773.1992.tb00566.x
[3] PING LI . Potentiation of nerve growth factor-action by picrosides I and II, natural iridoids, in PC12D cells[J]. European journal of pharmacology, 2000, 406 2: Pages 203-208. DOI: 10.1016/s0014-2999(00)00662-2
[4] PING LI. Picrosides I and II, selective enhancers of the mitogen-activated protein kinase-dependent signaling pathway in the action of neuritogenic substances on PC12D cells[J]. Life sciences, 2002, 71 15: Pages 1821-1835. DOI: 10.1016/s0024-3205(02)01949-5
[5] I A NAJAR. Modulation of P-glycoprotein ATPase activity by some phytoconstituents.[J]. Phytotherapy Research, 2010: 454-458. DOI: 10.1002/ptr.2951 |
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