| Identification | Back Directory | [Name]
Picroside II | [CAS]
39012-20-9 | [Synonyms]
AMPHICOSIDE
PICROSID II
Picroside-2
Picroside a…
Berberine II
PICROSIDE II
PICROSIDE ò
AMPHICOSIDE II
Vanilloyl catalpol
6'-VANILLOYL CATALPOL
Picroside II USP/EP/BP
Picroside II, ≥98% (HPLC)
Picroside II, 98%, from Picrorhiza scrophulariiflora Pennell.
6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl,[1aS-(1aα,1bβ,2β,5aβ,6β,6aα)]-
[(1aS)-1a,1bα,2,5aα,6,6aβ-Hexahydro-6α-[(4-hydroxy-3-methoxybenzoyl)oxy]-1aβ-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2α-yl]β-D-glucopyranoside
(1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-β-D-glucopyranoside
β-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl
(1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-1a,1b,2,5a,6,6a-Hexahydro-6-((4-hydroxy-3-methoxybenzoyl)oxy)-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl-beta-D-glucopyranoside
beta-d-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl, [1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha)]- | [EINECS(EC#)]
254-247-6 | [Molecular Formula]
C23H28O13 | [MDL Number]
MFCD00017402 | [MOL File]
39012-20-9.mol | [Molecular Weight]
512.46 |
| Questions And Answer | Back Directory | [Uses]
Picroside II similar to Picroside I (P437635), acts as an oxygen free radical scavenger and thus promotes anti-inflammatory activity and may be used in the treatment of arthritis or ischemic injury. |
| Chemical Properties | Back Directory | [Melting point ]
145 - 155oC | [Boiling point ]
780.8±60.0 °C(Predicted) | [density ]
1.66±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
ethanol: soluble1mg/mL, clear, colorless | [form ]
Solid | [pka]
8.07±0.20(Predicted) | [color ]
Pale Yellow | [InChIKey]
AKNILCMFRRDTEY-MRFBWRKESA-N | [SMILES]
C12(CO)OC1C(C1C=COC(O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO)O3)O)C21)OC(=O)C1=CC=C(O)C(OC)=C1 |&1:12,13,15,16,18,r| |
| Safety Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
3 | [HS Code ]
29389090 | [Storage Class]
13 - Non Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow needle-shaped crystals, soluble in methanol, derived from Picrorhizoma Coptidis. | [Definition]
ChEBI: Picroside ii is a tannin. | [Biological Activity]
Picroside II displaysmany anti-cancer properties such as anti-metastaticanti-angiogenicand anti-apoptotic activities in both in vitro and in vivo studies.It also exerts antioxidantanti-inflammatoryand antidiarrheal effectsagainst acute oxidative injuries such as severe acute pancreatitis-inducedintestinal barrier injury. PII has protective effects onischemia/reperfusion (I/R)-induced injury by interacting with differentmechanisms in various in vitro and in vivo models.''Phytochemical found in Traditional Chinese Medicine herbal preparations. Picroside IIa glucosideis reported to have hepatoprotectivecardioprotectiveand neuroprotective properties. | [in vivo]
Picroside II (0-20 mg/kg, i.g., given in two doses) protects liver cells from damage and prevents apoptosis[1].
Picroside II (20 mg/kg, intravenous injection, given in four doses) inhibits the activation of NLRP3 inflammasome and NF-κB pathway in mice, reducing the inflammatory response in sepsis and enhancing immune function[3].
Picroside II (20 mg/kg, intraperitoneal injection, a single dose) protects the blood-brain barrier by inhibiting oxidative signaling pathways in a rat model of ischemia-reperfusion injury[4].
Picroside II (5-20 mg/kg, i.g., once a day for seven days) has anti-lipid peroxidation effects and protects against mitochondrial damage in mice with liver injury[5]. | Animal Model: | DGalN and LPS(HY-D1056)-induced acute liver injury in mice[1] | | Dosage: | 0, 5, 10, 20 mg/kg; administered 10 min before and 4 h after D-GalN and LPS administration | | Administration: | i.g. | | Result: | Reduced the levels of alanine aminotransferase and aspartate aminotransferase in the serum, decreased MDA content, had a dose-dependent effect on hepatocyte apoptosis, and upregulated the expression of the bcl-2 gene. |
| Animal Model: | Sepsis mouse model[3] | | Dosage: | 20 mg/kg; four times injected (2 h, 14 h, 26 h and 38 h after CLP) | | Administration: | Intravenous injection (i.v.) | | Result: | Improved survival, reduced sepsis-related infiltration and attenuated lung injury, enhanced bacterial clearance, reduced IL-6, IL-1β, and TNF-α levels, inhibited splenic lymphocyte apoptosis, reduced p-NF-κB (p65) expression, and reduced IL-1β and caspase-1 levels. |
| Animal Model: | Rats with cerebral ischemia-reperfusion injury[4] | | Dosage: | 20 mg/kg; single dose | | Administration: | Intraperitoneal injection (i.p.) | | Result: | Reduced the nervous system score, neuronal injury, BBB damage, ROS content and NADPH oxidase activity, down-regulated the protein levels of Rac-1, Nox2, ROCK, MLCK and MMP-2, and up-regulated the expression of claudin-5. |
| Animal Model: | Mouse model of liver injury induced by CCl4, D-GalN and AP[5] | | Dosage: | 5, 10, 20mg/kg; daily; 7 days | | Administration: | i.g. | | Result: | Reduced the high levels of ALT and AST in serum caused by CCl4, D-GalN and AP, significantly alleviated liver cell damage, reduced MDA, and increased SOD and GSH-Px content in a dose-dependent manner, inhibited AP-induced liver toxicity in mice, enhanced ATPase activity, and improved mitochondrial swelling. |
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