ChemicalBook CAS DataBase List 69251-96-3

69251-96-3

Name	(+)-Piresil-4-O-beta-D-glucopyraside
CAS	69251-96-3
Molecular Formula	C26H32O11
MDL Number	MFCD17214935
Molecular Weight	520.53
MOL File	69251-96-3.mol

Synonyms

(+)-pinor Pinoresinol 4-glucoside Pinoresinol 4-O-glucoside (+)-pinoresinol-β-D-glucoside (+)-Piresil-4-O-β-D-glucopyraside Pinoresinol 4-O-β-D-glucopyranoside (+)-Piresil-4-O-beta-D-glucopyraside (+)-Pinoresinol-4-O-β-D-glucopyraside Pinoresinol 4-O-beta-D-glucopyranoside (+)-pinoresinol-4-O-β-D-glucopyranoside (+)-pinoresinol-4-O-beta-D-glucopyranoside 3,5-dibromo-benzoic acid,3,5-dibromobenzoic acid (+)-pinoresinol-β-D-glucoside(+)-pinoresinol-4-O-beta-D-glucopyranoside 4-[(1S,3aR,4S,6aR)-4-(4-Hydroxy-3-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxyphenylβ-D-glucopyranoside 4-[(1S,3aR,4S,6aR)-4-(4-Hydroxy-3-methoxyphenyl)tetrahydro-1H,3H- furo[3,4-c]furan-1-yl]-2-methoxyphenyl β-D-glucopyranoside β-D-Glucopyranoside, 2-methoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenyl

Chemical Properties

Melting point	102-104 °C(Solv: methanol (67-56-1))
Boiling point	752.5±60.0 °C(Predicted)
density	1.418±0.06 g/cm3(Predicted)
storage temp.	2-8°C
form	Solid
pka	9.84±0.35(Predicted)
color	White to light yellow
InChIKey	QLJNETOQFQXTLI-DUAOPOKGNA-N
SMILES	O(C1=C(C=CC([C@H]2OC[C@]3([H])[C@@H](C4C=CC(O)=C(OC)C=4)OC[C@]23[H])=C1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)C \|&1:6,9,11,23,27,28,29,31,33,r\|

Safety Data

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

Soluble in methanol, ethanol, DMSO and other organic solvents, derived from Forsythia.

Uses

(+)-Piresil-4-O-beta-D-glucopyraside is used for content determination/identification/pharmacological experiments, etc.

Definition

ChEBI: (+)-Pinoresinol 4-O-glucoside is a lignan and a glycoside.

Biological Activity

Pinoresinol 4-O-β-D-glucopyranoside ((+)-Pinoresinol 4-O-β-D-glucopyranoside) is the main active furofuranoside lignan in Forsythia. It has antioxidant, hypotensive and cyclic adenosine monophosphate (cAMP) phosphodiesterase inhibitory effects.

in vivo

Pinoresinol 4-O-β-D-glucopyranoside (50 mg/kg; p.o.; 20 days for hepatoprotective activity test, 10 days for antihyperglycaemic activity test) exhibits hepatoprotective activity by lowering AST and ALT levels in CCl₄ (HY-Y0298)-induced hepatotoxicity mice, and shows antihyperglycaemic activity by causing a prominent decline in serum glucose level and a promising elevation in insulin level in Streptozotocin (HY-13753)-treated mice^[4].
Pinoresinol 4-O-β-D-glucopyranoside (25-50 mg/kg; p.o.; twice with the second dose 1 h before pilocarpine injection) ameliorates the seizures in a dose-dependent manner in lithium/Pilocarpine (HY-B0726A)-induced epileptic seizures rats, manifested by retarding seizure onset, reducing the number of rats developing seizures, and enhancing the survival of animals after seizure exposure^[7].

Animal Model:	Male Swiss albino mice (weight: 27-30 g), CCl₄-induced hepatotoxicity model and Streptozotocin-induced hyperglycaemia model^[4]
Dosage:	50 mg/kg b.w.
Administration:	Oral gavage (p.o.), 20 days in the hepatotoxicity experiment; 10 days in the hyperglycaemia experiment
Result:	Led to a 33.94% decline in AST, a 3.01% decline in ALT, and a 49.96% decline in LPO levels (in the CCl₄-induced hepatotoxicity model). Significantly enhanced CAT, SOD, and TAS levels by 130%, 90.45%, and 61.39% respectively compared to the CCl₄-treated group (in the CCl₄-induced hepatotoxicity model). Caused a 37.83% reduction in serum glucose level and a 25.37% increase in insulin level (in the Streptozotocin-induced hyperglycaemia model). Reduced lipid peroxide levels by 51.77% and increased serum levels of CAT, SOD, and TAS by 93.02%, 70.79%, and 101.90%, respectively (in the Streptozotocin-induced hyperglycaemia model).

Spectrum Detail

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