ASPERULOSIDE CAS 14259-45-1

Introduction：Basic information about ASPERULOSIDE CAS 14259-45-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

ASPERULOSIDE Basic information

• Product Name: ASPERULOSIDE
• Synonyms: ASPERULOSIDE;RUBICHLORIC ACID;[2aS-(2aalpha,4aalpha,5alpha,7balpha)]-5-(beta-D-glucopyranosyloxy)-2a,4a,5,7b-tetrahydro-1-oxo-1H-2,6-dioxacyclopent[cd]inden-4-ylmethyl acetate;1H-2,6-Dioxacyclopentcdinden-1-one, 4-(acetyloxy)methyl-5-(.beta.-D-glucopyranosyloxy)-2a,4a,5,7b-tetrahydro-, (2aS,4aS,5S,7bS)-;Asperulosid;(2aS)-2a,4aα,5,7bα-Tetrahydro-4-acetoxymethyl-5α-(β-D-glucopyranosyloxy)-1H-2,6-dioxacyclopent[cd]inden-1-one;(2As-(2aalpha,4aalpha,5alpha,7balpha))-5-(beta-D-glucopyranosyloxy)-2A,4A,5,7B-tetrahydro-1-oxo-1H-2,6-dioxacyclopent(cd)inden-4-ylmethyl acetate;1H-2,6-Dioxacyclopent(cd)inden-1-one, 4-((acetyloxy)methyl)-5-(beta-D-glucopyranosyloxy)-2A,4A,5,7B-tetrahydro-, (2as-(2aalpha,5alpha,7balpha))-
• CAS: 14259-45-1
• MF: C18H22O11
• MW: 414.36
• EINECS: 238-137-5
• Product Categories: Miscellaneous Natural Products
• Mol File: 14259-45-1.mol

ASPERULOSIDE Chemical Properties

• Melting point: 131-132°
• alpha: D25 -198.6° (c = 1.44 in water)
• Boiling point: 704.2±60.0 °C(Predicted)
• density: 1.62±0.1 g/cm3(Predicted)
• storage temp.: -20°C
• solubility: Soluble in methanol and water
• form: powder
• pka: 12.76±0.70(Predicted)
• color: White
• Major Application: metabolomics vitamins, nutraceuticals, and natural products
• InChIKey: IBIPGYWNOBGEMH-BWDLRQFSNA-N
• SMILES: [C@]12([H])C(COC(=O)C)=C[C@]3([H])OC(=O)C(=COC1O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)[C@]23[H] |&1:0,9,19,20,22,23,25,30,r|
• EPA Substance Registry System: 1H-2,6-Dioxacyclopent[cd]inden-1-one, 4-[(acetyloxy)methyl]-5-(?-D-glucopyranosyloxy)-2a,4a,5,7b-tetrahydro-, (2aS,4aS,5S,7bS)- (14259-45-1)

Safety Information

• Hazard Codes: Xn
• Risk Statements: 22
• WGK Germany: 3
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral

ASPERULOSIDE Usage And Synthesis

Description

Asperuloside is an iridoid glycoside that has been found in G. tunetanum and has diverse biological activities, including anti-angiogenic, anti-inflammatory, and anti-obesity properties. It reduces microvessel formation by 67% in a chick embryo chorioallantoic membrane assay when used at a concentration of 2 μg/egg. Asperuloside (20, 40, and 80 mg/L) inhibits LPS-induced increases in TNF-α, IL-1β, and IL-6 production in RAW 264.7 macrophages in a concentration-dependent manner. It reduces lung myeloperoxidase (MPO) activity and bronchoalveolar lavage fluid (BALF) levels of TNF-α, IL-1β, and IL-6 in a mouse model of LPS-induced acute lung injury when administered at doses of 20, 40, and 80 mg/kg. Dietary administration of asperuloside decreases body weight gain, white adipose tissue (WAT) weight, and the ratio of WAT weight to body weight in a high-fat diet-induced mouse model of metabolic syndrome.

Uses

Asperuloside is an iridoid found in Paederia foetida and is an inhibitor of xanthine oxidase and is used in the treatment of various disorders including inflammatory and cardiovascular diseases.

Definition

ChEBI: A iridoid monoterpenoid glycoside isolated from Galium verum.

in vivo

Asperuloside (p.o., 3 mg/day, 0.3% in diet, daily, 12 weeks) reduces food intake, body weight, and adipose masses in rats consuming a high fat diet (HFD)^[2].
Asperuloside (30 and 60 mg/kg, i.p., 30 days) inhibits tumor growth of U937 xenografts mice model^[3].
Asperuloside (20-80 mg/kg, i.p.) relieves LPS-induced acute lung injury via inhibiting MAPK and NF-κB signaling in BALB/c mice^[4].

• Animal Model: Rats consuming a high fat diet (HFD)^[2]
• Dosage: 3 mg/day
• Administration: p.o., 0.3% in diet, daily, 12 weeks
• Result: Reduced body weight, energy intake, adiposity, blood glucose, and plasma insulin.

IC 50

iNOS

References

[1] CéSAR MU?OZ CAMERO . Anti-angiogenic activity of iridoids from Galium tunetanum[C]//28 3. 2018: Pages 374-377. DOI: 10.1016/j.bjp.2018.03.010
[2] JIAMING QIU . Pretreatment with the compound asperuloside decreases acute lung injury via inhibiting MAPK and NF-κB signaling in a murine model[J]. International immunopharmacology, 2016, 31: Pages 109-115. DOI: 10.1016/j.intimp.2015.12.013
[3] T. HIRATA . Anti-obesity compounds in green leaves of Eucommia ulmoides[J]. Bioorganic & Medicinal Chemistry Letters, 2011, 21 6: Pages 1786-1791. DOI: 10.1016/j.bmcl.2011.01.060

ASPERULOSIDE Preparation Products And Raw materials

• Preparation Products: (1S)-1α-(β-D-Glucopyranosyloxy)-5β-hydroxy-7-(acetoxymethyl)-1,4aα,5,7aα-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester