| Identification | Back Directory | [Name]
ASPERULOSIDE | [CAS]
14259-45-1 | [Synonyms]
Nsc 31760
Asperulosid
ASPERULOSIDE
RUBICHLORIC ACID
Einecs 238-137-5
Asperuloside >=95% (LC/MS-ELSD)
(2aS)-2a,4aα,5,7bα-Tetrahydro-4-acetoxymethyl-5α-(β-D-glucopyranosyloxy)-1H-2,6-dioxacyclopent[cd]inden-1-one
1H-2,6-Dioxacyclopent[cd]inden-1-one, 4-[(acetyloxy)methyl]-5-(β-D-glucopyranosyloxy)-2a,4a,5,7b-tetrahydro-, (2aS,4aS,5S,7bS)-
1H-2,6-Dioxacyclopentcdinden-1-one, 4-(acetyloxy)methyl-5-(.beta.-D-glucopyranosyloxy)-2a,4a,5,7b-tetrahydro-, (2aS,4aS,5S,7bS)-
1H-2,6-Dioxacyclopent(cd)inden-1-one, 4-((acetyloxy)methyl)-5-(beta-D-glucopyranosyloxy)-2A,4A,5,7B-tetrahydro-, (2as-(2aalpha,5alpha,7balpha))-
(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
[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 | [EINECS(EC#)]
238-137-5 | [Molecular Formula]
C18H22O11 | [MDL Number]
MFCD02094172 | [MOL File]
14259-45-1.mol | [Molecular Weight]
414.36 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [WGK Germany ]
3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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.1,2,3 It reduces microvessel formation by 67% in a chick embryo chorioallantoic membrane assay when used at a concentration of 2 μg/egg.1 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.2 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.3 | [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 |
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