| Identification | Back Directory | [Name]
ASARININ | [CAS]
133-04-0 | [Synonyms]
ASARININ
L-Asarinin
EPI-SESAMIN
(-)-SESAMINE
(-)-ASARININ
ASARININ(RG)(SEE SESAMIN)
Asarinin, 98%, from Aristolochia debilis Sieb. & Zucc.
5,5'-[(1R,3aα,4S,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(1,3-benzodioxole)
5-[4-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-1-yl]-1,3-benzodioxole
(-)-5,5'-[(1R,3aα,4S,6aα)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[1,3-benzodioxole] | [Molecular Formula]
C20H18O6 | [MDL Number]
MFCD00198067 | [MOL File]
133-04-0.mol | [Molecular Weight]
354.35 |
| Chemical Properties | Back Directory | [Melting point ]
121° | [alpha ]
D20 -118.6°; D23 -122° (chloroform) | [Boiling point ]
504.4±50.0 °C(Predicted) | [density ]
1.385±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Slightly), DMSO (Slightly, Sonicated) | [form ]
Solid | [color ]
White to Off-White | [Major Application]
food and beverages | [InChI]
1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2 | [InChIKey]
PEYUIKBAABKQKQ-UHFFFAOYSA-N | [SMILES]
O1C(C4C(C(OC4)c5cc6c(cc5)OCO6)C1)c2cc3c(cc2)OCO3 |
| Hazard Information | Back Directory | [Description]
Asarinin is a lignan that has been found in A. sieboldii.1 It is an epimer of sesamin (Item No. 70310) and a noncompetitive inhibitor of Δ5-desaturase (Ki = 0.28 mM).2 It is selective for Δ5-desaturase over Δ6- and Δ9-desaturase. Asarinin is cytotoxic to A2780 and SKOV3 ovarian cancer cells (IC50s = 38.45 and 60.87 μM, respectively) but not immortalized ovarian surface epithelial cells (IC50 = >200 μM).1 It induces apoptosis and activates caspase-3, -8, and -9 in A2780 and SKOV3 cells. | [Chemical Properties]
White needle-shaped crystals, soluble in boiling methanol, ethanol, chloroform, acetone, and benzene, almost insoluble in water, derived from A. sarum .sieboldii, Zanthoxylum piperitum, Paulownia tomentosa, and Zanthoxylum chinense. | [Uses]
l-Asarinin in combination with pellitorine is a potential larvicides for the control of insecticide-resistant mosquito populations. Possesses antimicrobial activity. | [in vivo]
(-)-Asarinin (5-20 mg/kg; gavage; once daily; 16 weeks) improves the morphology of gastric mucosal glands, alleviate intestinal metaplasia, inhibit the STAT3 pathway, promote ROS accumulation, and induce apoptosis of gastric mucosal cells in the N-Nitroso-N-methylurea (MNU) (HY-34758)-induced mouse model of gastric precancerous lesions[1].
(-)-Asarinin (5.0 mg/kg; oral administration; before intranasal OVA challenge) significantly inhibits the allergic reaction, reduces paw swelling and Evans blue exudation in mice, and decreases the degree of mast cell degranulation in the skin in the OVA-induced passive cutaneous anaphylaxis mouse model[3].
(-)-Asarinin (2.50 mg/kg; oral administration) reduces the concentrations of histamine, TNF-α, MCP-1, IL-4, and IL-5 in the serum of mice in the OVA - induced systemic anaphylaxis mouse model<[3].
(-)-Asarinin (5.0 mg/kg; oral administration; once daily; from day 21-28) significantly inhibits the scratching and sneezing responses of mice, reduces the concentrations of histamine, total IgE, and IL-4 in the serum of mice, and alleviates the inflammatory infiltration and thickening of the nasal mucosa in the OVA-induced allergic rhinitis mouse model[3].
(-)-Asarinin (2.5 mg/kg, 5.0 mg/kg, 10 mg/kg; oral administration) inhibits paw swelling and Evans blue exudation in mice and reduces the concentrations of histamine, TNF-α, MCP-1, and IL-8 in the serum in the C48/80-induced allergic reaction mouse model[3].
C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model3
5.0 mg/kg
Oral administration
Significantly suppressed passive cutaneous anaphylaxis (PCA) in mice, reduced the degree of swelling and Evens blue exudation of mice paw, and decreased the degree of degranulation of MCs in skin.
C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model3
2.50 mg/kg
Oral administration
Significantly reduced the concentration of histamine, TNF-α, MCP-1, IL-4 and IL-5 in mice serum.
C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model3
5.0 mg/kg
Oral administration, once daily, from day 21 - 28
Significantly inhibited the scratching and sneezing response of mice, reduced the concentration of histamine, total IgE, and IL - 4 in mice serum, and attenuated the inflammatory infiltrates and nasal mucosa incrassation in the AR mice.
C57BL/6 mice (male, 18-22 g), C48/80-induced allergic reaction model3
2.5 mg/kg, 5.0 mg/kg, 10 mg/kg
Oral administration
Reduced C48/80-induced paw swelling and Evens blue exudation, and decreased the concentration of histamine, TNF-α, MCP-1 and IL-8 in mice serum. | Animal Model: | Animal Model: SPF-grade BALB/c mice (male and female, 18-20 g, 4-week-old), established by administration of carcinogenic agent MNU[1] | | Dosage: | 20 mg/kg, 5 mg/kg | | Administration: | Gavage, once daily, 16 weeks | | Result: | Reversed the deterioration of the gastric mucosal glands' morphology, reduced the severity of intestinal metaplasia, promoted ROS accumulation, inhibited the STAT3 pathway, and induced apoptosis in the gastric mucosa of GPL mice. |
| Animal Model: | C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model[3] | | Dosage: | 5.0 mg/kg | | Administration: | Oral administration | | Result: | Significantly suppressed passive cutaneous anaphylaxis (PCA) in mice, reduced the degree of swelling and Evens blue exudation of mice paw, and decreased the degree of degranulation of MCs in skin. |
| Animal Model: | C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model[3] | | Dosage: | 5 mg/kg | | Administration: | Oral administration, once daily, from day 21-28 | | Result: | Significantly inhibited the scratching and sneezing response of mice, reduced the concentration of histamine, total IgE, and IL - 4 in mice serum, and attenuated the inflammatory infiltrates and nasal mucosa incrassation in the AR mice. |
| Animal Model: | C57BL/6 mice (male, 18-22 g), OVA-induced passive cutaneous anaphylaxis model3 | | Dosage: | 2.50 mg/kg | | Administration: | Oral administration | | Result: | Significantly reduced the concentration of histamine, TNF-α, MCP-1, IL-4 and IL-5 in mice serum. |
| Animal Model: | C57BL/6 mice (male, 18-22 g), C48/80-induced allergic reaction model3 | | Dosage: | 2.5 mg/kg, 5.0 mg/kg, 10 mg/kg | | Administration: | Oral administration | | Result: | Reduced C48/80-induced paw swelling and Evens blue exudation, and decreased the concentration of histamine, TNF-α, MCP-1 and IL-8 in mice serum. |
| [target]
IL Receptor | IFN-γ | CXCR | TLR | [References]
[1] MIRAN JEONG. (-)-Asarinin from the Roots of Asarum sieboldii Induces Apoptotic Cell Death via Caspase Activation in Human Ovarian Cancer Cells.[J]. Molecules, 2018, 23 8. DOI: 10.3390/molecules23081849
[2] SAKAYU SHIMIZU. Inhibition of Δ5-desaturase in polyunsaturated fatty acid biosynthesis by (?)-asarinin and (?)-epiasarinin[J]. Phytochemistry, 1992, 31 3: Pages 757-760. DOI: 10.1016/0031-9422(92)80008-3 |
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