| Identification | Back Directory | [Name]
Kinsenoside | [CAS]
151870-74-5 | [Synonyms]
Kinsenoside
(+)-Kinsenoside
(4R)-4-(beta-D-Glucopyranosyloxy)dihydro-2(3H)-furanone
2(3H)-Furanone, 4-(β-D-glucopyranosyloxy)dihydro-, (4R)-
(4R)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-one | [Molecular Formula]
C10H16O8 | [MDL Number]
MFCD11100290 | [MOL File]
151870-74-5.mol | [Molecular Weight]
264.229 |
| Questions And Answer | Back Directory | [Preparation]
Synthesis of Kinsenoside by Chemical Method: To date, there are three chemical methods for synthesizing Kinsenoside: (1) Using 1,2,4-butanetriol as a raw material, selectively protecting the two hydroxyl groups at the 1 and 4 positions as aglycones, and performing a glycosylation reaction with glucose trichloroacetylimide ester protected by benzoyl groups at the 2, 3, 4, and 6 hydroxyl groups. After removing the protection on the hydroxyl groups, a lactone is synthesized by ring cyclization. After resolving the epimers and separating the α-glycoside and β-glycoside, Kinsenoside is obtained. (2) Using furfural as a raw material, 5-(R)-(1-oxy)-2(5H)-furanone is used as a key intermediate to synthesize 3-R-hydroxy-γ-butane lactone as aglycone. Glycosylation reaction is performed with glucose trichloroacetylimide ester protected by benzyl groups at the 2, 3, 4, and 6 hydroxyl groups. Finally, the benzyl group is removed to obtain the target product. (3) Using D-malic acid as a raw material, 3-(R)-hydroxy-&gamma--butyrolactone was synthesized as the aglycone, and then glycosylated with 2,3,4,6-tetrabenzylglucose trichloroacetylimide to remove the benzyl group, yielding the target product. A significant problem with the chemical synthesis of Anoectochilus roxburghii glycosides is that the yields of both the glycosylation and deprotection reactions are relatively low; the α and β configurations of the glycosides obtained from the glycosylation reaction are very difficult to separate due to their similar configurations. A combination of chemical and enzymatic methods was used to synthesize Anoectochilus roxburghii glycosides: 3-R-hydroxy-&gamma--butyrolactone was synthesized from D-malic acid as a raw material, and then reacted with β-D-glucose in a reverse hydrolysis reaction catalyzed by amygdalinase to form Anoectochilus roxburghii glycosides. This method eliminates the need for protection and deprotection of the sugar donor, simplifying the reaction process; it improves the efficiency of the glycosylation reaction, with a Anoectochilus roxburghii glycoside yield as high as 17%; and after glycosylation, a single β configuration glycoside is formed. Because temperature has a significant impact on the activity of β-D-glucosidase, an unsuitable amount of enzyme can easily lead to the hydrolysis of the product, so the reaction conditions need to be strictly controlled. |
| Chemical Properties | Back Directory | [Boiling point ]
570.2±50.0 °C(Predicted) | [density ]
1.59±0.1 g/cm3(Predicted) | [storage temp. ]
4°C, protect from light | [solubility ]
DMF:14.0(Max Conc. mg/mL);52.98(Max Conc. mM)
DMSO:33.0(Max Conc. mg/mL);124.89(Max Conc. mM)
PBS (pH 7.2):10.0(Max Conc. mg/mL);37.85(Max Conc. mM) | [form ]
A crystalline solid | [pka]
12.81±0.70(Predicted) | [color ]
White to light yellow | [InChI]
InChI=1/C10H16O8/c11-2-5-7(13)8(14)9(15)10(18-5)17-4-1-6(12)16-3-4/h4-5,7-11,13-15H,1-3H2/t4-,5-,7-,8+,9-,10-/s3 | [InChIKey]
MQEPWBMWFIVRPS-MUOXDHKLNA-N | [SMILES]
O1C[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)CC1=O |&1:2,4,6,9,11,13,r| |
| Hazard Information | Back Directory | [Description]
Kinsenoside is a glycoside originally isolated from A. formosanus that has diverse biological activities, including antihyperlipidemic, immunosuppressive, and anti-inflammatory properties.1,2,3,4 It increases lipolysis mediated by adipose triglyceride lipase and increases hydrolysis of triglycerides in C3H10T1/2 adipocytes.2 It also increases phosphorylation of peroxisome proliferator-activated receptor α (PPARα) and CREB as well as protein levels of SIRT1, PGC-1α, and carnitine palmitoyltransferase I. Kinsenoside downregulates the expression and phosphorylation of VEGF receptor 2 (VEGFR2) and inhibits crosstalk between the JAK2/STAT3 and PI3K/AKT signaling pathways in dendritic cells in vitro.4 It decreases the production of IFN-γ, IL-17, and TNF-α and increases the production of IL-10 in splenocytes isolated from mice with collagen-induced arthritis (CIA).3 Kinsenoside (300 mg/kg per day) decreases the expression of IL-1β, TNF-α, and matrix metalloproteinase-9 (MMP-9) and increases the expression of IL-10 in inflamed joints in a mouse model of collagen-induced arthritis and prevents paw edema and reduces the severity of arthritis. | [Uses]
Kinsenoside is an anti-hyperlipidemic agent isolated from the plant Anoect chilus. | [Definition]
ChEBI: (3R)-5-Oxotetrahydro-3-furanyl beta-D-glucopyranoside is a glycoside. | [in vivo]
Kinsenoside (10 mg/kg; ip; every 3 days for 4 weeks) promotes the expression of Nrf2 and ameliorates intervertebral disc degeneration (IDD) induced by Pentobarbital (50 mg/kg) in vivo in rat model[1].
Kinsenoside (100 mg/kg, 300 mg/kg; ip; 1 h before LPS induction) inhibits LPS (40 mg/kg; ip)-induced inflammatory model in mice[3].
| [storage]
4°C, protect from light | [References]
[1] X M DU. Glycosidic constituents from in vitro Anoectochilus formosanus.[J]. Chemical & pharmaceutical bulletin, 2000, 48 11: 1803-1804. DOI: 10.1248/cpb.48.1803
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] HUNG-BO HSIAO. Kinsenoside inhibits the inflammatory mediator release in a type-II collagen induced arthritis mouse model by regulating the T cells responses[J]. BMC Complementary and Alternative Medicine, 2016, 16 1. DOI: 10.1186/s12906-016-1054-8
[4] MING XIANG. Effects of kinsenoside, a potential immunosuppressive drug for autoimmune hepatitis, on dendritic cells/CD8+T cells communication in mice[J]. Hepatology, 2016, 64 6: 2135-2150. DOI: 10.1002/hep.28825 |
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