94987-08-3 , Gypenoside XLIX ,
(3β)-3-{[6-Deoxy-α-L-mannopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-α-L-arabinopyranosyl]oxy}-20-hydroxy-19-oxodammar-24-en-21-yl β-D-glucopyranoside
Cas:94987-08-3
C52H86O21 / 1047.23
MFCD22124996
(3β)-3-{[6-Deoxy-α-L-mannopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-α-L-arabinopyranosyl]oxy}-20-hydroxy-19-oxodammar-24-en-21-yl β-D-glucopyranoside
Gypenoside XLIX is a natural compound that has been shown to have anti-inflammatory effects. It is extracted from the Chinese herb Gypsum officinale. This extract contains glycosides, which are compounds that contain a sugar molecule combined with a non-sugar molecule. The extract has been shown to inhibit the production of inflammatory mediators in liver cells and glomerular filtration rate. In addition, it has been shown to have an inhibitory effect on inflammatory skin diseases such as atopic dermatitis. Gypenoside XLIX also inhibits the production of pro-inflammatory cytokines and growth factors by inhibiting protein synthesis through inhibition of protein kinase C (PKC). This compound also inhibits urea nitrogen and stimulates the release of insulin by increasing glucose uptake in peripheral tissues. Gypenoside XLIX has also been shown to have beneficial effects for autoimmune diseases, including multiple sclerosis and rheumatoid arthritis, due to its ability to inhibit inflammatory responses
CAS Number | 94987-08-3 |
Product Name | Gypenoside XLIX |
IUPAC Name | (3S,5S,8R,9S,10S,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde |
Molecular Formula | C52H86O21 |
Molecular Weight | 1047.23 g/mol |
InChI | InChI=1S/C52H86O21/c1-24(2)9-8-15-52(65,23-68-45-40(63)38(61)36(59)30(19-53)70-45)27-12-16-49(6)26(27)10-11-32-50(49,7)17-13-31-48(4,5)33(14-18-51(31,32)22-54)71-47-43(73-46-41(64)37(60)34(57)25(3)69-46)42(29(56)21-67-47)72-44-39(62)35(58)28(55)20-66-44/h9,22,25-47,53,55-65H,8,10-21,23H2,1-7H3/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34-,35-,36+,37+,38-,39+,40+,41+,42-,43+,44-,45+,46-,47-,49+,50+,51+,52+/m0/s1 |
InChI Key | AFEVCSJFNQWWDF-AZFNEDKCSA-N |
SMILES | CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C(CCC6(C5(CCC4C3(C)C)C)C)C(CCC=C(C)C)(COC7C(C(C(C(O7)CO)O)O)O)O)C=O)O)OC8C(C(C(CO8)O)O)O)O)O)O |
Synonyms | 3-((O-6-deoxymannopyranosyl-1-2-O-(xylopyranosyl-1-3)arabinopyranosyl)oxy)-21-glucopyranosyloxy-20-hydroxydammar-24-en-19-al, gypenoside XLIX |
Canonical SMILES | CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C(CCC6(C5(CCC4C3(C)C)C)C)C(CCC=C(C)C)(COC7C(C(C(C(O7)CO)O)O)O)O)C=O)O)OC8C(C(C(CO8)O)O)O)O)O)O |
Isomeric SMILES | C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H](CC[C@]6([C@@]5(CC[C@H]4C3(C)C)C)C)[C@@](CCC=C(C)C)(CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)C=O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O |
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