Tubeimoside I

Tubeimoside I is a natural triterpenoid saponin isolated from the medicinal herb B. paniculatum which possesses broad anticancer activity. Tubeimoside I exhibits antiproliferative activity against hepatoma HepG2 cells (IC50 = 15.5 µM) and induces nuclear condensation and fragmentation, cell cycle arrest, mitochondrial membrane disruption, and activation of caspase-3 and caspase-9. Treatment of HeLa cells with tubeimoside I (IC50 = 25 µM) similarly initiates mitochondrial dysfunction, endoplasmic reticulum stress, and cytoskeletal rearrangement. In vivo, tubeimoside I (5 mg/kg) administration to nude mice with flank xenografts of human large-cell lung carcinoma cells decreases tumor volume and microvessel density. It also decreases metastasis of breast cancer cell line MDA-MB-231 in vivo by decreasing expression of C-X-C chemokine receptor type 4 (CXCR4).Formal Name: (2beta,3beta,4alpha)-olean-12-en-28-oic acid, 3-[[2-O-[4-O-[(3S)-4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-alpha-L-arabinopyranosyl]-beta-D-glucopyranosyl]oxy]-2,23-dihydroxy-28-(O-beta-D-xylopyranosyl-(1->3)-O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-alpha-L-arabinopyranosyl) ester, intramol. 4''(3)->4''(28)-ester. CAS Number: 102040-03-9. Synonyms: Lobatoside H, Tubeimoside A. Molecular Formula: C63H98O29. Formula Weight: 1319.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 1 mg/ml, DMSO: 1 mg/ml, PBS (pH 7.2): 10 mg/ml. SMILES: CC1(C)CC[C@]23CC[C@@]4(C)[C@]5(C)CC[C@@]6([H])[C@@](CO)(C)[C@](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@]8([H])OC[C@H](OC(C[C@@](O)(C)CC(O[C@@H]9[C@@H](O[C@@]%10([H])[C@H](O)[C@@H](O)[C@H](O)CO%10)[C@@H](O)[C@H](O[C@@]%11([H])[C@H](OC3=O)OC[C@H](O)[C@@H]%11O)O[C@H]9C)=O)=O)[C@H](O)[C@H]8O)([H])[C@@H](O)C[C@]6(C)[C@@]5([H])CC=C4[C@]2([H])C1. InChi Code: InChI=1S/C63H98O29/c1-26-46-47(88-51-43(76)38(71)30(67)22-81-51)45(78)53(84-26)90-48-39(72)31(68)23-82-54(48)92-56(79)63-15-13-57(2,3)17-28(63)27-9-10-35-59(5)18-29(66)50(60(6,25-65)34(59)11-12-62(35,8)61(27,7)14-16-63)91-55-49(42(75)40(73)32(21-64)86-55)89-52-44(77)41(74)33(24-83-52)85-36(69)19-58(4,80)20-37(70)87-46/h9,26,28-35,38-55,64-68,71-78,80H,10-25H2,1-8H3/t26-,28-,29-,30+,31-,32+,33-,34+,35+,38-,39-,40+,41-,42-,43+,44+,45+,46-,47-,48+,49+,50-,51-,52-,53-,54-,55-,58-,59-,60-,61+,62+,63-. InChi Key: MCPFEAJYKIXPQF-DXZAWUHFSA-N.