A triterpenoid saponin natural product
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Tubeimoside I

Item No. 22276

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2β,3β,4α)-olean-12-en-28-oic acid, 3-[[2-O-[4-O-[(3S)-4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-α-L-arabinopyranosyl]-β-D-glucopyranosyl]oxy]-2,23-dihydroxy-28-(O-β-D-xylopyranosyl-(1→3)-O-6-deoxy-α-L-mannopyranosyl-(1→2)-α-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(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/mlPBS (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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Tubeimoside I is a natural triterpenoid saponin isolated from the medicinal herb B. paniculatum which possesses broad anticancer activity.1,2,3,4 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-9.1 Treatment of HeLa cells with tubeimoside I (IC50 = 25 μM) similarly initiates mitochondrial dysfunction, endoplasmic reticulum stress, and cytoskeletal rearrangement.2 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.3 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).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, Y., Deng, L., Zhong, H., et al. Natural plant extract tubeimoside I promotes apoptosis-mediated cell death in cultured human hepatoma (HepG2) cells. Biol. Pharm. Bull. 34(6), 831-838 (2011).

    2. Xu, Y., Chiu, J.F., He, Q.Y., et al. Tubeimoside-1 exerts cytotoxicity in HeLa cells through mitochondrial dysfunction and endoplasmic reticulum stress pathways. J. Proteome Res. 8(3), 1585-1593 (2009).

    3. Gu, Y., Körbel, C., Scheuer, C., et al. Tubeimoside-1 suppresses tumor angiogenesis by stimulation of proteasomal VEGFR2 and Tie2 degradation in a non-small cell lung cancer xenograft model. Oncotarget 7(5), 5258-5272 (2016).

    4. Peng, Y., Zhong, Y., and Li, G. Tubeimoside-1 suppresses breast cancer metastasis through downregulation of CXCR4 chemokine receptor expression. BMB Rep. 49(9), 502-507 (2016).