Tubeimoside I

Names

[ CAS No. ]:
102040-03-9

[ Name ]:
Tubeimoside I

[Synonym ]:
TUBEIMOSIDE 1
β-D-Xylopyranosyl-(1->3)-6-deoxy-α-L-mannopyranosyl-(1->2)-1-O-{[(2R,3S,4S,4aR,5aS,8S,9S,9aR,17aR,17bR,19aR,19bS,21aS,25aS,27aR,27bR,29S,29aR,30aR)-3,4,8,9,13,29-hexahydroxy-2-(hydroxymethyl)-1 3,17a,19a,19b,24,24,27b-heptamethyl-11,15-dioxo-3,4,4a,7,8,9,9a,12,13,14,15,17a,18,19,19a,19b,20,21,22,23,24,25,25a,27,27a,27b,28,29,29a,30a-triacontahydro-2H,5aH,11H,17H-piceno[3,4-h]dipyrano[3,2-b:3 ;',2'-e][1,4,7,11]tetraoxacyclohexadecin-21a(
TubeimosideI
TUBELMOSIDEA
TUBEMOSIDE A
TUBEIMOSIDE I (RG)
(1S,4S,7S,8S,9R,11S,13S,14S,18S,22S,25S,27R,28S,29S,30R,32R,34R,35S,37R,38R,41R,42R,46S,53S,54R,55R,56R,57S,58R)-7,8,18,28,29,35,55,56,58-Nonahydroxy-30,54-bis(hydroxymethyl)-13,18,37,41,48,48,53,54-o ;ctamethyl-2,16,20-trioxo-3,5,10,12,15,21,24,26,31,33-decaoxadecacyclo[39.9.3.2.2.1.0.0.0.0.0]octapentacont-44-en-57-yl β-D-xylopyranoside
Olean-12-en-28-oicacid,3-[[2-O-[4-O-(4-carboxy-3
α-L-Arabinopyranose, O-β-D-xylopyranosyl-(1->3)-O-6-deoxy-α-L-mannopyranosyl-(1->2)-1-O-[[(2R,3S,4S,4aR,5aS,8S,9S,9aR,17aR,17bR,19aR,19bS,21aS,25aS,27aR,27bR,29S,29aR,30aR)-3,4,4a,5a,8,9,9a ,12,13,14,15,17a,18,19,19a,19b,20,21,22,23,24,25,25a,27,27a,27b,28,29,29a,30a-triacontahydro-3,4,8,9,13,29-hexahydroxy-2-(hydroxymethyl)-13,17a,19a,19b,24,24,27b-heptamethyl-11,15-dioxo-2H,7H,11H,17H- piceno[3,4-h]dipyrano[3,2-b:3',2'-e][1,4,7,1
Lobatoside H
Tubeimoside I

Biological Activity

[Description]:

Tubeimoside I(Lobatoside-H) is an extract from Chinese herbal medicine Bolbostemma paniculatum (MAXIM.) FRANQUET (Cucurbitaceae) has been shown as a potent anti-tumor agent for a variety of human cancers.IC50 value:Target: Anticancer natural compoundin vitro: TBMS I inhibited the proliferation of both HepG2 and L-02 cells in a dose- and time-dependent manner, but HepG2 cells appeared more sensitive to the agent. When exposed to TBMS I for 24, 48 and 72 h, IC50 for HepG2 cells versus L-02 cells were 15.5 vs. 23.1, 11.7 vs. 16.2, 9.2 vs. 13.1 (μM, p<0.01), respectively. TBMS I induced cell shrinkage, nuclear condensation and fragmentation, cell cycle arrest at the G2/M phase, mitochondrial membrane disruption, release of cytochrome c from the mitochondria, activation of caspase 3 and 9, and shifting Bax/Bcl-2 ratio from being anti-apoptotic to pro-apoptotic, all indicative of initiation and progression of apoptosis involving mitochondrial dysfunction [1]. TBMS1-induced molecular events were related to mitochondria-induced intrinsic apoptosis and P21-cyclin B1/cdc2 complex-related G2/M cell cycle arrest [2]. TBMS1 combined with CDDP promoted cell apoptosis, decreased proliferation activity and increased cytosolic Ca2+ levels. Bcl-2 protein expression was down-regulated but Bax was up-regulated. Moreover, GST-π mRNA and protein expression were decreased. TBMS1 reduced the resistance of the cells to CDDP-induced cytotoxicity [4]. Treatment with TBMS1 resulted in dose- and time-dependent inhibition of proliferation, led to arrest in phase G2/M of the cell cycle and increased the levels of intracellular Ca2?. Furthermore, TBMS1 up-regulated the levels of the glucose-regulated protein 78/immunoglobuin heavy chain binding protein (GRP78/Bip), C/EBP homologous protein (CHOP), Bax, and cleaved caspase-3 and down-regulated the levels of Bcl-2 [5].in vivo: TBMS1 significantly inhibited the production of the pro-inflammatory cytokines, TNF-α, IL-6 and IL-1β in vitro and in vivo. Pretreatment with TBMS1 markedly attenuated the development of pulmonary edema, histological severities and inflammatory cells infiltration in mice with ALI [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Wang Y, et al. Natural plant extract tubeimoside I promotes apoptosis-mediated cell death in cultured human hepatoma (HepG2) cells. Biol Pharm Bull. 2011;34(6):831-8.

[2]. Xu Y, et al. Intrinsic apoptotic pathway and G2/M cell cycle arrest involved in tubeimoside I-induced EC109 cell death. Chin J Cancer Res. 2013 Jun;25(3):312-21.

[3]. Wu Q, et al. Tubeimoside-1 attenuates LPS-induced inflammation in RAW 264.7 macrophages and mouse models. Immunopharmacol Immunotoxicol. 2013 Aug;35(4):514-23.

[4]. Liu HZ, et al. Tubeimoside I sensitizes cisplatin in cisplatin-resistant human ovarian cancer cells (A2780/DDP) through down-regulation of ERK and up-regulation of p38 signaling pathways. Mol Med Rep. 2011 Sep-Oct;4(5):985-92.

[5]. Chen WJ, et al. Tubeimoside-1 induces G2/M phase arrest and apoptosis in SKOV-3 cells through increase of intracellular Ca2+ and caspase-dependent signaling pathways. Int J Oncol. 2012 Feb;40(2):535-43.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Molecular Formula ]:
C₆₃H₉₈O₂₉

[ Molecular Weight ]:
1319.435

[ Exact Mass ]:
1318.619385

[ PSA ]:
445.19000

[ LogP ]:
6.38

[ Index of Refraction ]:
1.637

Safety Information

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Related Compounds

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