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Anemosapogenin

Names

[ CAS No. ]:
85999-40-2

[ Name ]:
Anemosapogenin

[Synonym ]:
(3β,13α)-3,23-Dihydroxylup-20(29)-en-28-oic acid
Lup-20(29)-en-28-oic acid, 3,23-dihydroxy-, (3β,13α)-
Anemosapogenin
(3β)-3,23-Dihydroxylup-20(29)-en-28-oic acid
23-Hydroxybetulinic acid
3|A,23-Dihydroxylup-20(29)-en-28-oic acid
Lup-20(29)-en-28-oic acid, 3,23-dihydroxy-, (3β)-
23-hydroxy butulinic acid
23-HBA

Biological Activity

[Description]:

23-hydroxybetulinic acid is one of the bioactive components responsible for its anticancer activity.In vitro: 23-hydroxybetulinic acid also shows different proliferation inhibitory activity against B16, HeLa, and HUVEC, with the IC50 value of 78.5, 80, and 94.8 uM, respectively. 23-hydroxybetulinic acid can promote cell cycle arrest at S phase and induce apoptosis via intrinsic pathway. 23-hydroxybetulinic acid disrupts mitochondrial membrane potential significantly (p<0.01) and selectively downregulates the levels of Bcl-2, survivin and upregulates Bax, cytochrome C, cleaved caspase-9 23-hydroxybetulinic acid can induce apoptosis in K562 cells. [1] 23-hydroxybetulinic acid enhances sensitivity of doxorubicin (DOX, ADR) on MCF-7/ADR cell lines, indicating its potential to be developed as a novel MDR modulator.[2] 23-HBA significantly improve the sensitivity of the tumor to doxorubicin. [3]

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Cancer
Natural Products >> Acids and Aldehydes

[References]

[1]. Liu M et al. Cytotoxicity of the compounds isolated from Pulsatilla chinensis saponins and apoptosis induced by 23-hydroxybetulinic acid. Pharm Biol. 2015 Jan;53(1):1-9.

[2]. Zhang DM et al. BBA, a derivative of 23-hydroxybetulinic acid, potently reverses ABCB1-mediated drug resistance in vitro and in vivo. Mol Pharm. 2012 Nov 5;9(11):3147-59.

[3]. Zheng Y et al. 23-Hydroxybetulinic acid from Pulsatilla chinensis (Bunge) Regel synergizes the antitumor activities of doxorubicin in vitro and in vivo. J Ethnopharmacol. 2010 Apr 21;128(3):615-22.


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
585.8±25.0 °C at 760 mmHg

[ Melting Point ]:
305 °C

[ Molecular Formula ]:
C30H48O4

[ Molecular Weight ]:
472.700

[ Flash Point ]:
322.1±19.7 °C

[ Exact Mass ]:
472.355255

[ PSA ]:
77.76000

[ LogP ]:
7.29

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.543

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds