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Taccalonolide A

Names

[ CAS No. ]:
108885-68-3

[ Name ]:
Taccalonolide A

[Synonym ]:
(1S,5S,5aS,5bR,6R,6aS,6bS,7R,8aS,9aS,10aS,11R,11aR,11bS,12S,13R,13aR,13bS)-5,7-Dihydroxy-1,5,5a,11a,13a-pentamethyl-4,8-dioxo-4,5,5a,5b,6,6a,6b,7,8,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-icosahydro-1H-oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-6,11,12,13-tetrayl tetraacetate
1H-Oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-4,8-dione, 6,11,12,13-tetrakis(acetyloxy)-5,5a,5b,6,6a,6b,7,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-octadecahydro-5,7-dihydroxy-1,5,5a,11a,13a-pentamethyl-, (1S,5S,5aS,5bR,6R,6aS,6bS,7R,8aS,9aS,10aS,11R,11aR,11bS,12S,13R,13aR,13bS)-

Biological Activity

[Description]:

Taccalonolide A is a microtubule stabilizer, which is a steroid isolated from Tacca chantrieri, with cytotoxic and antimalarial activities[1][2]. Taccalonolide A causes G2-M accumulation, Bcl-2 phosphorylation and initiation of apoptosis[1]. Taccalonolide A is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug resistance protein 7 (MRP7), with an IC50 of 622 nM for SK-OV-3 cells[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin
Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[Target]

microtubule[1]


[References]

[1]. Tinley TL, et al. Taccalonolides E and A: Plant -derived steroids with microtubule-stabilizing activity. Cancer Res. 2003 Jun 15;63(12):3211-20.

[2]. Risinger AL, et al. Taccalonolides: Novel microtubule stabilizers with clinical potential. Cancer Lett. 2010 May 1;291(1):14-9.

[3]. Risinger AL, et al. The taccalonolides: microtubule stabilizers that circumvent clinically relevant taxane resistance mechanisms. Cancer Res. 2008 Nov 1;68(21):8881-8.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
776.8±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C36H46O14

[ Molecular Weight ]:
702.742

[ Flash Point ]:
237.8±26.4 °C

[ Exact Mass ]:
702.288757

[ PSA ]:
201.56000

[ LogP ]:
2.49

[ Vapour Pressure ]:
0.0±6.1 mmHg at 25°C

[ Index of Refraction ]:
1.590

[ Storage condition ]:
2-8℃

Precursor & DownStream

Precursor

DownStream

Related Compounds