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Harpagide

Names

[ CAS No. ]:
6926-08-5

[ Name ]:
Harpagide

[Synonym ]:
4a,5,7-Trihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl hexopyranoside
einecs 230-050-0
Hexopyranoside, 1,4a,5,6,7,7a-hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta[c]pyran-1-yl

Biological Activity

[Description]:

Harpagide is a class of iridoid glycoside isolated from Scrophularia cryptophila and has antiparasitic activity, which exhibits good in vitro trypanocidal activities against African trypanosomes (T.b. rhodesiense) with an IC50 of 21 μg/mL. Harpagide exerts significant antileishmanial activity against L. donovani with an IC50 value of 2.0 μg/mL. Harpagide also possess significant anti-inflammatory activities[1][2].

[Related Catalog]:

Research Areas >> Infection

[In Vitro]

Harpagide shows cytotoxic activity over 50% in a concentration of 90 μg/mL, Harpagide on the A431 and HeLa cell lines. The cytotoxic effect of Harpagide on the MCF7 cell line in a concentration of 90 μg/mL[3].

[References]

[1]. Tasdemir D, et al. Evaluation of antiprotozoal and antimycobacterial activities of the resin glycosides and the other metabolites of Scrophularia cryptophila. Phytomedicine. 2008 Mar;15(3):209-15.

[2]. Zhang L, et al. Effects of β-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX-2) in vitro. Bioorg Med Chem. 2011 Aug 15;19(16):4882-6.

[3]. Háznagy-Radnai E, et al. Cytotoxic activities of Stachys species. Fitoterapia. 2008 Dec;79(7-8):595-7.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
637.1±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C15H24O10

[ Molecular Weight ]:
364.345

[ Flash Point ]:
339.1±31.5 °C

[ Exact Mass ]:
364.136932

[ PSA ]:
169.30000

[ LogP ]:
-3.69

[ Vapour Pressure ]:
0.0±4.3 mmHg at 25°C

[ Index of Refraction ]:
1.663

Safety Information

[ Safety Phrases ]:
24/25

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds