Verminoside

Names

[ Name ]:
Verminoside

[Synonym ]:
picroside-1
PicrosideI
2-Propenoic acid, 3-phenyl-, (1aS,1bS,2S,5aR,6S,6aS)-2-(β-D-glucopyranosyloxy)-1a,1b,2,5a,6,6a-hexahydro-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-6-yl ester, (2E)-
β-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl 6-O-[(2E)-1-oxo-3-phenyl-2-propen-1-yl]-
2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (1aS,1bS,2S,5aR,6S,6aS)-2-(β-D-glucopyranosyloxy)-1a,1b,2,5a,6,6a-hexahydro-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-6-yl ester, (2E)-
6'-O-trans-cinnamoylcatalpol
(1aS,1bS,2S,5aR,6S,6aS)-6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-2-yl 6-O-[(2E)-3-phenyl-2-propenoyl]-β-D-glucopyranoside
picrosides I
Picroside I
(1aS,1bS,2S,5aR,6S,6aS)-2-(β-D-Glucopyranosyloxy)-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-6-yl (2E)-3-(3,4-dihydroxyphenyl)acrylate
(1aS,1bS,2S,5aR,6S,6aS)-2-(β-D-Glucopyranosyloxy)-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[4,5]cyclopenta[1,2-c]pyran-6-yl (2E)-3-phenylacrylate
Verminoside

Biological Activity

[Description]:

Verminoside is an iridoid isolated from Kigelia africana, exhibits anti-inflammatory and remarkable antioxidant activity with a radical-scavenging activity of 2.5 μg/mL. The genotoxicity of Verminoside on human lymphocytes is associated with elevated levels of PARP-1 and p53 proteins[1][2][3].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PARP

Signaling Pathways >> Apoptosis >> MDM-2/p53

Signaling Pathways >> Cell Cycle/DNA Damage >> PARP

[Target]

PARP-1

[In Vitro]

Verminoside (Compound 1; 0.01-1 mM; 25 hours; J774.A1 macrophages) treatment shows significant and concentration-related inhibition of iNOS expression at 0.1 mM and 1 mM in LPS-stimulated J774.A1 macrophages[1]. Western Blot Analysis[1] Cell Line: J774.A1 macrophages Concentration: 0.01 mM, 0.1 mM or 1 mM Incubation Time: 25 hours Result: Showed significant and concentration-related inhibition of iNOS expression at 0.1 mM and 1 mM in LPS-stimulated J774.A1 macrophages.

[References]

[1]. Picerno P, et al. Anti-inflammatory activity of verminoside from Kigelia africana and evaluation of cutaneous irritation in cell cultures and reconstituted human epidermis. J Nat Prod. 2005 Nov;68(11):1610-4.

[2]. Boniface PK, et al. RP-HPLC-DAD method for the identification of two potential antioxidant agents namely verminoside and 1-O-(E)-caffeoyl-β-gentiobiose from Spathodea campanulata leaves. Nat Prod Res. 2015;29(7):676-80.

[3]. Santoro A, et al. Verminoside- and verbascoside-induced genotoxicity on human lymphocytes: involvement of PARP-1 and p53 proteins. Toxicol Lett. 2008 May 5;178(2):71-6.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
739.1±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₄H₂₈O₁₃

[ Molecular Weight ]:
492.473

[ Flash Point ]:
253.2±26.4 °C

[ Exact Mass ]:
492.163147

[ PSA ]:
208.13000

[ LogP ]:
-1.81

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.671