Picroside I

Names

[ Name ]:
Picroside I

[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]-
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-phenylacrylate

Biological Activity

[Description]:

Picroside I is the major ingredient of Picrorhiza kurroa. Picrorhiza kurroa is a high value medicinal herb due to rich source of hepatoprotective metabolites, Picroside-I and Picroside-II[1]. Picroside I is a promising agent for the management of asthma. Picroside I reduces the inflammation significantly at its higher dose. Picroside I also downregulates pSTAT6 and GATA3 expressions. Picroside I dose-dependently increases the serum levels of IFN-γ[2].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> STAT

Signaling Pathways >> JAK/STAT Signaling >> STAT

Research Areas >> Inflammation/Immunology

[Target]

STAT6

[References]

[1]. Ganeshkumar Y, et al. Picroside I and Picroside II from Tissue Cultures of Picrorhiza kurroa. Pharmacognosy Res. 2017 Dec;9(Suppl 1):S53-S56.

[2]. Sen Zhang, et al. Picroside I inhibits asthma phenotypes by regulating Tbet/GATA-3 ratio and Th1/Th2 balance in a murine model of asthma. Tropical Journal of Pharmaceutical Research September 2018; 17 (9): 1777-1782.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

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

[ Melting Point ]:
130 °C

[ Molecular Formula ]:
C₂₄H₂₈O₁₁

[ Molecular Weight ]:
492.473

[ Flash Point ]:
253.2±26.4 °C

[ Exact Mass ]:
492.163147

[ PSA ]:
167.67000

[ LogP ]:
-1.81

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

[ Index of Refraction ]:
1.671

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
ethanol: soluble1mg/mL, clear, colorless

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
29389090

Articles

Potentiation of nerve growth factor-action by picrosides I and II, natural iridoids, in PC12D cells.

Eur. J. Pharmacol. 406(2) , 203-8, (2000)

Natural iridoid, picroside I (beta-D-glucopyranoside, 1a,1b,2,5a,6, 6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1, 2-c]pyran-2-yl, 6-(3-phenyl-2-propenoate)) or II (beta-D-glucopyr...

Picrosides I and II, selective enhancers of the mitogen-activated protein kinase-dependent signaling pathway in the action of neuritogenic substances on PC12D cells.

Life Sci. 71(15) , 1821-35, (2002)

Picrosides I and II caused a concentration-dependent (> 0.1 microM) enhancement of basic fibroblast growth factor (bFGF, 2 ng/ml)-, staurosporine (10 nM)- and dibutyryl cyclic AMP (dbcAMP, 0.3 mM)-ind...

De novo sequencing and characterization of Picrorhiza kurrooa transcriptome at two temperatures showed major transcriptome adjustments.

BMC Genomics 13 , 126, (2012)

Picrorhiza kurrooa Royle ex Benth. is an endangered plant species of medicinal importance. The medicinal property is attributed to monoterpenoids picroside I and II, which are modulated by temperature...