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G0174

Sigma-Aldrich

Picroside II

Synonym(s):

(1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-[(4-hydroxy-3-methoxybenzoyl)oxy]-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-β-D-glucopyranoside, 6-Vanillylcatalpol, Amphicoside II, Vanilloyl catalpol

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About This Item

Empirical Formula (Hill Notation):
C23H28O13
CAS Number:
39012-20-9
Molecular Weight:
512.46
EC Number:
254-247-6
UNSPSC Code:
12352200
NACRES:
NA.25

Assay

≥98% (HPLC)

solubility

ethanol: 1 mg/mL, clear, colorless

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

OC1[C@@H](O)[C@H](O)C(CO)O[C@H]1O[C@@H]2OC=C[C@]3([H])[C@@]2([H])[C@](O4)(CO)[C@@H]4[C@H]3OC(C5=CC=C(O)C(OC)=C5)=O

InChI

1S/C23H28O13/c1-31-12-6-9(2-3-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3

InChI key

AKNILCMFRRDTEY-UHFFFAOYSA-N

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General description

PicrosideII (PII) is a monoterpene, iridoid glycoside, and one of the main bioactivecompounds sourced from Picrorhiza kurroa.

Application

PicrosideII has been used as a reference standard to analyze and validate picroside-II from Picrorhiza kurroa using high-performance liquid chromatography (HPLC).

Biochem/physiol Actions

Phytochemical found in Traditional Chinese Medicine herbal preparations. Picroside II, a glucoside, is reported to have hepatoprotective, cardioprotective, and neuroprotective properties.
Picroside II displaysmany anti-cancer properties such as anti-metastatic, anti-angiogenic, and anti-apoptotic activities in both in vitro and in vivo studies.It also exerts antioxidant, anti-inflammatory, and antidiarrheal effectsagainst acute oxidative injuries such as severe acute pancreatitis-inducedintestinal barrier injury. PII has protective effects onischemia/reperfusion (I/R)-induced injury by interacting with differentmechanisms in various in vitro and in vivo models.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP3867
MKCN8232
MKCL1347
MKCL1346
MKCK5434

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Chenghua Lou et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 120, 109494-109494 (2019-10-14)
Cancer is one of the leading causes of death worldwide. The development of novel anti-cancer agents from natural products is a promising approach to reduce cancer mortality. In this study, we investigated the anti-metastatic and anti-angiogenic activities of picroside II
Development and Validation of HPLC Method for Analysis of Picroside-I and Picroside-II in Picrorhiza kurroa
Sharma S, et al.,
International Research Journal of Pure and Applied Chemistry, 17, 1-10 (2019)
Shangying Ma et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 130, 110421-110421 (2020-07-17)
Picrorhiza kurroa, the dried rhizome of Picrorhiza kurroa Royle ex Benth, is a famous Chinese herb that has been traditionally used in China. Picroside II (PII), a glycoside derivative, is the main bioactive constituent of Picrorhiza kurroa. In the past
Xuehua Piao et al.
Oxidative medicine and cellular longevity, 2020, 3589497-3589497 (2020-05-01)
Picroside II exerts anti-inflammatory and antidiarrheal effects for treating the diseases associated with oxidative injury. However, its function on pancreatitis-induced intestinal barrier injury remains unclear. Hypothesis/Purpose. We hypothesized that picroside II will have protective effects against pancreatitis-induced intestinal barrier injury

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