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MedKoo Cat#: 574022 | Name: Pinoresinol diglucoside
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pinoresinol diglucoside is a lignan that inhibits peroxidation of linoleic acid emulsion, scavenges hydrogen peroxide and 2,2-diphenyl-1-picrylhydrazyl (DPPH), ABTS, and superoxide anion free radicals and has ferrous ion metal chelating activity. In vivo, pinoresinol diglucoside inhibits increases in serum levels of inorganic phosphate, IL-6, and TNF-α and decreases in serum calcium levels and transverse diameter, weight, bone mineral content, and bone mineral density of the right femur in a rat model of osteoporosis induced by dexamethasone.

Chemical Structure

Pinoresinol diglucoside
Pinoresinol diglucoside
CAS#63902-38-5

Theoretical Analysis

MedKoo Cat#: 574022

Name: Pinoresinol diglucoside

CAS#: 63902-38-5

Chemical Formula: C32H42O16

Exact Mass: 682.2473

Molecular Weight: 682.67

Elemental Analysis: C, 56.30; H, 6.20; O, 37.50

Price and Availability

Size Price Availability Quantity
5mg USD 235.00
10mg USD 390.00
25mg USD 670.00
50mg USD 1,150.00
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Synonym
(+)-Pinoresinol di-O-β-D-glucopyranoside, Pinoresinol diglucoside
IUPAC/Chemical Name
(2R,2'R,3S,3'S,4S,4'S,5R,5'R,6S,6'S)-6,6'-((((1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(2-methoxy-4,1-phenylene))bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)
InChi Key
ZJSJQWDXAYNLNS-FUPWJLLWSA-N
InChi Code
InChI=1S/C32H42O16/c1-41-19-7-13(3-5-17(19)45-31-27(39)25(37)23(35)21(9-33)47-31)29-15-11-44-30(16(15)12-43-29)14-4-6-18(20(8-14)42-2)46-32-28(40)26(38)24(36)22(10-34)48-32/h3-8,15-16,21-40H,9-12H2,1-2H3/t15-,16-,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31+,32+/m0/s1
SMILES Code
COC1=C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)C=CC([C@@H]3[C@@]4([H])CO[C@H](C5=CC(OC)=C(O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)C=C5)[C@@]4([H])CO3)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pinoresinol diglucoside is a lignan that inhibits peroxidation of linoleic acid emulsion, scavenges hydrogen peroxide and 2,2-diphenyl-1-picrylhydrazyl (DPPH), ABTS, and superoxide anion free radicals and has ferrous ion metal chelating activity.
In vitro activity:
The proliferation studies were performed under low and high calcium conditions with or without added growth stimulators at the time points of 2 and 6 days using AlamarBlue Cell Viability Reagent. The cytokine release assay was carried out by incubating the cells with the test articles for 18 h, after which the levels of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6, and IL-8 were measured in the supernatant by enzyme-linked immunosorbent assay. Resin and the purified lignan PINO (pinoresinol), but not p-coumaric acid or abietic acid (industrial tall oil rosin), enhanced the proliferation of human keratinocytes in vitro and inhibited the expression of TNF-α, and to a lesser extent the expression of IL-1β in peripheral blood mononuclear cells. Reference: Health Sci Rep. 2022 Dec 16;6(1):e998. https://pubmed.ncbi.nlm.nih.gov/36544622/
In vivo activity:
In this study, middle cerebral artery occlusion (MCAO) model was established with male C57BL/6 mice, and the mice were treated with 5 and 10 mg/kg PDG (pinoresinol diglucoside) via intravenous injection, respectively. It was revealed that PDG could significantly alleviate the MCAO-induced neurological dysfunction of the mice and reduce the infarct volume, brain water content, and neuron injury. PDG treatment decreased the levels of TNF-α, IL-1β, IL-6, NO, ROS, and MDA, and significantly increased the activities of SOD, GSH, and GSH-Px in the brain tissue of the mice. Additionally, PDG could repress the activation of p65 and promote Nrf2 and HO-1 expressions. Reference: Chem Biol Drug Des. 2021 Dec;98(6):986-996. https://pubmed.ncbi.nlm.nih.gov/34546621/
Solvent mg/mL mM comments
Solubility
DMF 10.0 14.65
DMSO 70.0 102.54
PBS (pH 7.2) 3.0 4.39
Water 100.0 146.48
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 682.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Haapakorva E, Raunio H, von Wright A, Harvima I. Pinoresinol stimulates keratinocyte proliferation and downregulates TNF-α secretion in peripheral blood mononuclear cells: An experimental in vitro study. Health Sci Rep. 2022 Dec 16;6(1):e998. doi: 10.1002/hsr2.998. PMID: 36544622; PMCID: PMC9758476. 2. Wei Y, Xiao L, Yingying L, Haichen W. Pinoresinol diglucoside ameliorates H/R-induced injury of cardiomyocytes by regulating miR-142-3p and HIF1AN. J Biochem Mol Toxicol. 2022 Oct;36(10):e23175. doi: 10.1002/jbt.23175. Epub 2022 Aug 13. PMID: 35962614. 3. Zhang Y, Lei Y, Yao X, Yi J, Feng G. Pinoresinol diglucoside alleviates ischemia/reperfusion-induced brain injury by modulating neuroinflammation and oxidative stress. Chem Biol Drug Des. 2021 Dec;98(6):986-996. doi: 10.1111/cbdd.13956. Epub 2021 Oct 3. PMID: 34546621; PMCID: PMC9293043. 4. Chen Y, Pan R, Zhang J, Liang T, Guo J, Sun T, Fu X, Wang L, Zhang L. Pinoresinol diglucoside (PDG) attenuates cardiac hypertrophy via AKT/mTOR/NF-κB signaling in pressure overload-induced rats. J Ethnopharmacol. 2021 May 23;272:113920. doi: 10.1016/j.jep.2021.113920. Epub 2021 Feb 16. PMID: 33607200.
In vitro protocol:
1. Haapakorva E, Raunio H, von Wright A, Harvima I. Pinoresinol stimulates keratinocyte proliferation and downregulates TNF-α secretion in peripheral blood mononuclear cells: An experimental in vitro study. Health Sci Rep. 2022 Dec 16;6(1):e998. doi: 10.1002/hsr2.998. PMID: 36544622; PMCID: PMC9758476. 2. Wei Y, Xiao L, Yingying L, Haichen W. Pinoresinol diglucoside ameliorates H/R-induced injury of cardiomyocytes by regulating miR-142-3p and HIF1AN. J Biochem Mol Toxicol. 2022 Oct;36(10):e23175. doi: 10.1002/jbt.23175. Epub 2022 Aug 13. PMID: 35962614.
In vivo protocol:
1. Zhang Y, Lei Y, Yao X, Yi J, Feng G. Pinoresinol diglucoside alleviates ischemia/reperfusion-induced brain injury by modulating neuroinflammation and oxidative stress. Chem Biol Drug Des. 2021 Dec;98(6):986-996. doi: 10.1111/cbdd.13956. Epub 2021 Oct 3. PMID: 34546621; PMCID: PMC9293043. 2. Chen Y, Pan R, Zhang J, Liang T, Guo J, Sun T, Fu X, Wang L, Zhang L. Pinoresinol diglucoside (PDG) attenuates cardiac hypertrophy via AKT/mTOR/NF-κB signaling in pressure overload-induced rats. J Ethnopharmacol. 2021 May 23;272:113920. doi: 10.1016/j.jep.2021.113920. Epub 2021 Feb 16. PMID: 33607200.
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Epub 2024 Jul 8. PMID: 39029355. 4: Zhao X, Qu Q, Zhang Y, Zhao P, Qiu J, Zhang X, Duan X, Song X. Research Progress of Eucommia ulmoides Oliv and Predictive Analysis of Quality Markers Based on Network Pharmacology. Curr Pharm Biotechnol. 2024;25(7):860-895. doi: 10.2174/0113892010265000230928060645. PMID: 38902931. 5: Hou YF, Liu Y, Bai L, Du J, Liu SJ, Jia L, Wang YL, Guo S, Ho CT, Bai NS. Explore the active ingredients and potential mechanism of action on Actinidia arguta leaves against T2DM by integration of serum pharmacochemistry and network pharmacology. J Pharm Biomed Anal. 2024 Jul 15;244:116105. doi: 10.1016/j.jpba.2024.116105. Epub 2024 Mar 13. PMID: 38552420. 6: Zuo Y, Chen C, Liu F, Hu H, Dong S, Shen Q, Zeng J, Huang L, Liao X, Cao Z, Zhong Z, Lu H, Chen J. Pinoresinol diglucoside mitigates dexamethasone-induced osteoporosis and chondrodysplasia in zebrafish. Toxicol Appl Pharmacol. 2024 Mar;484:116884. doi: 10.1016/j.taap.2024.116884. Epub 2024 Mar 3. 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