WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H463889
CAS#: 29388-59-8
Description: (–)-Secoisolariciresinol is a lignan that has been found in flaxseed and has diverse biological activities. It scavenges DPPH radicals. (–)-Secoisolariciresinol stimulates IgM production in HB4C5 hybridoma cells. It induces estrogen receptor-dependent gene expression in a reporter assay, as well as stimulates proliferation of MCF-7 human breast cancer cells, in a concentration-dependent manner. (–)-Secoisolariciresinol (5.8 mg/kg, p.o.) reduces weight gain and serum adiponectin levels in a mouse model of obesity induced by a high-fat diet (HFD).
Hodoodo Cat#: H463889
Name: (–)-Secoisolariciresinol
CAS#: 29388-59-8
Chemical Formula: C20H26O6
Exact Mass: 362.17
Molecular Weight: 362.422
Elemental Analysis: C, 66.28; H, 7.23; O, 26.49
Synonym: (–)-Secoisolariciresinol; (–) Secoisolariciresinol;
IUPAC/Chemical Name: (2R,3R)-2,3-bis(4-hydroxy-3-methoxybenzyl)butane-1,4-diol
InChi Key: PUETUDUXMCLALY-HOTGVXAUSA-N
InChi Code: InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
SMILES Code: COC1=C(O)C=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=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: >2 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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 362.42 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.
| 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Tavarini S, De Leo M, Matteo R, Lazzeri L, Braca A, Angelini LG. Flaxseed and Camelina Meals as Potential Sources of Health-Beneficial Compounds. Plants (Basel). 2021 Jan 14;10(1):156. doi: 10.3390/plants10010156. PMID: 33466939; PMCID: PMC7830963.
2: Kartha S, Weisshaar CL, Pietrofesa RA, Christofidou-Solomidou M, Winkelstein BA. Synthetic Secoisolariciresinol Diglucoside Attenuates Established Pain, Oxidative Stress and Neuroinflammation in a Rodent Model of Painful Radiculopathy. Antioxidants (Basel). 2020 Nov 30;9(12):1209. doi: 10.3390/antiox9121209. PMID: 33266301; PMCID: PMC7761466.
3: Zhuang CC, Feng X, Xu HY, Zhang L, Liu L, Zhang G, Zheng Z, Ma CM. Technical note: Quantification of lignans in the urine, milk, and plasma of flaxseed cake- fed dairy sheep. J Dairy Sci. 2021 Jan;104(1):391-396. doi: 10.3168/jds.2020-18470. Epub 2020 Nov 12. PMID: 33189295.
4: Decembrino D, Ricklefs E, Wohlgemuth S, Girhard M, Schullehner K, Jach G, Urlacher VB. Assembly of Plant Enzymes in E. coli for the Production of the Valuable (-)-Podophyllotoxin Precursor (-)-Pluviatolide. ACS Synth Biol. 2020 Nov 20;9(11):3091-3103. doi: 10.1021/acssynbio.0c00354. Epub 2020 Oct 23. PMID: 33095000.
5: Tannous S, Haykal T, Dhaini J, Hodroj MH, Rizk S. The anti-cancer effect of flaxseed lignan derivatives on different acute myeloid leukemia cancer cells. Biomed Pharmacother. 2020 Dec;132:110884. doi: 10.1016/j.biopha.2020.110884. Epub 2020 Oct 17. PMID: 33080470.
6: Scherbakov AM, Stasevich OV, Salnikova DI, Andreeva OE, Mikhaevich EI. Antiestrogenic and antiproliferative potency of secoisolariciresinol diglucoside derivatives on MCF-7 breast cancer cells. Nat Prod Res. 2020 Oct 7:1-7. doi: 10.1080/14786419.2020.1826479. Epub ahead of print. PMID: 33025821.
7: Dingeo G, Brito A, Samouda H, Iddir M, La Frano MR, Bohn T. Phytochemicals as modifiers of gut microbial communities. Food Funct. 2020 Oct 21;11(10):8444-8471. doi: 10.1039/d0fo01483d. PMID: 32996966.
8: Parikh M, Kura B, O'Hara KA, Dibrov E, Netticadan T, Slezak J, Pierce GN. Cardioprotective Effects of Dietary Flaxseed Post-Infarction Are Associated with Changes in MicroRNA Expression. Biomolecules. 2020 Sep 8;10(9):1297. doi: 10.3390/biom10091297. PMID: 32911872; PMCID: PMC7564197.
9: Lu M, Tan L, Zhou XG, Yang ZL, Zhu Q, Chen JN, Luo HR, Wu GS. Secoisolariciresinol Diglucoside Delays the Progression of Aging-Related Diseases and Extends the Lifespan of Caenorhabditis elegans via DAF-16 and HSF-1. Oxid Med Cell Longev. 2020 Jul 14;2020:1293935. doi: 10.1155/2020/1293935. PMID: 32733632; PMCID: PMC7378611.
10: García-Villalba R , Beltrán D , Frutos MD , Selma MV , Espín JC , Tomás- Barberán FA . Metabolism of different dietary phenolic compounds by the urolithin-producing human-gut bacteria Gordonibacter urolithinfaciens and Ellagibacter isourolithinifaciens. Food Funct. 2020 Aug 1;11(8):7012-7022. doi: 10.1039/d0fo01649g. Epub 2020 Jul 27. PMID: 32716447.
11: Zhang S, Cheng M, Wang Z, Liu Y, Ren Y, Rong S, Wang X. Secoisolariciresinol Diglucoside Exerts Anti-Inflammatory and Antiapoptotic Effects through Inhibiting the Akt/IκB/NF-κB Pathway on Human Umbilical Vein Endothelial Cells. Mediators Inflamm. 2020 Jun 24;2020:3621261. doi: 10.1155/2020/3621261. PMID: 32684834; PMCID: PMC7333043.
12: Chhillar H, Chopra P, Ashfaq MA. Lignans from linseed (Linum usitatissimum L.) and its allied species: Retrospect, introspect and prospect. Crit Rev Food Sci Nutr. 2020 Jul 3:1-23. doi: 10.1080/10408398.2020.1784840. Epub ahead of print. PMID: 32619358.
13: Navarro SL, Levy L, Curtis KR, Elkon I, Kahsai OJ, Ammar HS, Randolph TW, Hong NN, Carnevale Neto F, Raftery D, Chapkin RS, Lampe JW, Hullar MAJ. Effect of a Flaxseed Lignan Intervention on Circulating Bile Acids in a Placebo- Controlled Randomized, Crossover Trial. Nutrients. 2020 Jun 19;12(6):1837. doi: 10.3390/nu12061837. PMID: 32575611; PMCID: PMC7374341.
14: Morsy MA, El-Sheikh AAK, Ibrahim ARN, Venugopala KN, Kandeel M. In silico and in vitro identification of secoisolariciresinol as a re-sensitizer of P-glycoprotein-dependent doxorubicin-resistance NCI/ADR-RES cancer cells. PeerJ. 2020 Jun 10;8:e9163. doi: 10.7717/peerj.9163. PMID: 32566390; PMCID: PMC7293189.
15: Zaeem A, Drouet S, Anjum S, Khurshid R, Younas M, Blondeau JP, Tungmunnithum D, Giglioli-Guivarc'h N, Hano C, Abbasi BH. Effects of Biogenic Zinc Oxide Nanoparticles on Growth and Oxidative Stress Response in Flax Seedlings vs. In Vitro Cultures: A Comparative Analysis. Biomolecules. 2020 Jun 17;10(6):918. doi: 10.3390/biom10060918. PMID: 32560534; PMCID: PMC7355665.
16: Nzou G, Wicks RT, VanOstrand NR, Mekky GA, Seale SA, El-Taibany A, Wicks EE, Nechtman CM, Marrotte EJ, Makani VS, Murphy SV, Seeds MC, Jackson JD, Atala AJ. Multicellular 3D Neurovascular Unit Model for Assessing Hypoxia and Neuroinflammation Induced Blood-Brain Barrier Dysfunction. Sci Rep. 2020 Jun 17;10(1):9766. doi: 10.1038/s41598-020-66487-8. Erratum in: Sci Rep. 2020 Nov 18;10(1):20384. PMID: 32555384; PMCID: PMC7299970.
17: Khan I, Khan MA, Shehzad MA, Ali A, Mohammad S, Ali H, Alyemeni MN, Ahmad P. Micropropagation and Production of Health Promoting Lignans in Linum usitatissimum. Plants (Basel). 2020 Jun 9;9(6):728. doi: 10.3390/plants9060728. PMID: 32526854; PMCID: PMC7355781.
18: Asselin CY, Lam A, Cheung DYC, Eekhoudt CR, Zhu A, Mittal I, Mayba A, Solati Z, Edel A, Austria JA, Aukema HM, Ravandi A, Thliveris J, Singal PK, Pierce GN, Niraula S, Jassal DS. The Cardioprotective Role of Flaxseed in the Prevention of Doxorubicin- and Trastuzumab-Mediated Cardiotoxicity in C57BL/6 Mice. J Nutr. 2020 Sep 1;150(9):2353-2363. doi: 10.1093/jn/nxaa144. PMID: 32510147.
19: Aqeel T, Gurumallu SC, Bhaskar A, Hashimi SM, Javaraiah R. Secoisolariciresinol diglucoside protects against cadmium-induced oxidative stress-mediated renal toxicity in rats. J Trace Elem Med Biol. 2020 May 18;61:126552. doi: 10.1016/j.jtemb.2020.126552. Epub ahead of print. PMID: 32446210.
20: Kang J, Park J, Park WY, Jiao W, Lee S, Jung Y, Youn DH, Song G, Cho SY, Kim WY, Park JY, Ahn KS, Kwak HJ, Um JY. A phytoestrogen secoisolariciresinol diglucoside induces browning of white adipose tissue and activates non-shivering thermogenesis through AMPK pathway. Pharmacol Res. 2020 Aug;158:104852. doi: 10.1016/j.phrs.2020.104852. Epub 2020 May 11. PMID: 32438038.
