(–)-Secoisolariciresinol | CAS#29388-59-8 | Biologically diverse lignan

MedKoo Cat#: 463889 | Name: (–)-Secoisolariciresinol

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Description:

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

(–)-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).

Chemical Structure

(–)-Secoisolariciresinol

CAS#29388-59-8

Theoretical Analysis

MedKoo Cat#: 463889

Name: (–)-Secoisolariciresinol

CAS#: 29388-59-8

Chemical Formula: C20H26O6

Exact Mass: 362.1729

Molecular Weight: 362.42

Elemental Analysis: C, 66.28; H, 7.23; O, 26.49

Price and Availability

Size	Price	Availability
1mg	USD 250.00	2 Weeks
5mg	USD 500.00	2 Weeks
10mg	USD 750.00	2 Weeks

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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

Instruction

View handling instruction

Preparing Stock Solutions

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

1: Liu N, Yu S, Qu J, Tian B, Liu J. Dietary secoisolariciresinol diglucoside crude extract improves growth through modulating rumen bacterial community and epithelial development in lambs. J Sci Food Agric. 2024 Sep 18. doi: 10.1002/jsfa.13909. Epub ahead of print. PMID: 39291551. 2: Nguyen DH, Tran QH, Le LT, Nguyen HHT, Tran HT, Do TP, Ho AN, Tran QH, Thu HTN, Bui VN, Chu HH, Pham NB. Genomic characterization and identification of candidate genes for putative podophyllotoxin biosynthesis pathway in Penicillium herquei HGN12.1C. Microb Biotechnol. 2024 Sep;17(9):e70007. doi: 10.1111/1751-7915.70007. PMID: 39235571; PMCID: PMC11376216. 3: Moree SS, Böhm L, Hoffmann T, Schwab WG. Kinetics of Secoisolariciresinol Glucosyltransferase LuUGT74S1 and Its Mutants. J Agric Food Chem. 2024 Sep 11;72(36):20005-20013. doi: 10.1021/acs.jafc.4c06229. Epub 2024 Aug 30. PMID: 39213532; PMCID: PMC11403609. 4: Jia M, Ning F, Wen J, Wang X, Chen J, Hu J, Chen X, Liu Z. Secoisolariciresinol diglucoside attenuates neuroinflammation and cognitive impairment in female Alzheimer's disease mice via modulating gut microbiota metabolism and GPER/CREB/BDNF pathway. J Neuroinflammation. 2024 Aug 12;21(1):201. doi: 10.1186/s12974-024-03195-4. PMID: 39135052; PMCID: PMC11320852. 5: Wang S, Hu Y, Liu B, Li Y, Wang M, Sun Q. Lignan Intake and Type 2 Diabetes Incidence Among US Men and Women. JAMA Netw Open. 2024 Aug 1;7(8):e2426367. doi: 10.1001/jamanetworkopen.2024.26367. PMID: 39110458; PMCID: PMC11307137. 6: Liu Y, Zhao C, Tang X, Wang L, Guo R. Transcriptomic and Metabolomic Insights into ABA-Related Genes in Cerasus humilis under Drought Stress. Int J Mol Sci. 2024 Jul 11;25(14):7635. doi: 10.3390/ijms25147635. PMID: 39062878; PMCID: PMC11276642. 7: Li R, Ma X, Xiao Y. [Cloning and functional characterization of the pinoresinol-lariciresinol reductase gene IiPLR2 in Isatis indigotica]. Sheng Wu Gong Cheng Xue Bao. 2024 Jul 25;40(7):2270-2281. Chinese. doi: 10.13345/j.cjb.240017. PMID: 39044590. 8: Qiao Y, Huang D, Li Y, Jiang S, Chen X, Chen J, Xiao Y, Chen W. Construction of lignan glycosides biosynthetic network in Escherichia coli using mutltienzyme modules. Microb Cell Fact. 2024 Jul 5;23(1):193. doi: 10.1186/s12934-024-02467-1. PMID: 38970026; PMCID: PMC11225284. 9: Zhang W, Huang D, Liu Y, Guan H, Wang M, Chen H, Zou H, Li D. Effects of high pressure processing on structural changes, aggregation, and binding mechanisms of β-Lactoglobulin with typical polyphenols. Food Chem. 2024 Nov 15;458:140265. doi: 10.1016/j.foodchem.2024.140265. Epub 2024 Jun 28. PMID: 38968707. 10: Kim Y, Kim HW, Sung J, Kim Y. Optimal extraction conditions and quantification of lignan phytoestrogens in cereal grains using targeted LC- MS/MS. Front Nutr. 2024 Jun 11;11:1409309. doi: 10.3389/fnut.2024.1409309. PMID: 38933882; PMCID: PMC11201688. 11: Zhu J, Cai Z, Song Z, Li Y, Shim YY, Reaney MJT, Lee YY, Wang Y, Zhang N. Bioconversion of lignans in flaxseed cake by fermented tofu microbiota and isolation of Enterococcus faecium strain ZB26 responsible for converting secoisolariciresinol diglucoside to enterodiol. Food Chem. 2024 Nov 1;457:140077. doi: 10.1016/j.foodchem.2024.140077. Epub 2024 Jun 13. PMID: 38905833. 12: Giang LT, Lee S, Seo Y, Cuong NT, Tai BH, Van Kiem P, Hang NTM, Oanh NTT, Cuong PV, Ban NK, Park S, Nhiem NX. Symplosaponins A-D: New acylated oleanane- type triterpene saponins from Symplocos cochinchinensis and their hepatoprotective effect. Fitoterapia. 2024 Sep;177:106056. doi: 10.1016/j.fitote.2024.106056. Epub 2024 Jun 6. PMID: 38851515. 13: Ookoshi K, Sawane K, Fukumitsu S, Aida K. Availability of dietary secoisolariciresinol diglucoside on borderline blood cholesterol level in men: a randomized, parallel, controlled, double-blinded clinical trial. J Clin Biochem Nutr. 2024 May;74(3):261-266. doi: 10.3164/jcbn.23-122. Epub 2024 Mar 5. PMID: 38799144; PMCID: PMC11111469. 14: Zhuo LB, Yang Y, Xiao C, Li F, Lin L, Xi Y, Fu Y, Zheng JS, Chen YM. Gut microbiota-bile acid axis mediated the beneficial associations between dietary lignans and hyperuricemia: a prospective study. Food Funct. 2024 Jun 17;15(12):6438-6449. doi: 10.1039/d4fo00961d. PMID: 38775706. 15: Ghedini CP, Silva LHP, Moura DC, Brito AF. Supplementing flaxseed meal with sucrose, flaxseed oil, or both: Effects on milk enterolactone, ruminal microbiota profile, production performance, and nutrient utilization in dairy cows. J Dairy Sci. 2024 Sep;107(9):6834-6851. doi: 10.3168/jds.2024-24649. Epub 2024 May 17. PMID: 38762110. 16: Wu H, Zhang XH, Wang LP, Tian HD, Liu GR, Yang DH, Liu SL. Successful Outcome of a Patient with Concomitant Pancreatic and Renal Carcinoma Receiving Secoisolariciresinol Diglucoside Therapy Alone: A Case Report. Int Med Case Rep J. 2024 Mar 15;17:167-175. doi: 10.2147/IMCRJ.S446184. PMID: 38504721; PMCID: PMC10949998. 17: Chen J, Chen H, Feng C, Chen Q, Fang X, Wang Y, Zhang N. Anti-inflammatory effect of lignans from flaxseed after fermentation by lactiplantibacillus plantarum SCB0151 in vitro. World J Microbiol Biotechnol. 2024 Mar 14;40(4):134. doi: 10.1007/s11274-024-03945-9. PMID: 38480613. 18: Feng J, Yao Y, Qiao Y, Ma X, Wu Z, Duan Y, Di P, Chen W, Xiao Y. Effect of pinoresinol-lariciresinol reductases on biosynthesis of lignans with substrate selectivity in Schisandra chinensis. Phytochemistry. 2024 May;221:114053. doi: 10.1016/j.phytochem.2024.114053. Epub 2024 Mar 12. PMID: 38479587. 19: Feng C, Wu Y, Cai Z, Song Z, Shim YY, Reaney MJT, Wang Y, Zhang N. A comparative study on flaxseed lignan biotransformation through resting cell catalysis and microbial fermentation by β-glucosidase production Lactiplantibacillus plantarum. J Sci Food Agric. 2024 Aug 15;104(10):5869-5881. doi: 10.1002/jsfa.13412. Epub 2024 Mar 13. PMID: 38407005. 20: Chapple B, Woodfin S, Moore W. The Perfect Cup? Coffee-Derived Polyphenols and Their Roles in Mitigating Factors Affecting Type 2 Diabetes Pathogenesis. Molecules. 2024 Feb 6;29(4):751. doi: 10.3390/molecules29040751. PMID: 38398503; PMCID: PMC10891742.