Schisanhenol | CAS#69363-14-0 | lipid peroxidation inhibitor

MedKoo Cat#: 461922 | Name: Schisanhenol

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Description:

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

Schisanhenol, also known as Gomisin K3, is a compound isolated from Schisandrae Rubriflora that inhibits lipid peroxidation induced by ferrous-cysteine and NADPH-ascorbic acid.

Chemical Structure

Schisanhenol

CAS#69363-14-0

Theoretical Analysis

MedKoo Cat#: 461922

Name: Schisanhenol

CAS#: 69363-14-0

Chemical Formula: C23H30O6

Exact Mass: 402.2042

Molecular Weight: 402.48

Elemental Analysis: C, 68.64; H, 7.51; O, 23.85

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
25mg	USD 750.00	2 Weeks

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Related CAS #

No Data

Synonym

Schisanhenol; Gomisin K3; Gomisin-K3; NSC 330515; NSC330515; NSC-330515

IUPAC/Chemical Name

(6S,7R)-2,3,10,11,12-pentamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulen-1-ol

InChi Key

FYSHYFPJBONYCQ-QWHCGFSZSA-N

InChi Code

InChI=1S/C23H30O6/c1-12-8-14-10-16(25-3)21(27-5)20(24)18(14)19-15(9-13(12)2)11-17(26-4)22(28-6)23(19)29-7/h10-13,24H,8-9H2,1-7H3/t12-,13+/m0/s1

SMILES Code

OC1=C(C2=C(OC)C(OC)=C(OC)C=C2C[C@@H](C)[C@@H](C)C3)C3=CC(OC)=C1OC

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Schisanhenol inhibits lipid peroxidation induced by ferrous-cysteine and NADPH-ascorbic acid.

In vitro activity:

Schisanhenol has cardiovascular protective effects, but the exact mechanisms are still under investigation. Schisanhenol enhanced AMPK phosphorylation and reversed oxLDL-induced AMPK dephosphorylation and PKC phosphorylation, inhibiting NADPH oxidase subunit assembly and reducing ROS generation. Schisanhenol suppressed oxLDL-induced intracellular calcium rise, mitochondrial membrane potential collapse, altered Bcl-2/Bax ratio, and inhibited cytochrome c release and caspase-3 activation. Reference: Am J Chin Med. 2023;51(6):1459-1475. https://pubmed.ncbi.nlm.nih.gov/37518097/

In vivo activity:

Schisanhenol has potential in the treatment of cognitive disorders, such as Alzheimer’s disease by attenuating scopolamine-induced learning impairment and enhancing cognitive function. In a water morris maze, Schisanhenol increased the activity of SOD and GSH-px while decreasing the content of AChE and MDA in mouse brains. Schisanhenol significantly increased SIRT1 and PGC-1α levels and decreased phosphorylated Tau protein (Ser 396) levels in the hippocampal tissues. Reference: Int J Neurosci. 2019 Feb;129(2):110-118. https://pubmed.ncbi.nlm.nih.gov/30033800/

	Solvent	mg/mL	mM
Solubility
	DMSO	250.0	621.15

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 402.48 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:

1. Chiu TH, Ku CW, Ho TJ, Tsai KL, Hsu WC, Chen YA, Ou HC, Chen HI. Schisanhenol Attenuates OxLDL-Induced Endothelial Dysfunction via an AMPK-Dependent Mechanism. Am J Chin Med. 2023;51(6):1459-1475. doi: 10.1142/S0192415X23500660. Epub 2023 Jul 29. PMID: 37518097. 2. Yu LH, Liu GT. Schisanhenol attenuated ox-LDL-induced apoptosis and reactive oxygen species generation in bovine aorta endothelial cells in vitro. J Asian Nat Prod Res. 2008 Jul-Aug;10(7-8):799-806. doi: 10.1080/10286020802031072. PMID: 18696334. 3. Yu WJ, Chen CZ, Peng YX, Li Z, Gao Y, Liang S, Yuan B, Kim NH, Jiang H, Zhang JB. Schisanhenol improves early porcine embryo development by regulating the phosphorylation level of MAPK. Theriogenology. 2021 Nov;175:34-43. doi: 10.1016/j.theriogenology.2021.08.019. Epub 2021 Aug 17. PMID: 34481228. 4. Han Y, Yang H, Li L, Du X, Sun C. Schisanhenol improves learning and memory in scopolamine-treated mice by reducing acetylcholinesterase activity and attenuating oxidative damage through SIRT1-PGC-1α-Tau signaling pathway. Int J Neurosci. 2019 Feb;129(2):110-118. doi: 10.1080/00207454.2018.1503183. Epub 2018 Oct 30. PMID: 30033800.

In vitro protocol:

In vivo protocol:

1. Yu WJ, Chen CZ, Peng YX, Li Z, Gao Y, Liang S, Yuan B, Kim NH, Jiang H, Zhang JB. Schisanhenol improves early porcine embryo development by regulating the phosphorylation level of MAPK. Theriogenology. 2021 Nov;175:34-43. doi: 10.1016/j.theriogenology.2021.08.019. Epub 2021 Aug 17. PMID: 34481228. 2. Han Y, Yang H, Li L, Du X, Sun C. Schisanhenol improves learning and memory in scopolamine-treated mice by reducing acetylcholinesterase activity and attenuating oxidative damage through SIRT1-PGC-1α-Tau signaling pathway. Int J Neurosci. 2019 Feb;129(2):110-118. doi: 10.1080/00207454.2018.1503183. Epub 2018 Oct 30. PMID: 30033800.

1: Yu J, Yu W, Wu X, Han J. Schsphenines A and B, two new lignans from the fruit of Schisandra sphenanthera with cardioprotective Activities. Nat Prod Res. 2024 Oct 4:1-7. doi: 10.1080/14786419.2024.2410415. Epub ahead of print. PMID: 39365952. 2: Li B, Xiao Q, Zhao H, Zhang J, Yang C, Zou Y, Zhang B, Liu J, Sun H, Liu H. Schisanhenol ameliorates non-alcoholic fatty liver disease via inhibiting miR-802 activation of AMPK-mediated modulation of hepatic lipid metabolism. Acta Pharm Sin B. 2024 Sep;14(9):3949-3963. doi: 10.1016/j.apsb.2024.05.014. Epub 2024 May 17. PMID: 39309511; PMCID: PMC11413670. 3: Wang Y, Zhu J, Du X, Li Y. Simultaneous Extraction and Determination of Lignans from Schisandra chinensis (Turcz.) Baill. via Diol-Based Matrix Solid-Phase Dispersion with High-Performance Liquid Chromatography. Molecules. 2023 Sep 5;28(18):6448. doi: 10.3390/molecules28186448. PMID: 37764224; PMCID: PMC10535609. 4: Sobstyl E, Szopa A, Olszowy-Tomczyk M, Gnat S, Jafernik K, Choma IM. Chromatographic and Biological Screening of Chosen Species of Schisandraceae Family: Schisandra chinensis, S. rubriflora, S. sphenanthera, S. henryi and Kadsura japonica. Chem Biodivers. 2023 Oct;20(10):e202300741. doi: 10.1002/cbdv.202300741. Epub 2023 Sep 22. PMID: 37694741. 5: Chiu TH, Ku CW, Ho TJ, Tsai KL, Hsu WC, Chen YA, Ou HC, Chen HI. Schisanhenol Attenuates OxLDL-Induced Endothelial Dysfunction via an AMPK-Dependent Mechanism. Am J Chin Med. 2023;51(6):1459-1475. doi: 10.1142/S0192415X23500660. Epub 2023 Jul 29. PMID: 37518097. 6: Ruksiriwanich W, Linsaenkart P, Muangsanguan A, Sringarm K, Jantrawut P, Arjin C, Sommano SR, Phimolsiripol Y, Barba FJ. Wound Healing Effect of Supercritical Carbon Dioxide Datura metel L. Leaves Extracts: An In Vitro Study of Anti-Inflammation, Cell Migration, MMP-2 Inhibition, and the Modulation of the Sonic Hedgehog Pathway in Human Fibroblasts. Plants (Basel). 2023 Jul 4;12(13):2546. doi: 10.3390/plants12132546. PMID: 37447107; PMCID: PMC10346957. 7: Wen S, Yang K, Bai Y, Wu Y, Liu D, Wu X, Zhang X, Sun J. Investigating the Mechanism of Action of Schisandra chinensis Combined with Coenzyme Q10 in the Treatment of Heart Failure Based on PI3K-AKT Pathway. Drug Des Devel Ther. 2023 Mar 27;17:939-957. doi: 10.2147/DDDT.S393995. PMID: 37006723; PMCID: PMC10065024. 8: Chiu TH, Ku CW, Ho TJ, Tsai KL, Yang YD, Ou HC, Chen HI. Schisanhenol ameliorates oxLDL-caused endothelial dysfunction by inhibiting LOX-1 signaling. Environ Toxicol. 2023 Jul;38(7):1589-1596. doi: 10.1002/tox.23788. Epub 2023 Mar 31. PMID: 36999521. 9: Zhang Z, Zhao Y, Cai J, Wang T, Song Y, Lu J, Du H, Wang W, Zhao Y, Guo L. Optimized Extraction, Identification and Anti-Biofilm Action of Wu Wei Zi (Fructus Schisandrae Chinensis) Extracts against Vibrio parahaemolyticus. Molecules. 2023 Feb 28;28(5):2268. doi: 10.3390/molecules28052268. PMID: 36903518; PMCID: PMC10005123. 10: Zhang M, Tang Z. Therapeutic potential of natural molecules against Alzheimer's disease via SIRT1 modulation. Biomed Pharmacother. 2023 May;161:114474. doi: 10.1016/j.biopha.2023.114474. Epub 2023 Mar 4. PMID: 36878051. 11: Olas B. Cardioprotective Potential of Berries of Schisandra chinensis Turcz. (Baill.), Their Components and Food Products. Nutrients. 2023 Jan 23;15(3):592. doi: 10.3390/nu15030592. PMID: 36771299; PMCID: PMC9919427. 12: Ye J, Huang F, Zeng H, Xu X, Wu G, Tian S, Zhao J, Zhang W. Multi-omics and network pharmacology study reveals the effects of Dengzhan Shengmai capsule against neuroinflammatory injury and thrombosis induced by ischemic stroke. J Ethnopharmacol. 2023 Apr 6;305:116092. doi: 10.1016/j.jep.2022.116092. Epub 2022 Dec 29. PMID: 36587875. 13: Xue J, Zhang H, Zeng S. Integrate thermostabilized fusion protein apocytochrome b562 RIL and N-glycosylation mutations: A novel approach to heterologous expression of human UDP-glucuronosyltransferase (UGT) 2B7. Front Pharmacol. 2022 Aug 12;13:965038. doi: 10.3389/fphar.2022.965038. PMID: 36034790; PMCID: PMC9412022. 14: Sobstyl E, Szopa A, Dziurka M, Ekiert H, Nikolaichuk H, Choma IM. Schisandra rubriflora Fruit and Leaves as Promising New Materials of High Biological Potential: Lignan Profiling and Effect-Directed Analysis. Molecules. 2022 Mar 25;27(7):2116. doi: 10.3390/molecules27072116. PMID: 35408515; PMCID: PMC9000568. 15: Yang H, Li L, Jiao Y, Zhang Y, Wang Y, Zhu K, Sun C. Thioredoxin-1 mediates neuroprotection of Schisanhenol against MPP+-induced apoptosis via suppression of ASK1-P38-NF-κB pathway in SH-SY5Y cells. Sci Rep. 2021 Nov 3;11(1):21604. doi: 10.1038/s41598-021-01000-3. PMID: 34732784; PMCID: PMC8566484. 16: Deng L, Cheng S, Li J, Xu X, Hao X, Fan Y, Mu S. Synthesis and biological evaluation of novel schisanhenol derivatives as potential hepatoprotective agents. Eur J Med Chem. 2022 Jan 5;227:113919. doi: 10.1016/j.ejmech.2021.113919. Epub 2021 Oct 12. PMID: 34688010. 17: Yu WJ, Chen CZ, Peng YX, Li Z, Gao Y, Liang S, Yuan B, Kim NH, Jiang H, Zhang JB. Schisanhenol improves early porcine embryo development by regulating the phosphorylation level of MAPK. Theriogenology. 2021 Nov;175:34-43. doi: 10.1016/j.theriogenology.2021.08.019. Epub 2021 Aug 17. PMID: 34481228. 18: Min L, Wu Y, Cao G, Mi D, Chen C. A network pharmacology strategy to investigate the anti-osteoarthritis mechanism of main lignans components of Schisandrae Fructus. Int Immunopharmacol. 2021 Sep;98:107873. doi: 10.1016/j.intimp.2021.107873. Epub 2021 Jun 25. PMID: 34182246. 19: He X, Chen J, Mu Y, Zhang H, Chen G, Liu P, Liu W. The effects of inhibiting the activation of hepatic stellate cells by lignan components from the fruits of Schisandra chinensis and the mechanism of schisanhenol. J Nat Med. 2020 Jun;74(3):513-524. doi: 10.1007/s11418-020-01394-w. Epub 2020 Mar 19. PMID: 32193805. 20: Sobstyl E, Szopa A, Ekiert H, Gnat S, Typek R, Choma IM. Effect directed analysis and TLC screening of Schisandra chinensis fruits. J Chromatogr A. 2020 May 10;1618:460942. doi: 10.1016/j.chroma.2020.460942. Epub 2020 Feb 3. PMID: 32057448.