Yatein
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MedKoo CAT#: 341118

CAS#: 40456-50-6

Description: Yatein is a natural product isolated from from Cleistanthus boivinianu or Chamaecyparis obtusa. Yatein suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. The mechanisms of antiviral action of yatein seem to be mediated, by inhibiting HSV-1 α gene expression, including expression of the ICP0 and ICP4 genes, and by arresting HSV-1 DNA synthesis and structural protein expression in HeLa cells. Yatein showed antiproliferative activity against the HCT-116 human colon carcinoma cell line, with an IC50 > 10 uM.


Chemical Structure

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Yatein
CAS# 40456-50-6

Theoretical Analysis

MedKoo Cat#: 341118
Name: Yatein
CAS#: 40456-50-6
Chemical Formula: C22H24O7
Exact Mass: 400.1522
Molecular Weight: 400.427
Elemental Analysis: C, 65.99; H, 6.04; O, 27.97

Price and Availability

Size Price Availability Quantity
5.0mg USD 750.0 2 Weeks
10.0mg USD 1250.0 2 Weeks
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Synonym: Yatein; Dihydroanhydropodorhizol.

IUPAC/Chemical Name: 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-((3,4,5-trimethoxyphenyl)methyl)-, trans-(-)-

InChi Key: GMLDZDDTZKXJLU-JKSUJKDBSA-N

InChi Code: InChI=1S/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1

SMILES Code: C1(=O)[C@@H]([C@H](CO1)Cc1cc2c(OCO2)cc1)Cc1cc(c(c(c1)OC)OC)OC

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

Preparing Stock Solutions

The following data is based on the product molecular weight 400.427 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

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1: Picking D, Chambers B, Barker J, Shah I, Porter R, Naughton DP, Delgoda R. Inhibition of Cytochrome P450 Activities by Extracts of Hyptis verticillata Jacq.: Assessment for Potential HERB-Drug Interactions. Molecules. 2018 Feb 15;23(2). pii: E430. doi: 10.3390/molecules23020430. PubMed PMID: 29462868.

2: Corbin C, Drouet S, Mateljak I, Markulin L, Decourtil C, Renouard S, Lopez T, Doussot J, Lamblin F, Auguin D, Lainé E, Fuss E, Hano C. Functional characterization of the pinoresinol-lariciresinol reductase-2 gene reveals its roles in yatein biosynthesis and flax defense response. Planta. 2017 Apr 27. doi: 10.1007/s00425-017-2701-0. [Epub ahead of print] PubMed PMID: 28451749.

3: Liu Y, Young K, Rakotondraibe LH, Brodie PJ, Wiley JD, Cassera MB, Callmander MW, Rakotondrajaona R, Rakotobe E, Rasamison VE, TenDyke K, Shen Y, Kingston DG. Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest. J Nat Prod. 2015 Jul 24;78(7):1543-7. doi: 10.1021/np501020m. Epub 2015 Jun 19. PubMed PMID: 26091020; PubMed Central PMCID: PMC4517784.

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5: Rojas-Sepúlveda AM, Mendieta-Serrano M, Mojica MY, Salas-Vidal E, Marquina S, Villarreal ML, Puebla AM, Delgado JI, Alvarez L. Cytotoxic podophyllotoxin type-lignans from the steam bark of Bursera fagaroides var. fagaroides. Molecules. 2012 Aug 9;17(8):9506-19. doi: 10.3390/molecules17089506. PubMed PMID: 22878225.

6: da Silva JK, Andrade EH, Kato MJ, Carreira LM, Guimarães EF, Maia JG. Antioxidant capacity and larvicidal and antifungal activities of essential oils and extracts from Piper krukoffii. Nat Prod Commun. 2011 Sep;6(9):1361-6. PubMed PMID: 21941916.

7: Hendrawati O, Woerdenbag HJ, Michiels PJ, Aantjes HG, van Dam A, Kayser O. Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR. Phytochemistry. 2011 Dec;72(17):2172-9. doi: 10.1016/j.phytochem.2011.08.009. Epub 2011 Aug 31. PubMed PMID: 21889175.

8: Velázquez-Jiménez R, Torres-Valencia JM, Cerda-García-Rojas CM, Hernández-Hernández JD, Román-Marín LU, Manríquez-Torres JJ, Gómez-Hurtado MA, Valdez-Calderón A, Motilva V, García-Mauriño S, Talero E, Avila J, Joseph-Nathan P. Absolute configuration of podophyllotoxin related lignans from Bursera fagaroides using vibrational circular dichroism. Phytochemistry. 2011 Dec;72(17):2237-43. doi: 10.1016/j.phytochem.2011.07.017. Epub 2011 Aug 15. PubMed PMID: 21840559.

9: Harmatha J, Zídek Z, Kmoníčková E, Smidrkal J. Immunobiological properties of selected natural and chemically modified phenylpropanoids. Interdiscip Toxicol. 2011 Mar;4(1):5-10. doi: 10.2478/v10102-011-0002-1. PubMed PMID: 21577277; PubMed Central PMCID: PMC3090047.

10: Chen JJ, Hung HC, Sung PJ, Chen IS, Kuo WL. Aporphine alkaloids and cytotoxic lignans from the roots of Illigera luzonensis. Phytochemistry. 2011 Apr;72(6):523-32. doi: 10.1016/j.phytochem.2010.12.015. PubMed PMID: 21315382.

11: Santos EO, Lima LS, David JM, Martins LC, Guedes ML, David JP. Podophyllotoxin and other aryltetralin lignans from Eriope latifolia and Eriope blanchetii. Nat Prod Res. 2011 Sep;25(15):1450-3. doi: 10.1080/14786410902809500. Epub 2011 Jul 8. PubMed PMID: 20234970.

12: Maldini M, Montoro P, Piacente S, Pizza C. Phenolic compounds from Bursera simaruba Sarg. bark: phytochemical investigation and quantitative analysis by tandem mass spectrometry. Phytochemistry. 2009 Mar;70(5):641-9. doi: 10.1016/j.phytochem.2009.02.009. Epub 2009 Mar 28. PubMed PMID: 19329133.

13: Kuo YC, Kuo YH, Lin YL, Tsai WJ. Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Res. 2006 Jul;70(3):112-20. Epub 2006 Feb 20. PubMed PMID: 16540181.

14: Mohagheghzadeh A, Gholami A, Soltani M, Hemmati S, Alfermann AW. Linum mucronatum: organ to organ lignan variations. Z Naturforsch C. 2005 May-Jun;60(5-6):508-10. PubMed PMID: 16042353.

15: Usia T, Watabe T, Kadota S, Tezuka Y. Metabolite-cytochrome P450 complex formation by methylenedioxyphenyl lignans of Piper cubeba: mechanism-based inhibition. Life Sci. 2005 Apr 1;76(20):2381-91. PubMed PMID: 15748631.

16: Usia T, Watabe T, Kadota S, Tezuka Y. Potent CYP3A4 inhibitory constituents of Piper cubeba. J Nat Prod. 2005 Jan;68(1):64-8. PubMed PMID: 15679319.

17: Jang DS, Cuendet M, Su BN, Totura S, Riswan S, Fong HH, Pezzuto JM, Kinghorn AD. Constituents of the seeds of Hernandia ovigera with inhibitory activity against cyclooxygenase-2. Planta Med. 2004 Oct;70(10):893-6. PubMed PMID: 15490314.

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19: Hwang GS, Phuong NT, Park KR, Kim YH, Kim KH, Kang JS. Distribution of (-)-yatein in Cupressaceae family analysed by high performance liquid chromatography. Arch Pharm Res. 2004 Jan;27(1):35-9. PubMed PMID: 14969335.

20: Koulman A, Batterman S, van Putten FM, Bos R, Quax WJ. Lignan profiles of indoor-cultivated Anthriscus sylvestris. Planta Med. 2003 Oct;69(10):959-61. PubMed PMID: 14648404.

Yatein

5.0mg / USD 750.0