Nevadensin
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MedKoo CAT#: 584841

CAS#: 10176-66-6

Description: Nevadensin is a natural basil flavonoid that protects against a methyleugenol-induced marker of hepatocarcinogenicity in male F344 rat.


Price and Availability

Size Price Shipping out time Quantity
10mg USD 605 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-29. Prices are subject to change without notice.

Nevadensin purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584841
Name: Nevadensin
CAS#: 10176-66-6
Chemical Formula: C18H16O7
Exact Mass: 344.0896
Molecular Weight: 344.319
Elemental Analysis: C, 62.79; H, 4.68; O, 32.53


Synonym: Nevadensin

IUPAC/Chemical Name: 4H-1-Benzopyran-4-one, 5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-

InChi Key: KRFBMPVGAYGGJE-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)12-8-11(19)13-14(20)17(23-2)15(21)18(24-3)16(13)25-12/h4-8,20-21H,1-3H3

SMILES Code: O=C1C=C(C2=CC=C(OC)C=C2)OC3=C(OC)C(O)=C(OC)C(O)=C13


Technical Data

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


References

1: Al-Subeihi AA, Alhusainy W, Paini A, Punt A, Vervoort J, van Bladeren PJ, Rietjens IM. Inhibition of methyleugenol bioactivation by the herb-based constituent nevadensin and prediction of possible in vivo consequences using physiologically based kinetic modeling. Food Chem Toxicol. 2013 Sep;59:564-71. doi: 10.1016/j.fct.2013.06.043. Epub 2013 Jul 4. PubMed PMID: 23831728.

2: Liu H, Yan C, Li C, Lin L. LC-MS/MS determination of nevadensin in rat plasma and its application in pharmacokinetic studies. J Pharm Biomed Anal. 2013 Feb 23;74:56-61. doi: 10.1016/j.jpba.2012.10.021. Epub 2012 Nov 1. PubMed PMID: 23245233.

3: Alhusainy W, Williams GM, Jeffrey AM, Iatropoulos MJ, Taylor S, Adams TB, Rietjens IM. The natural basil flavonoid nevadensin protects against a methyleugenol-induced marker of hepatocarcinogenicity in male F344 rat. Food Chem Toxicol. 2014 Dec;74:28-34. doi: 10.1016/j.fct.2014.08.016. Epub 2014 Sep 10. PubMed PMID: 25218219.

4: Bernhardt B, Bernáth J, Gere A, Kókai Z, Komáromi B, Tavaszi-Sárosi S, Varga L, Sipos L, Szabó K. The Influence of Cultivars and Phenological Phases on the Accumulation of Nevadensin and Salvigenin in Basil (Ocimum basilicum). Nat Prod Commun. 2015 Oct;10(10):1699-702. PubMed PMID: 26669105.

5: Végh K, Riethmüller E, Hosszú L, Darcsi A, Müller J, Alberti Á, Tóth A, Béni S, Könczöl Á, Balogh GT, Kéry Á. Three newly identified lipophilic flavonoids in Tanacetum parthenium supercritical fluid extract penetrating the Blood-Brain Barrier. J Pharm Biomed Anal. 2018 Feb 5;149:488-493. doi: 10.1016/j.jpba.2017.11.029. Epub 2017 Nov 16. PubMed PMID: 29182998.

6: Alhusainy W, Paini A, Punt A, Louisse J, Spenkelink A, Vervoort J, Delatour T, Scholz G, Schilter B, Adams T, van Bladeren PJ, Rietjens IM. Identification of nevadensin as an important herb-based constituent inhibiting estragole bioactivation and physiology-based biokinetic modeling of its possible in vivo effect. Toxicol Appl Pharmacol. 2010 Jun 1;245(2):179-90. doi: 10.1016/j.taap.2010.02.017. Epub 2010 Mar 11. Erratum in: Toxicol Appl Pharmacol. 2010 Sep 15;247(3):250. PubMed PMID: 20226806.

7: Alhusainy W, Paini A, van den Berg JH, Punt A, Scholz G, Schilter B, van Bladeren PJ, Taylor S, Adams TB, Rietjens IM. In vivo validation and physiologically based biokinetic modeling of the inhibition of SULT-mediated estragole DNA adduct formation in the liver of male Sprague-Dawley rats by the basil flavonoid nevadensin. Mol Nutr Food Res. 2013 Nov;57(11):1969-78. doi: 10.1002/mnfr.201300144. Epub 2013 Jul 26. PubMed PMID: 23894034.

8: Liang C, Zhang X, Diao X, Liao M, Sun Y, Zhang L. Metabolism profiling of nevadensin in vitro and in vivo by UHPLC-Q-TOF-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 May 1;1084:69-79. doi: 10.1016/j.jchromb.2018.03.032. Epub 2018 Mar 16. PubMed PMID: 29573625.

9: Berim A, Gang DR. The roles of a flavone-6-hydroxylase and 7-O-demethylation in the flavone biosynthetic network of sweet basil. J Biol Chem. 2013 Jan 18;288(3):1795-805. doi: 10.1074/jbc.M112.420448. Epub 2012 Nov 26. PubMed PMID: 23184958; PubMed Central PMCID: PMC3548489.

10: Wang YQ, Weng ZM, Dou TY, Hou J, Wang DD, Ding LL, Zou LW, Yu Y, Chen J, Tang H, Ge GB. Nevadensin is a naturally occurring selective inhibitor of human carboxylesterase 1. Int J Biol Macromol. 2018 Dec;120(Pt B):1944-1954. doi: 10.1016/j.ijbiomac.2018.09.178. Epub 2018 Sep 27. PubMed PMID: 30268757.

11: Liu Y, Wagner H, Bauer R. Nevadensin glycosides from Lysionotus pauciflorus. Phytochemistry. 1996 Jul;42(4):1203-5. PubMed PMID: 8688190.

12: Berim A, Gang DR. Characterization of two candidate flavone 8-O-methyltransferases suggests the existence of two potential routes to nevadensin in sweet basil. Phytochemistry. 2013 Aug;92:33-41. doi: 10.1016/j.phytochem.2013.05.001. Epub 2013 Jun 6. PubMed PMID: 23747095.

13: Berim A, Kim MJ, Gang DR. Identification of a unique 2-oxoglutarate-dependent flavone 7-O-demethylase completes the elucidation of the lipophilic flavone network in basil. Plant Cell Physiol. 2015 Jan;56(1):126-36. doi: 10.1093/pcp/pcu152. Epub 2014 Nov 6. PubMed PMID: 25378691.

14: Tong X, Xiao X, Li G. On-line coupling of dynamic microwave-assisted extraction with high-speed counter-current chromatography for continuous isolation of nevadensin from Lyeicnotus pauciflorus Maxim. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Aug 15;879(24):2397-402. doi: 10.1016/j.jchromb.2011.06.035. Epub 2011 Jul 2. PubMed PMID: 21775221.

15: van den Berg SJ, Klaus V, Alhusainy W, Rietjens IM. Matrix-derived combination effect and risk assessment for estragole from basil-containing plant food supplements (PFS). Food Chem Toxicol. 2013 Dec;62:32-40. doi: 10.1016/j.fct.2013.08.019. Epub 2013 Aug 16. PubMed PMID: 23959103.

16: Sestili P, Ismail T, Calcabrini C, Guescini M, Catanzaro E, Turrini E, Layla A, Akhtar S, Fimognari C. The potential effects of Ocimum basilicum on health: a review of pharmacological and toxicological studies. Expert Opin Drug Metab Toxicol. 2018 Jul;14(7):679-692. doi: 10.1080/17425255.2018.1484450. Epub 2018 Jun 11. Review. PubMed PMID: 29865879.

17: Vieira RF, Grayer RJ, Paton AJ. Chemical profiling of Ocimum americanum using external flavonoids. Phytochemistry. 2003 Jul;63(5):555-67. PubMed PMID: 12809716.

18: Luo W, Wen Y, Tu Y, Du H, Li Q, Zhu C, Li Y. A New Flavonoid Glycoside from Lysionotus pauciflorus. Nat Prod Commun. 2016 May;11(5):621-2. PubMed PMID: 27319133.

19: Greenham J, Vassiliades DD, Harborne JB, Williams CA, Eagles J, Grayer RJ, Veitch NC. A distinctive flavonoid chemistry for the anomalous genus Biebersteinia. Phytochemistry. 2001 Jan;56(1):87-91. PubMed PMID: 11198823.

20: Song JY, He XZ, Chen XF, Hu JY, Luo GY, Mo YZ. [Hypotensive effect of nevadensin]. Zhongguo Yao Li Xue Bao. 1985 Jun;6(2):99-102. Chinese. PubMed PMID: 2934957.