Helioxanthin

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

MedKoo CAT#: 329645

CAS#: 18920-47-3

Description: Helioxanthin, also known as HE-145, is a potent inhibitor of HBV, HCV and HSV-1 virus. Helioxanthin suppresses the cross talk of COX-2/PGE2 and EGFR/ERK pathway to inhibit Arecoline-induced Oral Cancer Cell (T28) proliferation and blocks tumor growth in xenografted nude mice. Helioxanthin inhibits interleukin-1 beta-induced MIP-1 beta production by reduction of c-jun expression and binding of the c-jun/CREB1 complex to the AP-1/CRE site of the MIP-1 beta promoter in Huh7 cells.


Price and Availability

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Helioxanthin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329645
Name: Helioxanthin
CAS#: 18920-47-3
Chemical Formula: C20H12O6
Exact Mass: 348.0634
Molecular Weight: 348.31
Elemental Analysis: C, 68.97; H, 3.47; O, 27.56


Synonym: HE-145; HE 145; HE145. Helioxanthin

IUPAC/Chemical Name: 10-(benzo[d][1,3]dioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7(9H)-one

InChi Key: JUBRYHUFFFYTGR-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H12O6/c21-20-12-5-10-2-4-15-19(26-9-24-15)18(10)17(13(12)7-22-20)11-1-3-14-16(6-11)25-8-23-14/h1-6H,7-9H2

SMILES Code: O=C1OCC2=C(C3=CC=C(OCO4)C4=C3)C5=C6OCOC6=CC=C5C=C21


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:
>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).

Harmonized System Code:
293490


References

1: Janmanchi D, Lin CH, Hsieh JY, Tseng YP, Chen TA, Jhuang HJ, Yeh SF. Synthesis and biological evaluation of helioxanthin analogues. Bioorg Med Chem. 2013 Apr 1;21(7):2163-76. doi: 10.1016/j.bmc.2012.11.037. Epub 2012 Dec 5. PubMed PMID: 23465436.

2: Lin YM, Kuo WW, Velmurugan BK, Hsien HH, Hsieh YL, Hsu HH, Tu CC, Bau DT, Viswanadha VP, Huang CY. Helioxanthin suppresses the cross talk of COX-2/PGE2 and EGFR/ERK pathway to inhibit Arecoline-induced Oral Cancer Cell (T28) proliferation and blocks tumor growth in xenografted nude mice. Environ Toxicol. 2015 Oct 14. doi: 10.1002/tox.22204. [Epub ahead of print] PubMed PMID: 26464283.

3: Kao TT, Lin CC, Shia KS. The Total Synthesis of Retrojusticidin B, Justicidin E, and Helioxanthin. J Org Chem. 2015 Jul 2;80(13):6708-14. doi: 10.1021/acs.joc.5b00866. Epub 2015 Jun 15. PubMed PMID: 26047161.

4: Li Y, Fu L, Yeo H, Zhu JL, Chou CK, Kou YH, Yeh SF, Gullen E, Austin D, Cheng YC. Inhibition of hepatitis B virus gene expression and replication by helioxanthin and its derivative. Antivir Chem Chemother. 2005;16(3):193-201. PubMed PMID: 16004082.

5: Ying C, Tan S, Cheng YC. Helioxanthin analogue 8-1 inhibits duck hepatitis B virus replication in cell culture. Antivir Chem Chemother. 2010;21(2):97-103. doi: 10.3851/IMP1686. PubMed PMID: 21107018.

6: Nakajima K, Komiyama Y, Hojo H, Ohba S, Yano F, Nishikawa N, Ihara S, Aburatani H, Takato T, Chung UI. Enhancement of bone formation ex vivo and in vivo by a helioxanthin-derivative. Biochem Biophys Res Commun. 2010 May 14;395(4):502-8. doi: 10.1016/j.bbrc.2010.04.041. Epub 2010 Apr 9. Erratum in: Biochem Biophys Res Commun. 2010 Jul 2;397(3):631. Ihara, Sigeo [added]. PubMed PMID: 20382113.

7: Ohba S, Nakajima K, Komiyama Y, Kugimiya F, Igawa K, Itaka K, Moro T, Nakamura K, Kawaguchi H, Takato T, Chung UI. A novel osteogenic helioxanthin-derivative acts in a BMP-dependent manner. Biochem Biophys Res Commun. 2007 Jun 15;357(4):854-60. Epub 2007 Apr 9. PubMed PMID: 17451649.

8: Yeo H, Li Y, Fu L, Zhu JL, Gullen EA, Dutschman GE, Lee Y, Chung R, Huang ES, Austin DJ, Cheng YC. Synthesis and antiviral activity of helioxanthin analogues. J Med Chem. 2005 Jan 27;48(2):534-46. PubMed PMID: 15658867.

9: Song Y, Deng Y, Huang D, Wen J, Liu Z, Li F. LC-MS/MS determination and pharmacokinetic study of four lignan components in rat plasma after oral administration of Acanthopanax sessiliflorus extract. J Ethnopharmacol. 2012 Jun 14;141(3):957-63. doi: 10.1016/j.jep.2012.03.034. Epub 2012 Apr 4. PubMed PMID: 22497733.

10: Tseng PC, Hsu HC, Janmanchi D, Lin CH, Kuo YH, Chou CK, Yeh SF. Helioxanthin inhibits interleukin-1 beta-induced MIP-1 beta production by reduction of c-jun expression and binding of the c-jun/CREB1 complex to the AP-1/CRE site of the MIP-1 beta promoter in Huh7 cells. Biochem Pharmacol. 2008 Oct 30;76(9):1121-33. doi: 10.1016/j.bcp.2008.08.023. Epub 2008 Aug 27. PubMed PMID: 18789903.

11: Hajdu Z, Haskó J, Krizbai IA, Wilhelm I, Jedlinszki N, Fazakas C, Molnár J, Forgo P, Hohmann J, Csupor D. Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain. J Nat Prod. 2014 Dec 26;77(12):2641-50. doi: 10.1021/np500508y. Epub 2014 Dec 5. PubMed PMID: 25479041.

12: Tseng YP, Kuo YH, Hu CP, Jeng KS, Janmanchi D, Lin CH, Chou CK, Yeh SF. The role of helioxanthin in inhibiting human hepatitis B viral replication and gene expression by interfering with the host transcriptional machinery of viral promoters. Antiviral Res. 2008 Mar;77(3):206-14. doi: 10.1016/j.antiviral.2007.12.011. Epub 2008 Jan 18. PubMed PMID: 18249449.

13: Maeda Y, Hojo H, Shimohata N, Choi S, Yamamoto K, Takato T, Chung UI, Ohba S. Bone healing by sterilizable calcium phosphate tetrapods eluting osteogenic molecules. Biomaterials. 2013 Jul;34(22):5530-7. doi: 10.1016/j.biomaterials.2013.03.089. Epub 2013 Apr 23. PubMed PMID: 23623228.

14: Janmanchi D, Tseng YP, Wang KC, Huang RL, Lin CH, Yeh SF. Synthesis and the biological evaluation of arylnaphthalene lignans as anti-hepatitis B virus agents. Bioorg Med Chem. 2010 Feb;18(3):1213-26. doi: 10.1016/j.bmc.2009.12.038. Epub 2009 Dec 21. PubMed PMID: 20061158.

15: Parvez MK, Arbab AH, Al-Dosari MS, Al-Rehaily AJ. Antiviral Natural Products Against Chronic Hepatitis B: Recent Developments. Curr Pharm Des. 2016;22(3):286-93. Review. PubMed PMID: 26561057.

16: Kanke K, Masaki H, Saito T, Komiyama Y, Hojo H, Nakauchi H, Lichtler AC, Takato T, Chung UI, Ohba S. Stepwise differentiation of pluripotent stem cells into osteoblasts using four small molecules under serum-free and feeder-free conditions. Stem Cell Reports. 2014 May 22;2(6):751-60. doi: 10.1016/j.stemcr.2014.04.016. eCollection 2014 Jun 3. PubMed PMID: 24936463; PubMed Central PMCID: PMC4050355.

17: Ying C, Li Y, Leung CH, Robek MD, Cheng YC. Unique antiviral mechanism discovered in anti-hepatitis B virus research with a natural product analogue. Proc Natl Acad Sci U S A. 2007 May 15;104(20):8526-31. Epub 2007 May 8. PubMed PMID: 17488817; PubMed Central PMCID: PMC1895983.

18: Ban HS, Lee S, Kim YP, Yamaki K, Shin KH, Ohuchi K. Inhibition of prostaglandin E(2) production by taiwanin C isolated from the root of Acanthopanax chiisanensis and the mechanism of action. Biochem Pharmacol. 2002 Nov 1;64(9):1345-54. PubMed PMID: 12392817.

19: Leung YM, Tsou YH, Kuo CS, Lin SY, Wu PY, Hour MJ, Kuo YH. Arylnaphthalene lignans from Taiwania cryptomerioides as novel blockers of voltage-gated K+ channels. Phytomedicine. 2010 Dec 15;18(1):46-51. doi: 10.1016/j.phymed.2010.04.001. Epub 2010 Jun 1. PubMed PMID: 20684875.

20: Yoo HH, Lee SH, Jin C, Kim DH. Mechanism-based inactivation of cytochrome P450 3A4 by methylenedioxyphenyl lignans from Acanthopanax chiisanensis. Planta Med. 2008 Jun;74(8):822-7. doi: 10.1055/s-2008-1074556. Epub 2008 Jun 18. PubMed PMID: 18563665.