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MedKoo Cat#: 407827 | Name: Neobavaisoflavone
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Description:

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

Neobavaisoflavone is a natural isoflavone that was first isolated from seeds of P. corylifolia, which are used in traditional herbal medicine to treat various skin diseases. Neobavaisoflavone sensitizes apoptosis via the inhibition of metastasis in TRAIL-resistant human glioma U373MG cells.

Chemical Structure

Neobavaisoflavone
Neobavaisoflavone
CAS#41060-15-5

Theoretical Analysis

MedKoo Cat#: 407827

Name: Neobavaisoflavone

CAS#: 41060-15-5

Chemical Formula: C20H18O4

Exact Mass: 322.1205

Molecular Weight: 322.36

Elemental Analysis: C, 74.52; H, 5.63; O, 19.85

Price and Availability

Size Price Availability Quantity
5mg USD 325.00
25mg USD 950.00
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Synonym
Neobavaisoflavone,
IUPAC/Chemical Name
7-hydroxy-3-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-4H-1-benzopyran-4-one
InChi Key
OBGPEBYHGIUFBN-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H18O4/c1-12(2)3-4-14-9-13(5-8-18(14)22)17-11-24-19-10-15(21)6-7-16(19)20(17)23/h3,5-11,21-22H,4H2,1-2H3
SMILES Code
O=C1C(C2=CC=C(O)C(C/C=C(C)\C)=C2)=COC3=CC(O)=CC=C13
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Neobavaisoflavone inhibits DNA polymerase.
In vitro activity:
The present study investigated in vitro the anti-inflammatory activity of neobavaisoflavone. Neobavaisoflavone significantly inhibited the production of reactive oxygen species (ROS), reactive nitrogen species (RNS) and cytokines: IL-1β, IL-6, IL-12p40, IL-12p70, TNF-α in LPS+IFN-γ- or PMA- stimulated RAW264.7 macrophages. Reference: Molecules. 2011 May 3;16(5):3701-12. https://pubmed.ncbi.nlm.nih.gov/21540797/
In vivo activity:
As indicated by the results, NBIF (neobavaisoflavone) mitigated cartilage matrix degradation and chondrocyte apoptosis in the OA rat model. NBIF hampered IL-1β-mediated cell viability inhibition, apoptosis, inflammatory reactions, and oxidative stress of chondrocytes. Moreover, NBIF suppressed NF-κB phosphorylation and HIF-2α expression. HIF-2α overexpression induced inflammation, oxidative stress, and apoptosis in chondrocytes, while NBIF reversed HIF-2α overexpression-caused chondrocyte damage. Reference: J Physiol Pharmacol. 2022 Oct;73(5). https://pubmed.ncbi.nlm.nih.gov/36942811/
Solvent mg/mL mM
Solubility
Ethanol 1.0 3.10
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 322.36 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
Formulation protocol:
1. Guo J, Shen Y, Hu S, Rui T, Liu J, Yuan Y. Neobavaisoflavone inhibits antitumor immunosuppression via myeloid-derived suppressor cells. Int Immunopharmacol. 2022 Oct;111:109103. doi: 10.1016/j.intimp.2022.109103. Epub 2022 Aug 6. PMID: 35944461. 2. Szliszka E, Skaba D, Czuba ZP, Krol W. Inhibition of inflammatory mediators by neobavaisoflavone in activated RAW264.7 macrophages. Molecules. 2011 May 3;16(5):3701-12. doi: 10.3390/molecules16053701. PMID: 21540797; PMCID: PMC6263287. 3. Bai J, Liu T, Ren M, Wang X. Neobavaisoflavone improves medial collateral ligament-induced osteoarthritis through repressing the nuclear factor -κB/hypoxia-inducible factor-2α axis. J Physiol Pharmacol. 2022 Oct;73(5). doi: 10.26402/jpp.2022.5.08. Epub 2023 Mar 16. PMID: 36942811. 4. Liang R, Yuan Y, Bai Y, Liu X, Chen J, Jiang D, Meng D, Chen G, Li B, Zhou L, Guo W. Neobavaisoflavone inhibits allergic inflammatory responses by suppressing mast cell activation. Int Immunopharmacol. 2022 Sep;110:108953. doi: 10.1016/j.intimp.2022.108953. Epub 2022 Jun 17. PMID: 35724607.
In vitro protocol:
1. Guo J, Shen Y, Hu S, Rui T, Liu J, Yuan Y. Neobavaisoflavone inhibits antitumor immunosuppression via myeloid-derived suppressor cells. Int Immunopharmacol. 2022 Oct;111:109103. doi: 10.1016/j.intimp.2022.109103. Epub 2022 Aug 6. PMID: 35944461. 2. Szliszka E, Skaba D, Czuba ZP, Krol W. Inhibition of inflammatory mediators by neobavaisoflavone in activated RAW264.7 macrophages. Molecules. 2011 May 3;16(5):3701-12. doi: 10.3390/molecules16053701. PMID: 21540797; PMCID: PMC6263287.
In vivo protocol:
1. Bai J, Liu T, Ren M, Wang X. Neobavaisoflavone improves medial collateral ligament-induced osteoarthritis through repressing the nuclear factor -κB/hypoxia-inducible factor-2α axis. J Physiol Pharmacol. 2022 Oct;73(5). doi: 10.26402/jpp.2022.5.08. Epub 2023 Mar 16. PMID: 36942811. 2. Liang R, Yuan Y, Bai Y, Liu X, Chen J, Jiang D, Meng D, Chen G, Li B, Zhou L, Guo W. Neobavaisoflavone inhibits allergic inflammatory responses by suppressing mast cell activation. Int Immunopharmacol. 2022 Sep;110:108953. doi: 10.1016/j.intimp.2022.108953. Epub 2022 Jun 17. PMID: 35724607.
1: Sandoval-Ramírez BA, M Lamuela-Raventós R, Estruch R, Sasot G, Doménech M, Tresserra-Rimbau A. Beer Polyphenols and Menopause: Effects and Mechanisms-A Review of Current Knowledge. Oxid Med Cell Longev. 2017;2017:4749131. doi: 10.1155/2017/4749131. Epub 2017 Aug 17. Review. PubMed PMID: 28904736; PubMed Central PMCID: PMC5585550. 2: Stompor M, Świtalska M, Podgórski R, Uram Ł, Aebisher D, Wietrzyk J. Synthesis and biological evaluation of 4'-O-acetyl-isoxanthohumol and its analogues as antioxidant and antiproliferative agents. Acta Biochim Pol. 2017;64(3):577-583. doi: 10.18388/abp.2017_1608. Epub 2017 Aug 12. PubMed PMID: 28803257. 3: Stompor M, Uram Ł, Podgórski R. In Vitro Effect of 8-Prenylnaringenin and Naringenin on Fibroblasts and Glioblastoma Cells-Cellular Accumulation and Cytotoxicity. Molecules. 2017 Jun 30;22(7). pii: E1092. doi: 10.3390/molecules22071092. PubMed PMID: 28665345. 4: Liu M, Zhang W, Zhang W, Zhou X, Li M, Miao J. Prenylflavonoid Isoxanthohumol Sensitizes MCF-7/ADR Cells to Doxorubicin Cytotoxicity via Acting as a Substrate of ABCB1. Toxins (Basel). 2017 Jun 30;9(7). pii: E208. doi: 10.3390/toxins9070208. PubMed PMID: 28665335; PubMed Central PMCID: PMC5535155. 5: Quifer-Rada P, Chiva-Blanch G, Jáuregui O, Estruch R, Lamuela-Raventós RM. A discovery-driven approach to elucidate urinary metabolome changes after a regular and moderate consumption of beer and nonalcoholic beer in subjects at high cardiovascular risk. Mol Nutr Food Res. 2017 Jun 13. doi: 10.1002/mnfr.201600980. [Epub ahead of print] PubMed PMID: 28608394. 6: Luescher S, Urmann C, Butterweck V. Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells. J Nat Prod. 2017 Apr 28;80(4):925-931. doi: 10.1021/acs.jnatprod.6b00869. Epub 2017 Feb 24. PubMed PMID: 28234482. 7: Inui T, Okumura K, Matsui H, Hosoya T, Kumazawa S. Effect of harvest time on some in vitro functional properties of hop polyphenols. Food Chem. 2017 Jun 15;225:69-76. doi: 10.1016/j.foodchem.2017.01.002. Epub 2017 Jan 3. PubMed PMID: 28193435. 8: Yang L, Broderick D, Campbell Y, Gombart AF, Stevens JF, Jiang Y, Hsu VL, Bisson WH, Maier CS. Conformational modulation of the farnesoid X receptor by prenylflavonoids: Insights from hydrogen deuterium exchange mass spectrometry (HDX-MS), fluorescence titration and molecular docking studies. Biochim Biophys Acta. 2016 Dec;1864(12):1667-1677. doi: 10.1016/j.bbapap.2016.08.019. Epub 2016 Sep 3. PubMed PMID: 27596062; PubMed Central PMCID: PMC5071164. 9: Abdi F, Mobedi H, Roozbeh N. Hops for Menopausal Vasomotor Symptoms: Mechanisms of Action. J Menopausal Med. 2016 Aug;22(2):62-4. doi: 10.6118/jmm.2016.22.2.62. Epub 2016 Aug 30. PubMed PMID: 27617238; PubMed Central PMCID: PMC5016504. 10: Wang S, Dunlap TL, Howell CE, Mbachu OC, Rue EA, Phansalkar R, Chen SN, Pauli GF, Dietz BM, Bolton JL. Hop (Humulus lupulus L.) Extract and 6-Prenylnaringenin Induce P450 1A1 Catalyzed Estrogen 2-Hydroxylation. Chem Res Toxicol. 2016 Jul 18;29(7):1142-50. doi: 10.1021/acs.chemrestox.6b00112. Epub 2016 Jun 22. PubMed PMID: 27269377; PubMed Central PMCID: PMC4951797. 11: Venturelli S, Burkard M, Biendl M, Lauer UM, Frank J, Busch C. Prenylated chalcones and flavonoids for the prevention and treatment of cancer. Nutrition. 2016 Nov-Dec;32(11-12):1171-8. doi: 10.1016/j.nut.2016.03.020. Epub 2016 Apr 8. Review. PubMed PMID: 27238957. 12: Krajnović T, Kaluđerović GN, Wessjohann LA, Mijatović S, Maksimović-Ivanić D. Versatile antitumor potential of isoxanthohumol: Enhancement of paclitaxel activity in vivo. Pharmacol Res. 2016 Mar;105:62-73. doi: 10.1016/j.phrs.2016.01.011. Epub 2016 Jan 16. PubMed PMID: 26784390. 13: Zhang B, Chu W, Wei P, Liu Y, Wei T. Xanthohumol induces generation of reactive oxygen species and triggers apoptosis through inhibition of mitochondrial electron transfer chain complex I. Free Radic Biol Med. 2015 Dec;89:486-97. doi: 10.1016/j.freeradbiomed.2015.09.021. Epub 2015 Oct 8. PubMed PMID: 26453927. 14: Stompor M, Dancewicz K, Gabryś B, Anioł M. Insect Antifeedant Potential of Xanthohumol, Isoxanthohumol, and Their Derivatives. J Agric Food Chem. 2015 Aug 5;63(30):6749-56. doi: 10.1021/acs.jafc.5b02025. Epub 2015 Jul 27. PubMed PMID: 26176501. 15: Kim DW, Woo HS, Kim JY, Ryuk JA, Park KH, Ko BS. Phenols displaying tyrosinase inhibition from Humulus lupulus. J Enzyme Inhib Med Chem. 2016 Oct;31(5):742-7. doi: 10.3109/14756366.2015.1063621. Epub 2015 Jul 10. PubMed PMID: 26162028. 16: Martinez SE, Davies NM. Enantiospecific pharmacokinetics of isoxanthohumol and its metabolite 8-prenylnaringenin in the rat. Mol Nutr Food Res. 2015 Sep;59(9):1674-89. doi: 10.1002/mnfr.201500118. Epub 2015 Jul 1. PubMed PMID: 26079861. 17: Popoola OK, Marnewick JL, Rautenbach F, Ameer F, Iwuoha EI, Hussein AA. Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium. Molecules. 2015 Apr 20;20(4):7143-55. doi: 10.3390/molecules20047143. PubMed PMID: 25903365. 18: Żołnierczyk AK, Mączka WK, Grabarczyk M, Wińska K, Woźniak E, Anioł M. Isoxanthohumol--Biologically active hop flavonoid. Fitoterapia. 2015 Jun;103:71-82. doi: 10.1016/j.fitote.2015.03.007. Epub 2015 Mar 12. PubMed PMID: 25771121. 19: Gąsiorowska J, Teisseyre A, Uryga A, Michalak K. Inhibition of Kv1.3 Channels in Human Jurkat T Cells by Xanthohumol and Isoxanthohumol. J Membr Biol. 2015 Aug;248(4):705-11. doi: 10.1007/s00232-015-9782-0. Epub 2015 Feb 17. PubMed PMID: 25688010; PubMed Central PMCID: PMC4513206. 20: Büchter C, Havermann S, Koch K, Wätjen W. Isoxanthohumol, a constituent of hop (Humulus lupulus L.), increases stress resistance in Caenorhabditis elegans dependent on the transcription factor DAF-16. Eur J Nutr. 2016 Feb;55(1):257-65. doi: 10.1007/s00394-015-0843-z. Epub 2015 Feb 3. PubMed PMID: 25644181.

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