An unambiguous and practical synthesis of Oroxylin A: a commonly misidentified flavone

References

• Deka D, Kumar V, Prasad C, Kumar K, Gogoi B, Singh L, Srivastava R. 2013. Oroxylum indicum–a medicinal plant of North East India: An overview of its nutritional, remedial, and prophylactic properties. J Appl Pharm Sci. 3:S104–S112.
   Google Scholar
• Dinda B, SilSarma I, Dinda M, Rudrapaul P. 2015. Oroxylum indicum (L.) Kurz, an important Asian traditional medicine: from traditional uses to scientific data for its commercial exploitation. J Ethnopharmacol. 161:255–278.
   PubMed Web of Science ®Google Scholar
• Fuentes RG, Arai MA, Sadhu SK, Ahmed F, Ishibashi M. 2015. Phenolic compounds from the bark of Oroxylum indicum activate the Ngn2 promoter. J Nat Med. 69(4):589–594.
   PubMed Web of Science ®Google Scholar
• Fujita R, Hanaya K, Higashibayashi S, Sugai T. 2018. Synthesis of oroxylin A starting from naturally abundant baicalin. Heterocycles. 97:1165–1174.
   Web of Science ®Google Scholar
• Gao H, Nishioka T, Kawabata J, Kasai T. 2004. Structure-activity relationships for α-glucosidase inhibition of baicalein, 5, 6, 7-trihydroxyflavone: the effect of A-ring substitution. Biosci Biotechnol Biochem. 68(2):369–375.
   PubMed Web of Science ®Google Scholar
• Han DH, Lee Y, Ahn JH. 2016. Biological synthesis of baicalein derivatives using Escherichia coli. J Microbiol Biotechnol. 26(11):1918–1923.
   PubMed Web of Science ®Google Scholar
• He G, Gao Y, Li C, Wu G, Li Y, Dong L, Huang C, Chen H. 2016. A convenient and efficient approach to synthesize negletein from baicalin. Tetrahedron Lett. 57(18):2001–2005.
   Web of Science ®Google Scholar
• Huang W-H, Chien P-Y, Yang C-H, Lee A-R. 2003. Novel synthesis of flavonoids of Scutellaria baicalensis G EORGI. Chem Pharm Bull. 51(3):339–340.
   PubMed Web of Science ®Google Scholar
• Joshi B, Gawad D. 1977. Flavones of Pajanelia multijuga P. DC. and Ligustrum neilgherense var. obovata C.B. Cl. Proc Indian Acad Sci. 86(1):41–44.
   Google Scholar
• Kim DH, Jeon SJ, Son KH, Jung JW, Lee S, Yoon BH, Lee JJ, Cho YW, Cheong JH, Ko KH, et al. 2007. The ameliorating effect of oroxylin A on scopolamine-induced memory impairment in mice. Neurobiol Learn Mem. 87(4):536–546.
   PubMed Web of Science ®Google Scholar
• Komulainen P, Pedersen M, Hanninen T, Bruunsgaard H, Lakka TA, Kivipelto M, Hassinen M, Rauramaa TH, Pedersen BK, Rauramaa R. 2008. BDNF is a novel marker of cognitive function in ageing women: the DR's EXTRA Study. Neurobiol Learn Mem. 90(4):596–603.
   PubMed Web of Science ®Google Scholar
• Kostrzewa-Susłow E, Dmochowska-Gładysz J, Oszmiański J. 2007. Microbial transformation of baicalin and baicalein. J Mol Catal B: Enzym. 49(1-4):113–117.
   Google Scholar
• Li HB, Chen F. 2005. Isolation and purification of baicalein, wogonin and oroxylin A from the medicinal plant Scutellaria baicalensis by high-speed counter-current chromatography. J Chromatogr A. 1074(1-2):107–110.
   PubMed Web of Science ®Google Scholar
• Lu L, Guo Q, Zhao L. 2016. Overview of Oroxylin A: a promising flavonoid compound. Phytother Res. 30(11):1765–1774.
   PubMed Web of Science ®Google Scholar
• Panhekar D, Mahale G, Renalson K, Satpute S. 2015. Resolving structural ambiguity of Oroxylin synthesized by different approaches. J Chem Pharm Res. 7:174–180.
   Google Scholar
• Pham T, Che H, Phan P, Lee J, Kim S, Park H. 2012. Oroxylin A analogs exhibited strong inhibitory activities against iNOS-mediated nitric oxide (NO) production. Bioorg Med Chem Lett. 22(7):2534–2535.
   PubMed Web of Science ®Google Scholar
• Qidong Y, Zhiyu L, Yang B, Fu W, G Qinglong. 2009. Synthesis of oroxylin. Chinese Patent CN101508689A.
   Google Scholar
• Rajendran N, Subramaniam S, Christena LR, Muthuraman MS, Subramanian NS, Pemiah B, Sivasubramanian A. 2016. Antimicrobial flavonoids isolated from Indian medicinal plant Scutellaria oblonga inhibit biofilms formed by common food pathogens. Nat Prod Res. 30(17):2002–2006.
   PubMed Web of Science ®Google Scholar
• Rao J, Katragadda S, Tatipaka H, Khanapur M, Purohit M, Pullela V, Yadav J. 2007. Natural agent for treatment of gastrointestinal toxicity, associated symptoms and ulcers US Patent Application 2007/0213281 A1.
   Google Scholar
• Rao J, Katragadda S, Tatipaka H, Khanapur M, Purohit M, Pullela V, Yadav J. 2010. Method For Treatment Of Gastric Ulcers And Ulcers Induced By Aspirin. US Patent 2010/7855200 B2.
   Google Scholar
• Rao J, Katragadda S, Tiwari A, Tatipaka H, Pullela V, Suryadevara P, Sastry B, Ali A, Yadav J. 2017. Intestinal α-glucosidase inhibitors and a process for the isolation and use thereof. European Patent EP 1986670 B1, Int. Publication No. WO 2007/096739.
   Google Scholar
• Righi G, Antonioletti R, Silvestri I, D'Antona N, Lambusta D, Bovicelli P. 2010. Convergent synthesis of mosloflavone, negletein and baicalein from crysin. Tetrahedron. 66(6):1294–1298.
   Web of Science ®Google Scholar
• Shaw J, Lee A-R, Huang W-H. 2004. Methods of synthesizing flavonoids and chalcones US Patent Application 2004/0242907 A1.
   Google Scholar
• Song X, Chen Y, Sun Y, Lin B, Qin Y, Hui H, Li Z, You Q, Lu N, Guo Q. 2012. Oroxylin A, a classical natural product, shows a novel inhibitory effect on angiogenesis induced by lipopolysaccharide. Pharmacol Rep. 64(5):1189–1199.
   PubMed Web of Science ®Google Scholar
• Sun Y, Lu N, Ling Y, Gao Y, Chen Y, Wang L, Hu R, Qi Q, Liu W, Yang Y, et al. 2009. Oroxylin A suppresses invasion through down-regulating the expression of matrix metalloproteinase-2/9 in MDA-MB-435 human breast cancer cells. Eur J Pharmacol. 603(1-3):22–28.
   PubMed Web of Science ®Google Scholar
• Tan CX, Schrader KK, Khan IA, Rimando AM. 2015. Activities of wogonin analogs and other flavones against Flavobacterium columnare. Chem Biodivers. 12(2):259–272.
   PubMed Web of Science ®Google Scholar
• Várady J. 1965. Ring isomerization of flavones. New synthesis of oroxylin-A and 7-methyl-oroxylin-A. Tetrahedron Lett. 48:4281–4282.
   Google Scholar
• Yoon S-Y, Chun M-S, Lee Y-S, Park H-I, Shin C-Y, Ryu J-H, Cheong J-H. 2008. The scutellaria flavone, oroxylin A, improves attention-deficit/hyperactivity disorder related behaviors in spontaneously hypertensive rats. Biomol Ther (Seoul). 16(4):343–350.
   Web of Science ®Google Scholar