Abstract
Scutellarein has been prepared by the hydrolysis of scutellarin with sulfuric acid to provide this biologically important rare flavone in up to > 90% yield and on the 5 g scale in minutes. This protocol has been applied to five other flavonoid glycosides (rutin, hesperidin, naringin, baicalin and diosmin) which are readily hydrolysed to their corresponding aglycones.
References
1.
Luan L.-J.
,
Zhou Y.
,
Wu Y.-J.
,
Liu X.-S.
, and
Wang L.-H.
, J. Chem. Eng. Data , 2010 , 55 , 5299 .
2.
Ge Q.H.
,
Zhou Z.
,
Zhi X.J.
,
Ma L.L.
, and
Chen X.H.
, Chin. J. Pharm. , 2003 , 34 , 618 . (in Chinese).
3.
Xing J.-F.
,
You H.-S.
,
Dong Y.-L.
,
Lu J.
,
Chen S.-Y
,
Zhu H.-F.
,
Dong Q.
,
Wang M.-Y
, and
Dong W.-H.
, Acta Pharmacol. Sin. , 2011 , 32 , 655 .
4.
Che Q.M.
,
Pan L.Y.
,
Chen Y.
, and
He H.
, Chin. Pharm. J. , 2007 , 42 , 1418 . (in Chinese).
5.
Zhang J.L.
,
Che Q.M.
,
Li S.Z.
, and
Zhou T.H.
, J. Asian Nat. Prod. Res. , 2003 , 5 , 249 .
6.
Ran X.R.
,
Si S.Z.
,
Liang Q.L.
, and
Luo A.
, Chin. Chem. Lett. , 2006 , 17 , 1225 .
7.
Qiu F.
,
Xia H.J.
,
Zhang T.Y.
,
Di X.
,
Qu G.X.
, and
Yao X.S.
, Planta Med. , 2007 , 73 , 363 .
8.
Xia H.J.
,
Qiu F.
,
Zhu S.
,
Zhang T.Y.
,
Qu G.X.
, and
Yao X.S.
, Biol. Pharm. Bull. , 2007 , 30 , 1308 .
9.
Zhu B.-H.
,
Guan Y.-Y.
,
He H.
, and
Lin M.-J.
, Acta Pharmacol. Sin. , 2000 , 21 , 353 .
10.
Gao R.
,
Zhu B.-H.
,
Tang S.-B.
,
Wang J.-F.
, and
Ren J.
, Acta Pharmacol. Sin. , 2008 , 29 , 707 .
11.
Yu M.S.
,
Lee J.
,
Lee J.M.
,
Kim Y.
,
Chin Y.-W.
,
Jee J-G.
,
Keum Y.-S.
, and
Jeong Y.-J.
, Bioorg. Med. Chem. Lett. , 2012 , 22 , 4049 .
12.
Qian L.
,
Shen M.
,
Tang H.
,
Tang Y.
,
Zhang L.
,
Fu Y.
,
Shi Q.
, and
Li N.-G.
, Molecules , 2012 , 17 , 10667 .
13.
Chen V.
,
Staub R.E.
,
Baggett S.
,
Chimmani R.
,
Tagliaferri M.
,
Cohen I.
, and
Shtivelman E.
, PloS ONE , 2012 , 7 , e30107 .
14.
Farkas L.
,
Mezey-Vándor G.
, and
Nógrádi M.
, Chem. Ber. , 1974 , 107 , 3878 .
15.
Cui J.M.
,
Fang G.
,
Duan Y.B.
,
Liu Q.
,
Wu L.P.
,
Zhang G.H.
, and
Wu S.
, J. Asian Nat. Prod. Res. , 2005 , 7 , 655 .
16.
Righi G.
,
Silvestri I.P.
,
Barontini M.
,
Crisante F.
,
Manno A.D.
,
Pelagalli R.
, and
Bovicelli P.
, Nat. Prod. Res. , 2012 , 26 , 1278 .
17.
Li Y.Z.
,
Liu W.Y.
,
Li G.D.
,
Han G.X.
, and
Zhang W.D.
, Chin. J. Pharm. , 2002 , 33 , 281 . (in Chinese).
18.
Gao M.
,
Huang W.
, and
Liu C.Z.
, J. Chrom. B , 2007 , 858 , 22 .
19.
Li N.-G.
,
Song S.-L.
,
Shen M.-Z.
,
Tang Y.-P.
,
Shi Z.-H.
,
Tang H.
,
Shi Q.-P.
,
Fu Y.-F.
, and
Duan J.-A.
, Bioorg. Med. Chem. , 2012 , 20 , 6919 .
20.
Li N.-G.
,
Shen M.-Z.
,
Wang Z.-J.
,
Tang Y.-P.
,
Shi Z.-H.
,
Fu Y.-F.
,
Shi Q.-P.
,
Tang H.
, and
Duan J.-A.
, Bioorg. Med. Chem. Lett. , 2013 , 23 , 102 .
21.
Qian L.H.
,
Li N.-G.
,
Tang Y.-P.
,
Zhang L.
,
Tang H.
,
Wang Z.-J.
,
Liu L.
,
Song S.-L.
,
Song J.-M.
,
Guo J.M.
, and
Ding A.W.
, Int. J. Mol. Sci. , 2011 , 12 , 8208 .
22.
Fu X.Z.
,
Xing F.J.
,
Lan Y.Y.
,
Wang A.
,
Wang Y.
,
Li J.
,
Zhou W.
,
Zhang W.
, and
Liu Y.
, Chin. J. Org. Chem. , 2011 , 31 , 1043 . (in Chinese).
23.
Wang L.
,
Li X.
,
Zhang S.
,
Lu W.
,
Liao S.
,
Liu X.
,
Shan L.
,
Shen X.
,
Jiang H.
,
Zhang W.
,
Huang J.
, and
Li H.
, Bioorg. Med. Chem. Lett. , 2012 , 20 , 4164 .
24.
Correia-da-Silva M.
,
Sousa E.
,
Duarte B.
,
Marques F.
,
Carvalho F.
,
Cunha-Ribeiro L.M.
, and
Pinto M.M.M.
, J. Med. Chem. , 2011 , 54 , 95 .
25.
Kulesh N.I.
,
Vasilevskaya N.A.
,
Veselova M.V.
,
Denisenko V.A.
, and
Fedoreev S.A.
, Chem. Nat. Comp. , 2008 , 44 , 712 .
26.
Bhuyan R.
, and
Saikia C.N.
, Bioresource Tech. , 2005 , 96 , 363 .
27.
Gao H.
,
Kawabata J.
, Biosci. Biotechnol. Biochem. , 2004 , 68 , 1858 .