Resting cells of Fusarium oxysporum f. sp. Cucumerinum (F. oxsporum) were used for the biotransformation of salvianolic acid B (Sal B). Three transformed products, isolithospermic acid, prolithospermic acid and danshensu, were identified on the basis of chemical and spectroscopic data. The stability of the two ester bonds of Sal B was studied and two degradation routes were found. In the biotransformation system, Sal B was transformed into isolithospermic acid first which was then converted into prolithospermic acid. In alkaline solutions, Sal B was transformed into lithospermic acid first which was then converted into prolithospermic acid. This is the first reports of the NMR spectra of isolithospermic acid and this result may indicate the metabolic pathways of Sal B in vivo.
ZengJ., YangN., LiX.M., ShamiP.J., ZhanJ. (2010) 4′-O-methylglycosylation of curcumin by Beauveria bassiana. Natural Product Communications, 5, 77–80.
2.
RaoS.R., RavishankarG.A. (2000) Biotransformation of protocatechuic aldehyde and caffeic acid to vanillin and capsaicin in freely suspended and immobilized cell cultures of Capsicum frutescens. Journal of Biotechnology, 76, 137–146.
3.
YeH., YuanS., CongX. (2007) Biotransformation of puerarin into 3′-hydroxypuerarin by Trichoderma harzianum NJ01. Enzyme and Microbial Technology, 40, 594–597.
4.
(a) LiM.H., ChenJ.M., PengY., WuQ., XiaoP.G. (2008) Investigation of Danshen and related medicinal plants in China. Journal of Ethnopharmacology, 120, 419–426;(b) Xu M, Han J, Li H, Fan L, Liu A, Guo D. (2008) Analysis on the stability of total phenolic acids and salvianolic acid B from Salvia miltiorrhiza by HPLC and HPLC-MSn. Natural Product Communications, 3, 669–676; (c) Lu L, Hao Zhang H, Qian Y, and Yuan Yuan Y. (2010) Isolation of salvianolic acid A, a minor phenolic carboxylic acid of Salvia miltiorrhiza. Natural Product Communications, 5, 805–808.
5.
LuY., Yeap FooL. (2002) Polyphenolics of Salvia - A review. Phytochemistry, 59, 117–140.
6.
WuC.T., MulabagalV., NalawadeS.M., ChenC.L., YangT.F., TsayH.S. (2003) Isolation and quantitative analysis of cryptotanshinone, an active quinoid diterpene formed in callus of Salvia miltiorrhiza Bunge. Biological and Pharmaceutical Bulletin, 26, 845–848.
7.
ChenJ., WangF., LeeF.S.C., WangX., XieM., (2006) Separation and identification of water-soluble salvianolic acids from Salvia miltiorrhiza Bunge by high-speed counter-current chromatography and ESI-MS analysis. Talanta, 69, 172–179.
8.
ZhaoJ.F., LiuC.H., HuY.Y., XuL.M., LiuP., LiuC. (2004) Effect of salvianolic acid B on Smad3 expression in hepatic stellate cells. Hepatobiliary and Pancreatic Diseases International, 3, 102–105.
9.
WuY.J., HongC.Y., LinS.J., WuP., ShiaoM.S. (1998) Increase of vitamin E content in LDL and reduction of atherosclerosis in cholesterol-fed rabbits by a water-soluble antioxidant-rich fraction of Salvia miltiorrhiza. Arteriosclerosis Thrombosis and Vascular Biology, 18, 481–486.
10.
ChenY.H., LinS.J., KuH.H., ShiaoM.S., LinF.Y., ChenJ.W., ChenY.L. (2001) Salvianolic acid B attenuates VCAM-1 and ICAM-1 expression in TNF-alpha-treated human aortic endothelial cells. Journal of Cellular Biochemistry, 82, 512–521.
11.
TangM.K., RenD.C., ZhangJ.T., DuG.H. (2002) Effect of salvianolic acids from Radix Salviae miltiorrhizae on regional cerebral blood flow and platelet aggregation in rats. Phytomedicine, 9, 405–409.
12.
GuoY.X., XiuZ.L., ZhangD.J., WangH., WangL.X., XiaoH-B. (2007) Kinetics and mechanism of degradation of lithospermic acid B in aqueous solution. Journal of Pharmaceutical and Biomedical Analysis, 43, 1249–1255.
13.
TanakaT., MorimotoS., NonakaG.I., NishiokaI., YokozawaT., ChungH.Y., OuraH. (1989) Magnesium and ammonium-potassium lithospermates B, the active principles having a uremia-preventive effect from Salvia miltiorrhiza. Chemical & Pharmaceutical Bulletin, 37, 340–344.
14.
NagaiM., NoguchiM., IizukaT., OtaniK., KamataK. (1996) Vasodilator effects of des(α-carboxy-3,4-dihydroxyphenethyl)lithospermic acid (8-epiblechnic acid), a derivative of lithospermic acids in salviae miltiorrhizae radix. Biological and Pharmaceutical Bulletin, 19, 228–232.
15.
KimY.H., AhnJ.Y., MoonS.H., LeeJ. (2005) Biodegradation and detoxification of organophosphate insecticide, malathion by Fusarium oxysporum f. sp. pisi cutinase. Chemosphere, 60, 1349–1355.
16.
MoukouliM., TopakasE., ChristakopoulosP. (2008) Cloning, characterization and functional expression of an alkalitolerant type C feruloyl esterase from Fusarium oxysporum. Applied Microbiology and Biotechnology, 79, 245–254.
17.
KimY.H., MinJ., BaeK.D., GuM.B., LeeJ. (2005) Biodegradation of dipropyl phthalate and toxicity of its degradation products: A comparison of Fusarium oxysporum f. sp. pisi cutinase and Candida cylindracea esterase. Archives of Microbiology, 184, 25–31.
18.
JiangB., WuD.X., ZuoY.J., GaoL., LiZ.Y. (2007) Oxygenases and oxygenation of alkanes. Chinese Journal of Organic Chemistry, 27, 209–217.
19.
WackettL.P., (2002) Mechanism and applications of Rieske non-heme iron dioxygenases. Enzyme and Microbial Technology, 31, 577–587.
20.
HollandH. (1992) Organic Synthesis with Oxidative Enzymes, VCH Publishers, New York.
21.
SimsR.C., OvercashM.R. (1983) Fate of polynuclear aromatic compounds (PNAs) in soil-plant systems. Residue Reviews, 88, 1–68.
22.
KanS., LiJ., HuangW., ShaoL., ChenD. (2009) Microsphere resin chromatography combined with microbial biotransformation for the separation and purification of salvianolic acid B in aqueous extract of roots of Salvia multiorrihza Bunge. Journal of Chromatography A, 1216, 3881–3886.
