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Original articles

Biosynthesis of artemisinin – revisited

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Pages 265-273 | Received 28 Dec 2010, Accepted 08 Mar 2011, Published online: 12 Apr 2011

References

  • Akhila , A , Rani , K and Thakur , RS. 1990 . Biosynthesis of artemisinic acid in Artemisia annua . Phytochemistry. , 29 : 2129 – 2132 .
  • Akhila , A , Thakur , RS and Popli , SP. 1987 . Biosynthesis of artemisinin in Artemisia annua . Phytochemistry. , 26 : 1927 – 1930 .
  • Arigoni , D , Sagner , S , Latzel , C , Eisenreich , W , Bacher , A and Zenk , M. 1997 . Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement . Proc Natl Acad Sci USA. , 94 : 10600 – 10605 (and references cited therein) .
  • Bacher , A and Eisenreich , W. 2007 . 13CO2 as a universal metabolic tracer in isotopologue perturbation experiments . Phytochemistry. , 68 : 2273 – 2289 .
  • Bertea , CM , Voster , A , Verstappen , FWA , Maffei , M , Beekwilder , J and Bouwmeester , HJ. 2006 . Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichomes cDNA library . Arch Biochem Biophys. , 448 : 3 – 12 .
  • Bouwmeester , HJ , Wallaart , TE , Janssen , MHA , Loo , BV , Jansen , BJM , Posthumus , MA , Schmidt , CO , Kraker , JD , Kong , WA and Franssen , MCR. 1999 . Amorpha-4,11-diene synthase catalyses the first probable step in artemisinin synthesis . Phytochemistry. , 52 : 843 – 854 .
  • Brown , GD and Sy , L. 2004 . Synthesis of labeled dihydroartemisinic acid . Tetrahedron. , 60 : 1125 – 1138 .
  • Brown , GD and Sy , L. 2007a . In vivo transformation of artemisininc acid in Artemisia annua plants . Tetrahedron. , 63 : 9548 – 9566 .
  • Brown , GD and Sy , L. 2007b . In vivo transformation of dihydro-epi-deoxyarteannuin B in Artemisia annua plants . Tetrahedron. , 63 : 9536 – 9547 .
  • Covello , PS , Teoh , KH , Polichuk , DR , Reed , DW and Nowak , G. 2007 . Functional genomics and the biosynthesis of artemisinin . Phytochemistry. , 68 : 1864 – 1871 .
  • Delabays , N , Simonnet , X and Gaudin , M. 2001 . The genetics of artemisinin content in Artemisia annua L. and the breeding of yielding cultivars . Curr Med Chem. , 8 : 1795 – 1801 .
  • Eisenreich , W , Rohdich , F and Bacher , A. 2001 . Deoxyxylulose phosphate pathway to terpenoids . Trends Plant Sci. , 6 : 78 – 84 .
  • Eisenreich , W , Sagner , S , Zenk , MH and Bacher , A. 1997 . Monoterpenoid essential oils are not of mevalonoid origin . Tetrahedron Lett. , 38 : 3889 – 3892 .
  • Eisenreich , W , Schwarz , M , Cartayrade , A , Arigoni , D , Zenk , MH and Bacher , A. 1998 . The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms . Chem Biol. , 5 : 221 – 233 .
  • Ferreira , JFS , Laughlin , JC , Delabays , N and Magalhaes , PMD. 2005 . Cultivation and genetics of Artemisia annua L. for increased production of the antimalarial artemisinin . Plant Gen Res. , 3 ( 2 ) : 206 – 229 .
  • Hemmerlin , A , Hoeffler , J , Meyer , O , Tritsch , D , Kagan , IA , Grosdemange-Billiard , C , Rohmer , M and Bach , TJ. 2003 . Crosstalk between the cytosolic mevalonate and the plastidial methylerythritol phosphate pathways in tobacco bright yellow-2 cells . J Biol Chem. , 278 : 26666 – 26676 .
  • Hoeffler , J , Hammerlin , A , Grosdemange-Billiard , C , Bach , TJ and Rohmer , M. 2002 . Isoprenoid biosynthesis in higher plants and in Escherichia coli on the branching in the methylerythritol phosphate pathway and the independent biosynthesis of isopentenyl diphosphate and dimethylallyl diphosphate . Biochem J. , 366 : 573 – 583 .
  • Klayman , DL. 1985 . Qinghaosu (artemisinin): an antimalarial drug from China . Science. , 228 ( 4703 ) : 1049 – 1055 .
  • Klayman , DL , Lin , AJ , Acton , N , Scovill , JP , Hock , J , Milhous , WK and Theoharides , AD. 1984 . Isolation of artemisinin (qinghaosu) from Artemisia annua growing in the United States . J Nat Prod. , 47 : 715 – 717 .
  • Lichtenthaler , HK. 1999 . The 1-deoxy-D-xylulose -5-phosphate pathway of isoprenoid biosynthesis in plants . Annu Rev Plant Physiol Plant Mol Biol. , 50 : 47 – 65 .
  • Lichtenthaler , HK , Schwender , J , Disch , A and Rohmer , M. 1997 . Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate independent pathway . FEBS Lett. , 400 : 271 – 274 .
  • Liu , JM , Ni , MY , Fan , JF , Tu , YY , Wu , ZH , Wu , YL and Chou , WS. 1979 . Structure and reaction of arteannuin . Acta Chim Sinica. , 37 : 129 – 143 .
  • Mercke , P , Bengtsson , M , Bouwmeester , HJ and Posthumus , MA. 2000 . Molecular cloning, expression, and characterization of Amorpha-4,11-diene synthase, a key enzyme of artemisinin biosynthesis in Artemisia annua L . Arch Biochem Biophys. , 381 : 173 – 180 .
  • Olsson , ME , Olofsson , LM , Lindahl , AL , Lundgren , A , Brodelius , M and Brodelius , PE. 2009 . Localization of enzymes of artemisinin biosynthesis to the apical cells of grandular secretory trichomes of Artemisia annua L . Phytochemistry. , 70 : 1123 – 1128 .
  • Picaud , S , Mercke , P , He , X , Sterner , O , Brodelius , M , Cane , DE and Brodelius , PE. 2005 . Amorpha-4,11-diene synthase: mechanism and stereochemistry of the enzymatic cyclisation of farnesyl diphosphate . Arch Biochem Biophys. , 448 : 150 – 155 .
  • Putalun , W , Luealon , W , Eknamkul , WD , Tanaka , H and Shoyama , Y. 2007 . Improvement of artemisinin production by chitosan in hairy root cultures of Artemisia annua L . Biotechnol Lett. , 29 : 1143 – 1146 .
  • Rimada , RS , Gatti , WO , Jeandupeux , R and Cafferata , FR. 2009 . Isolation characterization and qualification of artemisinin by NMR from Argentinean Artemisia annua L . Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas. , 8 ( 4 ) : 275 – 281 .
  • Ro , D , Paradise , EM , Ouellet , M , Fisher , KJ , Newman , KL , Ndungu , JM , Ho , KA , Eachus , RA , Ham , TS Chang , MCY . 2006 . Schematic representation of engineered artemisinic acid biosynthetic pathway in S.cerevisiae strain EPY224 expressing CYP71AV1 and CPR . Nature. , 440 : 940 – 943 .
  • Rohmer , M . 1999 . The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants . Nat Prod Rep. , 16 : 565 – 574 .
  • Rohmer , M , Knani , M , Simonin , P , Sutter , B and Sahm , H. 1993 . Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate . Biochem J. , 295 : 517 – 524 .
  • Rohmer , M , Seemann , M , Horbach , S , Bringer-Meyer , S and Sahm , H. 1996 . Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis . J Am Chem Soc. , 118 : 2564 – 2566 .
  • Schramek , N , Wang , H , Romisch-Margl , W , Keil , B , Radykewicz , T , Winzenhorlein , B , Beerhues , L , Bacher , A and Rohdich , F. 2010 . Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study . Phytochemistry. , 71 : 179 – 187 .
  • Schuhr , CA , Radykewicz , T , Sagner , S , Latzel , C , Zenk , MH , Arigoni , D , Bacher , A , Rohdich , F and Eisenreich , W. 2003 . Quantitative assessment of crosstalk between the two isoprenoid biosynthesis pathways in plants by NMR spectroscopy . Phytochem Rev. , 2 : 3 – 16 .
  • Schwarz MK . 1994 . Terpen-biosynthese in Ginkgo biloba: Eine Oberraschende Geschichte . [Terpene biosynthesis in Ginkgo biloba: a surprising story] Thesis Nr. 10951, Schweiz: ETH Zurich .
  • Srivastava , N and Akhila , A. 2010 . Biosynthesis of andrographolide in Andrographis paniculata . Phytochemistry. , 71 : 1298 – 1304 .
  • Sy , L and Brown , GD. 2002 . The mechanism of the spontaneous autoxidation of dihydroartemisinic acid . Tetrahedron. , 58 : 897 – 908 .
  • Towler , MJ and Weathers , PJ. 2007 . Evidence of artemisinin production from IPP streaming from both the mevalonate and the nonmevalonate pathways . Plant Cell Rep. , 26 : 2129 – 2136 .
  • World Health Organization . 1981 . Report of the fourth meeting of the scientific working group on the chemotherapy of malaria. Beijing, People's Republic of China, October 6–10 . Geneva, , Switzerland : Office of Publications World Health Organization .

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