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Chemical Compound Review:

AC1L3XS1 2-[(4R)-4,7-dimethyl- 1,2,3,4,4a,5,6,8a...

Synonyms:

Van Nieuwerburgh, F.C. et al., Kohler, M. et al., Ro, D.K. et al., Jung, M. et al., Ferreira, J.F. et al., et al.

Jung, Lee, Kendrick, Robinson, Croft,

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High impact information on Artemisic acid

(+)-Deoxoartelinic acid (13), a new hydrolytically stable, water-soluble, and potent non-acetal-type antimalarial drug candidate, was successfully prepared from artemisinic acid by using sulfur ylide and photooxygenative cyclization in seven steps [1].
This study reports the development and validation of a rapid, sensitive and selective assay for the quantitation of artemisinin, arteannuin B, artemisitene and artemisinic acid in Artemisia annua L. by reversed phase high performance liquid chromatography (HPLC) electrospray (ESI) quadrupole time of flight (Q-TOF) tandem mass spectrometry (MS/MS) [2].
Although anti-artemisinin antibodies cross-reacted with artemisitene and dihydroartemisinin at all dilutions used, cross-reaction with deoxyartemisinin, artemisinic acid, and arteannuin B occurred only at high concentrations [3].
Here we report the engineering of Saccharomyces cerevisiae to produce high titres (up to 100 mg l(-1)) of artemisinic acid using an engineered mevalonate pathway, amorphadiene synthase, and a novel cytochrome P450 monooxygenase (CYP71AV1) from A. annua that performs a three-step oxidation of amorpha-4,11-diene to artemisinic acid [4].

Analytical, diagnostic and therapeutic context of Artemisic acid

Artemisinin (an antimalaric compound) and its major precursor artemisinic acid, isolated as the active principles of the medicinal plant Artemisia annua L., were extracted by supercritical fluid extraction (SFE) and analyzed by supercritical fluid chromatography (SFC) using a capillary column, coupled with a flame ionization detector (FID) [5].
X-ray crystallography of the dimer of artemisinic acid shows that the cyclization during intermolecular hydrogen bonding occurs by the opposite orientation of the alpha, beta-methylene group in each molecule [6].
Simultaneous densitometric determination of artemisinin, artemisinic acid and arteannuin-B in Artemisia annua using reversed-phase thin layer chromatography [7].

References

Synthesis, stability, and antimalarial activity of new hydrolytically stable and water-soluble (+)-deoxoartelinic acid. Jung, M., Lee, K., Kendrick, H., Robinson, B.L., Croft, S.L. J. Med. Chem. (2002) [Pubmed]
Quantitation of artemisinin and its biosynthetic precursors in Artemisia annua L. by high performance liquid chromatography-electrospray quadrupole time-of-flight tandem mass spectrometry. Van Nieuwerburgh, F.C., Vande Casteele, S.R., Maes, L., Goossens, A., Inzé, D., Van Bocxlaer, J., Deforce, D.L. Journal of chromatography. A. (2006) [Pubmed]
Immunoquantitative analysis of artemisinin from Artemisia annua using polyclonal antibodies. Ferreira, J.F., Janick, J. Phytochemistry (1996) [Pubmed]
Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Ro, D.K., Paradise, E.M., Ouellet, M., Fisher, K.J., Newman, K.L., Ndungu, J.M., Ho, K.A., Eachus, R.A., Ham, T.S., Kirby, J., Chang, M.C., Withers, S.T., Shiba, Y., Sarpong, R., Keasling, J.D. Nature (2006) [Pubmed]
Extraction of artemisinin and artemisinic acid from Artemisia annua L. using supercritical carbon dioxide. Kohler, M., Haerdi, W., Christen, P., Veuthey, J.L. Journal of chromatography. A. (1997) [Pubmed]
Crystal structure of artemisinic acid: a possible biogenetic precursor of antimalarial artemisinin from Artemisia annua. Misra, L.N., Ahmad, A., Thakur, R.S., Lotter, H., Wagner, H. J. Nat. Prod. (1993) [Pubmed]
Simultaneous densitometric determination of artemisinin, artemisinic acid and arteannuin-B in Artemisia annua using reversed-phase thin layer chromatography. Bhandari, P., Gupta, A.P., Singh, B., Kaul, V.K. Journal of separation science. (2005) [Pubmed]

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