Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams
Relative and absolute stereochemistry for hyperforin has been proposed by Brondz et al. was supported and new isomer of hyperforin-perforatrin has been discovered. Relative and absolute stereochemistry for perforatrin was proposed and elucidated by using gas-chromatography mass-spectrometry with supersonic molecular beams (SMB). The possibility of the existence of ambiguities in chirality as a hypothesis for the existence, and a new understanding, of chiral substances with shifting chirality is presented.
References
[1]
Gratia, A. (1925) Sur un remarquable example d’antagonisme entre deux souches de colibacille. Compt. Rend. Soc. Biol, 93, 1040-1042. Referred from: Gratia, J.P. (2000) Andre Gratia: A Forerunner in Microbial and Viral Genetics. Genetics, 156, 471-476.
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstrac t&list_uids=11014798\"PMID 11014798
[2]
Gratia, J.P. (2000) André Gratia: A Forerunner in Microbial and Viral Genetics. Genetics, 156, 471-476.
http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstrac t&list_uids=11014798\"PMID 11014798
[3]
Hugh, T.B. (2002) Howard Florey, Alexander Fleming and the Fairy Tale of Penicillin. The Medical Journal of Australia, 177, 52-53.
[4]
Maksyutina, N.P. and Koget, T.A. (1971) Polyphenols of the Herb Hypericum perforatum and the Preparation Novoimanin, Chemistry of Natural Compounds, 7, 338-341. https://doi.org/10.1007/BF00569009
[5]
Gurevich, A.I., Dobrynin, V.N., Kolosov, M.N., Popravko, S.A., Ryabova, I.D., Chernov, B.K., Derbentseva, N.A., Aizenman, B.E. and Garagulya, A.D. (1971) Hyperforin, an Antibiotic from Hypericum perforatum L. Antibiotiki Kimioterapi, 16, 510-513.
[6]
Bystrov, N.S., Chernov, B.K., Dobrynin, V.N. and Kolosov, M.N. (1975) The Structure of Hyperforin. Tetrahedron Letters, 16, 2791-2794.
https://doi.org/10.1016/S0040-4039(00)75241-5
[7]
Bystrov, N.S., Dobrynin, V.N., Kolosov, M.N., Popravko, S.A. and Chernov, B.K. (1978) Chemistry of Hyperforin. VI. General Chemical Characterization. Bioorganicheskaya Khimiya, 4, 791-797.
[8]
Bystrov, N.S., Dobrynin, V.N., Kolosov, M.N., Popravko, S.A. and Chernov, B.K. (1978) VIII. Differentiation of the Side Chains. Bioorganicheskaya Khimiya, 4, 943-947.
[9]
Bystrov, N.S., Dobrynin, V.N., Kolosov, M.N., Popravko, S.A. and Chernov, B.K. (1978) Chemistry of Hyperforin. IX. The Structure of Hyperforin. Bioorganicheskaya Khimiya, 4, 948-955.
[10]
Bystrov, N.S., Gupta, S.R., Dobrynin, V.N., Kolosov, M.N., Chernov, B.K., Chervin, I.I., Yakovlev, G.I., Aizenman, B.E. and Derbentseva, N.A. (1976) Structure of the antibiotic Hyperforin. Doklady Akademii Nauk SSSR, 226, 88-90.
[11]
Bystrov, N.S., Dobrynin, V.N., Kolosov, M.N., Chernov, B.K., Chervin, I.I. and Yakovlev, G.I. (1976) Stereokhimiya Antibiotika Hyperforina. Doklady Akademii Nauk SSSR, 226, 338-341.
[12]
Brondz, I. (1979) Antibiotikumet “Hyperforin” og andre innholdsstoffer i drogen Hypricum perforatum L. Thesis, University of Oslo, Oslo. (In Norwegian)
[13]
Brondz, I., Greibrokk, T. and Aasen, A.J. (1983) n-Alkanes of Hypericum perforatum: A Revision. Phytochemistry, 22, 295-296.
https://doi.org/10.1016/S0031-9422(00)80110-7
[14]
Brondz, I., Greibrokk, T. and Aasen, A.J. (1983) n-1-Alkohols of Hypericum perforatum. Journal of Natural Products, 46, 940-941.
https://doi.org/10.1021/np50030a025
[15]
Brondz, I., Greibrokk, T., Groth, P.A. and Aasen, A.J. (1982) The Relative Stereochemistry of Hyperforin—An Antibiotic from Hypericum perforatum L. Tetrahedron Letters, 23, 1299-1300. https://doi.org/10.1016/S0040-4039(00)87088-4
[16]
Brondz, I., Greibrokk, T., Groth, P. and Aasen, A.J. (1983) The Absolute Configuration of Hyperforin, an Antibiotic from Hypericum perforatum L., Based on the Crystal Structure Determination of its p-Bromobenzoate Ester. Acta Chemica Scandinavica, A37, 263-265. https://doi.org/10.3891/acta.chem.scand.37a-0263
[17]
Brondz, I., Fialkov, A.B. and Amirav, A. (2009) Analysis of Quinocide in Unprocessed Primaquine Diphosphate and Primaquine Diphosphate Tablets Using Gas Chromatography-Mass Spectrometry with Supersonic Molecular Beams. Journal of Chromatography A, 1216, 824-829. https://doi.org/10.1016/j.chroma.2008.11.043
[18]
Amirav, A. (2013) What Can Be Improved in GC-MS—When Multi Benefits Are Transformed into a GC-MS Revolution. International Journal of Analytical Mass Spectrometry and Chromatography (IJAMSC), 1, 31-47.
https://doi.org/10.4236/ijamsc.2013.11005
[19]
Brondz, I. (2013) Structure Elucidation of a New Toxin from the Mushroom Cortinarius rubellus by Using Gas Chromatography-Mass Spectrometry (GC-MS). International Journal of Analytical Mass Spectrometry and Chromatography, 1, 109-118. http://dx.doi.org/10.4236/ijamsc.2013.12014
[20]
Sparling, B.A., Moebius, D.C., Matthew, D. and Shair, M.D. (2013) Enantioselective Total Synthesis of Hyperforin. Journal of the American Chemical Society, 135, 644-647. https://doi.org/10.1021/ja312150d
[21]
Shimizu, Y., Shi, S.-L., Usuda, H., Kanai, M. and Shibasaki, M. (2010) Catalytic Asymmetric Total Synthesis of ent-Hyperforin. Angewandte Chemie International Edition, 49, 1103-1106. https://doi.org/10.1002/anie.200906678
[22]
Brondz, I. (2017) Super Antibiotics, Part III. Hyperforin, Revision of Relative and Absolute Stereochemistry Proposed by Bystrov et al. Voice of the Publisher, 3, 1-10.
https://doi.org/10.4236/vp.2017.32002
[23]
Zanoli, P. (2004) Role of Hyperforin in the Pharmacological Activities of St. John’s Wort. CNS Drug Reviews, 10, 203-218.
https://doi.org/10.1111/j.1527-3458.2004.tb00022.x
[24]
(Eds.: O’Neil, M.J., Smith, A., Heckelman, P.E., Obenchain, J.R., Gallipeau, J.A.R. and D’Arecca, M.A., Eds. (2001) The Merck Index, an Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Merck Research Laboratories Division of Merck & Co., Inc., Whitehouse Station, NJ, 871.
[25]
The Merck Index Online.
https://www.rsc.org/Merck-Index/searchresults?searchterm=Hyperforin
[26]
Adam, P., Duilio Arigoni, D., Bacher, A. and Eisenreich, W. (2002) Biosynthesis of Hyperforin in Hypericum perforatum. Journal of Medicinal Chemistry, 45, 4786-4793.
https://doi.org/10.1021/jm0209782
