Stereochemical Investigation of a Novel Biological Active Substance from the Secondary Metabolites of Marine Fungus Penicillium chrysogenum SYP-F-2720

Authors

  • Tiemin Sun Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education. Shenyang 110016, PR China

DOI:

https://doi.org/10.29356/jmcs.v59i1.15

Keywords:

(S)-2-(2-hydroxypropanamido) Benzoic Acid, Structural Elucidation, DFT, ECD, Anti-inflammatory

Abstract

The chemical structure and absolute configuration of a
novel benzoic acid (1) which is the secondary metabolites from the
marine fungus Penicillium chrysogenum SYP-F-2720, has been determined
by experimental spectroscopic data and quantum chemical
calculations of its electronic circular dichroism (ECD). The configurational
assignments were further confirmed by the highly consistent
spectra between natural compound and synthetic compound which
from raw material with a definite configuration. Furthermore, The
target compound exhibited more significant anti-inflammatory and
analgesic activities than aspirin when administered at 100 mg/kg,
however, it behaved no ulcerogenic effect.

Downloads

Download data is not yet available.

References

Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.;

Prinsep, M. R. Nat. Prod. Rep. 2006, 23, 26-78.

Donia, M.; Hamann, M. T. Lancet. 2003, 3, 338-348.

Bugni, T. S.; Ireland, C. M. Nat. Prod. Rep. 2004, 21, 143-163.

Saleem, M.; Ali, M. S. S.; Hussain, J. A.; Ashraf, M.; Lee, Y. S.

Nat. Prod. Rep. 2007, 24, 1142-1152.

Venkateswarlu, Y.; Srinivasa, R. N.; Venkatesham, U. Chem

Biomed Appl. 2001, 6, 101-128.

Boot, C. M; Amagata, T; Tenney, K; Compton, J. E; Pirtraszkiewicz,

H; Valeriote. F. A; Crews. P. Tetrahedron. 2007, 63, 9903-

Li, Q.; Wang, G. Microbiol Res, 2004, 52, 67-100.

Wu, B. W.; Hu, Y. H.; Fang, Z. J. Chin. Mar. Drugs. 2006, 25,

-43.

Walter, C.; Christopher, N.; Catherine, H. J. Methods 2007, 42,

-376.

Lin, W. H.; Fu, H. Z.; Li, J. Chin. Chem. Lett. 2001, 12, 235-

Gao, S. S.; Li, X. M.; Du, F. Y.; Li, C. S.; Proksch, P.; Wang, B.

G. Drugs, 2011, 9, 59-70.

Bugni, T. S.; and Ireland, C. Nat. Prod. Rep. 2004, 21, 143-163.

Wang, J. J.; Zhao, Y. L.; Men, L.; Zhang, Y. X.; Liu, Z.; Sun, T.

M.; Geng, Y. D.; Yu, Z. G. Chem. Nat. Compd. 2014, 50, 405-

Yu, Z.G; Zhao, Y.L; Wang, J.J. Chian patent, 201210541957.8,

(CN 103864638 A).

Guan, J.; Zhao, Y. L.; Zhu, H. Y.; An, Z. Z.; Yu, Y. M.; Li, R. J.;

Yu, Z. G. J. Pharm. Biomed. 2014, 95, 20-25.

Harada, N.; Nakanishi, K.; Circular dichroic spectroscopy: exciton

coupling in organic stereochemistry, University Science

Books, Mill Valley, 1983.

Giuseppe Mazzeo, G.; Santoro, E.; Andol, A.; Cimmino, A.;

Troselj, P.; Petrovic, A. G.; Superchi, S.; Evidente, A.; Berova,

N. J. Nat. Prod. 2013, 76, 588-599.

Miertuš, S.; Tomasi, J.; J. Chem. Phys. 1982, 65, 239-245.

Spartan 08, Wavefunction Inc., Irvine, CA 92612, USA, 2008.

Berova, N.; Nakanishi, K.; Woody R. W. Circular dichroism:

Principles and Applications, 2nd ed.; Wiley-VCH, NewYork,

USA, 2000.

Miertuš, S.; Scrocc, E.; Tomasi, J. J. Chem. Phys. 1982, 55, 117-

Evidente, A.; Superchi, S.; Cimmino, A.; Mazzeo, G.; Mugnai, L.;

Rubiales, D.; Andol, A. Eur. J. Org. Chem. 2011, 5564-5570.

Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;

Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci,

B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.;

Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg,

J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.;

Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.;

Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.;

Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.;

Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari,

K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi,

M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.;

Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.

E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski,

J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.;

Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D.

J.; Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT,

Romay, C.; Armesto, J.; Remirez, D.; Gonzalez, R.; Ledon, R.;

Garcia, N. J. Inflamm. Res. 1998, 47, 334-348.

Gu, K.; Bi, L.; Zhao, M.; Wang, C.; Kao, M.; Tok, J.; Peng, S.

Bioorg. Med. Chem. 2006, 14, 1339-1347.

Bi, L.; Zhang, Y.; Wang, M.; Tok, C.; Peng, J. Bioorg. Med.

Chem. 2005, 13, 5640-5646.

Siegmund, E. A.; Cadmus, R. A.; Lu, G. Proc. Soc. Exp. Biol.

Med. 1957, 95, 729-731.

Verma, M.; Sinha, J. N.; Gujrati, V. R. Pharmacol. Res. Commun.

, 13, 967-979.

Suleyman, H.; Akcay, F.; Altinkaynak, K. Pharmacol. Res. 2002,

, 155-158.

Downloads

Published

2017-10-12

Issue

Section

Regular Articles