Generic placeholder image

The Natural Products Journal

Editor-in-Chief

ISSN (Print): 2210-3155
ISSN (Online): 2210-3163

Research Article

Isocarpine as A New Peperidine Alkaloid from Adenocarpus Complicatus with Anticandidal Activity

Author(s): Mohammad Alhilal, Suzan Alhilal*, Sobhi Gomha* and Salama Ouf

Volume 12, Issue 5, 2022

Published on: 14 January, 2022

Article ID: e151021197237 Pages: 14

DOI: 10.2174/2210315511666211015085803

Price: $65

Open Access Journals Promotions 2
Abstract

Background: Adenocarpus complicatus L. is one of Adenocarpus genus, which has about 50 species, from Fabaceae (Papilionaceae) family. This plant is found in the Mediterranean basin as a southern west part of Europe and North Afric forestes.

Objective: Isolation of Isocarpine From Adenocarpus Complicatus as Anticandidal Agent.

Methods: A new piperidine alkaloid Isocarpine was isolated from the aerial parts of Adenocarpus complicatus L., which is gross in Syria. The structure of the new compound was determined by UV, IR, EI-Ms, 1H-NMR, 13C-NMR, DEPT-135, DQF-COSY and HMQC.

Results: The anticandidal activity of isocarpine was screened against 38 Candida strains and showed remarkable inhibitory effect compared with fluconazole as an antifungal reference drug.

Conclusion: Isocarpine is antifungal agent.

Keywords: Adenocarpus complicatus L, piperidine alkaloids, isocarpines, structure elucidation, fluconazole, antifungal activity.

Graphical Abstract
[1]
Cubas, P.; Pardo, C.; Tahiri, H.; Castroviejo, S. Phylogeny and evolutionary diversification of Adenocarpus DC. (Leguminosae). Taxon, 2010, 59, 720-732.
[http://dx.doi.org/10.1002/tax.593005]
[2]
Velari, T.C.; Chiapella, L.F.; Kosovel, V. Karyological diversity of Adenocarpus DC. (Fabaceae-Cytiseae). Webbia, 2010, 65, 229-240.
[http://dx.doi.org/10.1080/00837792.2010.10670874]
[3]
Geory Post, M.D.; Lld, D.D.S. Flore of Syria; Palestine and Sinai American press: Beirut, 1933, pp. 21-25.
[4]
Berber, A.; Zengin, G.; Aktumsek, A.; Sanda, M.A.; Uysal, T. Antioxidant capacity and fatty acid composition of different parts of Adenocarpus complicatus Fabaceae from Turkey. Rev Biol Trop., 2014, 62(1), 337-346.
[http://dx.doi.org/10.15517/rbt.v62i1.7887] [PMID: 24912363]
[5]
Schardl, C.L.; Grossman, R.B.; Nagabhyru, P.; Faulkner, J.R.; Mallik, U.P. Loline alkaloids: Currencies of mutualism. Phytochemistry, 2007, 68(7), 980-996.
[http://dx.doi.org/10.1016/j.phytochem.2007.01.010] [PMID: 17346759]
[6]
Cazarolli, L.H.; Zanatta, L.; Alberton, E.H.; Figueiredo, M.S.; Folador, P.; Damazio, R.G.; Pizzolatti, M.G.; Silva, F.R. Flavonoids: prospective drug candidates. Mini Rev. Med. Chem., 2008, 8(13), 1429-1440.
[http://dx.doi.org/10.2174/138955708786369564] [PMID: 18991758]
[7]
Ndjateu, F.S.T.; Tsafack, R.B.N.; Nganou, B.K.; Awouafack, M.D.; Wabo, H.K.; Tene, M. Antimicrobial and antioxidant activities of extracts and ten compounds from three Cameroonian medicinal plants: Dissotis perkinsiae (Melastomaceae), Adenocarpus mannii (Fabaceae) and Barteria fistulosa (Passifloraceae). S Afr J. Bot., 2014, 91, 37-42.
[http://dx.doi.org/10.1016/j.sajb.2013.11.009]
[8]
Yates, S.G.; Petroski, R.J.; Powell, R.G. Analysis of loline alkaloids in endophyte-infected tall fescue by capillary gas chromatography. J. Agric. Food Chem., 1990, 38, 182-185.
[http://dx.doi.org/10.1021/jf00091a040]
[9]
Essokne, R.S.; Grayer, R.J.; Porter, E.; Kite, G.C.; Simmonds, M.S.J.; Jury, S.L. Flavonoids as chemosystematic markers for the genus Adenocarpus. Biochem. Syst. Ecol., 2012, 42, 49-58.
[http://dx.doi.org/10.1016/j.bse.2011.12.023]
[10]
Greinwald, R.; Bachmann, P.; Witte, L.; Acebes-Grinoves, J.R.; Cyzgan, F.C. Taxonomic significance of alkaloids in the genus Adenocarpus (Fabaceae-Genisteae). Biochem. Syst. Ecol., 1992, 20, 69-73.
[http://dx.doi.org/10.1016/0305-1978(92)90073-M]
[11]
Nganou, B.K.; Selvaraj, J.; Tane, P.; Nchiozem, A.; Simo, I. A review on adenocarpus mannii; a main species of the genus adenocarpus. Curr. Tradit. Med., 2019, 6, 3-12.
[http://dx.doi.org/10.2174/2215083805666190708153634]
[12]
Sergeiko, A.; Poroikov, V.V.; Hanus, L.O.; Dembitsky, V.M. Cyclobutane-containing alkaloids: origin, synthesis, and biological activities. Open Med. Chem. J., 2008, 2, 26-37.
[http://dx.doi.org/10.2174/1874104500802010026] [PMID: 19696873]
[13]
Buckin gham, J.; Baggaley, K.H.; Roberts, A.D.; Szabó, L.F. Alkaloids. In: Dictionary of Alkaloids; Second edition, by CRC Press, Taylor and Francis Group.: Boca Raton London, New Yourk, USA, 2010.
[14]
Salatino, A.; Gottlieb, O.R. Quinolizidine alkaloids as systematic markers of the papilionoideae. Biochem. Syst. Ecol., 1980, 8, 133-147.
[http://dx.doi.org/10.1016/0305-1978(80)90006-X]
[15]
Donovan, D.G.O.; Creedon, P.B. Biosynthesis of santiaguine in Adenocarpus foliosus. Part II. J.C.S. Perkin, 1971, I, 2524-2528.
[16]
Donovan, D.G.O.; Creedon, P.B. The biosynthesis of santiaguine. J. Chem. Soc. C, 1971, 1604-1606.
[http://dx.doi.org/10.1039/j39710001604]
[17]
Fitch, W.L.; Djerassi, C. Mass spectrometry in structural and stereochemical problems. CCXLIII.1 Functional group interaction. Unusual fragmentations of amides as exemplified by bipiperidyl alkaloids. J. Am. Chem. Soc., 1974, 96, 4917-4927.
[http://dx.doi.org/10.1021/ja00822a032]
[18]
Wayne, P.A. Clinical and Laboratory Standards Institute (CLSI).. Reference method for broth dilution antifungal susceptibility testing of filamentous fungi; approved standard. CLSI document M38-A2, 2nd ed; Clinical and Laboratory Standards Institute, 2008.
[19]
Lamber, J.B.; Shurvell, H.F.; Lightner, D.A.; Cooks, R.G. Organic structural spectroscopy, by Prentice Hall Inc. In: Simon & Schuster Aviacom Company Upper Saddle; River New Jersy: USA, 1998.
[20]
Stiverstein, R.M.; Webster, F.X. Spectrometric Identification of Organic Compounds. Wikey and Inc: New Yourk, USA , 1996.
[21]
Dhamgaye, S.; Devaux, F.; Vandeputte, P.; Khandelwal, N.K.; Sanglard, D.; Mukhopadhyay, G.; Prasad, R. Molecular mechanisms of action of herbal antifungal alkaloid berberine, in Candida albicans. PLoS One, 2014, 9(8), e104554.
[http://dx.doi.org/10.1371/journal.pone.0104554] [PMID: 25105295]
[22]
Alhilal, M.; Sulaiman, Y.A.M.; Alhilal, S.; Gomha, S.M.; Ouf, S.A. Anti-fungal activity of new diterpenoid akaloids isolated by different chromatographic methods from Delphinium Peregrinum L. Var. Eriocarpum Boiss. Molecules, 2021, 26(5), 1375.
[http://dx.doi.org/10.3390/molecules26051375] [PMID: 33806579]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy