Isolation, characterization and antifungal activity of very long chain alkane derivatives from Cinnamomum obtusifolium, Elaeocarpus lanceifolius and Baccaurea sapida

• Published in: Journal of molecular structure Vol. 1142; pp. 200 - 210
• Main Authors: Bordoloi, Manobjyoti, Saikia, Surovi, Bordoloi, Prasanta K., Kolita, Bhaskor, Dutta, Partha P., Bhuyan, Purnajyoti D., Dutta, Subhas C., Rao, Paruchuri G.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-08-2017
• Subjects: Antifungal; Fatty acids; Long chain alkanes; Molecular docking; Protein modeling; Protein modeling; Long chain alkanes; Antifungal; Fatty acids; Molecular docking
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.04.027

The aim of this study was to isolate and characterize bioactive secondary metabolites from the flora of the Indo-Burma biodiversity belt for controlling leaf blight disease of Solanum khasianum Clarke (Solanaceae) caused by Alternaria tenuissima and Alternaria alternata during commercial cultivation, the berries of which contains 1.80–3.45% solasodine, a major raw material for steroid drug industries. Three new and two white powdered compounds were extracted from Cinnamomum obtusifolium (Roxb.) Nees (Lauraceae), Elaeocarpus lanceifolius (Roxb.) (Elaeocarpaceae) and Baccaurea sapida (Roxb.) Mull. Arg. (Euphorbiaceae). New compounds were characterized as Triacontanoic acid (1), octatriacontan-1-ol (2) and dotriacontane (3) isolated from C. obtusfolium and E. lanceofolius by 1H, 13C NMR and mass spectroscopy respectively. Other two known compounds were palmitic acid (4) and oleic acid (5) and from B. sapida. Complete inhibition of pathogenic fungi A.tenuissima and A. alternata were observed for compound 2 and 3. Further, in-silico molecular binding analysis of these compounds towards endopolygalacturonase, β-isopropyl dehydrogenase, plasma membrane ATPase, calmodulin, ACR-toxin biosynthesis hydroxylase and synthatase peptide (transcription regulator of Amt-gene) of A. tenuissima and A.alternata revealed that they are effective in inhibiting multiple targets. The antifungal potential of three new isolated compounds from C. obtusifolium and E. lanceifolius is reported for the first time. The results indicate the possible use of triacontanoic acid, octatriacontan-1-ol and dotriacontane as potential antifungal agents.
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•A very long chain alkane was isolated from Cinnamomum obtusifolium.•Two very long chain alkanes were isolated from Elaeocarpus lanceifolius.•Two known very long chain alkanes were isolated from Baccaurea sapida.•Good antifungal activity against Alternaria tenuissima and Alternaria alternata.•In-silico studies revealed inhibition of vital proteins of the pathogenic fungi.