Purification and Structural Elucidation of Three Bioactive Compounds Isolated from Streptomyces Coelicoflavus BC 01 and Their Biological Activity

Overview

Journal 3 Biotech

Publisher Springer

Specialty Biotechnology

Date 2017 Apr 13

PMID 28401462

Citations 11

Authors

Kothagorla Venkata Raghava Rao

Palla Mani

Botcha Satyanarayana

Tamanam Raghava Rao

Affiliations

Soon will be listed here.

Abstract

The strain Streptomyces coelicoflavus BC 01 was isolated from mangrove soil and used as inoculum for submerged fermentation. The fermented broth was extracted with ethyl acetate, the crude extract was subjected to silica gel column chromatography and the homogeneity of the isolated fractions was determined by TLC and then subjected to RP-HPLC for their purity. The purification steps led to the isolation of three pure bioactive compounds named as BC 01_C1, BC 01_C2 and BC 01_C3. The chemical structure of these three compounds was established on the basis of their spectroscopic studies like UV, IR, H and C NMR and GC-MS data by comparison with reference data from literature. The structure of the compound BC 01_C1 was established as 5-amino-2-(6-(2-hydroxyethyl)-3-oxononyl) cyclohex-2-enone. The compound BC 01_C2 was established as8-(aminomethyl)-7-hydroxy-1-(1-hydroxy-4-(hydroxylmethoxy)-2,3-dimethylbutyl)-2-methyl dodecahydro phenanthren-9(1H)-one and the compound BC 01_C3 was established as1-((E)-2-ethylhex-1-en-1-yl)2-((E)-2-ethylidenehexyl)cyclohexane-1,2-dicarboxylate. The MIC values of the three isolated compounds (BC 01_C1, BC 01_C2 and BC 01_C3) were found between 12.5-75 μg/ml for bacteria and 50-125 μg/ml for fungi used in this study. These compounds also possess in vitro antioxidant and anti-inflammatory activities.

Citing Articles

Assessment of Anticancer and Antimicrobial Potential of Bioactive Metabolites and Optimization of Culture Conditions of PB-St2 for High Yields.

Zameer M, Shahid I, Saleem R, Baig D, Zareen M, Malik K J Microbiol Biotechnol. 2025; 35:e2311041.

PMID: 39947697 PMC: 11883349. DOI: 10.4014/jmb.2311.11041.

Streptomyces sp. from desert soil as a biofactory for antioxidants with radical scavenging and iron chelating potential.

Shah I, Uddin Z, Hussain M, Khalil A, Amin A, Hanif F BMC Microbiol. 2024; 24(1):419.

PMID: 39434054 PMC: 11492556. DOI: 10.1186/s12866-024-03586-w.

Co-Expression of Transcriptional Regulators and Housekeeping Genes in spp.: A Strategy to Optimize Metabolite Production.

Cuervo L, Malmierca M, Garcia-Salcedo R, Mendez C, Salas J, Olano C Microorganisms. 2023; 11(6).

PMID: 37375086 PMC: 10301460. DOI: 10.3390/microorganisms11061585.

Phytoecdysteroids and Anabolic Effect of : UPLC-PDA-MS/MS Profiling, In Silico and In Vivo Models.

Zaghloul E, Handousa H, Singab A, Elmazar M, Ayoub I, Swilam N Plants (Basel). 2023; 12(1).

PMID: 36616335 PMC: 9824417. DOI: 10.3390/plants12010206.

Soil substrate culturing approaches recover diverse members of Actinomycetota from desert soils of Herring Island, East Antarctica.

Benaud N, Chelliah D, Wong S, Ferrari B Extremophiles. 2022; 26(2):24.

PMID: 35829965 PMC: 9279279. DOI: 10.1007/s00792-022-01271-2.

References

Lee S, Kim H, Park B, Ahn S, Lee H, Ahn J . Topical anti-inflammatory activity of dianemycin isolated fromStreptomyces sp. MT 2705-4. Arch Pharm Res. 1997; 20(4):372-4. DOI: 10.1007/BF02976203. View

Zaitlin B, Watson S . Actinomycetes in relation to taste and odour in drinking water: myths, tenets and truths. Water Res. 2006; 40(9):1741-53. DOI: 10.1016/j.watres.2006.02.024. View

Kim K, Kim M, Jung J . Antitumor and antioxidant activity of protocatechualdehyde produced from Streptomyces lincolnensis M-20. Arch Pharm Res. 2008; 31(12):1572-7. DOI: 10.1007/s12272-001-2153-7. View

Aitdafoun M, Mounier C, Heymans F, Binisti C, Bon C, Godfroid J . 4-Alkoxybenzamidines as new potent phospholipase A2 inhibitors. Biochem Pharmacol. 1996; 51(6):737-42. DOI: 10.1016/0006-2952(95)02172-8. View

Berdy J . Bioactive microbial metabolites. J Antibiot (Tokyo). 2005; 58(1):1-26. DOI: 10.1038/ja.2005.1. View

Fourati-Ben Fguira L, Fotso S, Ben Ameur-Mehdi R, Mellouli L, Laatsch H . Purification and structure elucidation of antifungal and antibacterial activities of newly isolated Streptomyces sp. strain US80. Res Microbiol. 2005; 156(3):341-7. DOI: 10.1016/j.resmic.2004.10.006. View

Parasuraman S, Kumar E, Kumar A, Emerson S . Free radical scavenging property and diuretic effect of triglize, a polyherbal formulation in experimental models. J Pharmacol Pharmacother. 2011; 1(1):38-41. PMC: 3142756. DOI: 10.4103/0976-500X.64535. View

Smaoui S, Mellouli L, Lebrihi A, Coppel Y, Fguira L, Mathieu F . Purification and structure elucidation of three naturally bioactive molecules from the new terrestrial Streptomyces sp. TN17 strain. Nat Prod Res. 2011; 25(8):806-14. DOI: 10.1080/14786410902986225. View

LECHEVALIER H . Production of the same antibiotics by members of different genera of microorganisms. Adv Appl Microbiol. 1975; 19:25-45. DOI: 10.1016/s0065-2164(08)70421-0. View

10.

Raghava Rao K, Raghava Rao T . Molecular characterization and its antioxidant activity of a newly isolated Streptomyces coelicoflavus BC 01 from mangrove soil. J Young Pharm. 2014; 5(4):121-6. PMC: 3930124. DOI: 10.1016/j.jyp.2013.10.002. View

11.

Taechowisan T, Tuntiwachwuttikul P, Lu C, Shen Y, Lumyong S, Taylor W . Anti-inflammatory activity of 4-arylcoumarins from endophytic Streptomyces aureofaciens CMUAc130 in murine macrophage RAW 264.7 cells. Immunol Invest. 2007; 36(2):203-11. DOI: 10.1080/08820130600992115. View

12.

Wiegand I, Hilpert K, Hancock R . Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat Protoc. 2008; 3(2):163-75. DOI: 10.1038/nprot.2007.521. View

13.

Baltz R . Genetic manipulation of antibiotic-producing Streptomyces. Trends Microbiol. 1998; 6(2):76-83. DOI: 10.1016/S0966-842X(97)01161-X. View

14.

Saurav K, Kannabiran K . Cytotoxicity and antioxidant activity of 5-(2,4-dimethylbenzyl)pyrrolidin-2-one extracted from marine Streptomyces VITSVK5 spp. Saudi J Biol Sci. 2013; 19(1):81-6. PMC: 3730557. DOI: 10.1016/j.sjbs.2011.07.003. View

15.

Prieto P, Pineda M, Aguilar M . Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: specific application to the determination of vitamin E. Anal Biochem. 1999; 269(2):337-41. DOI: 10.1006/abio.1999.4019. View

16.

Arumugam M, Mitra A, Jaisankar P, Dasgupta S, Sen T, Gachhui R . Isolation of an unusual metabolite 2-allyloxyphenol from a marine actinobacterium, its biological activities and applications. Appl Microbiol Biotechnol. 2009; 86(1):109-17. DOI: 10.1007/s00253-009-2311-2. View

17.

Kumagai K, Fukui A, Tanaka S, Ikemoto M, Moriguchi K, Nabeshima S . PC-766B, a new macrolide antibiotic produced by Nocardia brasiliensis. II. Isolation, physico-chemical properties and structure elucidation. J Antibiot (Tokyo). 1993; 46(7):1139-44. DOI: 10.7164/antibiotics.46.1139. View

18.

Mellouli L, Ben Ameur-Mehdi R, Sioud S, Salem M, Bejar S . Isolation, purification and partial characterization of antibacterial activities produced by a newly isolated Streptomyces sp. US24 strain. Res Microbiol. 2003; 154(5):345-52. DOI: 10.1016/S0923-2508(03)00077-9. View

19.

Martin J, Casqueiro J, Liras P . Secretion systems for secondary metabolites: how producer cells send out messages of intercellular communication. Curr Opin Microbiol. 2005; 8(3):282-93. DOI: 10.1016/j.mib.2005.04.009. View

20.

Newman D, Cragg G . Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007; 70(3):461-77. DOI: 10.1021/np068054v. View