Front. Microbiol. Frontiers in Microbiology Front. Microbiol. 1664-302X Frontiers Media S.A. 10.3389/fmicb.2023.1096826 Microbiology Original Research Antiproliferative activity of antimicrobial peptides and bioactive compounds from the mangrove Glutamicibacter mysorens Karthik Yalpi 1 Ishwara Kalyani Manjula 1 * Krishnappa Srinivasa 2 Devappa Ramakrishna 3 Anjali Goud Chengeshpur 4 Ramakrishna Krishnaveni 5 Wani Muneeb Ahmad 6 Alkafafy Mohamed 7 Hussen Abduljabbar Maram 8 Alswat Amal S. 9 Sayed Samy M. 10 Mushtaq Muntazir 11 12 * 1Department of Studies and Research in Microbiology, Mangalore University, Mangalore, Karnataka, India 2Department of Studies and Research in Biochemistry, Mangalore University, Mangalore, Karnataka, India 3Dr. C.D Sagar Centre for Life Sciences, Biotechnology Department, Dayananda Sagar College of Engineering, Dayananda Sagar Institutions, Bengaluru, India 4Department of Plant Biotechnology, School of Agricultural Sciences, Malla Reddy University, Hyderabad, India 5Department of Studies and Research in Microbiology, Vijayanagara Sri Krishnadevaraya University, Ballari, Karnataka, India 6Division of Floriculture, Sher-e-Kashmir University of Agricultural Sciences and Technology, Srinagar, Jammu and Kashmir, India 7Department of Cytology and Histology, Faculty of Veterinary Medicine, University of Sadat City, Sadat City, Egypt 8Department of Pharmacology and Toxicology, College of Pharmacy, Taif University, Taif, Saudi Arabia 9Department of Biotechnology, College of Science, Taif University, Taif, Saudi Arabia 10Department of Economic Entomology and Pesticides, Faculty of Agriculture, Cairo University, Giza, Egypt 11ICAR-National Bureau of Plant Genetic Resources, Division of Germplasm Evaluation, New Delhi, India 12MS Swaminathan School of Agriculture, Shoolini University of Biotechnology and Management, Bajhol, Himachal Pradesh, India

Edited by: Sumit Kumar, Amity University, India

Reviewed by: Amr Shehabeldine, Al-Azhar University, Egypt; Salma Mukhtar, Connecticut Agricultural Experiment Station, United States

 *Correspondence: Manjula Ishwara Kalyani, manjuganesh7176@gmail.com Muntazir Mushtaq, muntazirhuda@gmail.com

This article was submitted to Extreme Microbiology, a section of the journal Frontiers in Microbiology

 17 02 2023 2023 14 1096826 12 11 2022 26 01 2023 Copyright © 2023 Karthik, Ishwara Kalyani, Krishnappa, Devappa, Anjali Goud, Ramakrishna, Wani, Alkafafy, Hussen Abduljabbar, Alswat, Sayed and Mushtaq. 2023 Karthik, Ishwara Kalyani, Krishnappa, Devappa, Anjali Goud, Ramakrishna, Wani, Alkafafy, Hussen Abduljabbar, Alswat, Sayed and Mushtaq

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The Glutamicibacter group of microbes is known for antibiotic and enzyme production. Antibiotics and enzymes produced by them are important in the control, protection, and treatment of chronic human diseases. In this study, the Glutamicibacter mysorens (G. mysorens) strain MW647910.1 was isolated from mangrove soil in the Mangalore region of India. After optimization of growth conditions for G. mysorens on starch casein agar media, the micromorphology of G. mysorens was found to be spirally coiled spore chain, each spore visualized as an elongated cylindrical hairy appearance with curved edges visualized through Field Emission Scanning Electron Microscopy (FESEM) analysis. The culture phenotype with filamentous mycelia, brown pigmentation, and ash–colored spore production was observed. The intracellular extract of G. mysorens characterized through GCMS analysis detected bioactive compounds reported for pharmacological applications. The majority of bioactive compounds identified in intracellular extract when compared to the NIST library revealed molecular weight ranging below 1kgmole−1. The Sephadex G-10 could result in 10.66 fold purification and eluted peak protein fraction showed significant anticancer activity on the prostate cancer cell line. Liquid Chromatography–Mass Spectrometry (LC–MS) analysis revealed Kinetin-9-ribose and Embinin with a molecular weight below 1 kDa. This study showed small molecular weight bioactive compounds produced from microbial origin possess dual roles, acting as antimicrobial peptides (AMPs) and anticancer peptides (ACPs). Hence, the bioactive compounds produced from microbial origin are a promising source of future therapeutics.

 anticancer chromatography FESEM Glutamicibacter mysorens mangrove soil microbial peptides Introduction

The environmental conditions in a particular ecosystem play an important role in determining biodiversity composition. High tides, hypersaline water, significant temperature fluctuations, and optimal flora and fauna diversity are just a few of the distinctive environmental characteristics of the mangrove ecosystem (Karthik et al., 2020). Microbes can better adapt to any extreme environment in these vulnerable situations. The isolation of bioactive chemicals will be greatly aided by this habitat (Alongi, 2015).

Actinomyces word derived from the words “atkis” which means “a ray” and “mykes” which means “fungi” are filamentous, Gram–positive bacteria distinguished by different coloration and spore production at maturity (Chater, 2006). Actinomyces share the characteristics of bacteria and fungi. The Actinomyces group’s genetic and environmental flexibility facilitates the development of worthwhile bioactive substances. Actinomyces contribute more in enzyme production to pharmacological industries for the treatment, and prevention of various ailments (Chater, 2013).

The pharmaceutical industry is constantly looking for drugs with innovative structures and new modes of action as a result of the rise in antibiotic resistance. There are still many environmental niches to investigate as potential sources of antibiotics (Karthik and Kalyani, 2021, 2022). One such Actinomyces group Glutamicibacter genus is broadly utilized in the control, treatment, and prevention of diseases through the production of bioactive compounds, widely used as antibiotics (Phuong and Diep, 2020), anti-tumor, anti-tubercular (Khusro et al., 2020), anti-helminthic, anti-diabetic, anti-oxidant from an exo-polysaccharide (Xiong et al., 2020; Fukuda and Kono, 2021; Hidri et al., 2022), anti-angiogenic, growth hormones (Qin et al., 2018; Hidri et al., 2022), immuno-suppressors, neuritogenic (Tang et al., 2021), anti-inflammatory (Hui et al., 2021), anti-algal (Agamennone et al., 2018), anti-fungal with enzymatic source (Mihooliya et al., 2017; Asif et al., 2020), anti-proliferative (Baig et al., 2021), anti-parasitic, anti-malarial, anti-viral, anti-bacterial and many more biological applications (Nishioka and Katayama, 1978; Renner et al., 1999; Fernebro, 2011; Janardhan et al., 2014; Desouky et al., 2015; Abd-Elnaby et al., 2016).

The various species of genus Glutamicibacter shown huge biological importance as detailed above. Whereas G. creatinolyticus shown resistance to antibiotics as well as heavy metals (copper, arsenic, cadmium, cobalt, zinc, and chromium; Santos et al., 2020). The G. arilaitensis produced pink colored pigment and coprophorphyrin binds zinc and regulates in cheese rinds (Cleary et al., 2018). Another Gluamicibacter sps. Possessing genes that regulates the growth of plant under saline conditions, cold adaptation, efficient degradation and chitinase enzyme producing genes which help in control the growth of pathogenic bacteria (Borker et al., 2021; Fu et al., 2021). While G. nicotianae involved in heavy metals degradation (Wang et al., 2021). The G. mishrai and halophytocola isolated from Andaman sea sample. Genes involved in cell wall biogenesis, replication, recombination, repair mechanism and amino acid metabolism along possess important role in physiology and behavior of insects (Qin et al., 2018; Das et al., 2020; Wang W, et al., 2022).

Antimicrobial peptides (AMPs) are peptides with antimicrobial properties. In multicellular organisms, these positively charged host defense molecules, or AMPs, serve as the initial line of protection. Many AMP’s from both prokaryotes and eukaryotes have been categorized (Brandenburg et al., 2012; Desriac et al., 2013). Several genera of AMP’s -producing microorganisms have been discovered, including bacteriocins produced by Leuconostoc gelidum, Enterococcus faecium, and other species (Juturu and Wu, 2018; Khodaei and Sh, 2018). Microcins A and B, antimicrobial bacteriocins derived from Streptomyces pluripotens, have been shown to be effective against Escherichia coli, Salmonella typhimurium, Staphylococcus aureus, and Listeria monocytogenes (Collin and Maxwell, 2019; Kurnianto et al., 2021).These AMPs have been found to be effective in the treatment of a broad range of ailments (Sugrue et al., 2019; Karthik et al., 2020; Khadayat et al., 2020; Zhang et al., 2020). AMP’s are peptides derived from microbes that exhibit antimicrobial activity. AMPs have been shown to target cell walls or cell membranes, permitting them to penetrate cells and affect vital components while inhibiting growth (Desriac et al., 2013; Wang et al., 2020). As a result of their target-specific activity against resistant microbial species, AMPs are thought to be anti–microbial compounds.

Peptides with selective action and non-selective activity, i.e., those that have activity against bacteria, cancer cells, and healthy cells, can be categorized as having antitumor activity in Hoskin and Ramamoorthy’s investigations (Hoskin and Ramamoorthy, 2008).The peptides have antibacterial and anticancer properties, but not against normal cells. Cecropins, buforins, and magainins, among other peptides, have demonstrated anticancer effects without harming normal eukaryotic cells (Cruciani et al., 1991; Cho et al., 2009). These studies go into great detail and provide a compelling case for the fact that many peptides have biological activity in a variety of dimensions and properties and can possess dual activity as AMPs and ACPs. Therefore, we are searching for mangrove soil Actinomyces in the Mangalore region to isolate and characterize bioactive peptides that can function as both AMPs and ACPs.

In our previous study, we reported the detailed procedures for isolation, microscopic and macroscopic characters, identified as Glutamicibacter mysorens with GenBank accession number MW647910.1, the intracellular protein; extraction, estimation, along with their potential antimicrobial activity was observed against test pathogens Salmonella typhimurium (ATCC23564), Staphylococcus aureus (ATCC6538P),Bacillus cereus (ATCC10876), Proteus vulgaris (ATCC13315), and Pseudomonas aeruginosa (ATCC9027) cultures. The protein was characterized through LCMS and SDS PAGE techniques and small peptides were detected (Karthik and Kalyani, 2021).

In this study, the optimization of suitable growth media for G. mysorens and its micromorphology were analyzed using FESEM. The isolation of intracellular extract of G. mysorens was characterized through GCMS and LCMS. These GCMS studies revealed a large number of small bioactive compounds that possess significant biological activities are discussed. Whereas the LCMS studies resulted in the detection of low molecular weight Kinetin-9-ribose and Embinin showed significant anti-tumor potential against PC3 cell line in comparison to standard cisplatin drug.

 Materials and methods Mangrove soil collection

Soil samples were collected from Mangroves soil in Mangalore, Dakshina Kannada. Jeppinamogaru (JPMU) is located at 12°50′31.4”N 74°51′36.4″E. At the collecting site, the soil was brown with a powdery texture, and environmental parameters; the temperature of 21°C and pH of 7.2 was recorded. The collected samples were shifted to the Molecular Research Laboratory (MRL), Department of Microbiology, Jnana Kaveri, Mangalore University, India, in aseptic containers. To prevent fungal and bacterial growth, the soil sample was pre-heated for 2 h at 60°C prior to serial dilution and isolation (Mohan et al., 2013; Sridevi et al., 2015; Sapkota et al., 2020).

 Cultural characteristics

The isolated G. mysorens strain was subjected to FESEM analysis at different objectives distances; spore structure (1 and 2 μm) mycelial structure (10 and 20 μm) to visualize the complete micromorphological structures. The sequencing and identification of G. mysorens are reported by Karthik and Kalyani (2021).

 Intracellular extract

The G. mysorens strain was grown in SCN broth for 7 days at 30 ± 2°C with continuous shaking at 100 rpm. Centrifugation at 7000 rpm for 8 min separated the cultured biomass cells, which were then washed twice using phosphate-buffered saline devoid of Mg2+ and Ca2+ and centrifuged again. The cells were then re-suspended in 10 ml of chilled acetone for 5 min before being centrifuged at 7,000 rpm for 8 min. The intracellular extract was incubated for 2 min with 1.0 ml of 1% SDS after the traces of acetone was removed with a nitrogen stream (Bhaduri and Demchick, 1983). This intracellular extract was characterized using spectrometric (LCMS, GCMS) tools along with a comparison to the NIST library.

 Gas chromatography-mass spectroscopic analysis

The following equipment was assessed for the GC–MS studies of G. mysorens intracellular extract: a PerkinElmer Clarus 680 Gas Chromatograph and a PerkinElmer Clarus SQ 8C Mass Spectrometer. A PerkinElmer Elite-5MS standard column with dimensions of 30 m long x 0.250 mm inner diameter x 1 micron (60–350°C) is utilized in the equipment. With an equivalence ratio of 10:1, the injected volume of 2 μl was completely run for 26.6 min. Helium is used as the carrier gas, with a flow rate of 2 ml/min. The source temperature was set to 230 degrees Celsius, and the inlet temperature was set to 250 degrees Celsius. The oven temperature was initially set to 80°C with a hold time of 2.0 min; ramp1 was set to 10.0 /min to 150°C with a hold time of 1.0 min; and ramp2 was set to 15.0 /min to 250°C with a hold time of 10.0 min. The components were identified by comparing them to those contained in the NIST computer library, which was linked to the GC–MS apparatus, and the results were published.

 Gel filtration

The microbial proteins were purified using SephadexG-10. For 5 h, the Sephadex G-10 was allowed to swell in excess of dH2O in a boiling water bath. After decanting the gel to remove fines, it was equilibrated with 0.05 M sodium phosphate buffer, pH 7.0. Under gravity, the gel was packed into a 1.0 cm × 110.0 cm column. At a flow rate of 10 ml/h, the column was standardized with two-bed volumes of phosphate buffer of concentration 0.05 M, pH 7.0. The 20 mg of isolate protein sample was loaded onto the gel, eluted with 0.05 M sodium phosphate buffer, pH 7.0, and 2.0 ml fractions were collected and further analyzed (Bharadwaj et al., 2018).

 Liquid chromatography-mass spectrophotometer

The Sephadex G-10 peak fraction was analyzed using LC–MS, model Synapt G2, an analytical chemistry technique that combines the physical separation capabilities of liquid chromatography with mobile phases A: 0.1% Formic acid in Water and mobile phase B: 0.1% Formic acid in Acetonitrile with the mass analysis capabilities of mass spectrometry (MS) an Agilent 1100 LC system with a vacuum degasser, A BEH C18, 50 mm × 1.0 mm, 1.7 μm C18 column (Waters, United States) was used to achieve chromatographic separation in comparison to the NIST computer library.

 MTT assay

Prostate cancer cells (PC3) procured from NCCS Pune; were harvested in T-25 flasks for the in vitro studies. PC3 cells were trypsinized and aspirated into a 5 ml centrifuge tube. After centrifugation at 300 rpm for 10 min, the cell pellet was separated. The cell count was adjusted using DMEM HG medium so that 200 μl of suspension contained approximately 10,000 cells. In an ESCO model CLM170B-8-UV CO2 incubator, a 200 μl cell suspension was added to each well of the 96-well microtiter plate, and the plate was incubated for 24 h at 37°C and 5% CO2 atmosphere. After 24 h, the spent medium was aspirated. In each well, 200 μl of various test drug concentrations and the standard drug cisplatin were added. After that, the plates were incubated for 24 h at 37°C and 5% CO2. The drug-containing media was aspirated after the plate was removed from the incubator. The plate was then incubated for 3 h at 37\u00B0C and 5% CO2 atmosphere with 200 μl of medium containing 10% MTT reagent in each well to achieve a final concentration of 0.5 mg/ml. The culture medium was completely removed without disturbing the formed crystals. To solubilize the formed formazan, the plate was gently shaken in a gyrator shaker with 100 μl of solubilization solution (DMSO). The absorbance was read at 570 and 630 nm using the microplate reader of a Multiskan sky ELISA spectrophotometer.

 Results and discussion

The Mangrove region in Jeppinamogaru located at Mangalore, India, served as a suitable source for isolating G. mysorens strain. The G. mysorens strain received a GenBank accession number MW647910.1 and was isolated and their biological activities were reported by Karthik and Kalyani (2021). In continuation to previous work; initially, the G. mysorens strain was observed for morphological characteristics after performing FESEM analysis. Also, biologically important chemical components present in the intracellular extract of the G. mysorens strain were characterized using GCMS and a partially purified protein sample was characterized using LCMS and have a shown significant number of bioactive compounds.

The cultural characteristics of mangrove adapted G. mysorens strain upon growth on starch casein nitrate agar medium exhibited as white colored filamentous mycelia and at maturity showed ash-colored spores. Production of brown pigmentation on SCNA media was observed. Further microscopic analysis showed Gram staining positive. The isolate when further subjected to FESEM microscopic studies revealed mycelial morphological characteristics of the genus Glutamicibacter. Further, the culture showed filamentous mycelia possessing spirally coiled spore chains. Each spore is visualized as an elongated cylindrical hairy appearance with curved edges as shown in Figure 1. The G. mysorens when grown on different Actinomyces-specific media have shown distinctive phenotypic characteristics as listed in Table 1. Excellent growth was achieved on starch casein nitrate agar, whereas good growth was seen on, glucose leucine agar, yeast extract agar, and nutrient agar media. Moderate growth was seen on sucrose peptone agar, and malt extract agar.Whereas in another study, lysogeny agar was chosen as the best growth media for G. mysorens according to Wang Y. et al. (2022) and Deb et al. (2020).

Cultural characteristics of Glutamicibacter mysorens. (A) Front view of isolate. (B) Rear view of isolate. (C) Mycelia observations under FESEM. (D) Phase contrast microscopic analysis. (E,F) Mycelia along with spore analysis under FESEM. (G,H) Spore structure analysis using FESEM.

Phenotypic characteristics of Glutamicibacter mysorens on different media.

Media Growth Front view Rear view Pigment Spores
Sucrose peptone agar Moderate Cream Creamish white − No
Glucose luecine agar Good Cream White − Black
Nutrient agar Good Creamish Creamish − −
Malt extract agar Moderate Creamish white Creamish white − No
Yeast extract agar Good Cream Cream − White
Starch casein nitrate agar Excellent White ash Brown + Grey

In our previous report, the G. mysorens strain when subjected to simple and rapid disruption followed according to the method of Bhaduri yielded significant intracellular extraction in buffer (Bhaduri and Demchick, 1983). A 20 mg of protein was loaded on top of the column and 2 ml fractions were collected and about 2.5 times (216 ml) bed volumes of protein elutions were collected. The absorbance of protein fractions was checked at 280 nm and graphs were plotted. The X-axis indicates fraction numbers and absorbance plotted on Y-axis for each fraction collected from Sephadex G-10 column chromatography as showed in Figure 2. This column separation chromatography purifies 10.66 folds as detailed in Table 2. The GCMS studies depicted the presence of 155 bioactive molecules present in the intracellular extract of G. mysorens and the obtained elution profile is as shown in Figure 3. Whereas GCMS analysis depicted the highest probable compounds such as Cyclopentane undecanoic acid, methyl ester 22.7% and Glutaric acid, 2,2-dichloroethyl 3-fluorophenyl ester 34% probability as shown in Figure 4. All the compounds detected through GCMS showed low molecular weight below 1Kgmol−1with various pharmacological applications. The majority of bioactive compounds have shown antimicrobial, enzyme inhibitors, activators, antioxidants, anti-inflammatory, anticancer, agrochemical, insecticide, anti-obese, and many other applications as listed in Table 3. The intracellular extract of G. mysorens had shown potent antimicrobial activity to a broad spectrum of test pathogens such as Salmonella typhimurium (ATCC23564), Staphylococcus aureus (ATCC6538P), Pseudomonas aeruginosa (ATCC9027), Proteus vulgaris (ATCC13315), and Bacillus cereus (ATCC10876) cultures. In order to focus further on prominent bioactive compounds the intracellular extract was partially purified using a Sephadex G-10 column. The eluted peak fraction upon spectrophotometry and electrophoretic analysis revealed the presence of peptide and is reported in our previous article (Karthik and Kalyani, 2021). A similar study was illustrated on 41 different Actinomyces species and majority isolates shown antagonist activity against Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae (Sapkota et al., 2020).

Elution profile of Glutamicibacter mysorens by using Sephadex G-10 column chromatography.

Purification chart of Glutamicibacter mysorens intracellular protein.

Sample Protein (mg/ml) Fold purification % yield
Crude protein 2.0 1 100
Gel filtration (Sephadex G-10) 0.1875 10.66 9.38

Elution profile of GCMS analysis for Glutamicibacter mysorens intracellular extract.

GCMS depicted highest probable compounds. (A) Cyclopentaneundecanoic acid, methyl ester 22.7%. (B) Glutaric acid, 2,2-dichloroethyl 3-fluorophenyl ester 34% probability.

List of GC–MS analysis of bioactive compounds from Glutamicibacter mysorens intracellular extract.

Sl. No. R.T (min) Compound name Activity/Applications Molecular formula Molecular weight (g/mol) Area percentage References
1 4.5 2-Pentanone, 4-hydroxy-4-methyl- Photolysis C6H12O2 116 0.9 Qiu et al. (2019)
2 Tert-Butyl Hydroperoxide Oxidant C4H10O2 90 Gad (2014)
3 1,3-Dioxolane-2-methanol, 2,4-dimethyl- Chlorinating agent C6H12O3 132 Simon and Losada (2008), Fuentes et al. (2016)
4 2-Propanol, 2-nitroso-, acetate Cosmetics C5H9NO3 131 Lemieux and Nagabhushan (1968)
5 2-Hexanone, 4-methyl- Paints C7H14O 114 Rebbert and Ausloos (1962)
6 2-Acetoxyisobutyryl chloride Epoxides synthesis C6H9ClO3 164 Zibuck (2001)
7 6.0 Octanoic acid, methyl ester Oxidation C9H18O2 158 8.6 Schwabe et al. (1964)
8 Undecanoic acid, 2-methyl- Antifungal C12H24O2 200 Rossi et al. (2021)
9 Methyl 6-methyl heptanoate Biomolecule synthesis C9H18O2 158 Kroumova and Wagner (2003)
10 Decanoic acid, methyl ester Antibacterial C11H22O2 186 Damiano et al. (2020)
11 6.8 Dodecanoic acid, 3-hydroxy- Cytotoxic C12H24O3 216 5.3 Viegas et al. (1989)
12 Oleic Acid Anti-tumor C18H34O2 282 Carrillo Perez et al. (2012)
13 12-Methyl-E,E-2,13-octadecadien-1-ol Antioxidant C19H36O 280 Salem et al. (2016)
14 Z-8-Methyl-9-tetradecenoic acid Antibacterial C15H28O2 240 Jawad et al. (2016)
15 Z-(13,14-Epoxy)tetradec-11-en-1-ol acetate Anti-inflammatory C16H28O3 268 Abdul et al. (2020)
16 trans-13-Octadecenoic acid/ cis-Vaccenic acid Anti-protozoal/ Protects from Heart failure C18H34O2 282 Carballeira et al. (2009), Djoussé et al. (2014)
17 7-Hexadecenoic acid, methyl ester, (Z)- Antioxidant C17H32O2 268 Reza et al. (2021)
18 1-Octanol, 2,7-dimethyl- Antioxidant, hepatoprotective and anti-inflammatory C10H22O 158 Bentley et al. (2002)
19 Carbonic acid, prop-1-en-2-yl undecyl ester Beverages production C15H28O3 256 Millero et al. (2006)
20 1-Decanol, 2-ethyl- Surfactant C12H26O 186 Achimon et al., 2022
21 1-Decanol, 2-methyl- Lubricants, Plasticizers C11H24O 172 Halling et al. (1998)
22 Trichloroacetic acid, decyl ester Disinfectant C12H21Cl3O2 302 Anand et al. (2014)
23 1-Heptanol, 2-propyl- Pheromone C10H22O 158 Francke and Schulz (1999)
24 1-Octanol, 2-butyl- Antioxidant C12H26O 186 Abdillah et al. (2015)
25 Carbonic acid, decyl prop-1-en-2-yl ester Beverages production C14H26O3 242 Millero et al. (2006)
26 7.2 1,7-Octanediol, 3,7-dimethyl- Polymer C10H22O2 174 8.6 Reddy and Ananthaprasad (2021)
27 Octanoic acid, 7-oxo−/ Methyl 6-oxoheptanoate Antibacterial C8H14O3 158 Schwabe et al. (1964)
28 1,8-Nonanediol, 8-methyl- Agrochemicals C10H22O2 174 Kula et al. (2001)
29 7-Octen-2-ol, 2,6-dimethyl- Cosmetics C10H20O 156 Ham and Raymond Wells (2009)
30 3-Heptanol, 4-methyl- Therapeutics C8H18O 130 Ley and Madin (1991)
31 4-Heptanone, 2,3:5,6-diepoxy-2,6-dimethyl- Oxidant C9H14O3 170 Ley and Madin (1991)
32 3-Tridecanol Lubricant C13H28O 200 Chagnes et al. (2010)
33 2-Dodecanone Insecticide C12H24O 184 Wang et al. (2019)
34 7.7 3-(Prop-2-enoyloxy)dodecane Antibiotics C15H28O2 240 5.3 Fadhil et al. (2018)
35 3-(Prop-2-enoyloxy)tetradecane Phyto-constituent C17H32O2 268 Ezekwe et al. (2020)
36 2-Propenoic acid, 1-methylundecyl ester Antibacterial C15H28O2 240 Deryabin and Tolmacheva (2015)
37 5-(Prop-2-enoyloxy)pentadecane Antimicrobial C18H34O2 282 Xue et al. (2017), Gadhi et al. (2019)
38 3-Cyclopropylcarbonyloxydodecane Reducing Agent C16H30O2 254 Bolade et al. (2018)
39 9-Methyl-Z-10-pentadecen-1-ol Antioxidant C16H32O 240 Soleha et al. (2020)
40 Octadecane, 1-(ethenyloxy)- Anti-corrosion C20H40O 296 Zeitoun et al. (2021)
41 Dodecyl acrylate Polyemerization C15H28O2 240 Buback and Kowollik (1999)
42 Octanoic acid, 2-propenyl ester Antioxidant C11H20O2 184 Windey et al. (2012)
43 8.7 Octadecane, 6-methyl- Enzymatic C19H40 268 4.1 Holman et al. (1966)
44 Hydroxylamine, O-decyl- Reducing agent C10H23NO 173 (Gad, 2014)
45 Tetradecane, 2,6,10-trimethyl- Hydrocarbon C17H36 240 McCarthy and Calvin (1967)
46 Silane, trichlorodocosyl- Surfactant C22H45Cl3Si 442 Janneck et al. (2018)
47 Nonadecane Binding material C19H40 268 Li et al. (2010)
48 Oxirane, [(hexadecyloxy)methyl]- Antibacterial C19H38O2 298 Es (2014)
49 Decane, 1,1′-oxybis- Antimicrobial C20H42O 298 Fauzi et al. (2017)
50 1-Hexadecanol, 2-methyl- Antioxidant C17H36O 256 Hussein et al. (2015)
51 4-Hydroxy-4-methylhex-5-enoic acid, tert.-butyl ester Hydrocarbon C11H20O3 200 Ming Miao and Zhi (2018)
52 Z,Z-2,5-Pentadecadien-1-ol Pharmacological C15H28O 224 Millero et al. (2006)
53 l-Gala-l-ido-octose Neuritogenic, Anti-hyper cholesteromia C8H16O8 240 Jahan et al. (2020)
54 2-Cyclopropylcarbonyloxytridecane aphrodisiac, anti-inflammatory, antihypertensive C17H32O2 268 Sridhar et al. (2016)
55 Imidazole, 2-amino-5-[(2-carboxy)vinyl]- Therapeutic C6H7N3O2 153 Shalini et al. (2010)
56 9.5 4-Ethylacridine/3H-indole, 2-methyl-3-phenyl- Antioxidant C15H13N 207 4.2 Hosseini Hashemi et al. (2015)), Britten and Smith (1972)
57
58 4-Pyridinol 3,5-dichloro-2-ethyl-6-methyl- Herbicide C8H9Cl2NO 205 Ransom et al. (2012)
59 5-Methyl-2-phenylindolizine/3-Methyl-2-phenylindole/2-Methyl-7-phenylindole Antimicrobial, Antioxidant C15H13N 207 Onocha et al. (2011)
60 Pyridine, 2,4-dichloro-5-thiocyanato- Antimicrobial C6H2Cl2N2S 204 Al-Salahi et al. (2010)
61 Dichloroacetic acid, phenyl ester/ Benzoic acid, 2,5-dichloro-, methyl ester Therapeutic C8H6Cl2O2 204 Babar et al. (2008)
62 3,5-Dichloro-2,4-dimethyl-1-methoxybenzene Anticancer C9H10Cl2O 204 Dhakal et al. (2020)
63 1-Chloroundecane Precursor for fatty acid synthesis C11H23Cl 190 Gensler and Thomas (1952)
64 Dodecane, 1-chloro- Hydrocarbon C12H25Cl 204 Moldoveanu (2019)
65 Tetradecane, 1-chloro- Chlorination C14H29Cl 232 Assassi et al. (2005)
66 Nonane, 1-chloro- Hydrocarbon C9H19Cl 162 Moldoveanu (2019)
67 10.0 Benzene, 1,4-bis(trifluoromethyl)- Flurochrome C8H4F6 214 Skhirtladze et al. (2022)
68 Pyrimidine, 4,5-diamino-6-chloro-2-(trifluoromethyl)- Transcriptional activator C5H4ClF3N4 212 Palanki et al. (2000)
69 1H-Imidazole, 1-(2,2,3,3,3-pentafluoro-1-oxopropyl)- Anticancer C6H3F5N2O 214 Zhang et al. (2014)
70 Sulfaguanidine Enzyme inhibitor C7H10N4O2S 214 Akocak et al. (2021)
71 Anthracene, 2-chloro- Antibacterial C14H9Cl 212 de Bony et al. (1984)
72 Ethyl iodoacetate Enzyme activator C4H7IO2 214 Tanaka and Hayashi (2008)
73 8-Methyl-4-(1-pyrrolidinyl)pyrido[3,2-c]pyridazine Cancer therapies C12H14N4 214 Jubete et al. (2019)
74 [1,1’-Biphenyl]-4-carboxylic acid, 4′-hydroxy- Precursor for synthesis of bioactive molecules C13H10O3 214 Patel et al. (2004)
75 Benzoic acid, 2-(1,2,4-triazol-3-yl-aminocarbonyl)- Breast and prostate cancer therapy C10H8N4O3 232 Jamieson et al. (2012)
76 Succinic acid, 2-methylpent-3-yl pentafluorobenzyl ester Antioxidant C17H19F5O4 382 Cullere et al. (2004)
77 1,1’-Biphenyl, 2-iodo- Substrate C12H9I 280 Fang et al. (2017)
78 Benzamide, N-(1,4,6-trimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)- Substrate C16H16N4O 280 Jachak et al. (2006)
79 4-[N′-(4-Methoxy-benzoyl)-hydrazino]-4-oxo-butyric acid methyl ester Antibacterial C13H16N2O5 280 EL-Hashash et al. (2014)
80 Dibenzo[a,c]phenazine Flurochrome C20H12N2 280 Xie et al. (2019)
81 Benzofuro[3,2-d]pyrimidine, 4-(2-pyridylthio)- Therapeutic C15H9N3OS 279 Campos et al. (2022)
82 (9E)-Styrylanthracene Luminophore C22H16 280 Zhang et al. (2017)
83 1H-Purine-2,6-dione,3,7-dihydro-3-methyl-7-carboxymethyl-8-n-butyl Anti-inflammatory C12H16N4O4 280 Abou-Ghadir et al. (2014)
84 Methyl 2-phenyl-2,3-epoxyindan-1-one-3-carboxylate Catalyst C17H12O4 280 Godwin et al. (2012)
85 Propyl N-(heptafluorobutyryl)pyroglutamate Metabolite C12H12F7NO4 367 Hušek et al. (2016)
86 10.4 3-Trifluoroacetoxypentadecane Antimicrobial C17H31F3O2 324 1.3 Hussein et al. (2015)
87 3-Cyclopropylcarbonyloxytetradecane Antioxidant, Cytotoxic and Antibacterial C18H34O2 282 Upgade and Bhaskar (2013)
88 10-Undecenoic acid, octyl ester Antimicrobial C19H36O2 296 Van der Steen and Stevens (2009)
89 3-(Prop-2-enoyloxy)tetradecane Antioxidant C17H32O2 268 Ezekwe et al. (2020)
90 Z-10-Tetradecen-1-ol acetate Pharmaceutical C16H30O2 254 Bolade et al. (2018)
91 5-Amino-2-methoxy-4-(1H-1,2,3,4-tetrazol-5-yl)phenol Antimicrobial C8H9N5O2 207 Arulmurugan and Kavitha (2010)
92 4H-Pyrido[1,2-a]pyrimidine-3-carboxamide, 6,7,8,9-tetrahydro-6-methyl-4-oxo- Antimicrobial and antitumor C10H13N3O2 207 Al-Taisan et al. (2010)
93 1-Adamantanecarboxamide, N,N-dimethyl−/ Pent-3-yn-2-ol, 2-cyclopropyl-5-(1-piperidyl) Anticancer C13H21NO 207 Su et al. (2012)
94 trans-4-Ethoxy-β-methyl-β-nitrostyrene/ Carbamic acid, 4-methoxyphenyl-, allyl ester Cardiovascular therapy C11H13NO3 207 Alves-Santos et al. (2019)
95 Thiophen-2-methylamine, N-(2-fluorophenyl)- Catalytic activity C11H10FNS 207 Tanak et al. (2020)
96 2-(1-Piperidino)-3-nitropyridine Antimicrobial C10H13N3O2 207 Sivaprakash et al. (2019)
97 Benzoic acid, 4-amino-, pentyl ester Cytotoxicity C12H17NO2 207 Kratky et al. (2019)
98 10.5 Cyclopentaneundecanoic acid, methyl ester Antioxidant and Antibacterial C17H32O2 268 1.3 Daniels and Temikotan (2021)
99 Undecanoic acid, 10-methyl-, methyl ester Antioxidant C13H26O2 214 Narra et al. (2017)
100 Methyl 8-methyl-nonanoate Antimicrobial and Anti-inflammatory C11H22O2 186 Kaur et al. (2022)
101 Tetradecanoic acid, 12-methyl-, methyl ester Larvicidial C16H32O2 256 Xu et al. (2008)
102 Cyclopentanetridecanoic acid, methyl ester Cytotoxic C19H36O2 296 Joshi et al. (2020)
103 10.7 Glutaric acid, 2,2-dichloroethyl 3-fluorophenyl ester Anti-angiogenic C13H13Cl2FO4 322 1.0 Amaral et al. (2021)
104 Triethylgermanium bromide Oxidant C6H15BrGe 240 Satgé et al. (1973)
105 2,5-Cyclohexadien-1-one, 2,6-dichloro-4-(chloroimino)−/ benzene, 1,3,5-trichloro-2-nitroso- Surfactant C6H2Cl3NO 209 Yamamoto (2002)
106 Pyridine, 3,4,5-trichloro-2,6-dimethyl- Antimicrobial C7H6Cl3N 209 Khidre et al. (2011)
107 Ethaneselenoamide, N-(4-methylphenyl)- Anticancer C9H11NSe 213 Watanabe et al. (1997)
108 Stannane, chlorotriethyl- Polymerization C6H15ClSn 242 Qiu et al. (2013)
109 1-(2,4,5-Trichlorophenyl)ethanol Cytotoxic C8H7Cl3O 224 Shawky et al. (2021)
110 1,3-Dioxolane, 2-(5,5,5-trichloro-3-penten-1-yl)-, (E)- Flavoring agent C8H11Cl3O2 244 Ivankin (2017)
111 benzene, 1,1′-[oxybis(methyleneoxy)]bis[2,4,6-trichloro- Toxic agent C14H8Cl6O3 434 Holman et al. (1966)
112 11.5 Undecanoic acid Antifungal C11H22O2 186 0.9 Rossi et al. (2021)
113 n-Decanoic acid Beverage production C10H20O2 172 Viegas et al. (1989)
114 n-Hexadecanoic acid Anti-inflammatory C16H32O2 256 Aparna et al. (2012)
115 4-(Benzoylmethyl)-6-methyl-2H-1,4-benzoxazin-3-one Antimicrobial C17H15NO3 281 Ozden et al. (2000)
116 Adenine, N4-pentafluoropropionyl- Oxidization C8H4F5N5O 281 Tsunoda et al. (2011)
117 2-Furancarboxylic acid, N′-[(8-hydroxy-5-quinolinyl)methylidene]hydrazide Antioxidant C15H11N3O3 281 Gülerman et al. (2000)
118 1-Phenyl-4-(trifluoromethyl)-1H,4H,5H,6H,7H-pyrazolo[3,4-b]pyridin-6-one Antiproliferative C13H10F3N3O 281 Martín-Acosta et al. (2021)
119 Acetamide, 2-(2,4-difluorophenoxy)-N-(4-fluorophenyl)- Inhibitor C14H10F3NO2 281 Williams et al. (2015)
120 Succinic acid, 3,5-dinitrobenzyl 2-methylhex-3-yl ester Enzyme activator C18H24N2O8 396 Martinez et al. (2008)
121 Oxalic acid, monoamide, N-(2-fluorophenyl)-, heptyl ester Antioxidant C15H20FNO3 281 Ganyam et al. (2019)
122 Propanamide, 2,2,3,3,3-pentafluoro-N-(2,4,6-trimethylphenyl)- Inhibitor C12H12F5NO 281 Talley et al. (2000)
123 12.3 3-Trifluoroacetoxydodecane Antioxidant C14H25F3O2 282 Zagulyaeva et al. (2010)
124 12.5 Cyclopropanepentanoic acid, 2-undecyl-, methyl ester, trans- Anti-mycobacterial C20H38O2 310 1.5 Carballeira et al. (2007)
125 13,16-Octadecadiynoic acid, methyl ester Antioxidant C19H30O2 290 Hamalainen et al. (2001)
126 13-Tetradecynoic acid, methyl ester Anti-inflammatory C15H26O2 238 James and Martin (1956)
127 Oxiraneundecanoic acid, 3-pentyl-, methyl ester, cis- Antimicrobial C19H36O3 312 Al-Marzoqi et al. (2016)
128 9-Octadecenoic acid (Z)-, methyl ester/11-Octadecenoic acid, methyl ester Food and Pharmacological C19H36O2 296 Jiang and Jia (2015)
129 13-Docosenoic acid, methyl ester Food industires C23H44O2 352 Beare-Rogers (1977)
130 13.2 Z-(13,14-Epoxy)tetradec-11-en-1-ol acetate Anti-inflammatory C16H28O3 268 2.0 Abdul et al. (2020)
131 12-Methyl-E,E-2,13-octadecadien-1-ol/2-Methyl-Z,Z-3,13-octadecadienol Therapeutic C19H36O 280 Adeyemi (2017)
132 Z-8-Methyl-9-tetradecenoic acid Antimicrobial C15H28O2 240 Jawad et al. (2016)
133 Oxiraneoctanoic acid, 3-octyl-, cis- Antimicrobial C18H34O3 298 Hussein et al., 2016
134 Pentadecanoic acid Oxidation C15H30O2 242 Jenkins et al. (2015)
135 Heptadecanoic acid, heptadecyl ester Antimicrobial C34H68O2 508 Gautam et al. (2016)
136 2-Myristynoyl pantetheine Antimicrobial C25H44N2O5S 484 Srivastava et al. (2015)
137 9-Octadecenoic acid, (E)- Inhibitor C18H34O2 282 Carrillo Perez et al. (2012)
138 9-Hexadecenoic acid/1,2-15,16-Diepoxyhexadecane Cosmetics C16H30O2 254 Takigawa et al. (2005)
139 cis-13-Eicosenoic acid Anti-obesity C20H38O2 310 Senarath et al. (2018)
140 3-Heptafluorobutyroxytetradecane Polymerization C18H29F7O2 410 MacKenzie and Tenaschuk (1979)
141 n-Nonadecanol-1 Antifeedant C19H40O 284 Aznar-Fernandez et al. (2019)
142 14.7 Hexanedioic acid, mono(2-ethylhexyl)ester Antibacterial C14H26O4 258 0.4 Choi and Jiang (2014)
143 Hexanedioic acid, dioctyl ester Inhibitor C22H42O4 370 Chaler et al. (2004)
144 Cyclohexanecarboxylic acid, octyl ester C15H28O2 240 Andersson et al. (1965)
145 1-Dodecanol, 3,7,11-trimethyl- Cytotoxic C15H32O 228 Fahem et al. (2020)
146 Cyclohexanecarboxylic acid, decyl ester/2-Propenoic acid, tetradecyl ester Antioxidant C17H32O2 268 Matthew et al. (2022)
147 Hexanedioic acid, bis(2-ethylhexyl) ester Biomarker C22H42O4 370 Silva et al. (2013)
148 15.3 10-Octadecenal/4-Octadecenal Adjuvant/ pheromones C18H34O 266 0.4 Gil et al. (1995)
149 Cyclopropanetetradecanoic acid, 2-octyl-, methyl ester Pharmacological C26H50O2 394 Srivastava et al. (2015)
150 9-Methyl-Z-10-pentadecen-1-ol Antioxidant C16H32O 240 Soleha et al. (2020)
151 Hexadecane, 1,1-bis(dodecyloxy)- C40H82O2 594 Ser et al. (2015)
152 3-Chloropropionic acid, heptadecyl ester Antibiotic C20H39ClO2 346 Ikhsanov et al. (2018)
153 2-Tridecenoic acid, (E)- Antimicrobial C13H24O2 212 Chowdhury et al. (2021)
154 trans-2-undecenoic acid Larvicidal C11H20O2 184 Saxena and Stotzky (2001)
155 Ethanol, 2-(octadecyloxy)- Antimicrobial C20H42O2 314 Jaffar et al. (2015)

R.T (min): Retention Time.

One of the previous study; extracellular protein of Actinomyces are actively producers for enzyme ligno cellulase (Clark Mason et al., 1988). The eluted peak fraction for proteins of G. mysorens has shown significant activity for different concentrations 50 μg of protein fraction showed 24% antiproliferative activity against prostate cancer PC3 cell line, for 100 μg 35% antiproliferative activity was observed, for 150 μg 47% antiproliferative activity was observed and for 200 μg 56% antiproliferative activity was observed in comparison with standard drug cisplatin at 5 μg showed 47% antiproliferative activity as showed in Figure 5.

Anticancer activity of Glutamicibacter mysorens strain protein. MTT assay performed by using prostate cancer PC3 cell line. (A) Untreated cells of PC3 cell line, (B) Standard cisplatin at 5 μg/ml, (C) 56% Anticancer activity of Glutamicibacter mysorens protein at 200 μg/ml.

Similar studies reported that other bioactive compounds isolated from the genus Glutamicibacter have been characterized for antimicrobial activity (Phuong and Diep, 2020; Xiong et al., 2020). In another study reported that plant-growth promoting bioactive compounds was produced by Glutamicibacter halophytocola coastal region of China (Qin et al., 2018). Whereas another study describes the anti-fungal efficiency of the Glutamicibacter genus with chitin hydrolyzing activity (Asif et al., 2020). The intracellular protein extraction already reported in our previous studies characterized for an antimicrobial activity that can be considered as antimicrobial peptides (AMPs) from the microbial origin (Karthik and Kalyani, 2021). In the present work the G. mysorens protein fraction is also exhibiting antiproliferative activity against cancerous cells acting also as anticancer peptides (ACP’s) and the protein molecules detected and characterized by LC–MS analysis. We are also reporting GCMS analysis and detected bioactive compounds from G. mysorens.

As discussed above the Sephadex G-10 eluted peak protein fraction was further subjected to LCMS analysis. The LCMS analysis and elution profile as shown in Figure 6, revealed the detection of pharmacologically applicable bioactive peptide compounds. With respect to elution peak from LCMS analysis and detection through the NIST, the computer library resulted in the identification of Kinetin-9-riboside and Embinin. The detected Kinetin-9-riboside with 347 Da molecular weight structure and mass confirmation are shown in Figure 7. The mass confirmation and structure of Embinin with a molecular weight of 606 Da showed in Figure 8. These bioactive molecules are well-known for their effective activity in various biological applications.

Elution profile of intracellular protein extract from Glutamicibacter mysorens by LCMS.

(A) Mass confirmation and analysis record. (B) 2D structure of kinetin-9-ribose, (C) 3D structure of kinetin-9-ribose molecule.

(A) Mass confirmation of Embinin, (B) 2D structure of Embinin, (C) 3D structure of Embinin.

In a previous study, the therapeutic and biological studies of Kinetin-9-riboside as an immuno-stimulant; immuno-stimulatory activities, and their uses as an adjuvant were reported. Because mutations in induced putative kinase 1 (PINK1) induce severe Parkinson’s disease, there’s a lot of interest in finding small molecules that boost PINK1’s kinase activity. Several studies on the design, synthesis, serum stability and hydrolysis of four kinetin riboside ProTides have been published. These ProTides, in combination with kinetin riboside, activated PINK1 in cells that had not been depolarized by mitochondria. This demonstrates the therapeutic potential of modified nucleosides and their phosphate prodrugs for Parkinson’s disease, the second most common neurodegenerative disease (Osgerby et al., 2017).

Another study found that the epithelial-mesenchymal transition (EMT) is a molecular phenomenon associated with increased vimentin expression and raised activity of transcriptional factors (Snail, Twist) that inhibit E-cadherin. EMT has been linked to prostate cancer metastatic potential, therapy resistance, and poor outcomes. Kinetin riboside (KR) is a naturally occurring cytokinin with effective anticancer activity against several human cancer cell lines. mRNA and protein levels of AR, E-, N-cadherins, Vimentin, Snail, Twist, and MMPs were measured using Western Blot and RT-PCR or RQ-PCR techniques to determine the effect of KR on human prostate cell lines.KR inhibited the growth of human prostate cancer cells and, to a lesser extent, normal cells. The cell type and androgen sensitivity determined this effect. KR also decreased the level of p-Akt, which is involved in androgen signaling modulation. When cancer cell lines are exposed to KR, the anti-apoptotic Bcl-2 protein is down-regulated, whereas the Bax protein is up-regulated. KR was involved in E-cadherin re-expression as well as pivotal changes in cell migration. Taken together, the findings suggest that, for the first time, KR can be anticipated as a factor for signaling pathway regulation that involves the inhibition of the development of aggressive forms of prostate cancer, potentially leading to future therapeutic interventions. As a result, research indicates that KR is an effective inhibitor of EMT in human prostate cells (Thakor et al., 2016; Dulińska-Litewka et al., 2020).

Whereas Embinin is a C-Glycosyl flavone and has a wide therapeutic applications in cardiovascular diseases (Ivkin et al., 2018). Another study reports the production of Embinin frompetals of Iris germanica Linnaeus and Iris lactea Leaves (Kawase and Yagishita, 1968; Chen et al., 2018). Our study elucidates the cytotoxicity activity of G. mysorens bioactive peptide as characterized by LCMS/MS revealed the presence of Kinetin-9-Riboside and Embininin the peptide fraction showing its antiproliferative effect on the prostate cancer cell line. Thus microbial-originated intracellular peptides have potential antimicrobial (AMPs) and anticancer (ACPs) have been significantly substantiated in our studies.

 Conclusion

The present study is illustrative for exploring untapped mangrove habitat in the Mangalore region of Karnataka. In our study, we could demonstrate that mangrove G. mysorens is an efficient microbe to produce bioactive compounds and enzymes responsible for both antimicrobial and anticancer activity. The antimicrobial potentiality was detailed in our previous article. In this present study; anticancer activity on prostate cancer cell lines and to treat various other related ailments. Peptides from reliable sources such as Actinomyces could be demonstrated as having dual roles as AMPs as well as ACPs. Hence, this study supports and proves that the genus Glutamicibacter is an effective microbial group for the isolation of peptides to treat multidrug-resistant pathogens.

 Data availability statement

The datasets presented in this study can be found in online repositories. The names of the repository/repositories and accession number(s) can be found at: NCBI - MW647910.

 Author contributions

YK conducted the research and wrote the manuscript. MI, SK, RD, and CA performed the data analyses and reviewed the manuscript. SK, YK, KR, MAh, MAl, MH, AA, SS, and MM edited and reviewed the manuscript. MI provided experimental support, planned, supervised, and organized the experiment, and wrote and reviewed the manuscript. All authors contributed to the article and approved the submitted version.

 Funding

This work is supported by Science & Engineering Research Board, DST, Govt. of India and Vision Group of Science and Technology Govt. of Karnataka by providing financial and equipment grants.

 Conflict of interest

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

 Publisher’s note

All claims expressed in this article are solely those of the authors and do not necessarily represent those of their affiliated organizations, or those of the publisher, the editors and the reviewers. Any product that may be evaluated in this article, or claim that may be made by its manufacturer, is not guaranteed or endorsed by the publisher.

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