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Article

GC-MS-Based Metabolomics Analysis of Prawn Shell Waste Co-Fermentation by Lactobacillus plantarum and Bacillus subtilis

by
Yun Nian Tan
,
Jian Hua Zhang
and
Wei Ning Chen
*
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore 639798, Singapore
*
Author to whom correspondence should be addressed.
Polysaccharides 2020, 1(1), 31-50; https://doi.org/10.3390/polysaccharides1010004
Submission received: 14 September 2020 / Revised: 23 September 2020 / Accepted: 27 September 2020 / Published: 29 September 2020
Browse Figure
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Abstract

:
GC-MS-based metabolomics were used to investigate metabolic changes in prawn shell waste during fermentation. Microbial strains Lactobacillus plantarum and Bacillus subtilis were co-fermented in a shake flask comprising of 5% (w/v) prawn shell waste and 20% (w/v) glucose as a carbon source. Analysis of the prawn shell waste fermentation showed a total of 376 metabolites detected in the culture supernatant, including 14 amino acids, 106 organic acids, and 90 antimicrobial molecules. Results show that the liquid fraction of the co-fermentation is promising for harvesting valuable metabolites for probiotics application.

1. Introduction

The industrial seafood processing industry generates more than 1 million metric tons of dry weight of shellfish waste annually [1]. As the heads and exoskeletons of shellfish that comprise about 50–60% of their total weight are not suitable for human consumption, these shellfish residues are discarded as seafood processing waste by ocean dumping, incineration, or disposal in landfills [2]. This has contributed to both land and sea pollution, hence sparking scientific and environmental interest to develop techniques to recover and utilize the biopolymers in shellfish waste [3].
Prawn shell waste is chemically composed of 20–30% chitin, 20–40% protein, 30–60% minerals, and 0–14% lipids [4]. Currently, crustacean waste serves as the largest source of chitin or its deacetylated derivative chitosan [5]. Chitin, a polysaccharide with a similar structure to cellulose, is an N-acetyl-glucosamine biopolymer with α-1,4 bonds between each monomeric unit [6]. The isolation of chitin involves deproteinization, demineralization, and bleaching [7]. Traditional chemical methods involve the use of highly concentrated sodium hydroxide to carry out deproteinization and highly corrosive hydrochloric acid to carry out demineralization [8]. Other than the formation of toxic waste, undesired by-products such as irregularly deacetylated polymers result [9]. In addition, the protein and carotenoid components of the prawn shell waste are rendered useless [10].
Research has focused on using environmentally friendly processes such as biological co-fermentation by lactic acid bacteria and protease producing bacteria [11]. The lactic acid produced during fermentation reacts with the calcium carbonate in the prawn shell waste, leading to the formation of calcium lactate, which can be separated from the chitin fraction [12]. Proteolytic enzymatic action also simultaneously hydrolyzes the protein fraction of prawn shells to recover chitin [13]. Much attention has been directed at optimizing the extracellular production of the chitinase enzyme by the selection of appropriate micro-organisms [14]. Various factors such as glucose concentrations, inoculum sizes, pH, temperature, and length of fermentation influence the fermentation process as well as deproteinization and demineralization efficiencies [15].
The remains of shellfish heads and exoskeletons are also rich in lipid soluble carotenoid pigments and the recovery of an astaxanthin-rich carotenoprotein concentrate for its antioxidant properties have been a focal point of scientific study [16]. The extraction of protein hydrolysates from prawn shell waste for use as food flavoring agents or for aquaculture diets has received considerable scientific attention [17]. However, the study of these bioactive compounds in the liquor fraction has posed great challenges due to their inherent instability upon analysis [18].
In this study, GC-MS-based metabolomics profiling was performed on the co-culture supernatant of both microbial strains, lactic acid bacteria Lactobacillus plantarum subsp. plantarum ATCC 14,917 and protease producing bacteria Bacillus subtilis subsp. subtilis ATCC 6051, using prawn shell waste as the nitrogen source and 20% glucose in deionized water as the carbon source [19]. Lactobacillus plantarum was selected as previous studies found it to be starch-hydrolyzing, heterofermentative, and proteolytic when tested in skim milk agar, which are important properties for the deproteinization and demineralization of prawn shells [20]. Bacillus subtilis was chosen as it was affirmed in previous studies to produce a high protease yield, which retained maximum protease activity even in the presence of salt, surfactants, metal ions, and solvents [21].
The composition of totals phenols, polysaccharides, reducing sugars, free amino acids, and organic acids in the culture supernatant were determined by GC-MS analysis after GC derivatization to understand the fermentation characteristics of microbial extraction of chitin from prawn shell waste [22]. The remnants of the prawn shell waste were filtered off from the fermented supernatant, washed with deionized water, and sterilized with 70% (v/v) ethanol [23]. After being dried in a vacuum oven at 60°C overnight, chemical analysis was performed and it was found to be chitin [24].

2. Materials and Methods

2.1. Fermentation Conditions and Harvesting of Samples

Single colonies of Lactobacillus plantarum on De Man, Rogosa, and Sharpe (MRS) agar plates were picked to 5 mL MRS broth and cultured at 37 °C, 200 rpm, overnight for 12 to 16 h. Similarly, single colonies of Bacillus subtilis on Luria-Bertani (LB) agar plates were picked to 5 mL LB broth and cultured at 30 °C, 200 rpm, overnight for 12 to 16 h. The Lactobacillus plantarum and Bacillus subtilis bacterial cells were collected by centrifuging at 14,500× g, 25 °C, for 5 min and their respective supernatants were decanted, leaving the cell pellets behind.
A conical flask containing 5 g of prawn shell waste as well as 20 g of glucose dissolved in 100 mL of deionized water were autoclaved at 121 °C for sterilization [25]. The 100 mL 20% (w/v) glucose solution was poured into the sterile conical flask containing 5 g of prawn shell waste. Lactobacillus plantarum cells and Bacillus subtilis cells were picked up from the centrifuged bacterial cell pellets using inoculating loops and inoculated into the fermentation flask. The fermentation setup procedures were repeated twice and the triplicate flasks were incubated at 30 °C, 200 rpm, for 5 days.

2.2. Samples Preparation for Extracellular Metabolites Analysis

First, 1 mL culture supernatant was collected from each of the three fermentation setups after 5 days. Ten microliters of 2 g/L ribitol dissolved in water was added to 50 μL of each supernatant sample and mixed thoroughly in a fresh Eppendorf tube [26]. The addition of ribitol served as an internal standard to correct for metabolite loss during sample preparation [27]. The samples were lyophilized overnight using a Labconco freeze dryer set at −40 °C and 0.0002 mBar and GC-MS derivatization was performed the next day [28].

2.3. GC-MS Analysis of Extracellular Metabolites

GC derivatization was performed for metabolic profiling on the GC-MS [29]. The lyophilized samples were re-dissolved in 100 μL of 20 mg/mL methoxyamine hydrochloride in pyridine and incubated at 37 °C for 1 h for carbonyls protection [30]. One hundred microliters of N-methyl-N-(trimethylsilyl)-trifluoroacetamide (MSTFA) with 1% trimethyl-chlorosilane (TMCS) was added to each sample and silylation was carried out at 70 °C for 30 min [31]. The samples were centrifuged at 14,500× g for 15 min and the supernatant was used for GC-MS analysis [32]. Samples of 1 μL were injected into the HP-5MS capillary column (Agilent Technologies, Singapore) by splitless mode using an auto-injector [33]. Helium was used as a carrier gas at 1.1 mL/min [34]. The injector temperature and ion source temperature were set at 250 °C and 230 °C, respectively, on the GC-MS (Agilent Technologies, Singapore) [35]. The oven temperature was kept at 75 °C for 5 min, raised at 4 °C per minute to a final temperature of 280 °C, and held for 2 min [36]. Data were recorded from m/z 50 to 500 with a scan time of 0.1 s [37]. Metabolites were identified using the NIST08 mass spectral library and normalized using the internal standard ribitol before comparison [38].

2.4. Statistical Analysis of Metabolites

The peak area for ribitol from the GC-MS run was recorded and equated to 20 μg/200 μL. The peak areas for detected metabolites were tabulated and their concentrations calculated via multiplying by ribitol concentration 20 μg/200 μL and dividing over peak area for ribitol. Metabolite measurement results from the triplicate fermentation flasks were expressed as mean ± standard deviation.

2.5. Determination of Chitin Yield and Purity

The mass of the crude chitin obtained was weighed after being dried in the vacuum oven overnight to determine its yield. The Lowry’s test for residual protein was carried out to ascertain the purity of the recovered chitin. Firstly, 5, 10, 15, 20, 25, and 30 μL of 2 mg/mL bovine serum albumin (BSA) was added to 195, 190, 185, 180, 175, and 170 μL of deionized water respectively to form a range of 200 μL protein standards for the construction of a protein calibration curve. Then, 1 mL of Lowry’s solution was added to the protein standards and left to react for 15 min, after which 100 μL of 1 N Folin’s Phenol reagent was added and the protein standards were left to react for another 30 min. Absorbance was measured at 750 nm and the values were plotted into a graph of absorbance versus μg protein. Fifty milligrams of the extracted crude chitin was then treated with 10 mL of 1 M aqueous sodium hydroxide solution for 24 h at 70 °C. 1 mL of Lowry’s solution and 100 μL of 1 N Folin’s Phenol reagent was similarly added to the boiled NaOH supernatant to determine the residual protein content of the recovered chitin [39].

3. Results

3.1. Metabolomics Analysis by GC-MS

A total of 376 metabolites were detected by GC-MS. Fourteen amino acids were detected in the fermentation, with the highest quantity being alanine (4642.67 mg/L), followed by proline (91.76 mg/L), threonine (91.73 mg/L), leucine (63.91 mg/L), norleucine (53.57 mg/L), alanylthreonine (26.39 mg/L), glycine (25.56 mg/L), sarcosine (16.19 mg/L), isoleucine (13.96 mg/L), alloisoleucine (13.86 mg/L), glutamic acid (5.68 mg/L), valine (3.13 mg/L), 1,4-dihydrophenylalanine (2.92 mg/L), and lysine (0.44 mg/L). Ketoisocaproic acid, which is a metabolic intermediate in the metabolic pathway for the amino acid leucine, was detected at 44.06 mg/L; while ketoisovaleric acid, which is a metabolite of the amino acid valine, was detected at 1.2 mg/L.
One hundred and six organic acids were found in the culture supernatant, with the highest quantities being butanoic acid (4399.87 mg/L), mannonic acid (2567.14 mg/L), 2,3-dimethylbutanoic acid (2129.98 mg/L), carbamic acid (1432.07 mg/L), glucopyranuronic acid (1239.42 mg/L), D-glycero-L-manno-heptonic acid (1192.77 mg/L), 3-oxooctanoic acid (1185.00 mg/L), propanoic acid (1184.32 mg/L), and lactic acid (1055.38 mg/L). There were also significant quantities of mandelic acid (443.5 mg/L), gluconic acid (307.05 mg/L), 2-ketobutyric acid (222.57 mg/L), hexanedioic acid (200.31 mg/L), 2-hydroxyisocaproic acid (173.95 mg/L), xylonic acid (156.31 mg/L), butyric acid (153.36 mg/L), hexadecenoic acid (147.85 mg/L), octadecanoic acid (147.83 mg/L), dipropylacetic acid (120.83 mg/L), and 3-deoxy-D-arabino-hexonic acid (112.61 mg/L) detected.
Ninety metabolites were reported in the literature to possess antimicrobial properties, of which 37 metabolites were fatty or organic acids. The remaining 53 reportedly antimicrobial metabolites, which were non-acids, include acetamide (2999.12 mg/L), uridine (1277.01 mg/L), 2-hydroxybenzaldehyde (940.97 mg/L), acethydrazide (366.71 mg/L), 2-propenamide (338.39 mg/L), glycerol (336.23 mg/L), 2-quinolinone (284.36 mg/L), benzenesulfonamide (167.36 mg/L), thymol (68.98 mg/L), quinazoline (66.92 mg/L), sedoheptulose (64.36 mg/L), kaurene (58.27 mg/L), 1,2-benzisothiazole (56.13 mg/L), phenanthroline (49.88 mg/L), ethyl acetate (44.86 mg/L), pyrazine (33.19 mg/L), ethanol (31.01 mg/L), 1,4-benzoquinone (28.12 mg/L), benzoate (24.82 mg/L), benzisothiazolinone (23.64 mg/L), indole (22.32 mg/L), and 2-aminothiadiazole (20.98 mg/L).
Full detailed results for the detected metabolites are shown in Table 1, Table 2, Table 3 and Table 4 below.

3.2. Chitin Yield and Purity Calculations

From 5.0 g of prawn shell waste, 20 g of glucose, and 100 g of deionized water, the dry weight of crude extracted chitin was found to be 0.50 ± 0.01 g, translating to an overall fermentation yield of 0.50/125.0 × 100% = 0.4%.
Lowry’s test was performed on 1 mL of supernatant extracted from 50 mg chitin heated in 10 mL NaOH and its absorbance was found to be 0.213, corresponding to 20 μg of protein when compared against the protein calibration curve (Figure 1). This translates to a residual protein of 200 μg per 50 mg chitin, which is a residual protein content of 200/50,000 × 100% = 0.4%.

4. Discussion

Bacteria species coexist with neighboring microorganisms in a dynamic community by producing small metabolites in response to environmental changes such as biotic and abiotic stresses. These volatile organic and inorganic compounds are released during interspecies bacteria interactions due to competition and cooperation, forming soluble metabolites in the supernatant [134]. Detection and quantification of these bacteria volatile compounds have always been of great interest in the food, cosmetic, flavor, and fragrance bioprocessing industry as well as in the clinical and medical field. However, analysis of bacteria volatile compounds has remained challenging due to the wide abundance of metabolites and the complexity of the culture medium from where they are extracted.
The co-fermentation of prawn shell waste and 20% glucose by Lactobacillus plantarum and Bacillus subtilis for chitin extraction produced bacteria volatile metabolites of various chemical classes. Fatty acid derivatives such as hydrocarbons, ketones and alcohols, organic acids, as well as sulphur and nitrogen-containing compounds were detected in the culture supernatant. These metabolites were generally produced by different catabolic pathways such as glycolysis, proteolysis, and lipolysis to break down the proteins, fats, and minerals residual in the prawn shell waste [135]. Linear-chained hydrocarbons detected were most probably derived from products of the fatty acid biosynthetic pathway. Both short-chain alkanes and longer-chain hydrocarbons were found in the culture supernatant, testifying to the ability of the microbial strains to synthesize branched hydrocarbons.
Methyl ketones detected were probably produced from the decarboxylation of fatty acids [136]. For example, 3-hydroxy-2-butanone (72.50 mg/L) or acetoin detected might have been derived from pyruvate fermentation. Long-chain aliphatic alcohols such as 1-decanol (1.75 mg/L) were probably produced through the oxidation of fatty acid derivatives. Significant production of butanediol (139.50 mg/L) was detected due to the presence of glucose as the main nutrient in the growth medium. Short-chain branched alcohols such as 3,3-dimethyl-1-butanol (18.60 mg/L) detected might have been produced from the enzymatic conversion of branched chain amino acids such as leucine.
Several short-chain fatty acids were detected in the culture supernatant such as acetic acid (71.94 mg/L), propanoic acid (1184.32 mg/L), and butanoic acid (4399.87 mg/L). These saturated aliphatic organics acids most probably resulted from bacteria fermentation of carbohydrates. Glyoxylic acid (4.68 mg/L) detected could either have been produced in the tricarboxylic acid cycle or generated during amino acid metabolism, for example during the degradation of glycine (25.56 mg/L), threonine (91.73 mg/L), and proline (91.76 mg/L). Indole (22.32 mg/L) biosynthesis, another by-product of amino acid catabolism, was also detected in the fermentation supernatant [137].
An oxidative deamination of many amino acids might have also led to the production of aldehydes, ketones, or alcohols detected. For example, the degradation of 1,4-dihydrophenyalanine (2.92 mg/L) might have served as the first step of aromatic volatile compounds synthesis, producing benzene, its carbohydrate derivatives, as well as other benzenoid volatiles. Many volatile organic compounds produced by Lactobacillus plantarum and Bacillus subtilis have been reported to display antimicrobial activity. Among these known antimicrobial metabolites, benzenoids are the most represented in quantity compared to alkanes, aldehydes, ketones, acids, and alcohols. While a huge majority of antimicrobial benzenoid volatiles have a benzene core linked to a fatty acids derivative, benzenoids are very diverse and can be linked with carbohydrate chains containing nitrogen and sulphur [138].
The antimicrobial mode of action of these bacteria volatile organic compounds might arise from their lipophilic nature, which enables them to destabilize the cell membrane integrity of antagonistic pathogens, inhibiting their growth [139]. Besides benzenoids, nitrogen-containing volatile organic compounds are another important group of antimicrobial metabolites, consisting of non-cyclic amides and amines as well as cyclic azoles, pyrazines, pyridazines, and pyrimidines. Pyrazine (33.19 mg/L), pyridazine (3.29 mg/L), and pyrrolopyrimidine (3.33 mg/L) were detected in the Lactobacillus plantarum and Bacillus subtilis co-fermentation supernatant. Pyrazine, which is the most strongly represented in antimicrobial activity among them, is either formed from the non-enzymatic animation of acyloins or derived from aminoketone intermediates produced from amino acid catabolism. This testifies to the successful breakdown of amino acids from the prawn shell waste.
Antimicrobial active metabolites may have potential use as natural preservatives to control the growth and inactivate undesired microorganisms in food [140]. For example, lactic acid (1055.39 mg/L) and acetic acid (71.94 mg/L) are produced by Lactobacillus plantarum in probiotics to compete for nutrients with other foodborne pathogens. Other organic acids such as propanoic acid (1184.32 mg/L) and butanoic acid (4399.87 mg/L) are also produced, which further reduce the pH of the culture medium. The production of other substances such as ethanol (31.01 mg/L), fatty acids such as 3-hydroxybutyric acid (18.19 mg/L), 3-hydroxysebacic acid (4.09 mg/L), and 3-hydroxpyruvic acid (1.32 mg/L), as well as 3-hydroxy-2-butanone (72.5 mg/L) further intensify its antimicrobial activity. The metabolomics results show that Lactobacillus plantarum is more heterofermentative than homofermentative as a variety of metabolites are generated from the degradation of hexoses.

5. Conclusions

Many useful metabolites are produced when Lactobacillus plantarum and Bacillus subtilis are fermented with prawn shell waste together with 20% glucose as a carbon source. Besides lactic acid, a variety of organic acids such as fatty acids and amino acids as well as several antimicrobial molecules were detected in the culture supernatant. This shows that protease-mediated protein hydrolysis of the prawn shells is successful in removing proteins, minerals, and fats from the prawn shells. While harnessing the solid fraction of the fermentation as chitin, the nutrient-rich liquid fraction may be used for probiotics applications.

Author Contributions

Conceptualization, W.N.C.; methodology, Y.N.T. and J.H.Z.; software, Y.N.T. and J.H.Z.; validation, Y.N.T. and J.H.Z.; formal analysis, Y.N.T. and J.H.Z.; investigation, Y.N.T. and J.H.Z.; resources, W.N.C.; data curation, Y.N.T. and J.H.Z.; writing—original draft preparation, Y.N.T.; writing—review and editing, Y.N.T.; visualization, W.N.C.; supervision, W.N.C.; project administration, W.N.C.; funding acquisition, W.N.C. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by Nanyang Technological University, grant number M4062121.120.703012.

Acknowledgments

We thank Nanyang Technological University for support.

Conflicts of Interest

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

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Polysaccharides 01 00004 g001 550
Figure 1. Lowry’s test calibration curve (absorbance vs. μg protein).
Figure 1. Lowry’s test calibration curve (absorbance vs. μg protein).
Polysaccharides 01 00004 g001
Table
Table 1. Amino acids detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
Table 1. Amino acids detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
MetaboliteMolecular FormulaQuantity (mg/L)Biological Characteristic
AlanineC3H7NO24642.67 ± 3.90Amino acid
AlanylthreonineC7H14N2O426.39 ± 0.01Amino acid
AlloisoleucineC6H13NO213.86 ± 0.01Amino acid
1,4-DihydrophenylalanineC9H13NO22.92 ± 0.01Amino acid
Glutamic acidC5H9NO45.68 ± 0.01Amino acid
GlycineC2H5NO225.56 ± 0.02Amino acid
IsoleucineC6H13NO213.96 ± 0.06Amino acid
Ketoisocaproic acidC6H10O344.06 ± 0.13Leucine ketoacid
Ketoisovaleric acidC5H8O31.20 ± 0.01Valine ketoacid
LeucineC6H13NO263.91 ± 0.01Amino acid
LysineC6H14N2O20.44 ± 0.01Amino acid
ProlineC5H9NO291.76 ± 1.28Amino acid
ThreonineC4H9NO391.73 ± 0.05Amino acid
ValineC5H11NO23.13 ± 0.01Amino acid
Table
Table 2. Antimicrobial Compounds detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
Table 2. Antimicrobial Compounds detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
MetaboliteMolecular FormulaQuantity (mg/L)Biological Characteristic
AcetamideC2H5NO2999.12 ± 4.06Antimicrobial [40]
AcethydrazideC2H6N2O366.71 ± 0.01Antimicrobial [41]
Acetic acidC2H4O271.94 ± 0.17Antimicrobial [42]
AcridinedioneC13H7NO24.31 ± 0.01Antimicrobial [43]
Acrylic acidC3H4O20.72 ± 0.01Antimicrobial [44]
Allonic acidC6H12O718.89 ± 0.08Anti-tumor
4-Aminobenzoic acidC7H7NO27.00 ± 0.01Antimicrobial [45]
2-AminothiadiazoleC3H4N2S20.98 ± 0.01Antimicrobial [46]
Arachidonic acidC20H32O25.92 ± 0.01Antimicrobial [47]
Azelaic acidC9H16O40.50 ± 0.01Antimicrobial [48]
BenzamideC7H7NO11.18 ± 0.12Antimicrobial [49]
1,2-BenzenediolC6H6O21.31 ± 0.01Antimicrobial [50]
Benzeneacetic acidC8H8O29.04 ± 0.01Antimicrobial [51]
Benzenepropanoic acidC9H10O20.84 ± 0.01Antimicrobial [52]
BenzenesulfonamideC6H7NO2S167.36 ± 1.56Antimicrobial [53]
BenzenethiolC6H6S1.47 ± 0.01Antimicrobial [54]
1,2-BenzisothiazoleC7H5NS56.13 ± 0.59Antimicrobial [55]
BenzisothiazolinoneC7H5NOS23.64 ± 0.01Antimicrobial [56]
1,2-BenzisoxazoleC7H5NO1.75 ± 0.01Antimicrobial [57]
BenzoateC7H5O2−24.82 ± 0.01Antimicrobial [58]
1,3-BenzodioxoleC7H6O26.97 ± 0.01Antimicrobial [59]
Benzoic acidC7H6O227.37 ± 0.38Antimicrobial [60]
1,4-BenzoquinoneC6H4O228.12 ± 0.37Antimicrobial [61]
BenzoxazoleC7H5NO1.26 ± 0.01Antimicrobial [62]
1-BenzylindoleC15H13N7.92 ± 0.04Antimicrobial [63]
ButanolC4H10O1.81 ± 0.01Antimicrobial [64]
Butyric acidC4H8O2153.36 ± 0.26Antimicrobial [65]
CarbamateCH2NO2−0.92 ± 0.01Antimicrobial [66]
Carbamic acidCH3NO21432.07 ± 4.62Antimicrobial [67]
CephaloridineC19H17N3O4S26.53 ± 0.01Antibiotic
ColchicineC22H25NO615.06 ± 0.01Anti-inflammatory
Decanoic acidC10H20O270.50 ± 0.01Antimicrobial [68]
DihydroisosteviolC20H32O35.44 ± 0.01Antimicrobial [69]
Docosahexaenoic acidC22H32O25.79 ± 0.01Antimicrobial [70]
DocosanolC22H46O6.41 ± 0.01Antimicrobial [71]
DodecanamideC12H25NO5.28 ± 0.01Antimicrobial [72]
EthanolC2H6O31.01 ± 0.30Antimicrobial [73]
Ethyl acetateC4H8O244.86 ± 0.48Antimicrobial [74]
Galacturonic acidC6H10O75.03 ± 0.05Antimicrobial [75]
D-gluco-hexodialdodifuranosideC14H30O63.52 ± 0.01Anticancer
Gluconic acidC6H12O7307.05 ± 0.60Antimicrobial [76]
GlycerolC3H8O3336.23 ± 1.94Antimicrobial [77]
Glyoxylic acidC2H2O34.68 ± 0.01Antimicrobial [78]
GriseoviridinC22H27N3O7S3.14 ± 0.01Antibiotic
GuaiacolC7H8O28.43 ± 0.01Antimicrobial [79]
Hexadecanoic acidC16H32O2147.85 ± 1.49Antimicrobial [80]
2,4-Hexadienoic acidC6H8O20.87 ± 0.01Antimicrobial [81]
Hexanedioic acidC6H10O4200.31 ± 0.01Antimicrobial [82]
Hexanoic acidC6H12O220.24 ± 0.01Antimicrobial [83]
2-HydroxybenzaldehydeC7H6O2940.97 ± 1.64Antimicrobial [84]
3-Hydroxybutyric acidC4H8O318.19 ± 0.24Antimicrobial [85]
4-HydroxydiphenylamineC12H11NO1.77 ± 0.01Antimicrobial [86]
2-Hydroxyisocaproic acidC6H12O3173.95 ± 2.09Antimicrobial [87]
3-(4-Hydroxyphenyl)propionic acidC9H10O31.71 ± 0.01Anti-inflammatory
IndoleC8H7N22.32 ± 0.27Antimicrobial [88]
Indole-3-carboxylic acidC9H7NO28.27 ± 0.01Antimicrobial [89]
Isocitric acidC6H8O71.30 ± 0.01Antimicrobial [90]
3-IsoxazolidinoneC3H5NO23.31 ± 0.01Antimicrobial [91]
KaureneC20H3258.27 ± 0.10Antimicrobial [92]
2-Keto-D-glucoseC6H10O62.11 ± 0.01Antibiotic
Lactic acidC3H6O31055.38 ± 7.90Antimicrobial [93]
Linolenic acidC18H30O28.00 ± 0.01Antimicrobial [94]
LycopodineC16H25NO4.13 ± 0.01Antimicrobial [95]
Malic acidC4H6O521.02 ± 0.29Antimicrobial [96]
Mandelic acidC8H8O3443.50 ± 6.14Antimicrobial [97]
Meldrum’s acidC6H8O41.49 ± 0.01Antimicrobial [98]
MethanolCH4O10.15 ± 0.01Antimicrobial [99]
MethylenecyclopropaneC4H60.18 ± 0.01Antiviral [100]
Nonadecanoic acidC19H38O22.48 ± 0.01Anticancer [101]
Nonanoic acidC9H18O216.07 ± 0.01Antimicrobial [102]
Octadecanoic acidC18H36O2147.83 ± 1.66Antimicrobial [103]
Octanoic acidC8H16O21.38 ± 0.01Antimicrobial [104]
OctenidineC36H62N41.03 ± 0.01Antimicrobial [105]
Pentanedioic acidC5H8O450.59 ± 0.64Antimicrobial [106]
PhenanthrolineC12H8N249.88 ± 0.39Antimicrobial [107]
3-Phenyl-5-isoxazoloneC9H7NO22.14 ± 0.01Antimicrobial [108]
Phosphoric acidH3PO40.68 ± 0.01Antimicrobial [109]
PropanamideC3H7NO6.08 ± 0.01Antimicrobial [110]
PropanenitrileC3H5N8.05 ± 0.01Antimicrobial [111]
Propanoic acidC3H6O21184.32 ± 9.56Antimicrobial [112]
PropionamideC3H7NO10.84 ± 0.01Antimicrobial [113]
PteridineC6H4N43.82 ± 0.03Antimicrobial [114]
PyranoneC5H4O27.89 ± 0.07Antimicrobial [115]
PyrazineC4H4N233.19 ± 0.01Antimicrobial [116]
PyridazineC4H4N23.29 ± 0.01Antimicrobial [117]
PyrroleC4H5N3.04 ± 0.02Antimicrobial [118]
PyrrolopyrimidineC6H5N33.33 ± 0.01Antiviral [119]
Pyruvic acidC3H4O356.20 ± 0.02Antimicrobial [120]
QuinazolineC8H6N266.92 ± 0.01Antimicrobial [121]
QuinolineC9H7N1.87 ± 0.01Antimicrobial [122]
2-QuinolinoneC9H7NO284.36 ± 0.01Antimicrobial [123]
SedoheptuloseC7H14O764.36 ± 0.01Antimicrobial [124]
SesamolC7H6O39.33 ± 0.07Antimicrobial [125]
Tartaric acidC4H6O67.94 ± 0.01Antimicrobial [126]
ThiopheneC4H4S0.93 ± 0.01Antimicrobial [127]
ThioureaCH4N2S2.16 ± 0.01Antimicrobial [128]
ThymolC10H14O68.98 ± 0.01Antimicrobial [129]
1,2,4-Triazole-3-carboxylic acidC3H3N3O256.93 ± 0.01Antimicrobial [130]
Undecanoic acidC11H22O22.09 ± 0.01Antimicrobial [131]
UreaCH4N2O0.65 ± 0.01Antimicrobial [132]
UridineC9H12N2O61277.01 ± 3.34Antimicrobial [133]
Table
Table 3. Other organic compounds detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
Table 3. Other organic compounds detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
MetaboliteMolecular FormulaQuantity (mg/L)Biological Characteristic
Altronic acidC6H12O70.22 ± 0.01Organic acid
AmphetamineC9H13N1.35 ± 0.01Stimulant
AromadendreneC15H244.54 ± 0.01Essential oil
BenzeneC6H616.07 ± 0.01Aromatic
BenzocyclobuteneC8H87.98 ± 0.01Aromatic
BenzonitrileC7H5N91.31 ± 0.01Aromatic
ButanalC4H8O29.38 ± 0.19Aldehyde
ButaneC4H10543.18 ± 5.86Alkane
Butanedioic acidC4H6O431.11 ± 0.03Organic acid
ButanediolC4H10O2139.50 ± 0.03Alcohol
1,2,2,3,4-ButanepentacarbonitrileC9H5N50.55 ± 0.01Aromatic
Butanoic acidC4H8O24399.87 ± 6.20Organic acid
1-ButeneC4H8379.99 ± 5.33Alkene
1,4-ButenediolC4H8O246.28 ± 0.01Alcohol
2-Butenoic acidC4H6O252.41 ± 0.11Organic acid
3-Buten-1-olC4H8O2.31 ± 0.01Alcohol
ButylamineC4H11N84.67 ± 0.01Amine
ButyneC4H67.46 ± 0.01Alkyne
ButynolC4H10O0.43 ± 0.01Alcohol
ButyrateC4H7O2−0.72 ± 0.01Flavoring
Camphoric acidC10H16O40.81 ± 0.01Organic acid
Carbophenoxon sulfoneC11H16ClO5PS211.46 ± 0.01Organosulfone
CholestaneC27H483.63 ± 0.01Cholesterol
1-CholesteneC27H4631.64 ± 0.01Cholesterol
CholestenoneC27H44O7.61 ± 0.09Cholesterol
CholesterolC27H46O75.80 ± 0.66Cholesterol
ChromiumCr2.53 ± 0.01Mineral
CortisoneC21H28O52.09 ± 0.01Steroid
CyclobutanemethanolC5H10O25.00 ± 0.01Aromatic
CyclohexaneC6H124.64 ± 0.03Aromatic
CyclohexeneC6H101.31 ± 0.01Aromatic
3-Cyclohexene-1-methanolC7H12O2.78 ± 0.01Essential oil
1-Cyclohexyl-tetradecaneC20H405.00 ± 0.01Aromatic
Cyclopenta[de]naphthaleneC12H88.26 ± 0.01Aromatic
CyclopentaneC5H104.84 ± 0.01Aromatic
1,2,4-CyclopentanetrioneC5H4O37.93 ± 0.01Aromatic
CyclopenteneC5H80.61 ± 0.01Aromatic
Cyclopropanecarboxylic acidC4H6O23.04 ± 0.01Organic acid
DecaneC10H221.98 ± 0.01Alkane
1-DecanolC10H22O1.75 ± 0.01Fatty alcohol
2,6-Diamino-4-hexynoic acidC6H10N2O22.10 ± 0.01Organic acid
1,3-Diazepane-2,4,6-trioneC5H6N2O31.09 ± 0.01Aromatic
3-DibenzofuranamineC12H9NO19.35 ± 0.18Aromatic
Diethylene glycolC4H10O367.89 ± 0.68Solvent
2,3-Dihydroxybutanoic acidC4H8O413.75 ± 0.07Organic acid
1,1-DiisobutoxybutaneC12H26O21.72 ± 0.01Aldehyde
Diisopropyl malonateC9H16O41.30 ± 0.01Acid ester
DimethylbutanedioateC6H10O40.77 ± 0.01Flavoring
2,3-Dimethylbutanoic acidC6H12O22129.98 ± 3.01Fatty acid
3,3-Dimethyl-1-butanolC6H14O18.60 ± 0.01Alcohol
DimethylcyclohexanoneC8H14O89.00 ± 0.01Aromatic
DimethyldecahydronaphthaleneC12H2256.95 ± 0.01Aromatic
Dimethyl malonateC5H8O48.30 ± 0.01Acid ester
Dipropylacetic acidC8H16O2120.83 ± 0.01Organic acid
13,16-Docasadienoic acidC22H40O251.71 ± 0.35Fatty acid
Docosanoic acidC22H44O22.40 ± 0.01Fatty acid
13-DocosenamideC22H43NO64.20 ± 0.78Fatty amide
DodecaneC12H261462.61 ± 0.01Alkane
Dodecanedioic acidC12H22O44.84 ± 0.01Organic acid
5,8,11-Eicosatriynoic acidC20H28O20.97 ± 0.01Fatty acid
EstratetraenolC18H22O15.35 ± 0.01Steroid
EthaneC2H637.25 ± 0.01Alkane
Ethanedioic acidC2H2O416.61 ± 0.19Organic acid
Ethanesulfonic acidC2H6O3S3.13 ± 0.02Sulfonic acid
Ethanimidic acidC4H9NO0.63 ± 0.01Organic acid
Ethyl butyrateC6H12O27.25 ± 0.02Flavoring
EthyleneC2H41.99 ± 0.01Alkene
Ethylene glycolC2H6O2141.94 ± 0.01Solvent
3-FuranacetaldehydeC6H6O20.75 ± 0.01Aldehyde
2-Furancarboxylic acidC5H4O31.98 ± 0.01Organic acid
2-FuranoneC4H4O23.41 ± 0.02Flavoring
GlucuronolactoneC6H8O63.95 ± 0.04Lactone
Glyceraldehyde acetonideC6H10O3247.79 ± 0.01Carboxaldehyde
L-gulono-1,4-lactoneC6H10O621.25 ± 0.23Lactone
HeptadecaneC17H367.06 ± 0.01Alkane
Heptadecane-1,2-diolC17H36O254.71 ± 0.01Fatty alcohol
3-Heptyn-1-olC7H12O10.73 ± 0.01Fatty alcohol
HeptanamideC7H15NO14.97 ± 0.01Fatty amide
HexadecanamideC16H33NO5.81 ± 0.01Fatty amide
HexadecaneC16H3497.90 ± 0.01Alkane
1-HexeneC6H1210.50 ± 0.01Alkene
3-Hexenedioic acidC6H8O411.76 ± 0.01Fatty acid
3-Hexen-1-olC6H12O3.00 ± 0.01Fatty alcohol
4-Hexen-1-yneC6H82.27 ± 0.01Alkyne
3-Hydroxy-2-butanoneC4H8O272.50 ± 0.01Methyl ketone
2-Hydroxyglutaric acidC5H8O52.30 ± 0.01Organic acid
3-Hydroxypyruvic acidC3H4O41.32 ± 0.01Organic acid
3-Hydroxysebacic acidC10H18O54.09 ± 0.03Organic acid
InabenfideC19H15ClN2O23.19 ± 0.01Herbicide
IronFe3.25 ± 0.01Mineral
2-Ketobutyric acidC4H6O3222.57 ± 0.02Organic acid
2-Ketohexanoic acidC6H10O31.03 ± 0.01Fatty acid
Ketovaleric acidC5H8O317.59 ± 0.01Ketoacid
Malonic acidC3H4O40.25 ± 0.01Organic acid
MethanaminiumCH6N5.93 ± 0.05Conjugate acid
Methyl butyrateC5H10O29.83 ± 0.01Flavoring
MethylcyclopentadieneC6H8465.49 ± 0.01Aromatic
6-Methyl-3,5-heptadien-2-oneC8H12O106.73 ± 0.48Flavoring
Methyl phenyl sulfoxideC7H8OS2.38 ± 0.01Aromatic
2-Methylpropanoic acidC4H8O28.21 ± 0.01Organic acid
2-MethylpropeneC4H869.91 ± 0.31Alkene
2-Methyl-4-propyl-1,3-oxathianeC8H16OS53.44 ± 0.01Flavoring
Methyl tetradecanoateC15H30O23.53 ± 0.01Flavoring
4-Methyl-5-thiazoleethanolC6H9NOS120.92 ± 0.01Flavoring
Methyl valerateC6H12O2445.57 ± 0.01Flavoring
3-Methylvaleric acidC6H12O25.55 ± 0.01Fatty acid
Monoethyl malonic acidC5H8O413.41 ± 0.16Organic acid
MonostearinC21H42O435.76 ± 0.31Emulsifier
MorphineC17H19NO37.05 ± 0.01Painkiller
N-acetyl-glucosamineC8H15NO624.93 ± 0.33Chitosan
NickelNi6.56 ± 0.01Mineral
NonaneC9H202.28 ± 0.01Alkane
5-Norbornene-2-carboxylic acidC8H10O20.93 ± 0.01Organic acid
OctadecanamideC18H37NO47.22 ± 0.01Fatty amide
OctadecaneC18H38137.50 ± 0.01Alkane
OctadecenamideC18H35NO67.10 ± 0.77Fatty amide
17-Octadecynoic acidC18H32O218.04 ± 0.01Fatty acid
OctahydronaphthaleneC10H163.48 ± 0.01Aromatic
Octahydronaphthalene-1,4-diolC10H16O257.23 ± 0.01Alcohol
γ-OctalactoneC8H14O2238.91 ± 0.37Flavoring
OctaneC8H1825.30 ± 0.01Alkane
1-OcteneC8H1610.56 ± 0.01Alkene
Oleic acidC18H34O217.59 ± 0.01Fatty acid
3-Oxooctanoic acidC8H14O31185.00 ± 0.01Fatty acid
2-Oxovaleric acidC5H8O34.12 ± 0.01Ketoacid
Para-methoxy-N-methylamphetamineC11H17NO145.28 ± 0.01Stimulant
Pentadecanoic acidC15H30O211.42 ± 0.01Fatty acid
Pentaethylene glycolC22H46O66.10 ± 0.01Solvent
PentadecaneC15H322.32 ± 0.01Alkane
PentanamideC5H11NO1.41 ± 0.01Acid amide
PentaneC5H127.22 ± 0.09Alkane
Pentanoic acidC5H10O226.12 ± 0.20Flavoring
PentaoxacyclopentadecaneC10H20O51.60 ± 0.01Crown ether
PentenedioateC5H6O42−2.88 ± 0.01Organic acid
Pentenedioic acidC5H6O47.41 ± 0.07Organic acid
2-Pentenoic acidC5H8O270.15 ± 0.95Organic acid
9-O-pivaloyl-N-acetylcolchinolC25H31NO624.44 ± 0.17Aromatic
PregnenoloneC21H32O23.80 ± 0.01Steroid
PropanalC3H6O2.77 ± 0.02Aldehyde
PropaneC3H86.39 ± 0.02Alkane
Propanedioic acidC3H4O410.46 ± 0.01Organic acid
1,3-PropanediolC3H8O23.03 ± 0.01Alcohol
1,2,3-PropanetriolC3H8O31595.72 ± 0.02Polyol
PropanoneC3H6O114.26 ± 1.34Ketone
2-PropenamideC3H5NO338.39 ± 4.16Fatty amide
2-Propenoic acidC3H4O215.90 ± 0.01Organic acid
PropylamineC3H9N3.25 ± 0.01Fatty amine
Propylene glycolC3H8O22458.09 ± 1.26Solvent
PseudoephedrineC10H15NO24.34 ± 0.01Decongestant
PseudouridineC9H12N2O62.99 ± 0.01Nucleoside
PyrandiolC5H6O340.72 ± 0.01Alcohol
Pyruvate oximeC3H5NO314.13 ± 0.09Acid amine
ScopolinC16H18O9179.76 ± 2.08Phytochemical
Sebacic acidC10H18O43.53 ± 0.01Fatty acid
SuccinateC4H4O42-0.78 ± 0.01Flavoring
SuccinonitrileC4H4N20.16 ± 0.01Nitrile
Talonic acidC6H12O75.55 ± 0.01Organic acid
TetradecaneC14H3014.12 ± 0.01Alkane
Tetradecanoic acidC14H28O27.86 ± 0.03Fatty acid
1-TetradecanolC14H30O1.24 ± 0.01Fatty alcohol
Tetraethylene glycolC8H18O50.53 ± 0.01Solvent
1,2,4,5-TetramethylbenzeneC10H14650.91 ± 0.01Aromatic
ThiodiglycolC4H10O2S12.39 ± 0.14Alcohol
Tricyclodecenyl propionateC13H18O22.31 ± 0.01Fragrance
TridecaneC13H28207.98 ± 0.01Alkane
Tridecanoic acidC13H26O215.33 ± 0.01Fatty acid
Triethylene glycolC6H14O4120.91 ± 0.04Solvent
2,3,4-Trihydroxybutanoic acidC4H8O541.02 ± 0.31Organic acid
2,4,5-Trihydroxypentanoic acidC5H10O518.61 ± 0.01Organic acid
1,2,4-TrimethylbenzeneC9H1216.28 ± 0.01Aromatic
1-UndeceneC11H227.66 ± 0.03Alkene
Vitamin CC6H8O69.22 ± 0.01Ascorbic acid
Table
Table 4. Sugar derivatives detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
Table 4. Sugar derivatives detected in culture supernatant of dual Lactobacillus plantarum and Bacillus subtilis fermentation in prawn shell waste and 20% glucose in deionized water.
MetaboliteMolecular FormulaQuantity (mg/L)Biological Characteristic
Altro-heptuloseC7H14O76.79 ± 0.01Sugar substitute
ArabinitolC5H15O5115.06 ± 0.03Sugar alcohol
ArabinofuranoseC5H10O51714.08 ± 2.23Sugar substitute
ArabinofuranosideC5H9O5592.25 ± 0.06Sugar substitute
D-arabino-3-hexuloseC6H12O617.21 ± 0.01Sugar substitute
Arabinonic acidC5H10O681.43 ± 1.14Sugar acid
ArabinopyranoseC5H10O52350.31 ± 1.98Sugar substitute
ArabinoseC5H10O5912.65 ± 2.11Sugar substitute
ArabitolC5H10O51456.58 ± 0.56Sugar alcohol
3-Deoxy-D-arabino-hexonic acidC6H12O6112.61 ± 0.11Sugar acid
2-Deoxy-erythro-pentofuranoseC5H10O4596.47 ± 8.29Sugar substitute
3-Deoxy-erythro-pentonic acidC5H10O543.20 ± 0.03Sugar acid
2-Deoxy-erythro-pentopyranoseC5H10O42.50 ± 0.01Sugar substitute
2-Deoxy-erythro-pentoseC5H10O442.49 ± 0.36Sugar substitute
2-Deoxy-D-galactopyranoseC6H12O5281.36 ± 2.07Sugar substitute
2-Deoxy-D-glucoseC6H12O5677.13 ± 0.01Sugar substitute
Deoxy-riboseC5H10O419.08 ± 0.01Sugar substitute
3-Deoxy-D-ribohexonic acidC6H12O20.71 ± 0.01Sugar acid
DihydroxyacetoneC3H6O321.99 ± 0.01Sugar substitute
DulcitolC6H14O63323.48 ± 4.53Sugar alcohol
ErythritolC4H10O40.26 ± 0.01Sugar alcohol
Erythro-pentitolC5H12O29.50 ± 0.03Sugar alcohol
ErythroseC4H8O4522.45 ± 5.06Sugar substitute
Erythro-tetrofuranoseC5H10O522.65 ± 0.01Sugar substitute
FructopyranoseC6H12O66.94 ± 0.01Sugar substitute
FructoseC6H12O62462.43 ± 1.42Sugar substitute
Fructose oximeC6H13NO62421.99 ± 0.01Sugar substitute
GalactofuranoseC6H12O61076.99 ± 0.78Sugar substitute
GalactoheptuloseC7H14O72.20 ± 0.01Sugar substitute
GalactopyranoseC6H12O6943.28 ± 2.36Sugar substitute
GalactoseC6H12O68909.55 ± 1.18Sugar substitute
Galactose oximeC6H13NO6369.21 ± 0.39Sugar substitute
Glucaric acidC6H10O80.08 ± 0.01Sugar acid
GlucitolC6H14O6601.89 ± 7.85Sugar alcohol
GlucofuranoseC6H12O62035.95 ± 1.10Sugar substitute
GlucopyranoseC6H12O67024.77 ± 8.40Sugar substitute
Glucopyranuronic acidC6H10O71239.42 ± 0.13Sugar acid
GlucoseC6H12O62010.62 ± 1.31Sugar substitute
Glucose oximeC6H13NO6610.91 ± 0.23Sugar substitute
Glucuronic acidC6H10O77.58 ± 0.07Sugar acid
Glutaconic acidC5H6O40.77 ± 0.01Sugar acid
GlyceraldehydeC3H6O3422.51 ± 1.30Sugar substitute
D-glycero-D-galacto-heptoseC7H14O791.04 ± 0.01Sugar substitute
D-glycero-D-gluco-heptoseC7H14O7129.78 ± 1.66Sugar substitute
D-glycero-D-gulo-heptonic acidC7H14O840.26 ± 0.14Sugar acid
D-glycero-L-manno-heptonic acidC7H14O81192.77 ± 2.99Sugar acid
Gulonic acidC6H12O714.17 ± 0.10Sugar acid
GuloseC6H12O6361.01 ± 2.59Sugar substitute
LactoseC12H22O11125.72 ± 0.01Sugar substitute
LevoglucosanC6H10O51.32 ± 0.01Sugar substitute
LyxopyranoseC5H10O51654.75 ± 1.82Sugar substitute
LyxoseC5H10O5603.81 ± 2.35Sugar substitute
MaltoseC12H22O115653.05 ± 5.87Sugar substitute
MannitolC6H14O6177.42 ± 0.80Sugar alcohol
MannofuranoseC6H12O61009.76 ± 5.57Sugar substitute
Mannofuranuronic acidC6H8O651.35 ± 0.01Sugar acid
Mannonic acidC6H12O72567.14 ± 1.67Sugar acid
MannopyranoseC6H12O358.11 ± 0.21Sugar substitute
MannoseC6H12O65744.85 ± 7.73Sugar substitute
MelibioseC12H22O110.69 ± 0.01Sugar substitute
2,5-Methylene-D,L-rhamnitolC7H14O51.33 ± 0.01Sugar substitute
Methyl-D-galactofuranosideC7H14O6481.33 ± 1.13Sugar substitute
Methyl-D-glucopyranosideC7H14O64908.57 ± 6.54Sugar substitute
Methyl-D-lyxofuranosideC6H12O5499.24 ± 4.75Sugar substitute
Methyl-D-mannopyranosideC7H14O6131.27 ± 0.01Sugar substitute
Methyl-D-ribofuranosideC6H12O120.28 ± 0.01Sugar substitute
Methyl-D-xylopyranosideC6H12O51.23 ± 0.01Sugar substitute
Myo-inositolC6H12O6130.33 ± 0.50Sugar substitute
PentitolC5H12O5185.84 ± 0.01Sugar Alcohol
Phenyl-D-galactopyranosideC12H16O69584.87 ± 0.01Sugar substitute
D-ribo-2-hexuloseC6H12O65.77 ± 0.03Sugar substitute
Ribonic acidC5H10O689.50 ± 0.70Sugar acid
RibopyranoseC5H10O51427.89 ± 7.29Sugar substitute
RiboseC5H10O5249.45 ± 3.50Sugar substitute
SorbopyranoseC6H12O639.12 ± 0.11Sugar substitute
TaloseC6H12O6800.65 ± 2.15Sugar substitute
ThreitolC4H10O4121.12 ± 1.66Sugar alcohol
Threonic acidC4H8O530.15 ± 0.01Sugar acid
TuranoseC12H22O1166.04 ± 0.40Sugar substitute
XylitolC5H12O5508.27 ± 0.44Sugar alcohol
XylofuranoseC5H10O588.69 ± 0.01Sugar substitute
D-xylo-hexuloseC6H12O62.66 ± 0.02Sugar substitute
Xylonic acidC5H10O6156.31 ± 1.43Sugar acid
XylofuranoseC5H10O588.69 ± 0.01Sugar substitute
XylopyranoseC5H10O5915.86 ± 0.30Sugar substitute
XyloseC5H10O51417.45 ± 1.36Sugar substitute
XyluloseC5H10O57.30 ± 0.01Sugar substitute

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MDPI and ACS Style

Tan, Y.N.; Zhang, J.H.; Chen, W.N. GC-MS-Based Metabolomics Analysis of Prawn Shell Waste Co-Fermentation by Lactobacillus plantarum and Bacillus subtilis. Polysaccharides 2020, 1, 31-50. https://doi.org/10.3390/polysaccharides1010004

AMA Style

Tan YN, Zhang JH, Chen WN. GC-MS-Based Metabolomics Analysis of Prawn Shell Waste Co-Fermentation by Lactobacillus plantarum and Bacillus subtilis. Polysaccharides. 2020; 1(1):31-50. https://doi.org/10.3390/polysaccharides1010004

Chicago/Turabian Style

Tan, Yun Nian, Jian Hua Zhang, and Wei Ning Chen. 2020. "GC-MS-Based Metabolomics Analysis of Prawn Shell Waste Co-Fermentation by Lactobacillus plantarum and Bacillus subtilis" Polysaccharides 1, no. 1: 31-50. https://doi.org/10.3390/polysaccharides1010004

APA Style

Tan, Y. N., Zhang, J. H., & Chen, W. N. (2020). GC-MS-Based Metabolomics Analysis of Prawn Shell Waste Co-Fermentation by Lactobacillus plantarum and Bacillus subtilis. Polysaccharides, 1(1), 31-50. https://doi.org/10.3390/polysaccharides1010004

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