2020-02-10 17:14:13
1. Marine Microorganism Sources
Marine microorganisms, one of the main sources of natural pigments, are often isolated from algae, sponges, mangroves, and sediments. These pigments are mainly divided into indole derivatives (quinones and violacein), alkaloids (prodiginines and tambjamines), polyenes, macrolides, peptides, and terpe- noids.[4] Importantly, these compounds present different bio- logical properties.
1.1 Prodiginines
Bacteria as an important source of red pigments was first seen when prodigiosin compounds were first isolated from Serratia marcescens. The common aromatic chemical structure of these pigmented compounds was first named prodiginine by Gerber.[69] Prodiginines mainly includes compounds similar in chemical structures to compounds (37–39). A novel marine bacterium strain, Vibrio gazogenes, effectively produced prodiginine type pigments, including the typical prodigiosins compound 37 and 38 as well as two new prodiginines (40– 41).[70] These two new pigments had maximum absorption peaks at 533 nm and these colourants could dye wool, silk and synthetic fabrics such as polyester and polyacrylic and showed antibacterial properties against Escherichia coli and Staph- ylococcus aureus bacteria. Li Houjin et al. isolated two kinds of prodigiosin, prodigiosin A (42) and new derivative dimethyllinosin B (43) from the bacterial Pseudomonas sp. isolated from the surface of the sea water in Daya Bay, Guangdong province.[71] A marine bacterium (Serratia protea- macula 657) was screened out from 251 marine sponge- associated bacteria originated from San Juan Island and a prodigiosin-like pigment (44) with highly antitumor activity was isolated,[5] showing strong inhibition of HeLa and MGC803 cell lines. A gram-negative, red-pigment-producing marine bacterial strain (Zooshikella rubidus S1-1), was isolated from tidal flat sediment in Yellow Sea, Korea[73] with two red pigments (45–46) being extracted. These pigments are both prodigiosins and showed antimicrobial activity against Bacillus subtilis, Escheria coli, Salmonella serovar Typhimu- rium, Staphylococcus aureus, and Candida albicans. Interest- ingly they also both have anticancer activity to two human melanoma cell lines, SKMEL-28 and A375P.
1.2 Carotenoids
Carotenoids as terpenoids are also abundant in marine microorganisms. Astaxanthin (33) can also be isolated from marine microorgannisms such as being produced by the marine bacterium, Paracoccus haeundaensis.
Two novel Carotenoids (47–48) were isolated from marine bacteria (Bacillus indicus HU36).[75] The maximum UV-VIS absorption values of the two carotenoids were 454 nm and 468 nm respectively. The carotenoids and phenolic antioxi- dants displayed synergistic activities in the inhibition of linoleic acid peroxidation induced by heme iron, but not by free iron.
1.3 Violacein
The violet pigment violacein is an indole derivative, predom- inantly isolated from bacteria of the genus Chromobacte- rium.[76] Violacein has a variety of biological activities, including antiviral, antibacterial, antiulcerogenic, antileishma- nial, and anticancer properties.[77–80] Hamilton and Austin first isolated violacein from marine bacteria (Chromobacterium marinum).[81] A marine bacterium (Pseudomonas sp.) was isolated from the surface of the sea water of Daya Bay in the south China sea.[82] The bacterium can produce the violacein Blue-1 (49). A series of anti-tumour activity experimental results showed that Blu-1 had a strong inhibition on tumour cell growth. The IC50 of against MCG803 and BEL7402 were 4.6 and 6.8 ug/ml respectively. Hideki Kobayashi et al. have purified a new violet pigment derived from Shewanella violacea DSS12 isolated from the deep-sea sediment of the Ryukyu Trench at a depth of 5,110 m.[83] The absorption maximum of this violet pigment (50) in THF was 616 nm and 636 nm in chloroform. The violet pigment of DSS12 was very stable and showed no antibiotic activity to Escherichia coli, but this was dependent on low permeation into cells because of the crystals’ insolubility in water or hydrocarbons.
1.4 Phenazine Compounds
Phenazines are redox-active, small nitrogen-containing aro- matic compounds produced by a diverse range of bacterial genera. Maskey et al. reported the isolation of two yellow pigments from the marine Pseudonocardia sp. B6273, a member of the Actinomycetes. Structural investigations identi- fied the two pigments as novel phenazostatin D(51) and phenazostatin B(52), and found to be inactive against the tested microorganisms, and methyl saphenate, a known phenazine antibiotic.[84] Phenazostatin B possessed a positive optical rotation at 365 nm. Li et al. also reported seven new oxidized and reduced phenazine-type pigments, dermacozines A–G (53–59) extracted from strains MT1.1 and MT1.2. All pigment molecules had the maximum ultraviolet absorption at 520 nm.[85] The bacteria were isolated from Mariana Trench sediment at a depth of 10898 m. Dermacozines F(58) and G(59) exhibited moderate cytotoxic activity against leukaemia cell line K562 with IC50 values of 9 and 7 mM, respectively, while the highest radical scavenger activity was observed for dermacozine C (50) with an IC50 value of 8.4 mM. The novel 5, 10-dihydrophencomycin methyl ester (60) and phencomycin(61) were isolated from an unidentified marine Streptomyces sp..[86] Compound (60) shows weak antibiotic activity against Escherichia coli and Bacillus subtilis.
1.5 Tambjamines
Tambjamines are alkaloids always isolated from various marine organisms like bryozoans, nudibranchs, and asci- dians.[87–88] A yellow pigment (62) was isolated from Pseudoal- teromonas tunicata and was identified as a new member of the tambjamine class of compounds.[89] P. tunicata has the highest and broadest range of biological activities which linked to the production of the yellow pigment.[90] David M. Pinkerton et al conducted a series of biological activity evaluation experi- ments on compond (62) showing antibacterial, antifungal effects and cytotoxic activity. The IC50 against human cancer cell lines HL-60 (promyelocytic leukaemia cells), MDA-MB-
435 (derived from the M14 melanoma cell line), HCT-8 (ileocecal colorectal adenocarcinoma cell line), and SF-295 (glioblastoma cell line) as well as PBM cells are 0.69, 1.11, 0.98, 0.83, 0.64 mg/ml, respectively.
1.6 Quinones
Quinone derivatives range in colour from yellow to red, exhibit antiviral, anti-infection, antimicrobial, insecticidal, and anticancer activities, and have many commercial applications as natural and artificial dyes and pigments.[92] Two new anthracycline antibiotics, designated as himalomycin A (63) and B (64), were isolated from the culture broth of the marine Streptomyces sp. isolate B6921, derived from sandy sediment of a coastal site of Mauritius (Indian Ocean).[93] These two compounds are liposoluble yellow solid, with their maximum absorbance in MeOH at 254, 290, 441 and 256, 292, 434 nm, respectively. At concentrations of 50 mg/disk, compound 63 and 64 both exhibited strong antibacterial activity against Bacillus subtilis, Streptomyces viridochromogenes, Staphylo- coccus aureus and Escherichia coli.
Two novel pigmented antitumor, antibiotics, ellowish brown liposoluble solid chinikomycin A (65) and red lip- osoluble solid chinikomycin B (66) were isolated from a marine Streptomyces sp. Strain M045.[94] Chinikomycins A(65) and B (66) both exhibited moderate antitumor activity, Chinikomycins A (65) being significantly more potent. It selectively inhibited proliferation in cell lines of mammary cancer (MAXF 401NL, IC50 = 2.41 mg/mL), melanoma (MEXF 462NL, IC50 = 4.15 mg/mL) and renal cancer (RXF 944 L, IC50 = 4.02 mg/mL). The Chinikomycins B (66) showed selective antitumor activity against the mammary cancer cell line MAXF 401NL (IC50 = 3.04 mg/mL).
1.7 Azaphilones
Azaphilones are a family of fungal pigments characterized by a highly oxygenated pyrano-quinone bicyclic core. The coloured azaphilone derivatives are produced by species of ascomyceteous and basidiomyceteous fungi, including the genera Penicillium, Aspergillus, Chaetomium, Talaomyces, Emericella, Epicoccum, Pestalotiopsis, Phomopsis, Monascus and Hypoxylon.[95] One yellow new azaphilone (67), along with six known analogues (68–73), were isolated from the fungus Penicillium 303#, which was collected from sea water of Zhanjiang Mangrove National Nature Reserve in Guang- dong Province, China, in 2014. Evaluation of cytotoxicity of these compounds found that compound 69 showed potent cytotoxic activity with its IC50 values of 7.13 mM against MDA-MB-435.[96] Moreover, Weiyi Wang et al. isolated four new azaphilones, chaephilone C (74), chaetoviridides A–C (75–77) from a Chaetomium sp. strain NA-S01-R1 isolated from the seawater sample at a depth of 4050 m in the West Pacific Ocean in 2017.[95] Except chaephilone C is yellow, the other three compounds are all red. Through antibacterial assay and cytotoxicity assay found compounds 74, 76 and 77 displayed similar anti-MRSA activities in comparison to chloramphenicol and compounds 74 and 76 demonstrated relatively stronger cytotoxic activities than the other com- pounds against HeLa cell. In addition, compound 75 showed the most potent cytotoxic activities towards Hep G2 cell with IC50 below 5 mM.
1.8 Other Pigments from Marine Bacteria
Rui He et al. constructed a metagenomic library of the Japanese marine sponge discodermia calyx and screened out two clones producing porphyrins (78) as red pigments. The pigment has the UV absorption maximum at 405 nm.[97] The ability of porphyrins to generate reactive oxygen species had been utilized in cancer therapy. In addition, vitamin B12 composed of a porphyrin skeleton has been produced by a biotechnological process using bacteria.
A yellow pigment (79) was isolated from marine bacterial strain Vibrio sp.,[98] isolated from water samples of the Arabian Sea. This pigment has antioxidant activity and shows significant inhibition of Gram-positive organisms (MIC=31.25 to 62.5 mg/ml) in the attribute biological properties against pathogenic bacteria. Scytonemin (80) is a yellowgreen pigment isolated from aquatic cyanobacteria and its maximum UV absorption at 370 nm.[99] Scytonemin is an important UV- radiation protective synthesised biomolecule. It protects bacteria by preventing about 85–90 % of all UV-light from entering through the cell membrane.[100] Grossart H P et al. extracted a blue pigment named Glaukothalin from Two g- Proteobacteria strains, isolated from the German Wadden Sea and the Øresund, Denmark, respectively. Glaukothalin is readily soluble in pyridine or HMPT, moderately soluble in DMSO, DMF or CHCl3, and insoluble in acetone, methanol, water (acidic or alkaline), benzene or cyclohexane. The UV spectrum of glaukothalin in CHCl3 exhibits characteristic absorption maxima at 636 nm (log e = 4.51), 582 nm (sh), 286 nm (sh), 241 nm. The molecular formula of Glaukothalin is C34H56N4O4, but the structure of this compound has not been reported so far.[101] AM13,1 strain, which was identified to belong to the Cytophaga/Flexibacteria cluster of North Sea bacteria, was found to produce yellow liposoluble tryptanthrin (81). This pigment is anti-fungal and anti-microbial and was found to show an antibacterial activity against Bacillus subtilis and demonstrated its hitherto unknown activity against dermatophytes. Its absorption maximum in MeOH were 248, 252, 277, 311, 328 nm and vis lmax at 387 nm.
2. Future Prospects & Biotechnology
Although marine pigment sources are very extensive, some pigments are far from reaching the goal of mass production, especially those from marine animals. Use of microorganisms have advantages over marine animal sources due to simple culture conditions and rapid propagation; therefore, the pig- ment can be produced in high quantity in a short time by fermentation. In recent decades, scientists have made break- throughs in pigment production using genetic engineering and microbial fermentation. A novel gene involved in ketocom- pound biosynthesis, designated as crtW, was isolated from the marine bacteria Agrobacterium aurantiacum and Alcaligenes PC-1. When this gene was introduced into Escherichia coli, that accumulated b-carotene due to the Erwinia carotenogenic genes, the E. coli transformants synthesized canthaxanthin, one of ketocarotenoids.[103]
Carotenoids are the most omnipresent pigments in the oceans with important biological roles such as light capture and antioxidative activities and have made great achievements in biosynthesis. The early attempts led to the production of lycopene, b-carotene, and astaxanthin in Saccharomyces cerevisiae and Candida utilis by the expression of caroteno- genic enzymes from Pantoea ananatisi.[104–105] The lycopene synthetic pathway was engineered in Escherichia coli using the carotenoid genes (crtE, crtB and crtI) of Pantoea agglomerans and Pantoea ananatis. A two-fold higher lycopene production is obtained in E. coli by the expression of carotenogenic enzymes from P. agglomerans (27 mg/L) than from P. ananatis (12 mg/L).[106]
To improve the efficiency of carotenoid production, the biological system of the host organism also needs to be optimized. Direct efforts were focused on the modification of associated genes to these pathways. For example, deletion of pyruvate kinases PykFA can balance the availability of pyruvate and G3P for the MEP pathway, and increase lycopene production by 2.8-fold in E. coli.[107]
Astaxanthin, as previously mentioned, has multiple poten- tial uses due to its role as an antioxidant therefore it is under scrutiny by the biosynthetic industry. For example, an astaxanthin producing Saccharomyces cerevisiae strain was created by successively introducing the Haematococcus pluvialis b-carotenoid hydroxylase (crtZ) and ketolase (bkt) genes into a previously constructed b-carotene hyperproducer. Through codon optimization, gene copy number adjustment and iron cofactor supplementation led to significant increase in the astaxanthin production, reaching up to 4.7 mg/g DCW in the shake-flask cultures which is the highest astaxanthin content in Saccharomyces cerevisiae reported to date.[108]
Recently, the production of astaxanthin is mainly based on microbial fermentation, including yeast and algae. Interest- ingly, astaxanthin from yeast is 100 % right-handed (3R-3’R) with partial antioxidant activity, while astaxanthin from algae is 100 % left-handed (3S-3’S) with the strongest biological activity. Since 1990, Roche began a large-scale production of synthetic astaxanthin and practically fulfilled the world market for the pigment, estimated at 150–200 million dollars.
Due to harsh and extreme environments, marine organisms have developed unique adaptation mechanisms and metabolic pathways to survive. Most studies investigating marine organisms have shown that they have the excellent prospects in producing pigmented metabolites, which are found to have antibiotic, anticancer, and immunosuppressive activities. As these pigments have diverse and promising activities for different diseases, they can play an important role in both medical and agricultural research.
Overall, this review underscores the importance of finding new pigments in the vast oceans of the planet. These pigments have many bioactive properties and continue to provide promising avenues for basic science and applied biomedical research.
Acknowledgements
We acknowledged the grants supports from the National innovative and Entrepreneurship Training Program for College Students in China (201710338015), Agro-scientific Research in the Public Interest of Zhejiang province [grant number LGN18C190011], Science Foundation of Zhejiang Sci-Tech University [17042058-Y], 13th Five-year Plan Teaching Re- form Research in Higher Education of Zhejiang province [jg20180092] and Project for Jiaozhou Excellent Innovation Team [grant number 18-CX-1].We also acknowledged students of the Department of Development Technology of Marine Resources, College of Life Sciences, Zhejiang Sci-Tech University, Muhammad Ridwanur Rahman, Zengyi, Meng Fengbin, Ying Junjie, Ji Xiaofeng, Sun Shaokang, Li zhi, Song Jiaying, Meng Yuan, Wang Gaoyang, Zhang Shunli, Lei Yutong, Zhang Meiling, Yang Tianyong, Shi Xuhui, Huang Chaoyu, Ren Qingyu and Zhang Mengying, for their help in preparing this article.
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1-phenyl-2-(piperazin-1-yl)ethan-1-one dihydrochlorideCatalog No.:AA019PH4 CAS No.:109608-71-1 MDL No.:MFCD02671139 MF:C12H18Cl2N2O MW:277.1901 |
tert-Butyl (1,1-dimethyl-2-oxoethyl)carbamateCatalog No.:AA007SRV CAS No.:109608-77-7 MDL No.:MFCD09751786 MF:C9H17NO3 MW:187.2362 |
1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-[(5-methyl-2-furanyl)methylene]-Catalog No.:AA0095JY CAS No.:109610-93-7 MDL No.:MFCD00473856 MF:C12H12O5 MW:236.2207 |
(R)-N-Methyl-1-phenylethanamine hydrochlorideCatalog No.:AA01FSII CAS No.:1096105-18-8 MDL No.:MFCD28138033 MF:C9H14ClN MW:171.6672 |
4-Chloro-3-fluoro-2-methylanilineCatalog No.:AA00HBH4 CAS No.:1096113-25-5 MDL No.:MFCD20726431 MF:C7H7ClFN MW:159.5886 |
4-Acetylphenyl trifluoromethanesulfonateCatalog No.:AA003KK9 CAS No.:109613-00-5 MDL No.:MFCD00191706 MF:C9H7F3O4S MW:268.2097 |
2-Chloro-3-fluoro-4-nitropyridineCatalog No.:AA00822Q CAS No.:109613-90-3 MDL No.:MFCD16251524 MF:C5H2ClFN2O2 MW:176.5330 |
3,4-dimethoxypyridineCatalog No.:AA008Z03 CAS No.:109613-93-6 MDL No.:MFCD04037427 MF:C7H9NO2 MW:139.1519 |
2-Bromo-4-methoxypyridin-3-amineCatalog No.:AA00822P CAS No.:109613-97-0 MDL No.:MFCD11044243 MF:C6H7BrN2O MW:203.0366 |
2-bromo-3-fluoro-4-methoxypyridineCatalog No.:AA008UOO CAS No.:109613-98-1 MDL No.:MFCD18257613 MF:C6H5BrFNO MW:206.0124 |
"[1-(2-fluoro-4-methylphenyl)-1H-1,2,3-triazol-4-yl]methanol"Catalog No.:AA01FM6F CAS No.:1096130-69-6 MDL No.:MFCD16747696 MF:C10H10FN3O MW:207.2043 |
