Yingfang Lua,
Yinning Chenb,
Yulin Wua,
Huili Haoa,
Wenjing Liangc,
Jun Liu*d and
Riming Huang*a
aGuangdong Provincial Key Laboratory of Food Quality and Safety, College of Food Science, South China Agricultural University, Guangzhou 510642, China. E-mail: luyingfang@stu.scau.edu.cn; DanielWu@stu.scau.edu.cn; hhlhaohuili@stu.scau.edu.cn; huangriming@scau.edu.cn; Tel: +86 20 8528 3448
bGuangdong Polytechnic College, 526100, Zhaoqing, China. E-mail: Yinning_Chen@163.com
cLonggang No. 2 Vocational School, Shenzhen, 518104, China. E-mail: 345589207@qq.com
dLaboratory of Pathogenic Biology, Guangdong Medical University, Zhanjiang 524023, China. E-mail: lj2388240@gdmu.edu.cn; Tel: +86 7592388240
First published on 31st October 2019
Unsaturated fatty acids (UFAs) are an important category of monounsaturated and polyunsaturated fatty acids with nutritional properties. These secondary metabolites have been obtained from multitudinous natural resources, including marine organisms. Because of the increasing numerous biological importance of these marine derived molecules, this review covers 147 marine originated UFAs reported from 1978 to 2018. The review will focus on the structural characterizations, biological properties, proposed biosynthetic processes, and healthy benefits mediated by gut microbiota of these marine naturally originated UFAs.
Number | Names | Bioactivities | Sources | Reference(s) |
---|---|---|---|---|
1 | 10-Tricosenoic acid | — | Calyx podatypa | 9 |
2 | (6Z)-7-Methyloctadec-6-enoic acid A | — | Holothuria mexicana | 10 |
3 | Not given | — | Halichondria panicea | 11 |
4 | Not given | — | H. panicea | 11 |
5 | Not given | — | Ircinia sp. | 12 |
6 | Not given | Antiinflammatory properties | Gracilaria verrucosa | 13 |
7 | Not given | — | Ulva fasciata | 14 |
8 | Not given | — | U. fasciata | 14 |
9 | Not given | — | U. fasciata | 14 |
10 | (2E,4S,6S,8S)-2,4,6,8-Tetramethyl-2-undecenoic acid | — | Siphonaria capensis | 15 |
11 | Not given | — | S. denticulata | 16 |
12 | Not given | — | S. denticulata | 16 |
13 | Seco-patulolide | — | unidentified fungal strain | 17 |
14 | Not given | — | Sinularia sp. | 18 |
Number | Names | Bioactivities | Sources | Reference(s) |
---|---|---|---|---|
15 | Not given | — | Petrosia ficiformis | 19 |
16 | Not given | Antimicrobial | Oceanapia sp. | 20 |
17 | Carduusyne A | — | Phakellia carduus | 21 and 22 |
18 | Petroformynic acid | — | P. ficiformis | 23 |
19 | (5Z,7E,9E,14Z,17Z)-Icosa-5,7,9,14,17-pentaenoic acid | — | Ptilota jilicina | 24 |
20 | (5E,7E,9E,14Z,17Z)-Icosa-5,7,9,14,17-pentaenoicacid | — | P. jilicina | 24 |
21 | 5(Z),8(Z),10(E),12(E),14(Z)-Eicosapentaenoic acid | — | Bossiella orbigniana | 25 |
22 | (5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoic acid | Inhibiting growth of the green alga Monostroma oxyspermum | Neodilsea yendoana | 26 |
23 | (4Z,7Z,9E,11E,13Z,16Z,19Z)-Docosaheptaenoic acid | — | Anadyomene stellata | 27 |
24 | 10,15-Eicosadienoic acid | — | Haminaea templadoi | 28 and 29 |
25 | (5Z,15Z)-5,15-Eicosadienoic acid | — | Calyptogena phaseoliformis | 30 |
26 | (5Z,14Z)-5,14-Heneicosadienoic acid | — | C. phaseoliformis | 30 |
27 | (5Z,16Z)-5,16-Heneicosadienoic acid | — | C. phaseoliformis | 30 |
28 | (5Z,13Z,16Z)-5,13,16-Eicosatrienoic acid | — | C. phaseoliformis | 30 |
29 | (5Z,13Z,16Z)-5,13,16,19-Eicosatetraenoic acid | — | C. phaseoliformis | 30 |
30 | (5Z,14Z,17Z)-5,14,17-Heneicosatrienoic acid | — | C. phaseoliformis | 30 |
31 | 7,11,14,17-Eicosatetraenoic acid | Anti-inflammatory | Perna canaliculus | 31 |
32 | 7,13-Eicosadienoic acid | — | Ophiura sarsi | 32 |
33 | 7,13,17-Eicosatrienoic acid | — | O. sarsi | 32 |
34 | 9,15,19-Docosatrienoic acid | — | O. sarsi | 32 |
35 | 4,9,15,19-Docosatetraenoic acid | — | O. sarsi | 32 |
36 | (7Z,9Z,12Z)-Octadeca-7,9,12-trien-5-ynoic acid | — | Liagora farinosa | 33 |
37 | 4,7,10,13,16,19,22,25-Octacosaoctaenoic acid | — | Marine dinoflagellate species | 33 |
38 | 7,11-Tetradecadiene-5,9-diynoic acid | — | Marine dinoflagellate species | 33 |
Number | Names | Bioactivities | Sources | Reference(s) |
---|---|---|---|---|
39 | Not given | — | P. carduus | 21 |
40 | Not given | — | P. carduus | 21 |
41 | Not given | — | P. carduus | 21 |
42 | Not given | — | P. carduus | 21 |
43 | (Z,Z)-25-Methyl-5,9-hexacosadienoic acid | — | Jaspis stellifera | 35 |
44 | (Z,Z)-24-Methyl-5,9-hexacosadienoic acid | — | J. stellifera | 35 |
45 | (5Z,9Z)-Hexadeca-5,9-dienoic acid | — | Chondrilla nucula | 36 |
46 | 5,8,10,14,17-Eicosapentaenoic acid | — | Echinochalina mollis | 37 |
47 | Not given | — | E. mollis | 37 |
48 | 4,7,10,12,16,19-Docosahexaenoic acid | — | E. mollis | 37 |
49 | Not given | — | E. mollis | 37 |
50 | 5,9-Eicosadienoic acid | — | Erylus forrnosus | 38 and 39 |
51 | 5,9-Eicosadienoic acid | — | E. forrnosus | 38 and 39 |
52 | Petrosolic acid | Inhibited HIV reverse transcriptase | Petrosia sp. | 40 |
53 | Corticatic acid A | Antifungal | Petrosia corticata | 41 |
54 | Corticatic acid B | Antifungal | P. corticata | 41 |
55 | Corticatic acid C | Antifungal | P. corticata | 41 |
56 | Nepheliosyne A | — | Xestospon | 42 |
57 | Triangulynic acid | Against leukemia and colon tumour lines | Pellina triangulata | 43 |
58 | Pellynic acid | Inhibited inosine monophosphate dehydrogenase in vitro | P. triangulata | 44 |
59 | Aztequynol A | — | Petrosia sp. | 45 |
60 | Aztequynol B | — | Petrosia sp. | 45 |
61 | Osirisyne A | — | Haliclona osiris | 46 |
62 | Osirisyne B | — | H. osiris | 46 |
63 | Osirisyne C | — | H. osiris | 46 |
64 | Osirisyne D | — | H. osiris | 46 |
65 | Osirisyne E | — | H. osiris | 46 |
66 | Osirisyne F | — | H. osiris | 46 |
67 | Aikupikanyne F | — | Callyspongia sp. | 20 |
68 | Haliclonyne | — | Haliclona sp. | 47 |
69 | Callyspongynic acid | α-glucosidase inhibitor | P. corticata | 41, 48 and 49 |
70 | Corticatic acid D | Geranylgeranyltransferase type I inhibitor | P. corticata | 41, 48 and 49 |
71 | Corticatic acid E | P. corticata | 41, 48 and 49 | |
72 | (5Z,9Z)-22-Methyl-5,9-tetracosadienoic acid | Cytotoxic activity against mouse Ehrlich carcinoma cells and a hemolytic effect on mouse erythrocytes | Stelletta sp. | 50 |
73 | Stellettic acid C | Exhibited marginal to moderate toxicity to five human tumour cell lines | Stelletta sp. | 51 |
74 | Not given | Cytotoxic to human leukemia cells | Stelletta sp. | 52 |
75 | Petroformynic acid B | Cytotoxic | Petrosia | 53 |
76 | Petroformynic acid C | Petrosia | 53 | |
77 | Heterofibrin A1 | Inhibited lipid droplet formation | Spongia sp. | 54 |
78 | Officinoic acid B | — | Spongia officinalis | 55 |
79 | Fulvyne A | Against a chloramphenicol-resistant strain of Bacillus subtilis | Haliclona fulva | 56 |
80 | Fulvyne B | H. fulva | 56 | |
81 | Fulvyne C | H. fulva | 56 | |
82 | Fulvyne D | H. fulva | 56 | |
83 | Fulvyne E | H. fulva | 56 | |
84 | Fulvyne F | H. fulva | 56 | |
85 | Fulvyne G | H. fulva | 56 | |
86 | Fulvyne H | H. fulva | 56 | |
87 | Fulvyne I | H. fulva | 56 | |
88 | Petrosynic acid A | — | Petrosia sp. | 57 |
89 | Petrosynic acid B | — | Petrosia sp. | 57 |
90 | Petrosynic acid C | — | Petrosia sp. | 57 |
91 | Petrosynic acid D | — | Petrosia sp. | 57 |
Number | Names | Bioactivities | Sources | Reference(s) |
---|---|---|---|---|
92 | (10E,15Z)-(9S,12R,13S)-9,12,13-Trihydroxyoctadeca-10,14-dienoicacid | — | Lyngbya majuscula | 58 |
93 | (5Z,8E,10E)-11-Fomylundeca-5,8,10-trienoic acid | Antimicrobial | Laurencia hybrida | 59 |
94 | (2Z,5Z,7E,11Z,14Z)-9-Hydroxyeicosa-2,5,7,11,14-pentaenoic acid | Antimicrobial | L. hybrida | 59 |
95 | Acyclicditerpene | — | Bifurcaria bifurcate | 60 |
96 | Ptilodene | Inhibited both 5-lipoxygenase and Na+/K+A TPase | Ptilota filicina | 61 |
97 | 12-(S)-Hydroxyeicosapentaenoic acid | Inhibitor of platelet aggregation | Murrayella periclados | 62 |
98 | 9-Hydroxypentaenoic acid | — | Laurencia hybrid | 63 |
99 | Turbinaric acid | Cytotoxic | Turbinaria ornata | 64 |
100 | (12R,13R)-Dihydroxyeicosa-5(Z),8(Z),10(E),14(Z)-tetraeonic acid | Modulated fMLP-induced superoxide anion generation in human neutrophils; inhibited the conversion of arachidonic acid to lipoxygenase products by human neutrophils; inhibited the functioning of the dog kidney Na+/K+ ATPase | Farlowia mollis | 65 |
101 | (12R,13R)-Dihydroxyeicosa-5(Z),8(E),10(E),14(Z),17(Z)-pentaenoic acid | F. mollis | 65 | |
102 | (10R,11R)-Dihydroxyoctadeca-6(Z),8(E),12(Z)-trienoic acid | F. mollis | 65 | |
103 | (5Z,8Z,10E,12R,13R,14Z)-12,13-Dihydroxyeicosa,5,8,10,14-tetraenoic acid | — | F. mollis | 65 |
104 | (5Z,8Z,10E,12R,13S,14Z)-12,13-dihydroxyeicosa-5,8,10,14-tetraenoic acid | — | F. mollis | 66 |
105 | (6Z,9E,11E,13E)-9-Formyl-15-hydroxyheptadeca-6,9,11,13-tetraenoic acid | — | Acrosiphonia coalita | 67 |
106 | (9E,11E,13E)-9-Formyl-15-hydroxyheptadeca-9,11,13-trienoic acid | — | A. coalita | 67 |
107 | (6Z,9E,11E,13E)-9-formyl- 15-oxoheptadeca-6,9,11,13-tetraenoic acid | — | A. coalita | 67 |
108 | (10E,12Z,14E)-16-Hydroxy-9-oxooctadeca-10,12,14-trienoic acid | — | A. coalita | 67 |
109 | (10E,12E,14E)-16-hydroxy-9-oxooctadeca-10,12,14-trienoic acid | — | A. coalita | 67 |
110 | (9Z,11R,12S,13S,152)-12,13-Epoxy-11-hydroxyoctadeca-9,15-dienoic acid | — | A. coalita | 67 |
111 | (9Z,11R,12S,13S)-12,13-Epoxy-11-hydroxyoctadeca-9-enoic acid | — | A. coalita | 67 |
112 | (9R,10R,11S,12Z,152)-9,10-Epoxy-11-hydroxyoctadeca-12,15-dienoic acid | — | A. coalita | 67 |
113 | (9R,10R,11S,122)-9,10-Epoxy-11-hydroxyoctadeca- 12-enoic acid | — | A. coalita | 67 |
114 | Not given | — | Laminaria sincluirii | 68 |
115 | Not given | — | L. sincluirii | 68 |
116 | 9,11-Dodecadienoic acid | — | L. sincluirii | 68 |
117 | (13R)-13-hydroxyarachidonic acid | — | Lithothamnion coralloides | 69 and 70 |
118 | (12S)-12-Hydroxyeicosatetraenoic acid | — | M. periclados | 71 |
119 | (6E)-Leukotriene B4 | — | M. periclados | 71 |
120 | Hepoxilin B3 | — | M. periclados | 71 |
121 | Hepoxilin B3 | — | M. periclados | 71 |
122 | Hepoxilin B4 | — | M. periclados | 71 |
123 | Hepoxilin B4 | — | M. periclados | 71 |
124 | (5R,6S,7E,9E,11Z,14Z)-5,6-Dihydroxyicosa-7,9,11,14-tetraenoic acid | — | Rhodymenia pertusa | 72 |
125 | (5R*,6S*,7E,9E,11Z,14Z,17Z)-5,6-Dihydroxyicosa-7,9,11,14,17-pentaenoic acid | — | R. pertusa | 72 |
126 | (6E,8Z,11Z,14Z)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid | — | R. pertusa | 72 |
127 | (6E,8Z,11Z,14Z,17Z)-5-Hydroxyicosa-6,8,11,14,17-Pentaenoic acid | — | R. pertusa | 72 |
128 | 8,12-Octadecadienoic acid | — | Corallina officinalis | 73 |
129 | (8E,12Z,15Z)-10-Hydroxy-8,12,15-trien-4,6-diynoic acid | — | Caulerpa racemosa | 74 |
Number | Names | Bioactivities | Sources | Reference(s) |
---|---|---|---|---|
130 | Leiopathic acid | — | Leiopathes sp. | 75 |
131 | 5,9,11,14,17-Eicosapentaenoic acid | — | Leiopathes sp. | 75 |
132 | 5,9,11,14,17-Eicosapentaenoic acid | — | Leiopathes sp. | 75 |
133 | (11R)-Hydroxyeicosatetraenoic acid | — | Plexaurella dichotoma | 76 |
134 | (5Z,9Z)-14-methylpentadeca-5,9-dienoic acid | Inhibited the growth of Gram positive bacteria | Eunicea succinea | 77 |
135 | 6,9,12,16,18-Tetracosapentaenoic acid | Inhibited tube-formation in a human endothelial cell line model of angiogenesis | Sinularia numerosa | 78 |
136 | Dendryphiellic acid A | — | Dendryphiella salina | 79 and 80 |
137 | Dendryphiellic acid B | — | D. salina | 79 and 80 |
138 | Curvulalic acid | — | Curvularia sp. | 81 |
139 | 2,4-Decadienoic acid | — | Xylaria sp. | 82 |
140 | (5Z,8R,9E,11Z,14Z,17Z)-8-hydroxyeicosa-5,9,11,14,17-pentaenoic acid | — | Balanus balanoides, Eliminus modestus | 83 |
141 | 8,13-Dihydroxyeicosapentaenoic acid | A muscle stimulatory factor in the barnacle Balanus balanus | Balanus balanus | 84 |
142 | (9Z,12Z)-7-hydroxyoctadeca-9,12-dien-5-ynoic acid | Ichthyotoxic | L. farinosa | 33 |
143 | Macrolactic acid | — | Unidentified Gram-positive bacterium | 85 |
144 | Isomacrolactic acid | — | Unidentified Gram-positive bacterium | 85 |
145 | Ieodomycin C | Antimicrobial | Bacillus sp. | 86 |
146 | Ieodomycin D | Bacillus sp. | 86 | |
147 | Linieodolide B | Antibacterial; antifungal | Bacillus sp. | 87 and 88 |
Fig. 5 Structures of branched chain polyunsaturated fatty acids from Coelenterate, Marine fungus, Arthropoda, Bacterium. |
A cytotoxic fatty acid, (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid 72 was isolated from Geodinella robusta collected from the Sea of Okhotsk, Russia.50 An undescribed Korean species of Stelletta was found to contain a cytotoxic acetylenic acid: stellettic acid C 73 that exhibited marginal to moderate toxicity to five human tumour cell lines.51 From a seemingly identical Stelletta species, collected at a different Korean location, a desmethoxy analogue 74, was isolated; it was mildly cytotoxic to human leukemia cells.52 The cytotoxic petroformynic acids B 75 and C 76 were obtained from a Petrosia species (Katsuo-jim Is., Wakayama Pref., Japan).53 One acetylenic compound heterofibrin A1 77 was isolated from a Spongia (Heterofibria) sp. collected by dredging in the Great Australian Bight. Heterofibrin A1 inhibited lipid droplet formation at 10 mM yet was not cytotoxic at similar concentrations.54 Officinoic acid B 78 is linear diterpene from Spongia officinalis (off Mazara del Vallo, Sicily).55 An extract of Haliclona fulva (Procida Is., Gulf of Naples, Italy) contained the nine acetylenes fulvyne A–I 79–87.56 Petrosynic acids A–D 88–91 (Petrosia sp., Tutuila, American Samoa) all displayed similar activity versus various HTCLs and non-proliferative human fibroblasts and hence no therapeutic window is available.57
The green alga Acrosiphonia coalita contains the oxylipins coalital, which may be an artefact caused by photoisomerization of the natural product, racemic (6Z,9E,11E,13E)-9-formyl-15-hydroxyheptadeca-6,9,11,13-tetraenoic acid 105, (9E,11E,13E)-9-formyl-15-hydroxyheptadeca-9,11,13-trienoic acid 106, (6Z,9E,11E,13E)-9-formyl-15-oxoheptadeca-6,9,11,13-tetraenoic acid 107, (10E,12Z,14E)-16-hydroxy-9-oxooctadeca-10,12,14-trienoic acid 108, (10E,12E,14E)-16-hydroxy-9-oxooctadeca-10,12,14-trienoic acid 109, (9Z,11R,12S,13S,152)-12,13-epoxy-11-hydroxyoctadeca-9,15-dienoic acid 110, (9Z,11R,12S,13S)-12,13-epoxy-11-hydroxyoctadeca-9-enoic acid 111, (9R,10R,11S,12Z,152)-9,10-epoxy-11-hydroxyoctadeca-12,15-dienoic acid 112, and (9R,10R,11S,122)-9,10-epoxy-11-hydroxyoctadeca-12-enoic acid 113, the acids all being isolated as the corresponding methyl esters.67 Three divinyl ethers, 114–116, were isolated along with a number of hydroxylated fatty acids from the Oregon brown alga Laminaria sincluirii and were identified by interpretation of spectral evidence.68 The absolute stereochemistry of (13R)-13-hydroxyarachidonic acid 117, which is a known eicosanoid from Lithothamnion coralloides,69 was determined by degradation and its biosynthesis from arachidonic acid was studied.70
The Caribbean alga Murrayella periclados contains a number of eicosanoids that include (12S)-12-hydroxyeicosatetraenoic acid 118, (6E)-leukotriene B4, 119 and erythro and threo isomers of hepoxilins B3, 120/121 and B4, 122/123.71 Four oxylipins (5R,6S,7E,9E,11Z,14Z)-5,6-dihydroxyicosa-7,9,11,14-tetraenoic acid 124, (5R*,6S*,7E,9E,11Z,14Z,17Z)-5,6-dihydroxyicosa-7,9,11,14,17-pentaenoic acid 125, (6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid 126, and (6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid 127 were isolated from Rhodymenia pertusa.72 An oxylipin 128 was obtained from Aspergillus flavus, (red alga Corallina officinalis, Yantai, China).73 Studies on a Caulerpa racemosa (Zhanjiang coastline, China) led to the isolation of the acetylenic fatty acid (8E,12Z,15Z)-10-hydroxy-8,12,15-trien-4,6-diynoic acid 129.74
In addition, some polyunsaturated fatty acids from marine microalgae are found to modulate lipid metabolism disorders and gut microbiota.96 According to the survey results, high saturated fatty acid and high monounsaturated fatty acid diets have an adverse effect on the gut microbiota and high saturated fatty acids are associated with unhealthy metabolic status, while polyunsaturated fatty acid does not have a negative impact on gut microbiota.97 Through previous studies we find that connecting with gut microbiota, PUFAs can be more beneficial for human health. For example, increasing anti-obesogenic microbial species in the gut microbiota population by appropriate n-3 PUFAs can be an effective way to control or prevent metabolic diseases.98 Furthermore, a link has been established between n-3 PUFAs and gut microbiota especially with respect to inflammation (Fig. 7). A few related researchs show that after omega-3 PUFA supplementation, Faecalibacterium, often associated with an increase in the Bacteroidetes and butyrate-producing bacteria belonging to the Lachnospiraceae family, has decreased. Omega-3 PUFAs perform a positive action on diseases by reverting the microbiota composition and increasing the production of anti-inflammatory compounds like short-chain fatty acids.99 According to the link between n-3 PUFAs and gut microbiota, which is associated with inflammation, some scholars proposing that an optimal level of LC-PUFAs nurtures the suitable gut microbiota that will prevent dysbiosis. The synergy between optimal LC-PUFAs and gut microbiota helps the immune system overcome the immunosuppressive tumour microenvironment.100
Although many scholars have devoted themselves to the study of polyunsaturated fatty acids, they are limited to the more famous unsaturated fatty acids. There is still lack of investigation of the beneficial application of these polyunsaturated fatty acid derivatives with similar structural characteristics. Thus, more investigation should focus on fatty acid physiological roles and applications in human health and disease and the interaction with gut microbiota.101
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