. 2020 Sep 30;18(10):501. doi: 10.3390/md18100501

Table 1.

Phenolic compounds identified in different marine organisms: microalgae, cyanobacteria, fungus, seagrasses and sponges.

Marine Organism Extraction Chemical Analysis	Phenolic Compounds Antioxidant Activity (When Provided)	Ref.
Marine-derived Fungus
Alternaria sp. SCSIO41014 from sponge AC, EtOAc, US HPLC-UV, HRESIMS, NMR, ECD, XRay	Perylenequinone derivatives; altenusin derivative; phenol derivatives	[62]
Arthrinium sp. MeOH, MeCN HPLC, HRESIMS, NMR	2-(2,3-Dihydroxy-5-methyl benzoyl)-6-hydroxybenzoic acid	[63]
Aspergillus sydowii, from the sponge Stelletta sp. EtOAc, BuOH HPLC, UV, IR, HRESIMS, NMR, OP	Diorcinolic acid; β-d-glucopyranosyl aspergillusene A; diphenylethers; chromone; xanthone first glycoside of phenolic bisabolane sesquiterpenes	[64]
Aspergillus sp. from the sponge Xestospongia testudinaria EtOAc, AC RP-HPLC, HRESIMS, NMR	Phenolic bisabolane sesquiterpenoid dimers (disydonols A–C), (S)-(+)-sydonol	[65]
Aspergillus sp. from the sponge Chondrilla nucula EtOAc HPLC–PDA, UV, HRESIMS, NMR, OP	Phenolic bisabolane sesquiterpenes; asperchondol A; asperchondol B	[66]
Aspergillus sp., from the sponge Chondrilla nucula EtOAc, BuOH HPLC, UV, IR, HRESIMS, NMR, OP	Phenolic bisabolane sesquiterpenes; asperchondols A and B; diphenyl ethers	[64]
Aspergillus versicolor, deep-sea fungus EtOAc, BuOH HPLC, IR, TLC, HRESIMS, NMR, OP, ECD	Aspergilols A–F; diorcinal; cordyol E; 4-carboxydiorcinal; 4-methoxycarbonyldiorcinol; 4-carbethoxydiorcinal; cordyol C; methylgerfelin; violaceol II; averythrin; averantin, 1’-O-methylaverantin; lecanoric acid; orsellic acid; orcinol; 1- methylpyrogallol; fumaric acid ABTS = 0.1–5.4 mmol Trolox/g	[67]
Cladosporium cladosporioides from Sargassum wightii EtOAc LC-MS	N-(2-Iodophenyl)-2-[2-oxo-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazol-3-yl] acetamide; 2-[3-chloro-4-(4-chlorophenoxy)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid; 2-(2,4-dichlorophenyl)-2-oxoethyl 3,4-dihydro-2H-1,5-benzodioxepine-7-carboxylate; 4-bromo-N′-(4-fluoro-1-benzothiophene-2-carbonyl)-1H-pyrrole-2-carbohydrazide; (1R,2R,5S)-2-[3-({2-[(2,4-dichlorophenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl}methyl)-4-methyl-5 sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-6,8-dioxabicyclo [3.2.1]octan-4-one; methyl 2-({[5-bromo-2-(4 methoxybenzamido)phenyl] (phenyl)methyl}amino) acetate; 2-[4-(2,4-dichlorophenoxy)phenyl]-5-phenyl-octahydro-1H-isoindole-1,3-dione; N-({2-[(3,4-dichlorophenyl) methoxy]naphthalen-1-yl}methyl)-2,3-dihydro-1,4-benzodioxin- 6-amine; 2-({[(2,4-dichlorophenyl) carbamoyl] methyl}(propyl)amino)-N-(2,2,2-trifluoroethyl) acetamide; N-(4-bromo-2-fluorophenyl)-6-(2-tert-butylhydrazin1-yl)-5-nitropyrimidin-4-amine; N-(2-{3-[(3,4-di chlorophenyl)methyl]-2-oxo-1,3-diazina EC_50,DPPH = 50 mg/mL; EC_{50,DPPH, AS} = 18 mg/mL; RP = 0.81 mg/g	[68]
Penicillium brevicompactum EtOAc RP-HPLC, UV, HRESIMS, NMR	Anthranilic acid; syringic acid; sinapic acid; acetosyringone IC_{50, DPPH} = 20–30 µg/mL	[69]
Penicillium janthinellum EtOAc, MeOH HPLC, UV, IR, HRESIMS, GC-MS, NMR	6-(2-Acetyl-3,5-dihydroxybenzyl)-4-hydroxy-3-methyl-2H-pyran-2-one; 7-hydroxy-2-(hydroxymethyl)-5-methyl-4H-chromen4-one; 3,5-dihydroxy-2-(2-(2-hydroxy-6-methylphenyl)-2-oxoethyl)-4-methylbenzaldehyde; 3-hydroxy-5-methylphenyl 2,4-dihydroxy-6-methylbenzoate; lecanoric acid; orsellinic acid; orcinol	[70]
Penicillium griseofulvum EtOAc, BuOH HPLC, UV, IR, HRESIMS, NMR, OP	4,6-Dimethylcurvulinic acid	[64]
Penicillium expansum 091006 from the mangrove plant Excoecaria agallocha EtOAc, AC HPLC, UV, IR, HRESIMS, TLC, NMR, OP, ECD	Phenolic bisabolane sesquiterpenoid and diphenyl ether units, expansols A and B, (S)-(+)-11-dehydrosydonic acid,(7S,11S)-(+)-12-acetoxysydonic acid, (S)-(+)-sydonic acid, diorcinol,(S)-(+)-2-[3-hydroxy-4-(2-methoxy-6-methylheptan-2-yl)benzyl]-5- (3-hydroxy-5-methylphenoxy)-3-methylphenol, S-(+)-2-[3-hydroxy-4-(2-hydroxy-6- methylheptan-2-yl)benzyl]-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol, (S)-(+)-3-hydroxy-4-(2-hydroxy-6-methylhept-6-en-2-yl)benzoic acid, and 4-[(2S,6S)-7-acetoxy-2-hydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid	[71]
Scopulariopsis sp. EtOAc, MeOH, W, H HPLC-PDA, RP-HPLC, LC-MS, HRESIMS, TLC, NMR, OP	12-Dimethoxypinselin; 12-O-acetyl-AGI-B4, 11,12-dihydroxysydonic acid; 1-hydroxyboivinianic acid	[72]
ZSDS1-F11 from the sponge Phakellia fusca EtOAc, AC TLC, CC, HRESIMS, NMR	Phenolic bisabolane sesquiterpenoid and diphenyl ether units; expansols A–F; diorcinol	[73]
Cyanobacteria
Anabaena C5 E, US HPLC-MS/MS	Quinic acid; catechin EC_{50 DPPH} = 0.1 mg/mL; FRAP = 11.4 mg ASE/g	[74]
Arthrospira S1, S2 EtOH, US HPLC-MS/MS	Catechin EC_{50, DPPH} = 0.1 mg/mL; FRAP = 15.1–21.0 mg ASE/g	[74]
Calothrix sp. SI-SV MeOH, W HPLC-UV/VIS	Rutin; tannic acid; orcinol; phloroglucinol; protocatechuic acid EC_{50, ABTS} = 65.79 μg/mL, EC_{50, DPPH} = 69.38 μg/mL	[75]
Leptolyngbya sp. MeOH, W HPLC-UV/VIS	Rutin; tannic acid; orcinol; phloroglucinol; protocatechuic acid SI-SM (EC_{50, ABTS} = 63.45, EC_{50, DPPH} = 67.49 μg/mL)	[75]
Nostoc commune MeOH, W RP-HPLC-DAD	Gallic and chlorogenic acids	[76]
Nostoc sp EtOH, US HPLC-MS/MS	Gallic acid; chlorogenic acid; quinic acid; catechin; epicatechin; kaempferol; rutin; apiin IC_{50, DPPH} = 0.04–9.47 mg/mL; FRAP = 8.4–13.7 mg ASE/g	[74]
Microalgae
Ankistrodesmus sp. MeOH, W RP-HPLC-DAD	Protocatechuic acid DPPH scavenging_{10 mg/mL} = 29%	[76]
Euglena cantabrica MeOH, W RP-HPLC-DAD	Gallic acid; protocatechuic acid; chlorogenic acid; (+) catechin; (−)epicatechin DPPH scavenging_{10 mg/mL} = 71%	[76]
Nannochloropsis sp. EtOH, MeOH, H RP-HPLC-UV HPLC–ESI–MS/MS	Phenolic acids: chlorogenic; caffeic; gallic; protocatechuic; hydroxybenzoic; syringic; vanillic; ferulic	[27]
Spirulina sp. RP-HPLC-UV HPLC-ESI-MS/MS	Protocatechuic; gallic; chlorogenic; vanillic; hydroxybenzoic; syringic; vanillic acids	[27]
Spirogyra sp. MeOH, W RP-HPLC-DAD	Gallic acid DPPH scavenging_{10 mg/mL} = 62%	[76]
Seagrasses
Cymodocea nodosa MeOH, CH₂CL₂ HPLC-DAD, LC/MS-ESI, NMR	Diosmetin 7-sulfate; caftaric acid; coutaric acid	[77]
Halodule wrightii, Thalassia testudinum Agar, W HPLC	p-hydroxybenzoic acid; ferulic acid; p-coumaric acid; syringic acid; gallic acid	[78]
Halophila stipulacea MeOH, EtOAc, Hexane HR-LC-MS/MS GNPS	Luteolin; apigenin; matairesinol; cirsimarin; spiraeoside; 2,4-dihydroxyheptadec-16-ynyl acetate; 3-hydroxy-4-methoxycinnamic acid, alpha-cyano-4-hydroxycinnamic	[79]
Posidonia oceanica (L.) EtOH, W, Formic acid HPLC-ESI-MS/MS	Procyanidin B2; procyanidin C2; isorhamnetin-3-O-glucoside; quercetin-3-O-glucoside; quercetin-3-O-malonylglucoside; isorhamnetin-3-O-malonylglucoside EC_{50, DPPH} = 32 µg/mL	[80]
Ruppia cirrhosa (Petagna) Grande, Ruppia maritima L. MeOH, W, EtOAc HPLC-DAD, HR-LCMS-ESI+/TOF, NMR	Chicoric acid; quercetin 3-O-β-d-(6’’-O-malonyl)-glucopyranoside; quercetin 3-O-β-d-galactopyranoside; quercetin 3-O-β-d-glucopyranoside; quercetin 3-O-β-d-(6′’-O-malonyl)galactopyranoside; isorhamnetin 3-O-β-d-galactopyranoside; isorhamnetin 3-O-β-d-glucopyranoside; isorhamnetin 3-O-β-d-(6´´-O-malonyl) galactopyranoside; isorhamnetin 3-O-β-d-(6′’-O-malonyl)-glucopyranoside EC_{50 DPPH} = 23–176 µg/mL	[81]
Syringodium isoetifolium MeOH HPLC-EI-MS	Caftaric acid; 2 3-(4-Hydroxyphenyl)lactic acid; caffeic acid; caffeoyl-4′-O-phenyllactate; 3-phenyllactic acid; 4-coumaric acid; chicoric acid DPPH = 5.4 mg TE/g; ABTS = 9.6 mg TE; CUPRAC = 18.7 mg TE/g; FRAP = 9.5 mgTE/g; Chelating ability = 9.17 mg EDTAE/g	[82]
Thalassia testudinum AC, W, AA	3,4-Dihydroxybenzoic acid; p-hydroxybenzoic acid; p-coumaric acid; vanillin	[83]
T. testudinum EtOH, W RP-HPLC LC-MS, NMR	3,4-Dihydroxybenzoic acid, p-hydroxybenzoic acid, p-coumaric acid and vanillin	[84]
Zostera asiatica and Z. marina HPLC-MS	Rosmarinic acid; luteolin; 7,3′-disulfate luteolin ROS scavenger; protecting or enhancing endogenous antioxidants; metal chelation	[85]
Z. marina Hexane, AC HPLC-MS, NMR	Deoxycymodienol; isotedarene A	[86]
Z. marina SPA, IPA HPLC-MS/MS	3-Hydroxyhexanoic acid; 4-hydroxynonenoic acid; p-coumaric acid; caffeic acid; ferulic acid; zosteric acid; apigenin; luteolin; diosmetin; apigenin-7-sulfate; rosmarinic acid; luteolin-7-sulfate; diosmetin-7-sulfate; kaempferol-7,4′-dimethylether-3-O-sulfate	[5]
Z. noltii MeOH HPLC, NMR	Rosmarinic acid; caffeic acid; zosteric acid	[87]
Z. noltei MeOH HPLC-PDA-MS-ESI-QTOF, NMR	Rosmarinic acid; apigenin-7-O-glucoside; luteolin; apigenin; diosmetin; acacetin; luteolin-7-sulfate; apigenin-7-sulfate; diosmetin-7-sulfate; acacetin-7-sulfate	[88]
Zostera noltei leaves MeOH, W HPLC-DAD, LC-MS, NMR	Apigenin 7-sulfate; diosmetin 7-sulfate	[89]
Zostera noltii, Z. marina	Apigenin 7-sulphate; luteolin 7-sulphate; diosmetin 7-sulphate; rosmarinic acid; luteolin 7-glucoside; apigenin 7-glucoside; apigenin; luteolin 7-(6′’-malonyl) glucoside; apigenin 7-(6′’-malonyl) glucoside	[81]
Zostera muelleri MeOH, AA RP-HPLC	Proanthocyanidins; gallic acid; rosmarinic acid	[90]
Sponges
Didiscus aceratus MeOH, CH₂Cl₂, H HRESIMS, NMR	(S)-(+)-Curcuphenol; 10β-hydroxycurcudiol; 10α-hydroxycurcudiol; dicurcuphenols A–E; dicurcuphenol ether F	[91]
Hyrtios erectus MeOH, EtOAc HRAPCIMS, HRESIMS, NMR	Phenolic alkenes; erectuseneols A−F	[92]
Myrmekioderma sp. MeOH, CH₂Cl₂, EtOAc, BuOH, hexane HRESIMS, NMR	1-(2,4-Dihydroxy-5-methylphenyl)ethan-1-one; (1′Z)-2-(1′,5′-dimethylhexa-1′,4′-dieny1)-5- methylbenzene-1,4-diol; 1,8-epoxy-1(6),2,4,7,10-bisaborapentaen-4-ol; 6-(3-hydroxy-6-methyl-1,5- heptadien-2-yl)-3-methylbenzene-1,4-diol; 4-hydroxy-3,7-dimethyl-7-(3-methylbut-2- en-1-yl)benzofuran-15-one; 6-(2-methoxy-6-methylhept-5-en-2-yl)-3-methylbenzene-1,4-diol; 9-(3,3-dimethyloxiran-2-yl)-1,7-dimethyl-7-chromen-4-ol	[93]
Myrmekioderma sp. MeOH, EtOAc HRAPCIMS, HRESIMS, NMR	(R)-Biscurcudiol; (S)-biscurcudiol; myrmekiodermaral; myrmekioperoxide A; myrmekioperoxide B (4); myrmekiodermaral; (+)-curcudiol; (+)-dehydrocurcudiol; abolene; abolene epimer at C-5′; (+)-oxoabolene; (+)-curcuphenol; 5′α-hydroxycurcudiol; 5′β- hydroxycurcudiol; curcuepoxide A; curcuepoxide B	[94]

AA: ascorbic acid; AC: acetone; ASE: ascorbic acid equivalents; BuOH: butanol; CA: chelating ability; CAA: antioxidant assay for cellular antioxidant activity [95]; CLPAA: cellular lipid peroxidation antioxidant activity assay [95]; EA: ethyl acetate; ECD: electronic circular dichroism; EtOAc: ethyl acetate; EtOH: ethanol; GNPS: global natural product social molecular networking; H: hexane; HRAPCIMS: high resolution atmospheric pressure chemical ionization mass spectrometry; HRESIMS: high resolution electrospray ionization mass spectrometry; IPA: isopropanol; LPIA: lipid peroxidation inhibition assay [96]; MeCN: acetonitrile; MeOH: methanol; OP: polarimetry; PDA: photodiode array; PGU: phloroglucinol units; RP: reducing power; RP-HPLC: reversed phase HPLC; SPA: solid phase adsorption; SRSA: superoxide radical scavenging assay [96]; TAA: total antioxidant capacity [97]; TLC: thin-layer chromatography; US: ultrasound; W: water.