Phytosterols in Seaweeds: An Overview on Biosynthesis to Biomedical Applications
Abstract
:1. Introduction
2. Biosynthesis of Phytosterols
2.1. Biosynthesis of Isoprene
2.2. Condensation of Isoprene into Triterpenoids and Their Epoxidation
2.3. Phytosterol Synthesis
3. Extraction and Characterization of Phytosterols
4. Health Benefits and Biomedical Applications of Phytosterols
4.1. Phytosterols as Antioxidative Agents
4.2. Phytosterols as Antimicrobial Agents
4.3. Phytosterols as Anti-Inflammatory Agents
4.4. Phytosterols as Anticancer Agents
5. Safety of Phytosterols
6. Conclusions and Future Perspectives
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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---|---|---|---|---|
Gelidium spinosum | Soxhlet method | FTIR and GC–MS | Stigmasterol | [32] |
Saccharina latissima | saponified extract | GC–MS | cholesterol, desmosterol, 24-methylenecholesterol, fucosterol, cycloartenol, and unknown ∆5-sterol | [35] |
Palmaria decipiens, Plocamium cartilagineum, Iridaea cordata, and Pyropia endiviifolia | alkaline hydrolysis | GC–MS | cholesterol, brassicasterol, campesterol, stigmasterol, β-sitosterol, and fucosterol | [33] |
Ecklonia radiata | alkaline saponification | LC-MS/MS and GC–MS | fucosterol, Sitostanol, 24α-methyl cholesterol, and 24α-ethyl cholesterol | [36] |
Padina australis and Stoechospermum marginatum, and Ahnfeltiopsis pygmaea | acid and alkaline hydrolysis followed by solvent extraction, derivatization, and GC determination | gas chromatography coupled with a flame ionization detection system (GC–FID) | sitostanol, campestanol ergosterol, campesterol, delta-5-avenasterol, stigmasterol, sistenol, cholesterol, and 24-methylenecholesterol | [37] |
Adenocystis utricularis, Desmarestia confervoides, Curdiea racovitzae, Myriogramme manginii, and Ulva intestinalis | Soxhlet method | GC–MS and FT-IR | fucosterol, cholesterol, and hydroxymethylcholesterol | [38] |
Phaeophyta (Cystoseira barbata, Cystoseira compressa, Fucus virsoides) and chlorophyta (Codium bursa) | agitation-assisted extraction and pressurized liquid extraction | TLC | cholesterol, brassicasterol, campesterol, campestanol, stigmasterol, β-sitosterol, fucosterol, and isofucosterol | [39] |
Cystoseira trinodis | solvent extraction and column chromatography | 1H, 13C NMR, heteronuclear multiple-bond correlation (HMBC), heteronuclear single-quantum coherence (HSQC), GC–MS, and electron ionization-mass spectra (EI-MS) | saringosterol, β-sitosterol | [40] |
Sargassum horneri | high-speed countercurrent chromatography | NMR | fucosterol and saringosterol | [41] |
S. fusiforme | Folch method | GC–MS | 24(S)-Saringosterol | [42] |
Halimeda tuna, Codium bursa, and Cystoseira barbata | solvent extraction | GC and GC–MS | fucosterol, campesterol and β-sitosterol | [43] |
Sargassum elegans | solvent extraction and column chromatography | NMR (1H and 13C), IR and mass spectral data | β-sitosterol, fucosterol | [44] |
Phaeophyta (Cystophora pectinata, Pyllospora comoasa, Scytothalia dorycarpa, Carpoglossum confluens, E. radiata, Sargassum lacerifolium, Perithalia caudata, Codium harveyi, Scytothalia dorycarpa, Hypnea valida, Cystophora monilifera, Hormosira banksia, Myriodesma integrifolium, Epiphytic algae sp., Cystophora subfarcinata), Rhodophyta (Austrophyllis harveyana, Rhodophyllis membaneacea), and chlorophyta (Codium fragile) | maceration | post-chromatographic derivatization and HPTLC | β-sitosterol | [45] |
Ascoseira mirabilis, A. utricularis, Desmarestia anceps, and Phaeurus antarcticus | saponification | GC–MS | cholesterol, desmosterol, brassicasterol, campesterol, stigmasterol, fucosterol, and β-sitosterol | [46] |
Ecklonia stolonifera | silica gel column chromatography | 1H and 13C NMR | fucosterol | [47] |
Rhodophyta (Gracilaria vermiculophylla, Pterocladiella tenuis, Palisada intermedia, Chrysymenia wrightii, Gracilaria elegans, Grateloupia asiatica, Laurencia okamurae) and Phaeophyta (Eckloniopsi radicosa, Sargassum thunbergia, Ecklonia kurome, Eisenia arborea, Sargassum piluliferum, S. fusiforme, U. pinnatifida, Ecklonia cava) | saponification | HPLC with fluorescence detection | cholesterol, β-sitosterol, ergosterol, stigmasterol, and fucosterol | [48] |
S. horneri | total lipid extraction using methanol | RP-HPLC | fucosterol | [49] |
Hizikia fusiformein | ethanol extraction and chromatographic separation | LC/ electrospray ionization (ESI)-MS | fucosterol | [50] |
A. utricularis, Ascoseira mirabilis, Cystosphaera jacquinotii, D. anceps, Durvillaea antarctica, and Himantothallus grandifolius | ultrasound irradiation | LC-MS/MS | ergosterol, brassicasterol, fucosterol, β-sitosterol, campesterol, cholesterol, and stigmasterol) | [6] |
Porphyra dentata | methanol extraction and silica gel column chromatography | HPLC- evaporative light scattering detector (ELSD) | cholesterol, β -sitosterol, and campesterol | [51] |
Seaweed Names | Cell Lines Used | Therapeutic Compounds | Anticancer Activity | References |
---|---|---|---|---|
Ulva fasciata, Ulva lactuca, Amphiroa anceps, Corallina mediterranea, and Sargassum filipendula | human breast adenocarcinoma cell line (MCF-7) and colorectal carcinoma cell line (HCT-116) | palmitic acid, oleic acid, retinoic acid, dihydroactinidiolide, thiosemicarbazide, diisobutyl phthalate, and phytol | anticancer agents against human breast and colon cancers | [134] |
Sargassum spp. | SMMC-7721, Huh7, and HCCLM3 liver | fucoidan | deactivates the integrin αVβ3/SRC/E2F1 signaling pathway; Antimetastatic | [135] |
Ulva lactuca, Codium tomentosum, Cystoseira crinita, Cystoseira stricta, Sargassum vulgare, Gelidium latifolium, Hypnea musciformis and Jania rubens | human colorectal carcinoma (Caco2) and human corneal epithelial cells (HCEC) | polyphenols and flavonoids | human colorectal carcinoma | [136] |
Ecklonia maxima | HeLa, H157 and MCF7 cancer cell lines | phlorotannins and sterol | cytotoxic activity | [137] |
Sargassum spp., Turbinaria spp. and Padina spp. | breast cancer (MCF-7) and colon cancer cells (WiDr) | fucoidan | showed potential selective cytotoxicity | [138] |
Sargassum hemiphyllum | HCT116 | oligo-fucoidan | DNA damage; cell cycle checkpoint; prevents HCT116 tumorigenicity and regulate the cancer cell death | [139] |
Ulva lactuca and Eucheuma cottonii | breast MCF-7 and colorectal HCT-116 cancer cells | steroids, glycosides, flavonoids, and tannins | anti-breast and anticolorectal cancer agents | [140] |
Carpodesmia tamariscifolia | hepatocellular carcinoma Hep G2, AGS and HCT-15 cell lines | isololiolide | caspase-3 activation, decreased Bcl-2 levels, increased p53 expression and PARP cleavage | [141] |
Fucus vesiculosus | human hepatoma cell line MHCC-97H | fucoidan | macrophages M2 anti-inflammatory reduction; inhibition of tumor cell migration | [142] |
Brown algae spp. | MCF-7 cell line | phloroglucinol | decreased CD44+ cancer cell population, expression of CSC regulators such as Sox2, CD44, Oct4, Notch2, and β-catenin; inhibited KRAS and its downstream PI3K/AKT and RAF-1/ERK signaling pathway | [143] |
U. pinnatifida | human hepatocellular carcinoma SMMC-7721 cells | fucoidan | apoptosis via the ROS mediated mitochondrial pathway | [144] |
U. pinnatifida | PC-3 human prostate cancer cells | fucoidan | induced intrinsic and extrinsic apoptosis pathways | [145] |
Laminaria digitata | HT-29 colon cancer cells | laminarin | induction of apoptosis; affected insulin-like growth factor (IGF-IR); decreased MAPK and ERK phosphorylation; decreased IGF-IR-dependent proliferation | [146,147] |
Sargassum muticum | MCF-7 cells | Sargassum muticum methanol extract (SMME) | induced apoptosis; showed antiangiogenic activity in the chorioallantoic membrane (CAM) assay; antioxidant effects | [148] |
Porphyra dentata | 4T1 cancer cells | cholesterol, β-sitosterol, and campesterol | induced apoptosis; decreased the ROS and arginase activity of MDSCs in tumor-bearing mice | [51] |
Sargassum spp. | MCF-7 (breast cancer) and Hep-2 (liver cancer) cell line | ethanol extract | induced cell shrinkage, cell membrane blebbing and formation of apoptotic bodies | [149] |
U. pinnatifida | A549 human lung carcinoma cells | fucoidan | induced apoptosis through down-regulation of p38, PI3K/Akt, and the activation of the ERK1/2 MAPK pathway | [150] |
Sargassum oligocystum | K562 and Daudi human cancer cell lines | fucoidans | antitumor activity | [151] |
U. pinnatifidasporophylls | leukemia A20 cells | fucoidan | T-cell mediated and NK cell response; tumor destruction by immune cells | [152] |
Amphiroa zonata | human leukemic cells | palmitic acid | showed selective cytotoxicity | [153] |
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Sohn, S.-I.; Rathinapriya, P.; Balaji, S.; Jaya Balan, D.; Swetha, T.K.; Durgadevi, R.; Alagulakshmi, S.; Singaraj, P.; Pandian, S. Phytosterols in Seaweeds: An Overview on Biosynthesis to Biomedical Applications. Int. J. Mol. Sci. 2021, 22, 12691. https://doi.org/10.3390/ijms222312691
Sohn S-I, Rathinapriya P, Balaji S, Jaya Balan D, Swetha TK, Durgadevi R, Alagulakshmi S, Singaraj P, Pandian S. Phytosterols in Seaweeds: An Overview on Biosynthesis to Biomedical Applications. International Journal of Molecular Sciences. 2021; 22(23):12691. https://doi.org/10.3390/ijms222312691
Chicago/Turabian StyleSohn, Soo-In, Periyasamy Rathinapriya, Sekaran Balaji, Devasahayam Jaya Balan, Thirukannamangai Krishnan Swetha, Ravindran Durgadevi, Selvaraj Alagulakshmi, Patchiappan Singaraj, and Subramani Pandian. 2021. "Phytosterols in Seaweeds: An Overview on Biosynthesis to Biomedical Applications" International Journal of Molecular Sciences 22, no. 23: 12691. https://doi.org/10.3390/ijms222312691