Green Extraction of Bioactive Compounds From Marine Constituents

Keywords: Marine biology, Pharmacology, Phytochemicals, Ultrasonics, Ultrasound-assisted enzyme extraction, Chromatography, supercritical fluid, Solvent, SFE, PSE, Green extraction technology

Abstract


Marine organisms house diverse bioactive compounds, making them a prime focus in marine pharmacology. This abstract explores eco-friendly extraction methods for isolating bioactive marine constituents and peptides from marine sources, underscoring their sustainability and environmental responsibility. Green extraction technologies include supercritical fluid extraction (SFE), pressurised solvent extraction (PSE) and enzyme extraction using microwaves and ultrasounds. Since there is less chemical interference, these newer, greener technologies would be safer. The extraction, isolation and characterisation of these marine constituents can lead to the identification of novel constituents from marine sources. Marine components and bioactive peptides made by marine species have a wide range of pharmacological capabilities, such as antioxidant, anti-inflammatory, antibacterial and anticancer activity. These attributes position marine-derived constituents as promising candidates for drug development and the creation of functional foods and nutraceuticals. Application of sustainable extraction methods aligns with responsible marine resource management principles; particularly important as marine ecosystems face increasing challenges from overexploitation and environmental stressors. Green extraction harmonises scientific exploration with ecological preservation within the area of marine pharmacology, promising advancements and responsible utilisation of marine resources.

 

Author Biographies

Bincy Raj, T. John College of Pharmacy, Bengaluru

Department of Pharmacognosy

 T. John College of Pharmacy,

Bengaluru – 560 083, Karnataka, India.

DS Seetharam, Osmania University, Hyderabad, Telangana State

Department of Botany,

Osmania University,

Hyderabad – 500007,

Telangana, India.

Sharangouda J Patil, NMKRV College for Women, Bengaluru

Department of Zoology,

NMKRV College for Women,

Bengaluru – 560011,

Karnataka, India.

References

Donia M, Hamann MT. Marine natural products and their potential applications as anti-infective agents. Lancet Infect Dis. 2003 Jun;3(6):338-48. doi: 10.1016/s1473-3099(03)00655-8.

Malve H. Exploring the ocean for new drug developments: Marine pharmacology. J Pharm Bioallied Sci. 2016 Apr-Jun;8(2):83-91. doi: 10.4103/0975-7406.171700.

Peñalver R, Lorenzo JM, Ros G, Amarowicz R, Pateiro M, Nieto G. Seaweeds as a functional ingredient for a healthy diet. Mar Drugs. 2020 Jun 5;18(6):301. doi: 10.3390/md18060301.

Rocha DHA, Seca AML, Pinto DCGA. Seaweed secondary metabolites in vitro and in vivo anticancer activity. Marine Drugs. 2018; 16(11):410. doi: 10.3390/md16110410.

Zhang QW, Lin LG, Ye WC. Techniques for extraction and isolation of natural products: a comprehensive review. Chin Med. 2018 Apr 17;13:20. doi: 10.1186/s13020-018-0177-x.

David E, Niculescu VC. Volatile Organic Compounds (VOCs) as environmental pollutants: occurrence and mitigation using nanomaterials. Int J Environ Res Public Health. 2021 Dec 13;18(24):13147. doi: 10.3390/ijerph182413147.

Gałuszka A, Migaszewski Z, Namieśnik J. The 12 principles of green analytical chemistry and the SIGNIFICANCE mnemonic of green analytical practices. TrAC Trends Anal Chem. 2013;50:78-84.

Winterton N. The green solvent: a critical perspective. Clean Technol Environ Policy. 2021;23(9):2499-522. doi: 10.1007/s10098-021-02188-8.

Getachew AT, Jacobsen C, Holdt SL. Emerging technologies for the extraction of marine phenolics: opportunities and challenges. Mar Drugs. 2020 Jul 27;18(8):389. doi: 10.3390/md18080389.

Rotter A, Barbier M, Bertoni F, Bones AM. The essentials of marine biotechnology. Frontiers Mar Sci. 2021;8: 629629. doi: 10.3389/fmars.2021.629629.

Sithranga Boopathy N, Kathiresan K. Anticancer drugs from marine flora: an overview. J Oncol. 2010;2010:214186. doi: 10.1155/2010/214186.

Kurhekar JV. Antimicrobial lead compounds from marine plants. In: C. Egbuna, et al. (Eds.), Phytochemicals as lead compounds for new drug discovery Amsterdam, NA: Elsevier 2020; pp. 257-274. doi: 10.1016/B978-0-12-817890-4.00017-2.

Cheng Z, Lin X, Wu M, Lu G, Hao Y, Mo C, et al. Combined effects of polyamide microplastics and hydrochemical factors on the transport of bisphenol a in groundwater. Separations. 2023; 10(2):123. doi: 10.3390/separations10020123.

Martins R, Barbosa A, Advinha B, Sales H, Pontes R, Nunes J. Green extraction techniques of bioactive compounds: a state-of-the-art review. Processes. 2023; 11(8):2255. doi: 10.3390/pr11082255.

Ullah N, Haseeb A, Tuzen M. Application of recently used green solvents in sample preparation techniques: a comprehensive review of existing trends, challenges, and future opportunities. Crit Rev Anal Chem. 2024;54(8):2714-33. doi: 10.1080/10408347.2023.2197495

Chemat F, Vian MA, Cravotto G. Green extraction of natural products: concept and principles. Int J Mol Sci. 2012;13(7):8615-8627. doi: 10.3390/ijms13078615.

Wibowo JT, Ahmadi P, Rahmawati SI, Bayu A, Putra MY, Kijjoa A. marine-derived indole alkaloids and their biological and pharmacological activities. Mar Drugs. 2021 Dec 21;20(1):3. doi: 10.3390/md20010003.

Ibrahim SR, Mohamed GA. Marine pyridoacridine alkaloids: biosynthesis and biological activities. Chem Biodivers. 2016 Jan;13(1):37-47. doi: 10.1002/cbdv.201400434.

Hu Y, Chen S, Yang F, Dong S. Marine indole alkaloids-isolation, structure and bioactivities. Mar Drugs. 2021 Nov 24;19(12):658. doi: 10.3390/md19120658.

Munir S, Shahid A, Aslam B, Ashfaq UA, Akash MSH, Ali MA, et al. The therapeutic prospects of naturally occurring and synthetic indole alkaloids for depression and anxiety disorders. Evid Based Complement Alternat Med. 2020 Oct 16;2020:8836983. doi: 10.1155/2020/8836983.

Galasso C, Corinaldesi C, Sansone C. Carotenoids from marine organisms: biological functions and industrial applications. Antioxidants (Basel). 2017 Nov 23;6(4):96. doi: 10.3390/antiox6040096.

Venkatesan J, Keekan KK, Anil S, Bhatnagar I, Kim SK. Phlorotannins. Encycl Food Chem. 2019:515–27. doi: 10.1016/B978-0-08-100596-5.22360-3.

Gil-Martín E, Forbes-Hernández T, Romero A, Cianciosi D, Giampieri F, Battino M. Influence of the extraction method on the recovery of bioactive phenolic compounds from food industry by-products. Food Chem. 2022 Jun 1;378:131918. doi: 10.1016/j.foodchem.2021.131918.

Uddin MS, Ferdosh S, Akanda JH, Ghafoor K, Rukshana AH, Ali E, et al. Techniques for the extraction of phytosterols and their benefits in human health: a review, Sep Sci Technol. 2018;53:14;2206-23. doi: 10.1080/01496395.2018.1454472.

Chen Y, Mu T. Revisiting greenness of ionic liquids and deep eutectic solvents. Green Chemical Engineering. 2021:2(2); 174-186. doi: 10.1016/j.gce.2021.01.004.

Iloki-Assanga SB, Lewis-Luján LM, Lara-Espinoza CL, Gil-Salido AA, Fernandez-Angulo D, Rubio-Pino JL, et al. Solvent effects on phytochemical constituent profiles and antioxidant activities, using four different extraction formulations for analysis of Bucida buceras L. and Phoradendron californicum. BMC Res Notes. 2015 Sep 1;8:396. doi: 10.1186/s13104-015-1388-1.

Abdullah Ali H, Kamal Omer H. Solubility enhancement of a poorly water-soluble drug using hydrotropy and mixed hydrotropy-based solid dispersion techniques. Adv Pharmacol Pharm Sci. 2022 Nov 28;2022:7161660. doi: 10.1155/2022/7161660.

Arjaria P, Goyal M, Jain S. Hydrotropic solubilization. Int J Pharmaceutical Phytopharmacol Res. 2013;3(1):17-23.

Dhapte V, Mehta P. Advances in hydrotropic solutions: An updated review. St. Petersburg Polytechnical Univ J: Physics Mathemat. 2015;1(4) 424–35. doi: 10.1016/j.spjpm.2015.12.006.

Patel AD, Desai MA. Progress in the field of hydrotropy: mechanism, applications and green concepts. Rev Chem Eng. 2023;39(4):601-30. doi: 10.1515/revce-2021-0012.

Fierascu RC, Fierascu I, Ortan A, Georgiev MI, Sieniawska E. Innovative approaches for recovery of phytoconstituents from medicinal/aromatic plants and biotechnological production. Molecules. 2020 Jan 12;25(2):309. doi: 10.3390/molecules25020309.

Kulkarni NS, Ghule SB, Dhole SN. A review on hydrotropic solubilization for poorly water-soluble drugs: analytical application and formulation development. Research J Pharm Tech. 2019;12(7):3157-62. doi: 10.5958/0974-360X.2019.00532.8.

Mangal A, Bhadoriya SS, Joshi S, Agrawal G, Gupta A, Mandoria N. Extraction of herbal drugs by using hydrotropy solublization phenomenon. Int Res J Pharm. App Sci. 2012;2(1):63-74.

Awad AM, Kumar P, Ismail-Fitry MR, Jusoh S, Ab Aziz MF, Sazili AQ. Green extraction of bioactive compounds from plant biomass and their application in meat as natural Antioxidant. Antioxidants (Basel). 2021 Sep 15;10(9):1465. doi: 10.3390/antiox10091465.

Uwineza PA, Waśkiewicz A. Recent Advances in supercritical fluid extraction of natural bioactive compounds from natural plant materials. Molecules. 2020; 25(17):3847. doi: 10.3390/molecules25173847.

Carreira-Casais A, Otero P, Garcia-Perez P, Garcia-Oliveira P, Pereira AG, Carpena M, et al. Benefits and drawbacks of ultrasound-assisted extraction for the recovery of bioactive compounds from marine algae. Int J Environ Res Public Health. 2021 Aug 30;18(17):9153. doi: 10.3390/ijerph18179153.

Assunção J, Amaro HM, Malcata FX, Guedes AC. Factorial optimization of ultrasound-assisted extraction of phycocyanin from synechocystis salina: towards a biorefinery approach. Life 2022; 12:1389. doi: 10.3390/life12091389.

Babich O, Budenkova E, Kashirskikh E, Dolganyuk V, Ivanova S, Prosekov A, Anokhova V, Andreeva A, Sukhikh S. Study of the polysaccharide production by the microalga vischeria punctata in relation to cultivation conditions. Life (Basel). 2022 Oct 15;12(10):1614. doi: 10.3390/life12101614.

Dobrinčić A, Zorić Z, Pedisić S, Repajić M, Roje M, Herceg Z, et al. Application of ultrasound-assisted extraction and non-thermal plasma for fucus virsoides and Cystoseira barbata polysaccharides pre-treatment and extraction. Processes. 2022; 10(2):433. doi: 10.3390/pr10020433.

Adam F, Abert-Vian M, Peltier G, Chemat F. "Solvent-free" ultrasound-assisted extraction of lipids from fresh microalgae cells: a green, clean and scalable process. Bioresour Technol. 2012 Jun;114:457-65. doi: 10.1016/j.biortech.2012.02.096.

Blanco-Llamero C, García-García P, Señoráns FJ. Combination of synergic enzymes and ultrasounds as an effective pretreatment process to break microalgal cell wall and enhance algal oil extraction. Foods. 2021 Aug 19;10(8):1928. doi: 10.3390/foods10081928.

Yucetepe A. A combination of osmotic shock and ultrasound pre-treatments and the use of enzyme for extraction of proteins from Chlorella vulgaris microalgae: Optimization of extraction conditions by RSM. Food Measure. 2022;16:1516–27.

Mittal R, Tavanandi HA, Mantri VA, Raghavarao KSMS. Ultrasound assisted methods for enhanced extraction of phycobiliproteins from marine macro-algae, Gelidium pusillum (Rhodophyta). Ultrasonics Sonochem. 2017;38:97-102. doi: 10.1016/j.ultsonch.2017.02.030.

Zhao X, Zhang X, Liu H, Zhu H, Zhu Y. Enzyme-assisted extraction of astaxanthin from Haematococcus pluvialis and its stability and antioxidant activity. Food Sci Biotechnol. 2019 Apr 17;28(6):1637-47. doi: 10.1007/s10068-019-00608-6.

Tzanova M, Atanasov V, Yaneva Z, Ivanova D, Dinev T. Selectivity of current extraction techniques for flavonoids from plant materials. Processes. 2020; 8(10):1222. doi: 10.3390/pr8101222.

Bitwell C, Indra SS, Luke C, Kakoma MK. A review of modern and conventional extraction techniques and their applications for extracting phytochemicals from plants. Sci African. 2023:19. doi: 10.1016/j.sciaf.2023.e01585.

Gupta A, Naraniwal M, Kothari V. Modern extraction methods for preparation of bioactive plant extracts. Int J Appl Nat Sci. 2012;1(1):8-26.

Chaves JO, de Souza MC, da Silva LC, Lachos-Perez D, Torres-Mayanga PC, Machado APDF, et al. Extraction of flavonoids from natural sources using modern techniques. Front Chem. 2020 Sep 25;8:507887. doi: 10.3389/fchem.2020.507887.

Motlagh SR, Elgharbawy AA, Khezri R, Harun R, Omar R. Ionic liquid‑based microwave‑assisted extraction of protein from Nannochloropsis sp. Biomass Conv Bioref. 2023;13:8327–38. doi: 10.1007/s13399-021-01778-2.

Berthod A, Ruiz-Angel MJ, Carda-Broch S. Elution-extrusion counter current chromatography. Use of the liquid nature of the stationary phase to extend the hydrophobicity window. Anal Chem. 2003 Nov 1;75(21):5886-94. doi: 10.1021/ac030208d.

Liang J, Qiao B, Syed N, Sun W. A mass spectrometry guided elution-extrusion counter-current chromatography protocol for isolation of eighteen terpenoids from Fructus Corni and assessment of their anti-glioma activities. Microchem J. 2018;137:464-72. doi: 10.1016/j.microc.2017.12.008.

Berthod A, Maryutina T, Spivakov B, Shpigun O, Sutherland I. Countercurrent chromatography in analytical chemistry Pure Appl. Chem. 2009;81(2) 355–87.

Chen D, Jin Y, Hu D, Ye J, Lu Y, Dai Z. One-step preparative separation of fucoxanthin from three edible brown algae by elution-extrusion countercurrent chromatography. Marine Drugs. 2022; 20(4):257. doi: 10.3390/md20040257.

Xia M, Liu C, Gao L, Lu Y. One-Step preparative separation of phytosterols from edible brown seaweed Sargassum horneri by high-speed countercurrent chromatography. Mar Drugs. 2019; 17(12):691. doi: 10.3390/md17120691.

Liu Y, Zhou X, Naman CB, Lu Y, Ding L, He S. Preparative separation and purification of trichothecene mycotoxins from the marine Fungus fusarium sp. LS68 by high-speed countercurrent chromatography in stepwise elution mode. Mar Drugs. 2018;16(2):73. doi: 10.3390/md16020073.

Kulinowski L, Luca SV, Skalicka‐Woźniak K. Liquid-liquid chromatography as a promising technology in the separation of food compounds. eFood. 2023;4:e87. doi: 10.1002/efd2.87.

Vafaei N, Rempel CB, Scanlon MG, Jones PJH, Eskin MNA. Application of supercritical fluid extraction (SFE) of tocopherols and carotenoids (hydrophobic antioxidants) compared to non-SFE methods. Applied Chem. 2022;2(2):68-92. doi: 10.3390/appliedchem2020005.

Cragg GM, Newman DJ. Natural products: a continuing source of novel drug leads. Biochim Biophys Acta. 2013 Jun;1830(6):3670-95. doi: 10.1016/j.bbagen.2013.02.008.

Khaw KY, Parat MO, Shaw PN, Falconer JR. Solvent supercritical fluid technologies to extract bioactive compounds from natural sources: a review. Molecules. 2017 Jul 14;22(7):1186. doi: 10.3390/molecules22071186.

Zhou J, Gullón B, Wang M, Gullón P, Lorenzo JM, Barba FJ. The application of supercritical fluids technology to recover healthy valuable compounds from marine and agricultural food processing by-products: a review. Processes. 2021;9(2):357. doi: 10.3390/pr9020357.

Macías-Sánchez MD, Fernandez-Sevilla JM, Fernández FA, García MC, Grima EM. Supercritical fluid extraction of carotenoids from Scenedesmus almeriensis. Food Chem. 2010;123:928–35. doi: 10.1016/j.foodchem.2010.04.076.

Molino A, Larocca V, Di Sanzo G, Martino M, Casella P, Marino T, et al. Extraction of Bioactive compounds using supercritical carbon dioxide. Molecules. 2019 Feb 21;24(4):782. doi: 10.3390/molecules24040782.

Barp L, Višnjevec AM, Moret S. Pressurized liquid extraction: a powerful tool to implement extraction and purification of food contaminants. Foods. 2023;12(10):2017. doi: 10.3390/foods12102017.

Perez-Vazquez A, Carpena M, Barciela P, Cassani L, Simal-Gandara J, Prieto MA. Pressurized liquid extraction for the recovery of bioactive compounds from seaweeds for food industry application: a review. Antioxidants. 2023; 12(3):612. doi: 10.3390/antiox12030612.

Johnson TA, Morgan MV, Aratow NA, Estee SA, Sashidhara KV, Loveridge ST, et al. Assessing pressurized liquid extraction for the high-throughput extraction of marine-sponge-derived natural products. J Nat Prod. 2010 Mar 26;73(3):359-64. doi: 10.1021/np900565a.

Román-Hidalgo C, Barreiros L, Villar-Navarro M, López-Pérez G, Martín-Valero MJ, Segundo MA. Electro membrane extraction based on biodegradable materials: Biopolymers as sustainable alternatives to plastics. TrAC Trends Anal Chem. 2023;162:117048.

Martins RO, de Araújo GL, Simas RC, Chaves AR. Electromembrane extraction (EME): fundamentals and applications. Talanta Open. 2023 Mar 15:100200. doi: 10.1016/j.talo.2023.100200.

Tabani H, Asadi S, Nojavan S, Parsa M. Introduction of agarose gel as a green membrane in electromembrane extraction: An efficient procedure for the extraction of basic drugs with a wide range of polarities. J Chromatogr A. 2017 May 12;1497:47-55. doi: 10.1016/j.chroma.2017.03.075.

Román-Hidalgo C, Martín-Valero MJ, López-Pérez G, Villar-Navarro M. Green method for the selective electromembrane extraction of parabens and fluoroquinolones in the presence of NSAIDs by using biopolymeric chitosan films. Membranes (Basel). 2023 Mar 12;13(3):326. doi: 10.3390/membranes13030326.

Kotnik T, Rems L, Tarek M, Miklavčič D. Membrane electroporation and electropermeabilization: mechanisms and models. Annu Rev Biophys. 2019 May 6;48:63-91. doi: 10.1146/annurev-biophys-052118-115451.

Kotnik T, Frey W, Sack M, Haberl Meglič S, Peterka M, Miklavčič D. Electroporation-based applications in biotechnology. Trends Biotechnol. 2015 Aug;33(8):480-8. doi: 10.1016/j.tibtech.2015.06.002.

Grimi N, Dubois A, Marchal L, Jubeau S, Lebovka NI, Vorobiev E. Selective extraction from microalgae Nannochloropsis sp. using different methods of cell disruption. Bioresour Technol. 2014 Feb;153:254-9. doi: 10.1016/j.biortech.2013.12.011.

Eleršek T, Flisar K, Likozar B, Klemenčič M, Golob J, Kotnik T, et al. Electroporation as a solvent-free green technique for non-destructive extraction of proteins and lipids from Chlorella vulgaris. Front Bioeng Biotechnol. 2020 May 13;8:443. doi: 10.3389/fbioe.2020.00443.

Luengo E, Martínez JM, Bordetas A, Álvarez I, Raso J. Influence of the treatment medium temperature on lutein extraction assisted by pulsed electric fields from Chlorella vulgaris. Innov Food Sci Emerg Technol. 2015;29:15–22. doi: 10.1016/j.ifset.2015.02.012,

Parniakov O, Barba FJ, Grimi N, Marchal L, Jubeau S, Lebovka N, et al. Pulsed electric field and pH assisted selective extraction of intracellular components from microalgae Nannochloropsis. Algal Res. 2015;8:128–34. doi: 10.1016/j.algal.2015.01.014.

Houssen WE, Jaspars M. Isolation of marine natural products. Methods Mol Biol. 2012;864:367-92. doi: 10.1007/978-1-61779-624-1_14.

Sherma J, Fried B. Chapter 2: preparative thin layer chromatography. J Chrom Library. 1987;38:105-27. doi: 10.1016/S0301-4770(08)60365-6.

Tobiszewski M, Namieśnik J. Greener organic solvents in analytical chemistry. Curr Op Green Sust Chem. 2017;5:1-4. doi: 10.1016/j.cogsc.2017.03.002.

Bucar F, Wubea A, Schmidb M. Natural product isolation – how to get from biological material to pure compounds. Nat Prod Rep. 2013;30:525. doi: 10.1039/c3np20106f.

Sun YY, Wang H, Guo GL, Pu YF, Yan BL, Wang CH. Isolation, purification, and identification of antialgal substances in green alga Ulva prolifera for antialgal activity against the common harmful red tide microalgae. Environ Sci Pollut Res Int. 2016 Jan;23(2):1449-59. doi: 10.1007/s11356-015-5377-7.

Hua-Li Zuo, Feng-Qing Yang, Wei-Hua Huang, Zhi-Ning Xia, Preparative gas chromatography and its applications. J Chromatogr Sci. 2013;51(7)704–15. doi: 10.1093/chromsci/bmt040.

Braithwaite A, Smith FJ. Gas chromatography. In: Braithwaite A, Smith FJ, Eds. Chromatographic methods. Dordrecht: Springer 1999. pp. 165-257.

De Grazia G, Cucinotta L, Rotondo A, Donato P, Mondello L, Sciarrone D. Expanding the knowledge related to flavors and fragrances by means of three-dimensional preparative gas chromatography and molecular spectroscopy. Separations. 2022; 9(8):202. doi: 10.3390/separations9080202.

Hinchcliffe PR, Riley JP. The docosahexaenoic acid of marine organisms. J Am Oil Chem Soc. 1971;48:514. doi: 10.1007/BF02544673.

Zapata M, Rodríguez F, Garrido JL. Separation of chlorophylls and carotenoids from marine phytoplankton:a new HPLC method using a reversed phase C8 column and pyridine-containing mobile phases. Mar Ecol Progr Ser. 2000;195:29–45. doi: 10.3354/meps195029.

Wang X, Liang Y, Peng C, Xie H, Pan M, Zhang T, Ito Y. Preparative isolation and purification of chemical constituents of eBlamcanda by MPLC, HSCCC and PREP-HPLC. J Liq Chromatogr Relat Technol. 2011;34(4):241-57. doi: 10.1080/10826076.2011.547058.

Ebada SS, Edrada RA, Lin W, Proksch P. Methods for isolation, purification and structural elucidation of bioactive secondary metabolites from marine invertebrates. Nat Protoc. 2008;3(12):1820-31. doi: 10.1038/nprot.2008.182.

Youssef DT, Shaala LA, Mohamed GA, Badr JM, Bamanie FH, Ibrahim SR. Theonellamide G, a potent antifungal and cytotoxic bicyclic glycopeptide from the Red Sea marine sponge Theonella swinhoei. Mar Drugs. 2014 Apr 1;12(4):1911-23. doi: 10.3390/md12041911.

Ibrahim AE, Deeb SE, Abdelhalim EM, Al-Harrasi A, Sayed RA. Green stability indicating organic solvent-free hplc determination of remdesivir in substances and pharmaceutical dosage forms. Separations. 2021; 8(12):243. doi: 10.3390/separations8120243.

Suarez Garcia E, Miranda CF, Cesario MT, Wijffels RH, van den Berg C, Eppink MHM. Ionic liquid-assisted selective extraction and partitioning of biomolecules from macroalgae. ACS Sustain Chem Eng. 2023 Jan 24;11(5):1752-62. doi: 10.1021/acssuschemeng.2c05823.

Guler BA, Tepe U, Imamoglu E. Sustainable point of view: life cycle analysis for green extraction technologies. Chem Bio Eng Reviews. 2024;11(2):348-62. doi: 10.1002/cben.202300056.

Mbimbo P, D’Elia L, Liberti D, Olivieri G, Monti DM. Towards green extraction methods from microalgae learning from the classics. Appl Microbiol Biotechnol. 2020;104:9067–77. doi: 10.1007/s00253–020–10839–x.

Rao KV, Donia MS, Peng J, Garcia-Palomero E, Alonso D, Martinez A, et la. Manzamine B and E and ircinal. A related alkaloids from an Indonesian Acanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer's diseases. J Nat Prod. 2006 Jul;69(7):1034-40. doi: 10.1021/np0601399.

Netz N, Opatz T. Marine indole alkaloids. Mar Drugs. 2015;13(8):4814-914. doi: 10.3390/md13084814.

Carletti I, Banaigs B, Amade P. Matemone, a new bioactive bromine-containing oxindole alkaloid from the indian ocean sponge Iotrochota purpurea. J Nat Prod. 2000 Jul;63(7):981-3. doi: 10.1021/np990408d..

Tsuda M, Takahashi Y, Fromont J, Mikami Y, Kobayashi J. Dendridine A. A bis-indole alkaloid from a marine sponge Dictyodendrilla Species. J Nat Prod. 2005 Aug;68(8):1277-8. doi: 10.1021/np050076e.

Pecoraro C, Terrana F, Panzeca G, Parrino B, Cascioferro S, Diana P, et al. Nortopsentins as leads from marine organisms for anticancer and anti-inflammatory agent development. Molecules. 2023; 28(18):6450. doi: 10.3390/molecules28186450.

Kochanowska-Karamyan AJ, Araujo HC, Zhang X, El-Alfy A, Carvalho P, Avery MA, et al. Isolation and synthesis of veranamine, an antidepressant lead from the marine sponge Verongula rigida. J Nat Prod. 2020 Apr 24;83(4):1092-1098. doi: 10.1021/acs.jnatprod.9b01107.

Liu SS, Yang L, Kong FD, Zhao JH, Yao L, Yuchi ZG, et al. three new quinazoline-containing indole alkaloids from the marine-derived fungus Aspergillus sp. HNMF114. Front Microbiol. 2021 Jun 2;12:680879. doi: 10.3389/fmicb.2021.680879.

Kong F, Zhao C, Hao J, Wang C, Wang W, Huang X, et al. New α-glucosidase inhibitors from a marine sponge-derived fungus, Aspergillus sp. OUCMDZ-1583. RSC Advances. 2015;5(84):68852-63. doi: 10.1039/C5RA11185D.

Nenkep V, Yun K, Son BW. Oxysporizoline, an antibacterial polycyclic quinazoline alkaloid from the marine-mudflat-derived fungus Fusarium oxysporum. J Antibiot (Tokyo). 2016 Sep;69(9):709-11. doi: 10.1038/ja.2015.137.

Chen S, Jiang M, Chen B, Salaenoi J, Niaz SI, He J, Liu L. Penicamide A, A unique N,N'-ketal quinazolinone alkaloid from ascidian-derived fungus Penicillium sp. 4829. Mar Drugs. 2019 Sep 5;17(9):522. doi: 10.3390/md17090522.

De AK, Muthiyan R, Mondal S, Mahanta N, Bhattacharya D, Ponraj P, et al. A natural quinazoline derivative from marine sponge Hyrtios erectus induces apoptosis of breast cancer cells via ROS production and intrinsic or extrinsic apoptosis pathways. Mar Drugs. 2019 Nov 23;17(12):658. doi: 10.3390/md17120658.

Pereira JR, Hilário FF, Lima AB, Silveira ML, Silva LM, Alves RBet al. Cytotoxicity evaluation of marine alkaloid analogues of viscosaline and theonelladin C. Biomed Prev Nutr. 2012;2(2):145-8. doi: 10.1016/j.bionut.2012.01.003.

De Rop AS, Rombaut J, Willems T, De Graeve M, Vanhaecke L, Hulpiau P, et al. Novel alkaloids from marine actinobacteria: discovery and characterization. Mar Drugs. 2021 Dec 22;20(1):6. doi: 10.3390/md20010006.

Kiichi Y, Fukuoka K, Kitano A, Ishino K, Kotoku N. Unified synthesis and biological evaluation of makaluvamine j and its analogs. Molecules. 2024; 29(6):1389. doi: 10.3390/molecules29061389.

Boucle S, Melin C, Clastre M, Guillard J. Design, synthesis and evaluation of new marine alkaloid-derived pentacyclic structures with anti-tumoral potency. Mar Drugs. 2015 Jan 19;13(1):655-65. doi: 10.3390/md13010655.

Munekata PES, Pateiro M, Conte-Junior CA, Domínguez R, Nawaz A, Walayat N, et al. Marine alkaloids: compounds with in vivo activity and chemical synthesis. Mar Drugs. 2021 Jun 28;19(7):374. doi: 10.3390/md19070374.

Berlinck RG, Britton R, Piers E, Lim L, Roberge M, Moreira da Rocha R, et al. Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum: structure elucidation and synthesis. J Organic Chem. 1998:63(26):9850-6. doi: 10.1021/jo981607p.

Cao B, Ding H, Yang R, Wang X, Xiao Q. Total Synthesis of a marine alkaloid—rigidin E. Marine Drugs. 2012; 10(6):1412-1421. doi: 10.3390/md10061412.

Cafieri F, Fattorusso E, Mangoni A, Taglialatela-Scafati, O. Dispacamides, anti-histamine alkaloids from Caribbean Agelas sponges. Tetrahedron Lett. 1996;37(20):3587-90. doi: 10.1016/0040-4039(96)00629-6.

Loaëc N, Attanasio E, Villiers B, Durieu E, Tahtouh T, Cam M, et al. Marine-derived 2-aminoimidazolone alkaloids. leucettamine b-related polyandrocarpamines inhibit mammalian and protozoan DYRK & CLK kinases. Mar Drugs. 2017 Oct 17;15(10):316. doi: 10.3390/md15100316.

Rogers EW, Molinski TF. A cytotoxic carotenoid from the marine sponge Prianos osiros. J Nat Prod. 2005 Mar;68(3):450-2. doi: 10.1021/np0497797.

Matsuno T, Maoka T, Katagiri K, Komori T. A new carotenoid, isorenieradicistene from the sea sponge Suberites sericeus. Nippon Suisan Gakkaishi. 1984;50(6):1071-5. doi: 10.2331/SUISAN.50.1071.

Look SA, Fenical W, Jacobs RS, Clardy J. The pseudopterosins: anti-inflammatory and analgesic natural products from the sea whip Pseudopterogorgia elisabethae. Proc Natl Acad Sci U S A. 1986 Sep;83(17):6238-40. doi: 10.1073/pnas.83.17.6238.

Alves A, Sousa E, Kijjoa A, Pinto M. Marine-derived compounds with potential use as cosmeceuticals and nutricosmetics. Molecules. 2020; 25(11):2536. doi: 10.3390/molecules25112536.

Ullah A, Munir S, Badshah SL, Khan N, Ghani L, Poulson BG, Emwas AH, Jaremko M. Important flavonoids and their role as a therapeutic agent. Molecules. 2020 Nov 11;25(22):5243. doi: 10.3390/molecules25225243.

Kalinin VI, Ivanchina NV, Krasokhin VB, Makarieva TN, Stonik VA. Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles. Mar Drugs. 2012 Aug;10(8):1671-1710. doi: 10.3390/md10081671.

Li K, Cai J, Su Z, Yang B, Liu Y, Zhou X, Huang J, Tao H. Glycosylated natural products from marine microbes. Front Chem. 2020 Jan 10;7:879. doi: 10.3389/fchem.2019.00879.

Chen S, Zhang D, Chen M, Zhang Z, Lian XY. A rare diketopiperazine glycoside from marine-sourced Streptomyces sp. ZZ446. Nat Prod Res. 2020 Apr;34(7):1046-1050. doi: 10.1080/14786419.2018.

Hoffmann A, Steffens U, Maček B, Franz-Wachtel M, Nieselt K, Harbig TA, et al. The unusual mode of action of the polyketide glycoside antibiotic cervimycin C. mSphere. 2024 May 29;9(5):e0076423. doi: 10.1128/msphere.00764-23.

Mayer AMS, Rodríguez AD, Taglialatela-Scafati O, Fusetani N. Marine pharmacology in 2012-2013: marine compounds with antibacterial, antidiabetic, antifungal, anti-inflammatory, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous systems, and other miscellaneous mechanisms of action. Mar Drugs. 2017 Aug 29;15(9):273. doi: 10.3390/md15090273.

D'Armas HT, Mootoo BS, Reynolds WF. Steroidal compounds from the Caribbean octocoral Eunicea laciniata. J Nat Prod. 2000 Dec;63(12):1669-71. doi: 10.1021/np000315s.

Sang VT, Hung ND, Se-Kwon K. Pharmaceutical properties of marine polyphenols: An overview. ACTA Pharmaceutica Sci 2019;57(2):217. doi: 10.23893/1307-2080.APS.05714.

Published
2025/04/30
Section
Review article