Bioactive Marine Natural Products

Code:

RM10

Acronym:

PNMB

Keywords
Classification	Keyword
OFICIAL	Marine Sciences

Instance: 2025/2026 - 1S (of 15-09-2025 to 13-02-2026)

Active?	Yes
Responsible unit:	Chemistry
Course/CS Responsible:	Master Degree in Marine Sciences - Marine Resources

Cycles of Study/Courses

Acronym	No. of Students	Study Plan	Curricular Years	Credits UCN	Credits ECTS	Contact hours	Total Time
MCMRM	5	Oficial Plan 2018	1	-	5	50	135

Teaching language

Suitable for English-speaking students
Obs.: Português

Objectives

- Understand the scientific foundations of organic chemistry, biochemistry, and cell biology applied to the study of marine natural products.

- Recognize the diversity and importance of marine natural products (corals, sponges, algae, cyanobacteria, fungi, etc.) as sources of bioactive compounds with applications in medicine, cosmetics, food, and biotechnology.

- Acquire knowledge and apply methods of extraction, fractionation, and purification of secondary metabolites derived from marine organisms.

- Master concepts and instrumental analytical techniques (HPLC, infrared spectroscopy, mass spectrometry, and NMR) for the structural characterization of natural products.

- Explore the mechanisms of action of marine bioactive compounds in the context of cytotoxicity, cancer, and antimicrobial resistance.

- Develop practical laboratory skills in the extraction, isolation, characterization, and evaluation of the bioactivity of natural compounds.

- Discuss the processes of screening, preclinical validation, and drug discovery from marine organisms, from laboratory research to potential clinical trials.

- Foster critical and scientific thinking, enhancing the ability to analyze experimental data, interpret spectra, solve problems, and present group work results.

- Raise awareness of current and future challenges in the sustainable exploitation of marine resources and the development of innovative therapeutic solutions.

Learning outcomes and competences

By the end of this course unit, students should be able to:

- Identify and describe the main classes of marine natural products and their potential bioactive effects.

- Apply extraction, fractionation, and purification techniques to secondary metabolites obtained from marine organisms.

- Interpret and analyze data from instrumental techniques (HPLC, IR, MS, NMR) to structurally characterize bioactive compounds.

- Evaluate the bioactivity of marine compounds through cytotoxicity and antimicrobial activity assays.

- Relate the mechanisms of action of bioactive compounds to biological processes such as apoptosis, cell cycle, carcinogenesis, and antibiotic resistance.

- Develop and perform laboratory protocols with safety, accuracy, and critical thinking.

- Integrate interdisciplinary knowledge (chemistry, biology, biotechnology, pharmacology) in the analysis of potential therapeutic applications.

- Communicate scientific results clearly and effectively in oral presentations and group projects.

- Critically reflect on the ethical, environmental, and scientific challenges of exploiting marine resources for pharmaceutical purposes.

Working method

Presencial

Pre-requirements (prior knowledge) and co-requirements (common knowledge)

PREREQUISITES (PREVIOUS KNOWLEDGE)

- General and basic organic chemistry:  atomic and molecular structure, chemical bonds, functional groups, stereochemistry, fundamental organic reactions.

- Fundamental biochemistry: primary and secondary metabolism, classes of biomolecules (proteins, lipids, carbohydrates, nucleic acids). Basic notions of secondary metabolite biosynthesis.

- Cell and molecular biology: structure and function of the cell, mechanisms of cell division, apoptosis, and basics of the cell cycle.

- Basic microbiology: structure and diversity of microorganisms, ecological roles, basic knowledge of antibiotics and resistance.

- Laboratory methods: basic concepts of solution preparation, use of micropipettes, sterility, good laboratory practices, and safety.

 

 

SKILLS AND COMPETENCIES

- Mastery of extraction, purification, and characterization techniques for natural products.

- Ability to interpret spectra and chromatographic data.

- Knowledge of drug discovery and development processes from marine sources.

- Execution of experimental procedures with safety and good laboratory practices.

- Ability to plan and carry out cytotoxicity and antibacterial assays.

- Analysis and interpretation of experimental results.

- Problem-solving in theoretical and practical contexts related to natural products chemistry and biology.

- Teamwork and scientific collaboration.

- Oral and written communication in a scientific context.

Program

Theoretical and Theoretical-Practical Classes

1 – Introduction to the course unit (30 min) – Objectives, learning outcomes, syllabus, assessment, and schedule.

2 – Introduction to organic chemistry (1.5h) – Molecular structure and chemical bonding, functional groups and nomenclature, stereochemistry and isomerism, reaction mechanisms and biosynthesis of Natural Products.

3 – Applications of marine natural products (2h) – Natural Products, secondary metabolites (plants, algae, and fungi), applications of marine natural products in medicine, cosmetics, and food.

4 – Extraction and screening methods (2h) – Efficient methods for extracting secondary metabolites from various sources (plants, marine invertebrates, and microorganisms). Traditional extraction methods: maceration, infusion, decoction, and percolation; advanced extraction methods: Soxhlet extraction, ultrasound-assisted extraction, microwave-assisted extraction, supercritical fluid extraction, pressurized liquid extraction, enzyme-assisted extraction, and ionic liquid extraction.

5 – Fractionation and purification methods (2h) – Crystallization. Chromatography: origin, classification of chromatographic processes, liquid chromatography (components of the chromatographic system, column chromatography, thin-layer chromatography).

6 – High-Performance Liquid Chromatography (HPLC) (4h) – Principles of chromatographic separation. Components of an HPLC system: solvent reservoir, pump, injector, column, detector, and data processor. Types of stationary phases and mobile phases. Normal-phase vs. reversed-phase chromatography. Isocratic and gradient elution. Detection methods (UV-Vis, fluorescence, mass spectrometry coupling). Interpretation of chromatograms: retention time, resolution, selectivity, efficiency. Applications of HPLC in the isolation and analysis of marine natural products. Problem-solving exercises.

7 – Infrared spectroscopy (2h) – Electromagnetic radiation. Infrared spectroscopy. The infrared spectrum: regions, characteristic absorption bands, intensity of absorption bands, position and shape of absorption bands. Analysis of an infrared spectrum. Problem-solving.

8 – Mass spectrometry (2h) – Sample ionization. Detection of fragments. The mass spectrum: molecular ion, base peak, fragmentation, isotopes. Determination of molecular formula using the rule of 13. High-resolution mass. Problem-solving.

9 – Nuclear magnetic resonance (12h) – Applications and history of nuclear magnetic resonance. Nuclear magnetic resonance: alpha and beta spin states, spin inversion, spectrometer, sample preparation, Fourier transform. The NMR spectrum: shielding/deshielding effects, number of signals, chemical shift, characteristic chemical shifts in proton NMR, diamagnetic anisotropy, integration, signal splitting, coupling constants. Carbon-13 NMR: advantages/disadvantages compared with proton NMR, characteristic chemical shifts in carbon-13 NMR. DEPT (Distortionless Enhancement by Polarization Transfer). 2D NMR: COSY (Homonuclear Correlation Spectroscopy), HSQC (Heteronuclear Single Quantum Correlation), and HMBC (Heteronuclear Multiple Bond Correlation). Problem-solving. Challenge class – to which compounds do these spectra belong?

10 – Group work presentation (1h).

11 – Exploring the cytotoxic effect of marine bioactive compounds (2h) – Cytotoxicity, mechanisms of cytotoxicity, cytotoxicity assessment methods, types of cytotoxicity, cancer, carcinogenic process, targets of bioactive compounds in tumor cells, marine bioactive compounds, introduction to usnic acid, mechanism of action of usnic acid in cancer cells, studies on the cytotoxic effects of usnic acid, combination with anticancer drugs, additive and synergistic effects, general procedures for drug discovery from marine sources.

12 – From the sea to innovative therapeutic solutions: in vitro screening of marine bioactive compounds (4h) – Marine Natural Products: bioactive compounds from corals, sponges, algae, or seaweed. In Vitro Screening of Marine Bioactive Compounds, In Vivo Validation, General Procedures for Marine-Derived Drug Discovery, Clinical Trials.

13 – Marine bioactive compounds: a promising frontier in cancer treatment (2h) – Overview, case study, drug resistance, mechanisms of drug resistance: efflux pumps, DNA repair, cell cycle alterations, tumor microenvironment.

14 – The ecology of antimicrobial resistance (2h) – Antibiotics: what they are, brief history, classification of resistance. Emergence and spread of resistance: why are so many antibiotics used? what are we releasing into the environment?. We must do more and better: monitoring antibiotic use and resistance, reducing use, containing dissemination, better understanding bacterial evolutionary versatility, discovering new antibiotics, and new infection control strategies.

 

Laboratory Practical Classes

Practical Work 1 – Extraction and isolation of pigments from marine organisms. Comparison of chromatographic profiles of pigments from an alga (Chlorella vulgaris) vs. a cyanobacterium (Spirulina platensis) (3h).

Practical Work 2 – Isolation and characterization of usnic acid extracted from lichens (Cladonia portentosa) (3h).

Practical Work 3 – Exploration of the cytotoxic effect of Usnic Acid (3h).

Practical Work 4 – Screening of antibacterial activity and synergy – Disk diffusion assay – Kirby-Bauer method (2h).

Mandatory literature

E. Ibañez, F. Rindi, M. Hayes; Marine Bioactive Compounds: Source, Characterization and Application, Maria Hyes , 2014. ISBN: 13: 978- 1489986108
David R. Klein; Organic Chemistry, 4th Edition, Wiley, 2021. ISBN: 978-1-119-77674-1
Hiromasa Kiyota; Marine Natural Products, Springer, 2021. ISBN: Hardcover ISBN 978-981-16-4636-2
Ernö Pretsch , Philippe Bühlmann , Martin Badertscher; Structure Determination of Organic Compounds, Springer, 2020. ISBN: 978-3-662-62438-8
Pallaval Veera Bramhachari, Chanda Vikrant Berde; Marine Bioactive Molecules for Biomedical and Pharmacotherapeutic Applications, Springer, 2023. ISBN: 978-981-99-6769-8

Teaching methods and learning activities

- Theoretical classes: oral lectures supported by audiovisual resources (slides, videos, molecular models) to introduce fundamental concepts of chemistry, biology, and pharmacology of marine natural products.

- Theoretical-practical classes: solving exercises on the interpretation of spectra (IR, MS, NMR) and chromatograms; analysis of extraction, purification, and screening methodologies for bioactive compounds.

- Laboratory practical classes: group experimental work including extraction, isolation, characterization, and bioactivity assays of marine compounds. Application of good laboratory practices, safety procedures, and recording of results in a laboratory notebook.

- Group project development: preparation of a group project with oral presentation and class discussion.

- Challenge class: interpretation of real spectra and compound identification.

- Reading of reference bibliography and scientific articles.

- Preparation for tests, laboratory reports, and project presentations.

keywords

Physical sciences > Chemistry > Applied chemistry > Pharmaceutical chemistry
Physical sciences > Chemistry > Organic chemistry
Natural sciences
Technological sciences > Technology > Biotecnology

Evaluation Type

Distributed evaluation without final exam

Assessment Components

Designation	Weight (%)
Participação presencial	5,00
Apresentação/discussão de um trabalho científico	15,00
Teste	60,00
Trabalho laboratorial	20,00
Total:	100,00

Amount of time allocated to each course unit

Designation	Time (hours)
Estudo autónomo	100,00
Total:	100,00

Eligibility for exams

75% attendance.

Calculation formula of final grade

Continuous evaluation: 100%

Observations

This course unit requires a basic background in Chemistry, particularly in General and Organic Chemistry, to support the understanding of the topics covered.