Macroalgae are increasingly viewed as a source of secondary metabolites with great potential for the development of new drugs. In this development, in vitro studies are only the first step in a long process, while in vivo studies and clinical trials are the most revealing stages of the true potential and limitations that a given metabolite may have as a new drug. This literature review aims to give a critical overview of the secondary metabolites that reveal the most interesting results in these two steps. Phlorotannins show great pharmaceutical potential in in vivo models and, among the several examples, the anti-dyslipidemia activity of dieckol must be highlighted because it was more effective than lovastatin in an in vivo model. The IRLIIVLMPILMA tridecapeptide that exhibits an in vivo level of activity similar to the hypotensive clinical drug captopril should still be stressed, as well as griffithsin which showed such stunning results over a variety of animal models and which will probably move onto clinical trials soon. Regarding clinical trials, studies with pure algal metabolites are scarce, limited to those carried out with kahalalide F and fucoxanthin. The majority of clinical trials currently aim to ascertain the effect of algae consumption, as extracts or fractions, on obesity and diabetes.
Chalcones and flavanones are isomeric structures and also classes of natural products, belonging to the flavonoid family. Moreover, their wide range of biological activities makes them key scaffolds for the synthesis of new and more efficient drugs. In this work, the synthesis of hydroxy and/or methoxychalcones was studied using less common bases, such as sodium hydride (NaH) and lithium bis(trimethylsilyl)amide (LiHMDS), in the aldol condensation. The results show that the use of NaH was more effective for the synthesis of 2′-hydroxychalcone derivatives, while LiHMDS led to the synthesis of polyhydroxylated chalcones in a one-pot process. During this study, it was also possible to establish the conditions that favor their isomerization into flavanones, allowing at the same time the synthesis of hydroxy and/or methoxyflavanones. The chalcones and flavanones obtained were evaluated to disclose their antioxidant, anticholinesterasic, antibacterial and antitumor activities. 2′,4′,4-Trihydroxychalcone was the most active compound in terms of antioxidant, anti-butyrylcholinesterase (IC50 26.55 ± 0.55 μg/mL, similar to control drug donepezil, IC50 28.94 ± 1.76 μg/mL) and antimicrobial activity. 4′,7-Dihydroxyflavanone presented dual inhibition, that is, the ability to inhibit both cholinesterases. 4′-Hydroxy-5,7-dimethoxyflavanone and 2′-hydroxy-4-methoxychalcone were the compounds with the best antitumor activity. The substitution pattern and the biological assay results allowed the establishment of some structure/activity relationships.
17 July 2017 in ACS Sustainable Chemistry & Engineering
Seaweed beach-casts are a seasonal phenomenon that regularly deposits tons of algae biomass on beaches, which are usually disposed of in landfills. The present work aimed to contribute to the valorization of this biomass by studying bioactivities that reveal its potential in the pharmaceutical and/or cosmeceutical industries. Methanol and ethanol extracts and fractions from 15 beach-casts biomass were tested for a range of bioactivities. Eight of the most active samples exhibit IC50 values between 11.38 µg/mL and 19.28 µg/mL and selectivity indexes higher than 3.8, against NCI-H1299 (lung cancer) and T47D (breast cancer). Concerning antiaging potential, all the extracts tested presented UV protection, with SPF values above 30, like the standard sunscreen. Regarding aging-related enzymes, 24 samples were tyrosinase inhibitors exhibiting IC50 values from 9.01 µg/mL to 200.09 µg/mL. Eight extracts inhibited collagenase (IC50 < 248.76 µg/mL), two of them more actively than positive control EDTA (IC50 = 59.26 µg/mL). In addition to UV protection, the cumulative effect of antityrosinase and anticollagenase activities shown by the samples suggest that they may play a significant role in preventing skin photoaging. The results obtained demonstrate the high potential of beach-cast seaweed biomass as sources of cosmetic bioproducts with antiaging effects, and of selective cytotoxic metabolites.