New Aromatic Bisabolane Derivatives with Lipid-Reducing Activity from the Marine Sponge Myrmekioderma sp.

Costa, Margarida; Coello, Laura; Urbatzka, Ralph; Pérez, Marta; Þorsteinsdóttir, Margrét

doi:10.3390/md17060375

Cited by 14 publications

(10 citation statements)

References 34 publications

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“…Our work evidenced the lipid-reducing activity of some extracts (EL, ML) with EC 50 values of 1.2-2.2 µg/mL using the zebrafish Nile red fat metabolism assay as a whole small animal model in vivo. This assay was used previously to show the lipid-lowering effects of extracts of raw materials or marine organisms (wine lee, actinobacteria, cyanobacteria, sponges), or isolated compounds (polyphenols, chlorophyll derivatives) [19][20][21][22][23]. The original paper from Jones et al [24] demonstrated that zebrafish responded to lipid modulator drugs in the same way as humans.…”

Section: Discussionmentioning

confidence: 99%

The Marine Seagrass Halophila stipulacea as a Source of Bioactive Metabolites against Obesity and Biofouling

et al. 2020

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Marine organisms, including seagrasses, are important sources of biologically active molecules for the treatment of human diseases. In this study, organic extracts of the marine seagrass Halophila stipulacea obtained by different polarities from leaves (L) and stems (S) (hexane [HL, HS], ethyl acetate [EL, ES], and methanol [ML, MS]) were tested for different bioactivities. The screening comprehended the cytotoxicity activity against cancer cell lines grown as a monolayer culture or as multicellular spheroids (cancer), glucose uptake in cells (diabetes), reduction of lipid content in fatty acid-overloaded liver cells (steatosis), and lipid-reducing activity in zebrafish larvae (obesity), as well as the antifouling activity against marine bacteria (microfouling) and mussel larval settlement (macrofouling). HL, EL, HS, and ES extracts showed statistically significant cytotoxicity against cancer cell lines. The extracts did not have any significant effect on glucose uptake and on the reduction of lipids in liver cells. The EL and ML extracts reduced neutral lipid contents on the larvae of zebrafish with EC50 values of 2.2 µg/mL for EL and 1.2 µg/mL for ML. For the antifouling activity, the HS and ML extracts showed a significant inhibitory effect (p < 0.05) against the settlement of Mytilus galloprovincialis plantigrade larvae. The metabolite profiling using HR-LC-MS/MS and GNPS (The Global Natural Product Social Molecular Networking) analyses identified a variety of known primary and secondary metabolites in the extracts, along with some unreported molecules. Various compounds were detected with known activities on cancer (polyphenols: Luteolin, apeginin, matairesinol), on metabolic diseases (polyphenols: cirsimarin, spiraeoside, 2,4-dihydroxyheptadec-16-ynyl acetate; amino acids: N-acetyl-L-tyrosine), or on antifouling (fatty acids: 13-decosenamide; cinnamic acids: 3-hydroxy-4-methoxycinnamic acid, alpha-cyano-4-hydroxycinnamic), which could be, in part, responsible for the observed bioactivities. In summary, this study revealed that Halophila stipulacea is a rich source of metabolites with promising activities against obesity and biofouling and suggests that this seagrass could be useful for drug discovery in the future.

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Section: Discussionmentioning

confidence: 99%

The Marine Seagrass Halophila stipulacea as a Source of Bioactive Metabolites against Obesity and Biofouling

et al. 2020

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“…Another four new aromatic bisabolanes, including 6-(3-hydroxy-6-methyl-1,5-heptadien-2-yl)-3-methylbenzene-1,4-diol ( 86 ), 4-hydroxy-3,7-dimethyl-7-(3-methylbut-2-en-1-yl)benzofuran-15-one ( 87 ), 6-(2-methoxy-5-methylhept-4-en-2-yl)-3-methylbenzene-1,4-diol ( 88 ), and 9-(3,3-dimethyloxiran-2-yl)-1,7-dimethyl-7-chromen-4-ol ( 89 ), were obtained from an organic extract of the marine sponge Myrmekioderma sp. ( Costa et al, 2019 ). All of the isolated compounds represented cyclic bisabolanes bearing rich oxo functionality.…”

Section: Chemical Diversity Of the Newly-discovered Marine-derived Bi...mentioning

confidence: 99%

“…It appeared that the acetoxy group at C-11 could significantly enhance inhibitory ability against marine phytoplanktons. Zebrafish Nile red fat metabolism assay revealed that compounds 86 , 87 , and 89 had significant lipid-reducing activity with IC 50 values of 7.89, 12.61, and 1.22 μM, respectively ( Costa et al, 2019 ). 92 containing an isonitrile group exerted strong brine shrimp lethal activity with an LC 50 of 0.1 μg/ml ( Iwashima et al, 2002 ).…”

Section: Biological Activities Of Bisabolanesmentioning

confidence: 99%

Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

Liu

Yang

et al. 2022

Front. Chem.

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Natural products, characterized by intriguing scaffold diversity and structural complexity, as well as significant agricultural and medicinal activities, have been a valuable source of agrochemicals/drugs development and have historically made a huge contribution to pharmacotherapy. Structurally, bisabolanes are a family of naturally occurring sesquiterpenoids that featured a hexatomic ring core incorporating with eight continuous carbons, which cause high structural variability along the alkyl side chain to form abundant functionalities. Moreover, apart from their interesting structures, bisabolanes have shown multitudinous bioactivities. Bisabolanes are distributed in a variety of marine invertebrates, terrestrial plant, and microbial sources. Interestingly, bisabolanes characterized from marine environment possess unique characteristics both structurally and biologically. A total of 296 newly-discovered bisabolanes were searched. Among them, 94 members were isolated from marine organisms. This review particularly focuses on the new bisabolanes characterized from marine organisms (covering from 2000 to 2021), including marine-derived fungi, algae, soft corals, and sponges, with emphasis on the diversity of their chemical structures as well as the novelty and differences between terrestrial and marine sources. Moreover, a wide range of bioactivities of marine-derived bisabolanes, including antimicrobial, anti-inflammatory, enzyme inhibitory, and cytotoxic properties, are presented herein, which is considered to be a promising resource for the discovery of new drug leads and agrochemicals.

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“…Despite being a rich source of highly bioactive compounds [ 93 ], there are few studies in the literature regarding the extraction and identification of polyphenols in sponges. Methanol and dichloromethane were normally used for extraction, while new phenolic compounds have been identified using HRAPCIMS, HRESIMS and NMR.…”

Section: Marine Phenolics: Sources and Phenolic Compositionmentioning

confidence: 99%

Bioactive Properties of Marine Phenolics

2020

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Phenolic compounds from marine organisms are far less studied than those from terrestrial sources since their structural diversity and variability require powerful analytical tools. However, both their biological relevance and potential properties make them an attractive group deserving increasing scientific interest. The use of efficient extraction and, in some cases, purification techniques can provide novel bioactives useful for food, nutraceutical, cosmeceutical and pharmaceutical applications. The bioactivity of marine phenolics is the consequence of their enzyme inhibitory effect and antimicrobial, antiviral, anticancer, antidiabetic, antioxidant, or anti-inflammatory activities. This review presents a survey of the major types of phenolic compounds found in marine sources, as well as their reputed effect in relation to the occurrence of dietary and lifestyle-related diseases, notably type 2 diabetes mellitus, obesity, metabolic syndrome, cancer and Alzheimer’s disease. In addition, the influence of marine phenolics on gut microbiota and other pathologies is also addressed.

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New Aromatic Bisabolane Derivatives with Lipid-Reducing Activity from the Marine Sponge Myrmekioderma sp.

Cited by 14 publications

References 34 publications

The Marine Seagrass Halophila stipulacea as a Source of Bioactive Metabolites against Obesity and Biofouling

The Marine Seagrass Halophila stipulacea as a Source of Bioactive Metabolites against Obesity and Biofouling

Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

Bioactive Properties of Marine Phenolics

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