Antioxidant and anti-inflammatory oxygenated meroterpenoids from the thalli of red seaweed Kappaphycus alvarezii

Makkar, Fasina; Chakraborty, Kajal

doi:10.1007/s00044-018-2210-0

Cited by 22 publications

(11 citation statements)

References 18 publications

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“…The histidine-related dipeptides carnosine (228) and anserine (229) were shown to exert comparable antioxidant activities, as measured by ferric thiocyanate and TBARS (85.2% and 84.1% inhibition for 228 and 94.4% and 89.1% inhibition for 229, respectively), to those of α-tocopherol (88.2% and 86.7%, respectively) and BHT (99.8% and 98.2%, respectively) [198]. Moreover, Cermeno et al (2019) isolated a series of bioactive peptides (232)(233)(234)(235)(236)(237)(238) from Porphyra dioica that displayed significant antioxidant activity as assessed using the ORAC assay [200]. It appears that peptides containing tyrosine in their structure (compounds 232, 233, 235, and 237) possessed higher levels of antioxidant activity.…”

Section: Nitrogenous Compoundsmentioning

confidence: 99%

Metabolites with Antioxidant Activity from Marine Macroalgae

et al. 2021

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Reactive oxygen species (ROS) attack biological molecules, such as lipids, proteins, enzymes, DNA, and RNA, causing cellular and tissue damage. Hence, the disturbance of cellular antioxidant homeostasis can lead to oxidative stress and the onset of a plethora of diseases. Macroalgae, growing in stressful conditions under intense exposure to UV radiation, have developed protective mechanisms and have been recognized as an important source of secondary metabolites and macromolecules with antioxidant activity. In parallel, the fact that many algae can be cultivated in coastal areas ensures the provision of sufficient quantities of fine chemicals and biopolymers for commercial utilization, rendering them a viable source of antioxidants. This review focuses on the progress made concerning the discovery of antioxidant compounds derived from marine macroalgae, covering the literature up to December 2020. The present report presents the antioxidant potential and biogenetic origin of 301 macroalgal metabolites, categorized according to their chemical classes, highlighting the mechanisms of antioxidative action when known.

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Section: Nitrogenous Compoundsmentioning

confidence: 99%

Metabolites with Antioxidant Activity from Marine Macroalgae

et al. 2021

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“…Sargassum muticum can produce tetraprenyltoluquinol meroterpenoid that has antioxidant activity and can give protection against oxidative damage [63]. Likewise, highly oxygenated meroterpenoids with antioxidant property have been found from Kappaphycus alvarezii, a red macroalgae [64]. Hypnea musciformis has meroterpenoid like 2-(tetrahydro-5-(4-hydroxyphenyl)-4-pentylfuran-3-yl)ethyl-4-hydroxy benzoate which shows antioxidative properties comparable to gallic acid [65].…”

Section: Meroterpenoidsmentioning

confidence: 99%

Algal Terpenoids: A Potential Source of Antioxidants for Cancer Therapy

Ferdous¹,

Yusof²

2021

Biochemistry

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In cancer treatment, increase in drug resistance and decrease in new chemotherapeutic drugs have become a pressing problem. Hence, searching for novel anticancer agents with less toxicity and high sensitivity is expanding gradually. Many preclinical and clinical studies indicate that natural antioxidants can help combating carcinogenicity and reduce the adverse effects on cancer therapy, when used alone or as adjuvant in chemotherapy. Consequently, marine algae pave the way for exploring more potential antioxidant compounds which have pharmaceutical importance. Algal terpenoids comprise a large group of bioactive compounds that have excellent antioxidative property and can be used as source of antioxidant in cancer therapy. This chapter summarizes the potential role of terpenoids from algal sources in inhibiting cancer cells, blocking cell cycle, hindering angiogenesis and metastasis as well as in inducing apoptosis.

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“…Natural products are extensively known to be a major resource of biologically active compounds that hold manifold and unusual platforms [1]. Terpenoids are structurally differing secondary metabolites with more than 40,000 reported structural diversity bearing valuable bioactive characters [2,3] Their structures are chiefly sourced from plants and microbes, which are mainly biosynthesized by the 2-C-methylerythritol 4-phosphate pathway or the mevalonate pathway [4,5]. Terpenoids were known to have potential pharmacological properties against fatal diseases, such as malaria [6], cardiovascular disease [7], and cancer [3,8].…”

Section: Introductionmentioning

confidence: 99%

“…Meroterpenoids are hybrid secondary metabolites that moderately obtain from the terpenoid pathways [9,10]. Especially, meroterpenoids derived from polyketide and terpenoid precursors have sp 3 -rich terpenoid scaffolds and sp 2 -rich polyketide scaffolds, which argue different pharmacological activities [11]. Their carbon skeletons come from intra-and intermolecular cyclizations and/or rearrangements of terpene chains to give unique polycyclic or macrocyclic structures often possessing varied functional groups [12,13].…”

Section: Introductionmentioning

confidence: 99%

“…Terretonintype ( Figure 10) congeners bearing a δ-lactone in ring D are derived from terrenoid (andrastin-type) by D-ring expansion and bizarre rearrangement of the methoxy group [78]. Berkeleyone-type (or protoaustinoid-type) ( Figure 11) derivatives being the caspase-1 inhibitor is the meroterpenoids defining a set of unique and functionalized chemical scaffolds, which are identified by the existence bicyclo [3.3,1]nonane or its rearranged bicyclo [3,2,1]octane unit in rings C and D [79], and are originated by the same intermediate as for andrastins with miscellaneous rearrangement. Austinol ( Figure 12) and its analogs displayed a pentacyclic scaffold with a spiro-δlactone in ring A and a γ-lactone in ring E, that was originated from protoaustinoid through oxidation and ring rearrangement [80].…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Meroterpenes: A Review

2020

J Pharmacol Pharm Res

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Meroterpenes are mixed natural products. They consist of one terpene and one polyketide skeletons. Due to their structural varieties, meroterpenoids display diverse bioactivities, like anticancer, anti-inflammatory, antibiotic , and antifibrotic activities. Our aim is to highlight the importance of the meroterpenes which have been the most studied on and reported among the bioactive natural products last years. According to our literature survey, the three most effective meroterpene groups have been determined. One group is the meroterpenes isolated from the brown alga Sargassum siliquastrum: Sargachromanol E, D, and P have exerted strong cytotoxicity against AGS (gastric cancer cells), HT-29 (colorectal adenocarcinoma cancer cell), and HT-1080 (human fibrosarcoma cells) cell lines, with IC 50 values varying from 0.5 to 5.7 μg/mL [100]. The other most effective meroterpene is Eucalypglobulusal F, which is isolated from E. globulus fruit, has shown cytotoxicity against the human acute lymphoblastic cell line (CCRF-CEM) with an IC 50 value of 3.3 μM [89]. Also, the last one is 11-dehydroxy epoxyphomalin A (4), from the endophytic fungus Peyronellaea coffeae-arabicae FT238, which was obtained from the native Hawaiian plant Pritchardia lowreyana showed a strong antiproliferative effect with an IC 50 of 0.5 μM against OVCAR3 (Ovarian carsinoma cells) [102]. Conclusively, meroterpenes have potential nominees as an anticancer drug. Moreover, the structure of naturally isolated meroterpenes has a moderate anticancer activity that can easliy be modified by semi-synthetic ways due to their simple structures comparing to other natural compounds such as triterpenes or phenolic compounds.

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Antioxidant and anti-inflammatory oxygenated meroterpenoids from the thalli of red seaweed Kappaphycus alvarezii

Cited by 22 publications

References 18 publications

Metabolites with Antioxidant Activity from Marine Macroalgae

Metabolites with Antioxidant Activity from Marine Macroalgae

Algal Terpenoids: A Potential Source of Antioxidants for Cancer Therapy

Cytotoxic Meroterpenes: A Review

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