Neuroinhibitory meroterpenoid compounds from Cordia oncocalyx

Matos, Taynara Simão; Silva, Ana Karine O.; Quintela, Amanda Lemos; Pinto, L. Francisco das Chagas; Canuto, Kirley Marques; Braz‐Filho, Raimundo; Fonseca, Maria Júlia Sousa; Luna-Costa, Angélica Maria; Paz, Iury A.; Nascimento, Nilberto Robson Falcão do; Silveira, Edilberto R.; Pessoa, Otília Deusdênia Loiola

doi:10.1016/j.fitote.2017.09.021

Cited by 9 publications

(3 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They isolated a new compound rel-1,4,8α-trihydroxy-5-furanyl-2-methoxy-8aβ-methyl-6,7,8,8a,9,10-hexahydro-10-anthracenone, reported to possess the neuroinhibitory activity, and none of the pharmacological antagonists was reversed. Additionally, compounds rel-1,4,8α-trihydroxy-5-furanyl-2-methoxy- 8aβ-methyl-6,7,8, 8a, 9,10-hexahydro-10-anthracenone and 6-formyl-2-methoxy-9-methyl-1,4-phenanthrendione were able to inhibit the 69% and 63% contractions, respectively ( Matos et al, 2017 ).…”

Section: Biological Activities Of Meroterpenoidsmentioning

confidence: 99%

Biological activities of meroterpenoids isolated from different sources

et al. 2022

View full text Add to dashboard Cite

Meroterpenoids are natural products synthesized by unicellular organisms such as bacteria and multicellular organisms such as fungi, plants, and animals, including those of marine origin. Structurally, these compounds exhibit a wide diversity depending upon the origin and the biosynthetic pathway they emerge from. This diversity in structural features imparts a wide spectrum of biological activity to meroterpenoids. Based on the biosynthetic pathway of origin, these compounds are either polyketide-terpenoids or non-polyketide terpenoids. The recent surge of interest in meroterpenoids has led to a systematic screening of these compounds for many biological actions. Different meroterpenoids have been recorded for a broad range of operations, such as anti-cholinesterase, COX-2 inhibitory, anti-leishmanial, anti-diabetic, anti-oxidative, anti-inflammatory, anti-neoplastic, anti-bacterial, antimalarial, anti-viral, anti-obesity, and insecticidal activity. Meroterpenoids also possess inhibitory activity against the expression of nitric oxide, TNF- α, and other inflammatory mediators. These compounds also show renal protective, cardioprotective, and neuroprotective activities. The present review includes literature from 1999 to date and discusses 590 biologically active meroterpenoids, of which 231 are from fungal sources, 212 are from various species of plants, and 147 are from marine sources such as algae and sponges.

show abstract

Section: Biological Activities Of Meroterpenoidsmentioning

confidence: 99%

Biological activities of meroterpenoids isolated from different sources

et al. 2022

View full text Add to dashboard Cite

show abstract

“…About 350 species of that genus have been identified worldwide, mainly in warmer regions [8]. Previous phytochemical investigations of plants from this genus reported the isolation and characterization of different classes of secondary metabolites including naphthoquinones, hydroquinones [8], cromenes [9], terpenenoids [10] or polyphenols [11]. Meanwhile and based on some pharmacological surveys, essential oils from C. curassivica and C. gilletii appeared as active against some microbial strains [12,13] Some biological activities and in silico investigations of C. dichotoma were recently reported [14,15]; the plant is also known to contain, apart from allantoin (1) [16,17] which has been the subject of many quantum calculations [18,19], fatty acids (FA) [20].…”

Section: Introductionmentioning

confidence: 99%

“…Structures of the isolated compounds(1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) from the stems of C. batesii.…”

mentioning

confidence: 99%

Density Functional Theory of a New Derivative of Allantoin with Antiplasmodial Properties, Antimycobacterial Activities of Essential Oil from Cordia Batesii WERNHAM (Boraginaceae)

Tiam

Bikobo

Ndassa

et al. 2020

Preprint

View full text Add to dashboard Cite

Background: some chemical and pharmacological investigations were performed on the EtOAc and/or CH2Cl2 extracts of the stems of Cordia batesii (Boraginaeae); one of its components was subjected to some quantum calculations to get improvement in the understanding of its 13C–NMR and UV properties along with geometric, electronic, thermodynamic data and reactivity descriptors. Results: a new allantoin (1) derivative named batesiin (2) was characterized from the EtOAc extract; thirteen known compounds including allantoin (1) were either isolated or identified by means of MS, NMR, LC–MS and GC–MS. GC–MS was applied on a fraction of essential oil which was composed of a mixture of fatty acids (9–14). Density functional theory (DFT) calculations were applied on batesiin (2). Data were simulated using B3LYP and MPW1PW91 functionals; calculated chemical shifts at B3LYP/6–31G(d,p) and MPW1PW91/6–31G+(d,p) showed much better correlations with the experimental data. Time dependent DFT applied on 2 at B3LYP/6–31G+(d,p) displayed a major absorption band at λmax = 299.01 nm using chloroform as solvent, 3.01 nm higher than the experimental value. In addition, The MeOH extract of the stems and some isolated compounds were tested in vitro against Pf7G8 CQS and Pf Dd2 CQR strains of Plasmodium falciparum; meanwhile, the CH2Cl2 extract and the mixture of fatty acids (9–14) were tested on a resistant mycobacterial strain of Mycobacterium tuberculosis codified AC45. Stems disclosed a moderate antiplasmodial activity (IC50 = 50 μg/mL) and the mixture 9–14 a potent antimycobacterial activity with a MIC = 9.52 μg/mL.Conclusion: these results tend to emphasize on the use of DFT studies when trying to learn more about the chemical structure through spectroscopic data of a natural compound, especially the case of a derivative of allantoin (1); essential oil from Cordia batesii presents interesting antimycobacterial activities which need to gain more visibility; further antiplasmodial tests should rely on batesiin (2) and other components of the species.

show abstract

Quinones from Cordia species from 1972 to 2023: isolation, structural diversity and pharmacological activities

Dongmo Zeukang,

Kalinski,

Tembeni

et al. 2023

Nat. Prod. Bioprospect.

View full text Add to dashboard Cite

Plants of the genus Cordia (Boraginaceae family) are widely distributed in the tropical regions of America, Africa, and Asia. They are extensively used in folk medicine due to their rich medicinal properties. This review presents a comprehensive analysis of the isolation, structure, biogenesis, and biological properties of quinones from Cordia species reported from 1972 to 2023. Meroterpenoids were identified as the major quinones in most Cordia species and are reported as a chemotaxonomic markers of the Cordia. In addition to this property, quinones are reported to display a wider and broader spectrum of activities, are efficient scaffold in biological activity, compared to other classes of compounds reported in Cordia, hence our focus on the study of quinones reported from Cordia species. About 70 types of quinones have been isolated, while others have been identified by phytochemical screening or gas chromatography. Although the biosynthesis of quinones from Cordia species is not yet fully understood, previous reports suggest that they may be derived from geranyl pyrophosphate and an aromatic precursor unit, followed by oxidative cyclization of the allylic methyl group. Studies have demonstrated that quinones from this genus exhibit antifungal, larvicidal, antileishmanial, anti-inflammatory, antibiofilm, antimycobacterial, antioxidant, antimalarial, neuroinhibitory, and hemolytic activities. In addition, they have been shown to exhibit remarkable cytotoxic effects against several cancer cell lines which is likely related to their ability to inhibit electron transport as well as oxidative phosphorylation, and generate reactive oxygen species (ROS). Their biological activities indicate potential utility in the development of new drugs, especially as active components in drug-carrier systems, against a broad spectrum of pathogens and ailments. Graphical Abstract

show abstract

Neuroinhibitory meroterpenoid compounds from Cordia oncocalyx

Cited by 9 publications

References 15 publications

Biological activities of meroterpenoids isolated from different sources

Biological activities of meroterpenoids isolated from different sources

Density Functional Theory of a New Derivative of Allantoin with Antiplasmodial Properties, Antimycobacterial Activities of Essential Oil from Cordia Batesii WERNHAM (Boraginaceae)

Quinones from Cordia species from 1972 to 2023: isolation, structural diversity and pharmacological activities

Contact Info

Product

Resources

About