A Novel Chlorinated Diphenyl Ether from<i>Byrsonima microphylla</i>(Malpighiaceae)

Rocha, João H. C.; Cardoso, Manuela; David, Juceni P.; David, Jorge M.

doi:10.1271/bbb.60196

Cited by 3 publications

(13 citation statements)

References 10 publications

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“…Naphthoquinones, their derivatives, xanthones, and terpene derivatives have been isolated previously from members of this genus. 4,19,20,23 Quinones are derived from the oxidation of phenolic compounds; the oxidation of catechols (1,2-dihydroxybenzenes) leads to orthoquinones, and the oxidation of quinols (1,4-dihydroxybenzenes) leads to para-quinones. Accordingly, terpenoid quinones are built up from shikimate and terpenoid pathways.…”

Section: Resultsmentioning

confidence: 99%

“…The phytochemical investigation of the leaves and stems afforded the flavonoids (+)-catechin, (-)-epicatechin, quercitrin and isoquercitrin, which are frequently found in Byrsonima species including B. basiloba, 6,7 B. bucidaefolia, 8 B. crassa, 9,10 B. crassifolia, [11][12][13][14] B. fagifolia, [15][16][17] B. intermedia, 18 B. microphylla, 19,20 and B. verbascifolia; 21,22 the investigation also afforded the tannins 3,5-di-O-galloylquinic acid, 5-O-galloylquinic acid, 5-O-(3-methylgalloyl)-quinic acid, 3,4,5-tri-O-galloylquinic acid and gallic acid, which have been previously described in B. crassa 9,10 and B. fagifolia. [15][16][17] Among the compounds isolated from the stems of B. coccolobifolia, (+)-syringaresinol and trigonostemone are new in the genus Byrsonima.…”

Section: Resultsmentioning

confidence: 99%

“…[3][4][5] The compounds most commonly isolated from this genus are flavonoids, terpenes, gallic acids and quinic acid derivatives. 1 Among the constituents, flavonoids (flavanones, bioflavonoids, flavonols and procyanidins), triterpenes (with oleanolic and ursolic skeletons) and modified triterpenoids (steroids) are commonly found in B. basiloba, 6,7 B. bucidaefolia, 8 B. crassa, 9,10 B. crassifolia, [11][12][13][14] B. fagifolia, [15][16][17] B. intermedia, 18 B. microphylla, 19,20 and B. verbascifolia. 21,22 Previous studies on the leaves of B. coccolobifolia revealed the presence of flavonoids, gallic acid and xanthones.…”

Section: Introductionmentioning

confidence: 99%

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NEW DEGRADED QUINONE DITERPENOID FROM THE STEMS OF Byrsonima coccolobifolia Kunth. (Malpighiaceae)

et al. 2017

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A chemical investigation of two specimens of Byrsonima coccolobifolia collected in the southeast cerrado and from central Brazil was performed. A new degraded diterpenoid, byrsonimaquinone, was isolated from the stems along with known compounds. This is the first study on the roots of B. coccolobifolia, and several triterpenes, such as α-amyrin, β-amyrin, oleanolic acid, and glochidonol, along with a mixture of stigmasterol, β-sitosterol and campesterol, were identified. These compounds were identified by spectroscopic analysis techniques, including 1D and 2D NMR, GC-MS and high-resolution mass spectrometry.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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NEW DEGRADED QUINONE DITERPENOID FROM THE STEMS OF Byrsonima coccolobifolia Kunth. (Malpighiaceae)

et al. 2017

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“…Methyl asterrate (3) was reported to perform weak cytotoxic activities against diverse tumor cell lines, including HepG2, HL-60, MOLT-3, MCF-7, NCI-H460, and SF-268 cell lines. 63,64 Asterric acid (1), geodin hydrate (12), methyl dichloroasterrate (17), methyl chloroasterrate (18), neogeodin hydrate (27), and iizukine A (29) all manifested cytotoxic effects on HL-60, BEL-7402, and A-549 cell lines to various degrees. 32 Butyl 2,4-dichloroasterrate ( 22) and 3-methylpentyl-2,4-dichloroasterrate (30) performed weak cytotoxic activity against HL-60, HCT116, PC-3, and HT-29 cancer cell lines.…”

Section: Cytotoxic Activitiesmentioning

confidence: 99%

“…72−75 Asterric acid analogs (48−51) were found to exert potent scavenging effects on the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical with max radical scavenging rates of 88.6− 103.3% and antioxidant activity in oxygen radical absorbance capacity (ORAC) assay with 3.2−12.8 ORAC units. 43 Corynether A (57) also displayed moderate antioxidant activity with 4.3 ORAC units, 47 and neogeodin hydrate (27) showed inhibition against superoxide anion radical formation by xanthine/xanthine oxidase (XXO) with an IC 50 value of 179.1 ± 13.1 μM but no inhibitory activity against aromatase enzyme. 30 The investigators suggested that the phenolic hydroxy group might be the functional group.…”

Section: Cytotoxic Activitiesmentioning

confidence: 99%

Naturally Occurring Asterric Acid Analogs: Chemistry and Biology

Tan,

Chen,

Ding

2024

J. Agric. Food Chem.

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Asterric acid and its analogs belong to diphenyl ethers (DPEs) with multiple substitutions on A/B aromatic rings. This member of DPEs originates from the polyketide pathway and displays a wide range of biological effects. Though the structures of asterric acid analogs are not complex, there were only more than 50 asterric acid analogs found in nature from 1960 to 2023. In this review, the structures, bioactivities, and biosynthesis of asterric acid analogs are summarized. More importantly, the empirical rule about the shielding effect of B-ring on H-6 is suggested, and this provides a convenient and useful way to analyze the NMR spectral data of asterric acid analogs, based on which the chemical shift values of the A-ring in some asterric acid analogs are revised.

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Espécies vegetais descritas em área de reserva da biosfera da Mata Atlântica como fonte para novos compostos bioativos

Silva,

Silva

2024

Rev Fitos

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This work consists of a systematic review of the literature related to the plant species cataloged in Parque das Dunas, Salvador-BA, a region acclaimed by the title of Atlantic Forest biosphere reserve by UNESCO (United Nations Educational, Scientific and Cultural Organization). We included studies containing data on pharmacological activity, phytochemical and toxic profile of the species, from PUBMED, SCIELO and SCIENCE DIRECT databases, in Portuguese and English, without a delimited period. The scientific names of the thirty cataloged species were used as descriptors. The physicochemical parameters and prediction in silico toxicity were evaluated for the isolated and active compounds. As a result, it was verified that of the thirty species, twelve were investigated for pharmacological activity and/or phytochemical and toxic profile, and 33% of the studies involving Chrysobalanus icaco L. (Chrysobalanaceae). Twenty-five bioactive compounds isolated predominantly of the terpene and flavonoid classes, and in eighteen studies the safety of seven species was evaluated. The in silico analysis showed ten compounds did not violate the Lipinski and Veber rules, and only three with high toxic potential. This review gathers data that point to the use of natural products from Brazilian territory in research that may culminate in development of innovative drugs.

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A Novel Chlorinated Diphenyl Ether fromByrsonima microphylla(Malpighiaceae)

Cited by 3 publications

References 10 publications

NEW DEGRADED QUINONE DITERPENOID FROM THE STEMS OF Byrsonima coccolobifolia Kunth. (Malpighiaceae)

NEW DEGRADED QUINONE DITERPENOID FROM THE STEMS OF Byrsonima coccolobifolia Kunth. (Malpighiaceae)

Naturally Occurring Asterric Acid Analogs: Chemistry and Biology

Espécies vegetais descritas em área de reserva da biosfera da Mata Atlântica como fonte para novos compostos bioativos

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