FLAVONOID GLYCOSIDES FROM<i>Erythroxylum pulchrum</i>A. St.-Hil. (Erythroxylaceae)

Albuquerque, Camila Holanda de; Tavares, Josean Fechine; Oliveira, Steno L.; Silva, Tainá Souza; Gonçalves, Gregório Fernandes; Costa, Vicente Carlos O.; Agra, Maria de Fátima; Pessôa, Hilzeth de Luna Freire; Silva, Marcelo Sobral da

doi:10.5935/0100-4042.20140104

Cited by 14 publications

(5 citation statements)

References 9 publications

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“…Albuquerque and collaborators have described the presence of epicatechin in the aerial parts of E. pulchrum, 46 and catechin is being reported for the first time in the three species of this study. ) was also generated by cleavage of the ester bond between the units, followed by dehydration in the quinic acid unit (Figure S5).…”

Section: Liquid Chromatography Coupled With Esi-ms N and Hresims Analysissupporting

confidence: 57%

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS

Dantas

Abreu

Cunha

et al. 2021

Phytochemical Analysis

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Introduction: Given the diversity of secondary metabolites produced by species of the genus Erythroxylum, in addition to the many methods that have already been described in the literature, modern screening and identification methodologies, such as dereplication, represent an efficient and quick strategy compared to the classic techniques linked to natural product research. Objective: The objective of the present study was to determine the phenolic profiles obtained from three species of Erythroxylum (Erythroxylum pauferrense Plowman, Erythroxylum pulchrum A.St.-Hil. and Erythroxylum simonis Plowman) by dereplication using liquid chromatography coupled with ESI-MS n and HRESIMS. Material and Methods: Ethyl acetate and n-butanolic fractions from crude ethanolic extract of Erythroxylum species were analyzed by HPLC-ESI-MS n and HPLC-HRESIMS, in order to identify its corresponding compounds. Experiments were performed in negative ionization mode, and the metabolites were provisionally identified based on deprotonated molecules, molecular formulas, fragmentation patterns and literature data. The corresponding isolated compounds were characterized by 1 H and 13 C NMR spectroscopy.Results: According to the dereplication method, it was possible to establish and compare the phenolic profile of the corresponding species by the assignment of 55 compounds, most of which were first described in these species and among which some were also new to the Erytroxylum genus. Additionally, nine compounds were isolated, including biphenyl-3,3 0 ,4,4 0 -tetraol, where the mass spectral data were not sufficient for their identification, and reported for the first time in the Erythroxylaceae family. Conclusion: This research contributes to the phytochemical knowledge of theErythroxylum genus and demonstrates the importance of the dereplication method regarding the investigation of natural products, enabling accurate identification of the metabolites while avoiding the efforts and material expenses involved in the isolation of known compounds.

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Section: Liquid Chromatography Coupled With Esi-ms N and Hresims Analysissupporting

confidence: 57%

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS

Dantas

Abreu

Cunha

et al. 2021

Phytochemical Analysis

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“…Compounds quercetin, quercitrin and kaempferol were found in both species, while (epi)catechin, (epi)catechin dimer (procyanidin dimer), rutin, eriodictyol-rhamnoside, and ombuin-rutinoside were found only in the ethyl acetate partition of E. ovalifolium . Quercitrin, ombuin-rutinoside, and eriodictyol-rhamnoside have already been described in species of the Erythroxylum genus [28,29,30]. Quercetin, rutin, and quercitrin were also isolated from ethyl acetate and butanol partitions.…”

Section: Resultsmentioning

confidence: 99%

Protective Effect of the Plant Extracts of Erythroxylum sp. against Toxic Effects Induced by the Venom of Lachesis muta Snake

et al. 2016

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Snake venoms are composed of a complex mixture of active proteins that induce toxic effects, such as edema, hemorrhage, and death. Lachesis muta has the highest lethality indices in Brazil. In most cases, antivenom fails to neutralize local effects, leading to disabilities in victims. Thus, alternative treatments are under investigation, and plant extracts are promising candidates. The objective of this work was to investigate the ability of crude extracts, fractions, or isolated products of Erythroxylum ovalifolium and Erythroxylum subsessile to neutralize some toxic effects of L. muta venom. All samples were mixed with L. muta venom, then in vivo (hemorrhage and edema) and in vitro (proteolysis, coagulation, and hemolysis) assays were performed. Overall, crude extracts or fractions of Erythroxylum spp. inhibited (20%-100%) toxic effects of the venom, but products achieved an inhibition of 4%-30%. However, when venom was injected into mice before the plant extracts, hemorrhage and edema were not inhibited by the samples. On the other hand, an inhibition of 5%-40% was obtained when extracts or products were given before venom injection. These results indicate that the extracts or products of Erythroxylum spp. could be a promising source of molecules able to treat local toxic effects of envenomation by L. muta venom, aiding in the development of new strategies for antivenom treatment.

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“… Compounds name Plant source Refs. 108 ombuin E. nummularia [ 44 ] 109 ombuin-3- O -rutinoside E. alaternifolium , E. campestre , E. barbatum , E. argentinum , E. tenue , E. daphnites , E. loefgrenii , E. engleri , E. cuneifolium , E. lucidum , E. pruinosum , E. pulchrum , E. squamatum , E. subracemosum , E. subrotundum , E. vacciniifolium , E. novogranatense [ 59 , 66 – 71 ] 110 ombuin-3- O -rutinoside-5- O -glucoside E. argentinum , E. cuneifolium , E. pulchrum , E. macrocalyx [ 49 , 67 , 70 , 71 ] 111 quercetin E. rimosum , E. lucidum , E. suberosum , E. ovalifolium [ 14 , 46 , 59 ] 112 quercetin-3- O -rutinoside E. argentinum , E. cambodianum , E. alaternifolium , E. engleri , E. loefgrenii , E. leal - costae , E. lucidum , E. pruinosum ...…”

Section: Chemical Compositionmentioning

confidence: 99%

Advances in chemistry and bioactivity of the genus Erythroxylum

Tian

Wang

et al. 2022

Nat. Prod. Bioprospect.

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Erythroxylum P. Browne is the largest and most representative genus of Erythroxylaceae family. It contains approximately 230 species that are mainly distributed in tropical and subtropical regions. Some species in this genus, such as E.monogynum and E.coca, have been used as folk medicines in India or South America for a long history. It is well known that Erythroxylum plants are rich in tropane alkaloids, and the representative member cocaine shows remarkable activity in human central nervous system. However, many other types of active compounds have also been found in Erythroxylum along with the broadening and deepening of phytochemical research. To date, a total of 383 compounds from Erythroxylum have been reported, among which only 186 tropane alkaloids have been reviewed in 2010. In this review, we summarized all remained 197 compounds characterized from 53 Erythroxylum species from 1960 to 2021, which include diterpenes, triterpenes, alkaloids, flavonoids, and other derivates, providing a comprehensive overview of phytoconstituents profile of Erythroxylum plants. In addition, the biological activities of representative phytochemicals and crude extracts were also highlighted. Graphical Abstract

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FLAVONOID GLYCOSIDES FROMErythroxylum pulchrumA. St.-Hil. (Erythroxylaceae)

Abstract: FLAVONOID GLYCOSIDES FROM

Cited by 14 publications

References 9 publications

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS

Protective Effect of the Plant Extracts of Erythroxylum sp. against Toxic Effects Induced by the Venom of Lachesis muta Snake

Advances in chemistry and bioactivity of the genus Erythroxylum

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FLAVONOID GLYCOSIDES FROMErythroxylum pulchrumA. St.-Hil. (Erythroxylaceae)

Abstract: FLAVONOID GLYCOSIDES FROM

Cited by 14 publications

References 9 publications

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSn and HRESIMS

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSn and HRESIMS

Protective Effect of the Plant Extracts of Erythroxylum sp. against Toxic Effects Induced by the Venom of Lachesis muta Snake

Advances in chemistry and bioactivity of the genus Erythroxylum

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Product

Resources

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Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS

Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI‐MSⁿ and HRESIMS