Chemical composition of four different species of the Waltheria genus

Caridade, Taíza Nayara S.; Araújo, Rusceli Diego de; Oliveira, Anne Natália A.; Souza, Taiannie Soriano A.; Ferreira, Nara Cristina Frutuoso; Avelar, Deusielly S.; Teles, Yanna Carolina Ferreira; Silveira, Edilberto R.; Araújo, Renata Mendonça

doi:10.1016/j.bse.2018.07.003

Cited by 6 publications

(4 citation statements)

References 33 publications

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“…These compounds have been previously reported from Malvaceae species such as Sidastrum micranthum (Gomes et al, 2011), Sida galheirensis (Silva et al, 2006), Sida tuberculata (Vadivel, et al, 2016), and Wissadula periplocifolia (Teles et al, 2015b). Among the flavonoids identified, tiliroside (5) is referred to as the most prevailing flavonoid produced by Malvaceae species (Caridade et al, 2018). Several biological activities have been demonstrated to tiliroside (5), such as antioxidant, vasorelaxant, modulator of bacterial resistance, and anti-inflammatory and larvicidal activity against Ae.…”

Section: Discussionmentioning

confidence: 56%

Sidastrum paniculatum (L.) Fryxell (Malvaceae): A Promising Source of Bioactive Sulfated Flavonoids Against Aedes aegypti L

et al. 2022

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Aedes aegypti L. is known as the most relevant vector mosquito for viruses such as yellow fever, chikungunya, dengue, and Zika, especially in places with unplanned urbanization, and erratic water supply. Plants used in folk medicine have become a useful source of active compounds with the potential to control the dissemination of Ae. aegypti. Compounds isolated from Malvaceae sensu lato have been previously reported as larvicides, repellents, and insecticides. Recent studies have demonstrated the anti Ae. aegypti activity of sulfated flavonoids, an uncommon type of flavonoid derivatives. This research reports the phytochemical investigation of Sidastrum paniculatum (L.) Fryxell, a Malvaceae species with the potential against Ae. aegypti. Chromatographic procedures resulted in the isolation of the compounds: stearic acid (1), N-trans-feruloyltyramine (2), acacetin (3), apigenin (4), tiliroside (5), along with the sulfated flavonoids: wissadulin (6), 7,4′-di-O-methyl-8-O-sulfate flavone (7), yannin (8), beltraonin (9a), 7-O-sulfate isoscutellarein (paniculatumin) (9b), and condadin (10). This is the first report of compound 7-O-sulfate isoscutellarein (9b). The structures were elucidated by spectroscopic analysis (NMR, LC-HRMS and FT-IR). The sulfated flavonoids identified were submitted to a ligand-based and structure-based virtual screening against two targets: 1YIY (from adult Ae. aegypti) and 1PZ4 (from Ae. aegypti larvae). The results indicated that when the O-sulfate group is bearing the position 7, the structures are potentially active in 1PZ4 protein. On the other hand, flavonoids with the O-sulfate group bearing position 8 were showed to be more likely to bind to the 1YIY protein. Our findings indicated that S. paniculatum is a promising source of sulfated flavonoids with potential against Ae. aegypti.

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Section: Discussionmentioning

confidence: 56%

Sidastrum paniculatum (L.) Fryxell (Malvaceae): A Promising Source of Bioactive Sulfated Flavonoids Against Aedes aegypti L

et al. 2022

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“…This was followed by Jandouba, with 36.94 CE mg/g DM in male plants, and Nabeul, also with 30.35 CE mg/g DM in male plants, while the provenance of Beja displayed for both male (4.27 CE mg/g DM) and female (4.16 CE mg/g DM) leaves the lowest doses (Figure 2). Richness in TFC in aerial parts of plants was previously reported by Caridade et al (2018) [20]. This affluence in phenolic compounds is probably the cause of the use of M. annua against hair loss in Tunisia.…”

Section: Antioxidant Activity (Aoa)mentioning

confidence: 67%

Phytochemicals, Antioxidant Attributes and Larvicidal Activity of Mercurialis annua L. (Euphorbiaceae) Leaf Extracts against Tribolium confusum (Du Val) Larvae (Coleoptera; Tenebrionidae)

Nasr

Baudelaire²,

Dıcko³

et al. 2021

Biology

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This study reports the link between larvicidal activity and the phytochemical composition of male and female leaf extracts of Mercurialis annua L. (M. annua) from four Tunisian regions: Bizerte, Jandouba, Nabeul and Beja. Their antioxidant activity was evaluated using DPPH (2, 2-diphenyl-1-picrylhydrazyl) assays. Phenolic compounds were identified and quantified using liquid chromatography coupled with a UV detector and mass spectrometry (LC-UV-ESI/MS). Higher antioxidant activity (AOA) was found in the leaves of male plant extracts than of female ones. The leaves of male and female plant extracts from Bizerte exhibited the highest AOA: 22.04 and 22.78 mg Trolox equivalent/g dry matter (mg TE/g DM), respectively. For both sexes, plant extracts from Beja had the lowest AOA with 19.71 and 19.67 mg TE/g DM for male and female plants, respectively. Some phenolic compounds such as narcissin, gallocatechin, rutin, epigallocatechin and epicatechin were identified and quantified using LC-MS, which highlighted the abundance of narcissin and rutin in the male leaves of M. annua. We noted that the interaction between the sex of plants and the provenance had a significant effect on TFC (F = 6.63; p = 0.004) and AOA (F = 6.53; p = 0.004) assays, but there was no interaction between sex and origins for TPC (F = 1.76; p = 0.19). The larvicidal activity of aqueous leaf extracts of M. annua against Tribolium confusum (Du Val) (T. confusum), an insect pest of flour and cereal seeds, showed that the mortality could reach 100% after 48 h of exposure in the Bizerte region. The LC50 values for the leaf extract were low in Bizerte, with 0.003 and 0.009 g/mL for male and female plants, respectively, succeeded by Jandouba, which displayed 0.006 and 0.024 g/mL for male and female plants, respectively. Nabeul showed 0.025 g/mL for male plants and 0.046 g/mL for female plants and Beja showed 0.037 and 0.072 g/mL for male and female plants, respectively. This is the first time that a study has revealed a negative correlation between the antioxidant activity and the larvicidal activity of the leaf extracts of M. annua with the following correlation coefficients of Perason: r = −0.975 and r = −0.760 for male and female plants, respectively.

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“…Asperphenamate, first discovered from Aspergillus flavipes in 1977 ( Clark et al, 1977 ), was since found to be produced by a wide range of Aspergillus ( Samson et al, 2011 ; Zheng et al, 2013 ; Ratnaweera et al, 2016 ; Hou et al, 2017 ) and Penicillium ( Frisvad et al, 2004 , 2013 ) species. Additionally, the compound has also been isolated in trace amounts from a number of unrelated plant species ( Wu et al, 2004 ; Dang et al, 2014 ; Zhou et al, 2017 ; Bunteang et al, 2018 ; Caridade et al, 2018 ), suggesting endophytic fungi being the actual producers, rather than the plants. Although asperphenamate is mainly known for its antitumour activity and immense synthetic chemists interest in asperphenamate backbone modification ( Li et al, 2012 ; Yuan et al, 2012 , 2018 , 2019 , 2020 ; Liu et al, 2016 ), recent studies have also shown asperphenamate to be a potential neuroinflamatory inhibitor ( Zhou et al, 2017 ), and to possess anti-HIV ( Bunteang et al, 2018 ) and antidiabetic ( Del Valle et al, 2016 ) properties.…”

Section: Introductionmentioning

confidence: 99%

Mass Spectrometry Guided Discovery and Design of Novel Asperphenamate Analogs From Penicillium astrolabium Reveals an Extraordinary NRPS Flexibility

et al. 2021

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Asperphenamate is a small peptide natural product that has gained much interest due to its antitumor activity. In the recent years numerous bioactive synthetic asperphenamate analogs have been reported, whereas only a handful of natural analogs either of microbial or plant origin has been discovered. Herein we describe a UHPLC-HRMS/MS and amino acid supplement approach for discovery and design of novel asperphenamate analogs. Chemical analysis of Penicillium astrolabium, a prolific producer of asperphenamate, revealed three previously described and two novel asperphenamate analogs produced in significant amounts, suggesting a potential for biosynthesis of further asperphenamate analogs by varying the amino acid availability. Subsequent growth on proteogenic and non-proteogenic amino acid enriched media, revealed a series of novel asperphenamate analogs, including single or double amino acid exchange, as well as benzoic acid exchange for nicotinic acid, with the latter observed from a natural source for the first time. In total, 22 new asperphenamate analogs were characterized by HRMS/MS, with one additionally confirmed by isolation and NMR structure elucidation. This study indicates an extraordinary nonribosomal peptide synthetase (NRPS) flexibility based on substrate availability, and therefore the potential for manipulating and designing novel peptide natural products in filamentous fungi.

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Chemical composition of four different species of the Waltheria genus

Cited by 6 publications

References 33 publications

Sidastrum paniculatum (L.) Fryxell (Malvaceae): A Promising Source of Bioactive Sulfated Flavonoids Against Aedes aegypti L

Sidastrum paniculatum (L.) Fryxell (Malvaceae): A Promising Source of Bioactive Sulfated Flavonoids Against Aedes aegypti L

Phytochemicals, Antioxidant Attributes and Larvicidal Activity of Mercurialis annua L. (Euphorbiaceae) Leaf Extracts against Tribolium confusum (Du Val) Larvae (Coleoptera; Tenebrionidae)

Mass Spectrometry Guided Discovery and Design of Novel Asperphenamate Analogs From Penicillium astrolabium Reveals an Extraordinary NRPS Flexibility

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