On the identity of two Mexican species of  Ageratina  (Eupatorieae, Asteraceae):  A. grandifolia  and  A. rivalis

Hinojosa-Espinosa, Óscar; Villaseñor, José Luis; Ortíz, Enrique

doi:10.17129/botsci.2143

Cited by 6 publications

(13 citation statements)

References 16 publications

(13 reference statements)

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“…(Asteraceae) is widespread in Guerrero, Michoacán, Morelos, México, Hidalgo, and Oaxaca states and Mexico City . This species is used as a traditional remedy for treating stomach discomfort and skin afflictions …”

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confidence: 99%

“…1 This species is used as a traditional remedy for treating stomach discomfort and skin afflictions. 2 A. grandifolia has not been previously investigated phytochemically. However, several specialized metabolites have been characterized from other members of the genus Ageratina, including flavonoids, sesquiterpenes, diterpenoids, benzyl benzoates, thymol derivatives, chromenes, benzofurans, and p-hydroxyacetophenones, which are regarded as the precursors of the chromenes and benzofurans.…”

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α-Glucosidase Inhibitors from Ageratina grandifolia

et al. 2021

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Fractionation of an aqueous extract from the aerial parts of Ageratina grandifolia yielded a new natural product, namely, 4-hydroxy-3-((S)-1′-angeloyloxy-(R)-2′,3′-epoxy-3′methyl)butylacetophenone (1), along with eight known compounds, including three flavonoids (2−4) and five chromenes (5− 9). NMR data interpretation and DFT-calculated chemical shifts combined with DP4+ statistical and J-DP4 probability analyses allowed for the complete characterization of compound 1. The presence of compound 1 in a plant that biosynthesizes 2,2dimethylchromenes is noteworthy, because an epoxy derivative has long been postulated as the reaction intermediate from the prenylated p-hydroxyacetophenones to cyclic dimethylchromenes. So far, this key intermediate has not been isolated, due to its purported chemical instability. Thus, this is the first report of a potential epoxide intermediate, leading to any of the chromene constituents of this plant. Compounds 1−9 inhibited yeast α-glucosidase with IC 50 values ranging from 0.79 to 460 μM (acarbose, IC 50 = 278.7 μM). The most active compounds were quercetagetin-7-O-(6-O-caffeoyl-β-D-glucopyranoside (3) and 6hydroxykaempferol-7-O-(6-O-caffeoyl-β-D-glucopyranoside (4). Kinetic analysis of 3 revealed its mixed-type inhibitor nature. Docking studies into the crystallographic structure of yeast α-glucosidase (pdb 3A4A) predicted that 3 and 4 bind at the catalytic site of the enzyme.

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α-Glucosidase Inhibitors from Ageratina grandifolia

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“…However, structural revisions are still not uncommon, and the revision and confirmation of the molecular architectures of natural products is fundamental for the discovery of novel bioactive compounds Ageratina grandifolia is a perennial herb used as a traditional remedy for treating stomach discomfort and skin afflictions . 2,2-Dimethyl-3-hydroxy-4-(1′-angeloyloxy)-6-acetylchromane is a natural product isolated from the aerial parts of A.…”

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Asymmetric Synthesis of Four Stereoisomers of 2,2-Dimethyl-3-hydroxy-4-(1′-angeloyloxy)-6-acetylchromane from Ageratina grandifolia and Plausible Absolute Stereochemistry of the Natural Product

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Im,

Bae

et al. 2023

ACS Omega

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2,2-Dimethyl-3-hydroxy-4-(1′-angeloyloxy)-6-acetylchromane is a natural product isolated from Ageratina grandifolia that exhibits inhibitory activity against yeast α-glucosidase. Initially, its structure was proposed to be 4-hydroxy-3-((S)-1′-angeloyloxy-(R)-2′,3′-epoxy-3′-methyl)butylacetophenone with an epoxide, but the structure was later revised to 2,2-dimethyl-3R-hydroxy-4S-(1-angeloyloxy)-6-acetylchromane. In this study, we present a total synthesis of 2,2-dimethyl-3-hydroxy-4-(1′-angeloyloxy)-6-acetylchromane from A. gradifolia and its stereoisomers. The key features of their synthesis include Sharpless asymmetric dihydroxylation of a readily available benzopyran substrate and subsequent Mitsunobu or Steglich reaction to provide both cis- and trans-isomers with chiral control. The absolute stereochemistry of the natural product was determined to be 2,2-dimethyl-3S-hydroxy-4R-(1′-angeloyloxy)-6-acetylchromane based on optical rotations of the synthesized compounds. The absolute configuration of the synthesized stereoisomers was confirmed by Mosher ester analysis. In addition, we provided ECD spectra for the four stereoisomers, which will allow verification of the absolute configuration of the natural product. Synthesis of all four stereoisomers of 2,2-dimethyl-3-hydroxy-4-(1′-angeloyloxy)-6-acetylchromane would facilitate the exploration of their potential biomedical applications.

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“…La altura se midió con una vara de 8 m (dividida en un metro). La identificación de plantas se llevó a cabo con base en Lot et al (2015), Hinojosa-Espinosa et al (2019) y Espinosa-Méndez et al (2020.…”

Section: Muestreo De Vegetaciónunclassified

“…Especies de plantas y número de individuos registrados en el río Lerma en Temascalcingo, Estado de México. La identificación se hizo con base en Lot et al (2015), Hinojosa-Espinosa et al (2019) Anexo 4. Número de registros de las especies especialistas por tipo de ambiente.…”

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Comparación de la avifauna riparia del río Lerma y su relación con el uso de suelo en el municipio de Temascalcingo, Estado de México

Guerra

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Riparian ecosystems are the interface between terrestrial and aquatic ecosystems. Despite its relevance, the riparian vegetation of these ecological systems is threatened, since it is being displaced by agricultural, industrial and human settlement activities. The objective of this work was to compare the avifauna between sites that belong to different environments (riparian vegetation, scrub, grazing areas and crops) of the upper part of the Lerma River. The demonstration was carried out from April to November 2020, through counting points established in the four main types of environments adjacent to the Lerma River in the municipality of Temascalcingo, State of Mexico. 11 bird orders, 33 families and 94 species were recorded: 62 residents and 32 migrants. Species accumulation curves were generated. The richness, diversity and similarity of the avifaunas of the four environments were estimated. The riparian vegetation was the environment that presented the greatest richness and diversity of birds (45 species). The abundance of bird species was higher in grazing areas. According to the Jaccard index, the greatest similarity was between the same sites of riparian vegetation and crops. Group species were grouped into nine guilds; the most abundant in all types of environments were the granivores. There were significant differences (p<0.05) in the abundances of guilds. The bird species were related to the herbaceous stratum and the abundance of the plants. The modified environments adjacent to the Lerma River wetland serve differentially as an alternate refuge for bird species.

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On the identity of two Mexican species of Ageratina (Eupatorieae, Asteraceae): A. grandifolia and A. rivalis

Cited by 6 publications

References 16 publications

α-Glucosidase Inhibitors from Ageratina grandifolia

α-Glucosidase Inhibitors from Ageratina grandifolia

Asymmetric Synthesis of Four Stereoisomers of 2,2-Dimethyl-3-hydroxy-4-(1′-angeloyloxy)-6-acetylchromane from Ageratina grandifolia and Plausible Absolute Stereochemistry of the Natural Product

Comparación de la avifauna riparia del río Lerma y su relación con el uso de suelo en el municipio de Temascalcingo, Estado de México

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