Three new caryophyllane-type sesquiterpenoids, linariophyllenes A−C (1−3), two new hamamelitol derivatives, linaritols A (4) and B (5), two new chromones, linariosides A (6) and B (7), and three known chromones, cnidimol C (8), monnieriside A (9), and undulatoside A (10), were identified from the aerial parts of Evolvulus linarioides. The structures of these compounds were elucidated by NMR, MS, and IR data. The absolute configurations of compounds 1−5 and 7 were established via electronic circular dichroism data. The anti-inflammatory potential of compounds 1−5 and 7−10 was evaluated by determining their ability to inhibit the production of nitric oxide (NO) and proinflammatory cytokine IL-1β by stimulated J774 macrophages. Compounds tested at noncytotoxic concentrations inhibited NO production by macrophages, exhibiting IC 50 values between 17.8 and 66.2 μM, and inhibited IL-1β production by stimulated macrophages by 72.7−96.2%.
Herein, the isolation of secondary metabolites from the aerial parts of Justicia aequilabris guided by HPLC-MS n and molecular networking analyses is reported. Twenty-two known compounds were dereplicated. Three new lignans (aequilabrines A− C (1−3)) and three known compounds (lariciresinol-4′-O-β-glucose (4), roseoside (5), and allantoin (6)) were obtained. The antiinflammatory activity of compounds 1−3 was evaluated in vitro by inhibiting the nitric oxide production (NO) and proinflammatory activity on the cytokine IL-1β. Compounds 2 and 3 showed significant inhibitory activity against NO production, with IC 50 values of 9.1 and 7.3 μM, respectively. The maximum inhibition of IL-1β production was 23.5% (1), 27.3% (2), and 32.5% (3).
Mandevilla Lindl. is an important genus of the Apocynaceae family, not only as ornamental plants but also for its medicinal uses. In Brazil, Mandevilla species are indicated to treat asthma and skin infections, their anti-inflammatory potential and wound healing properties are also reported in the literature. Concerning their chemical composition, this group of plants is a conspicuous producer of pregnane glycosides. Mandevilla dardanoi is an endemic species from the Brazilian semiarid region not studied by any phytochemical methods. In view of the medicinal potential of Mandevilla species, this study aimed to isolate new pregnane glycosides from M. dardanoi. To achieve this main goal, modern chromatography techniques were employed. Five new pregnane glycosides, dardanols A-E, were isolated from the roots of M. dardanoi by HPLC. Their structures were determined using extensive 1D and 2D-NMR and mass spectrometry (MSn and HRESIMS) data. The cytotoxicity and the anti-inflammatory potential of these compounds were evaluated. The first was evaluated by measuring proinflammatory cytokines and nitric oxide production by stimulated macrophages. Dardanols were able to inhibit the production of nitric oxide and reduce IL-1β and TNF-α. The current work demonstrates the chemodiversity of Brazilian semiarid species and contributes to amplifying knowledge about the biological potential of the Mandevilla genus.
The aim of this study was to obtain bioactive compounds from Mandevilla dardonoi (Apocynaceae), in order to contribute positively to the discovery of new sources of active natural substances. Based on this, the compounds obtained from the ethyl acetate phase were isolated by medium pressure column chromatography and high performance liquid chromatography and identified by nuclear magnetic resonance (1 H) and electrospray mass spectrometry. It was possible to isolate 6 chlorogenic acids: 3-caffeoylquinic (3-ACQ), 4-caffeoylquinic (4-ACQ), 5-caffeoylquinic (5-ACQ), 3,4-dicaffeoylquinic 4-diACQ), 3,5dicaffeoylquinic (3,5-diACQ) and 4,5dicaffeoylquinic (4,5-diACQ) acids. The research contributed positively to the expansion of the knowledge about the genus Mandevilla and especially of the species M. dardonoi, which did not exist reports of phytochemical studies in the literature.
Evolvulus (Convolvulaceae family) composed of about seventy species widely distributed in Brazil, with some of its species showed a spasmolytic effect in some smooth muscles. Evolvulus linarioides Meisn. is a erect sub-shrub with small blue flowers. Previous phytochemical studies have resulted in the identification of chromones and sesquiterpenes. Therefore, the aim of this study was to do phytochemical investigation and evaluate the tocolytic activity of the methanolic extract of E. linarioides (EL-MeOH) on rats. After euthanasia, the rat uterus was placed in baths for isolated organ where isotonic contractions were monitored (n = 5). The Ethics Committee on Animal Use of UFPB approved all experiments (Protocol 3559100918). Following the extraction of aerial parts of E. linarioides with methanol, the dried extract was successive partitioning in hexane, dichloromethane, ethyl acetate and n-butanol. The n-butanol phase was column chromatographed using Sephadex LH-20 and then further purified by HPLC on C-18 reverse phase (methanol:water, 17:83) affording compound 1 (5 mg). The structure of the compound was elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Thus, compound 1 was characterized as a 5-hydroxy-7-O-(β-D-glucopyranosyl)-2-methylchromone (undulatoside A). In addition, EL MeOH antagonized in a concentration-dependent and equipotent manner both phasic contractions induced by 10-2 IU/mL oxytocin (Emax = 100%; IC50 = 253.8 ± 54.6 μg/mL) and 10-5 M carbachol (Emax = 93.6 ± 2.2%; IC50 = 195.5 ± 47.5 μg/mL), indicating that the tocolytic effect of EL-MeOH probably involves a common pathway between these agonists. In conclusion, we report for the first time the undulatoside A from Convolvulaceae family, in addition, the species E. linarioides presents tocolytic activity on uterus.
The aim of this study was to obtain bioactive compounds from Mandevilla dardonoi (Apocynaceae), in order to contribute positively to the discovery of new sources of active natural substances. Based on this, the compounds obtained from the ethyl acetate phase were isolated by medium pressure column chromatography and high performance liquid chromatography and identified by nuclear magnetic resonance ( 1 H) and electrospray mass spectrometry. It was possible to isolate 6 chlorogenic acids: 3-caffeoylquinic (3-ACQ), 4-caffeoylquinic (4-ACQ), 5-caffeoylquinic (5-ACQ), 3,4-dicaffeoylquinic 4-diACQ), 3,5dicaffeoylquinic (3,5-diACQ) and 4,5dicaffeoylquinic (4,5-diACQ) acids. The research contributed positively to the expansion of the knowledge about the genus Mandevilla and especially of the species M. dardonoi, which did not exist reports of phytochemical studies in the literature.
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