Chemical constituents from Aspidosperma illustre (Apocynaceae)

Barbosa, Lara Fonseca; Mathias, Lêda; Braz-Filho, Raimundo; Vieira, Ivo José Curcino

doi:10.1590/s0103-50532010000800004

Cited by 13 publications

(9 citation statements)

References 13 publications

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“…The effects induced by EEAT on the cardiovascular system in rats are in agreement with literature data, related with bioactivity of Apocynaceae species and with bioactive chemical compounds isolated from species of the Aspidosperma, which are rich alkaloids, including aspidospermine, quebrachamine, and yohimbine (Lyon et al, 1973;Craveiro et al, 1983;Sperling et al, 2002). Also, other natural products have been documented, such as the occurrence of triterpenes (Barbosa et al, 2010), flavonol glycosides, quercetin, kaempferol and isorhamnetin derivatives (Pelotto and Del Pero, 1995) in genus Aspidosperma. The EEAT was analyzed by ESI-MS in the positive and negative ion mode.…”

Section: Discussionsupporting

confidence: 87%

Antihypertensive and Vasorelaxant effects of the ethanolic extract from the stem bark of Aspidosperma tomentosum Mart

Furtado¹,

Menezes²,

Bernardo³

et al. 2017

J App Pharm Sci

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Aspidosperma species have been traditionally used for the treatment of cardiovascular disease. These species are important sources of indole alkaloids, which are responsible for different cardiovascular effects. Based on this premise, and as there are still no studies related to the cardiovascular effects of the ethanolic extract from the stem bark of Aspidosperma tomentosum (EEAT). The goal of the survey was to characterize the mechanism of the vasorelaxant action of EEAT in isolated rat mesenteric rings and to establish its antihypertensive activity. The mean arterial pressure (MAP) and Heart Rate (HR) were measured in hypertensive rats through a catheter implanted in abdominal aorta via the femoral artery. The vasodilator effect of EEAT in isolated pre-contracted rat mesenteric rings was examined. The bioactive extract was investigated via mass spectrometry fingerprinting. EEAT induced relaxation in mesenteric rings pre-contracted with Phe independent of the endothelium. In denuded rings, when incubation with KCl 20 mM or TEA did not change the relaxation. EEAT inhibited the concentration-response curves induced by CaCl2 or Phe and inhibited 80 mM KCl-induced contraction. In precontracted preparations with BayK 8644, the EEAT induced relaxation. The transient contraction induced by Phe was inhibited. The oral administration of EEAT reduced MAP and did not alter the HR. Phenolic acids, flavonoids, and indole alkaloids were identified in EEAT. In conclusion, the EEAT induced vasorelaxation through a blockade of Ca 2+ channels and inhibition of the mobilization of Ca 2+ of the IP3-sensitive Ca 2+ stores and caused an antihypertensive effect.

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Section: Discussionsupporting

confidence: 87%

Antihypertensive and Vasorelaxant effects of the ethanolic extract from the stem bark of Aspidosperma tomentosum Mart

Furtado¹,

Menezes²,

Bernardo³

et al. 2017

J App Pharm Sci

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“…The known compounds were identified by analysing the spectroscopic data (1D and 2D NMR) and comparing their data with those in the literature to be α -amyrin acetate ( 1 ) (Virgilio et al 2015), α -amyrin ( 2 ) (Virgilio et al 2015), 3 β -acetoxy-20-taraxasten-22-one ( 3 ) (Ramadan et al 2009; Ahmed 2010), 3 β -acetoxy-11 α -methoxy-olean-12-ene ( 4 ) (Kuo and Chiang 2000; Mallavadhani et al 2006; Barbosa et al 2010), 3 β -acetoxy-11 α -methoxy-12-ursene ( 5 ) (Mathias et al 2000; Barbosa et al 2010), 11-oxo- α -amyrin acetate ( 6 ) (Fingolo et al 2013), 11-oxo- β -amyrin acetate ( 7 ) (Fingolo et al 2013), palmitic acid ( 8 ) (Ajoku et al 2015), stigmast-4,22-diene-3,6-dione ( 9 ) (Itokawa et al 1973), stigmast-4-ene-3,6-dione ( 10 ), stigmasterol ( 12 ) (Mohamed and Ibrahim 2007; Kamboj and Salujai 2011; Chaturvedula and Prakash 2012), β -sitosterol ( 13 ) (Al-Musayeib et al 2013), stigmast-22-ene-3,6-dione ( 14 ) (Wei et al 2004), stigmastane-3,6-dione ( 15 ) (Wei et al 2004; Lim et al 2005), 3 β ,21 β -dihydroxy-11 α -methoxy-olean-12-ene ( 16 ) (Cáceres-Castillo et al 2008), 3 β -hydroxy-11 α -methoxyurs-12-ene ( 18 ) (Fujita et al 2000), 6-hydroxystigmast-4,22-diene-3-one ( 19 ) (Kontiza et al 2006; Georges et al 2006), 6-hydroxystigmast-4-ene-3-one ( 20 ) (Kontiza et al 2006; Georges et al 2006) and β -sitosterol-3- O - β -D-glucopyranoside ( 22 ) (Khatun et al 2012). …”

Section: Resultsmentioning

confidence: 95%

New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors

et al. 2016

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Phytochemical investigation of Ficus pandurata Hance (Moraceae) fruits has led to the isolation of two new triterpenoids, ficupanduratin A [1β-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (11) and ficupanduratin B [21α-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (17), along with 20 known compounds: α-amyrin acetate (1), α-amyrin (2), 3β-acetoxy-20-taraxasten-22-one (3), 3β-acetoxy-11α-methoxy-olean-12-ene (4), 3β-acetoxy-11α-methoxy-12-ursene (5), 11-oxo-α-amyrin acetate (6), 11-oxo-β-amyrin acetate (7), palmitic acid (8), stigmast-4,22-diene-3,6-dione (9), stigmast-4-ene-3,6-dione (10), stigmasterol (12), β-sitosterol (13), stigmast-22-ene-3,6-dione (14), stigmastane-3,6-dione (15), 3β,21β-dihydroxy-11α-methoxy-olean-12-ene (16), 3β-hydroxy-11α-methoxyurs-12-ene (18), 6-hydroxystigmast-4,22-diene-3-one (19), 6-hydroxystigmast-4-ene-3-one (20), 11α,21α-dihydroxy-3β-acetoxy-urs-12-ene (21), and β-sitosterol-3-O-β-D-glucopyranoside (22). Compound 21 is reported for the first time from a natural source. The structures of the 20 compounds were elucidated on the basis of IR, 1D (1H and 13C), 2D (1H–1H COSY, HSQC, HMBC and NOESY) NMR and MS spectroscopic data, in addition to comparison with literature data. The isolated compounds were evaluated for their anti-microbial, anti-malarial, anti-leishmanial, and cytotoxic activities. In addition, their radioligand displacement affinity on opioid and cannabinoid receptors was assessed. Compounds 4, 11, and 15 exhibited good affinity towards the CB2 receptor, with displacement values of 69.7, 62.5 and 86.5 %, respectively. Furthermore, the binding mode of the active compounds in the active site of the CB2 cannabinoid receptors was investigated through molecular modelling.

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“…Figure S10), as characteristic of sugar residue protons (Primahana & Darmawan 2017). This indicates the presence of glycosides in both flavonoids (δ H 7.0-7.5), as well as triterpenes (δ H 2.5-1.0) (Barbosa et al 2010, Ibrahim et al 2019. Finally, in Ts-MeOH9 the presence of two doublets at δ H 0.33 (J = 4.2 Hz) and at δ H 0.55 (J = 4.2 Hz), is indicative of cyclopropane protons in the cycloartane framework (Table 3.…”

Section: Inhibition Of Biofilm Formation and Swarming Inmentioning

confidence: 89%

Anti-virulence activities of some Tillandsia species (Bromeliaceae)

et al. 2020

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Background: Using molecules that inhibit bacterial virulence is a potential strategy to fight infections, with the advantage that, in contrast to bactericidal compounds, they do not induce resistance. Several compounds with anti-virulence properties have been identified in plants, however, they represent a small portion of the total diversity, and in Mexico there are still few studies on this matter. Hypothesis: Extracts of species of the Tillandsia genus inhibit the expression of diverse virulence factors without affecting the bacterial growth. Studied species: Tillandsia recurvata (L.) L., T. schiedeana Steud. and T. fasciculata Sw. Study site and date: These species were collected in December 2016 in the municipalities of Ixtlahuaca and Santo Tomás de los Plátanos, State of Mexico. Methods: The ability of dichloromethane (CH2Cl2) and methanol (CH3OH) extracts to inhibit production of violacein in Chromobacterium violaceum was evaluated, as well as the virulence factors regulated by quorum sensing, motility and biofilm in Pseudomonas aeruginosa. In addition, the bioactive fractions obtained were partially identified by 1H NMR. Results: CH2Cl2 and CH3OH extracts reduced violacein production from 43 to 85 %, but only those from CH2Cl2 reduced protease activity, biofilm formation and swarming. Interestingly, CH3OH extracts stimulated the formation of biofilms by up to 37 %. Presence of terpenes and phenolic compounds in these species was confirmed. In T. schiedeana glycosylated compounds and cycloartane-type triterpenes were identified. Conclusion: The species of Tillandsia show anti-virulence activity, mainly on factors related to adhesion and dispersion in Pseudomonas aeruginosa.

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Chemical constituents from Aspidosperma illustre (Apocynaceae)

Cited by 13 publications

References 13 publications

Antihypertensive and Vasorelaxant effects of the ethanolic extract from the stem bark of Aspidosperma tomentosum Mart

Antihypertensive and Vasorelaxant effects of the ethanolic extract from the stem bark of Aspidosperma tomentosum Mart

New ursane triterpenoids from Ficus pandurata and their binding affinity for human cannabinoid and opioid receptors

Anti-virulence activities of some Tillandsia species (Bromeliaceae)

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