Anti-inflammatory and antioxidative effects of six pentacyclic triterpenes isolated from the Mexican copal resin of Bursera copallifera

Romero-Estrada, Antonio; Maldonado-Magaña, Amalia; González-Christen, Judith; Bahena, Silvia Marquina; Garduño-Ramı́rez, Marı́a Luisa; Rodríguez-López, Verónica; Álvarez, Laura

doi:10.1186/s12906-016-1397-1

Cited by 58 publications

(60 citation statements)

References 48 publications

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“…These results were significantly (P < 0.05) different from that of the negative control group. Chromatographic purification of the most active BC-3-1 subfraction allowed us to obtain the triterpenes α-amyrin (3) and 3epilupeol (4), which were previously described as the major anti-inflammatory constituents of the resin of this plant species [13], and were identified by direct comparison (co-chromatography and 1 H NMR) with authentic samples. These two triterpenes are well known for their anti-inflammatory properties.…”

Section: Resultsmentioning

confidence: 99%

“…These two triterpenes are well known for their anti-inflammatory properties. α-amyrin (3) has showed topical dose-dependent effect in reducing TPA-induced ear edema, inhibits the LPS-induced NO production in RAW 264.7 macrophages, and is able to decrease the expression of COX-2, levels of PGE2 [13]. This pentacyclic triterpene also inhibited the activity of nuclear transcription factors like NF-kB reducing the synthesis of pro-inflammatory proteins [21].…”

Section: Resultsmentioning

confidence: 99%

“…NMR spectra were acquired on a Varian Unity NMR spectrometer operating at 400 MHz for 1 H and 100 MHz for 13 C nuclei. Chemical shifts are listed in parts per million (ppm), referenced to CDCl3 and were made on the basis of 1 H-1 H gCOSY, 1 H-1 H NOESY, gHSQC and gHMBC spectral analysis as required.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…In our research team, the quantitative phytochemical analysis of the copal resin of B. copallifera resulted in the isolation and characterization of six pentacyclic triterpenes: 3-epilupeol formiate, lupenone, αamyrin, 3-epilupeol and their acetates. The pharmacological study demonstrated that the anti-inflammatory activity showed by the resin can be attributed to the potent nitric oxide (NO) production inhibitory activity on RAW 264.7 macrophages, together with the moderate inhibitory activity of PLA2 enzyme displayed by all the natural triterpenes, and the COX-2 inhibitory activity showed by α-amyrin and 3-epilupeol [13].…”

Section: Introductionmentioning

confidence: 99%

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Antiproliferative and anti-inflammatory acyl glucosyl flavones from the leaves of Bursera copallifera

et al. 2019

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Bursera copallifera(DC) Bullock (Burseraceae) is a plant species used in folk medicine for the treatment of inflammation (bronchitis, cough). The dichloromethane-methanol extract (DML) of B. copallifera leaves was found to possess important antiproliferative and anti-inflammatory activities. In order to further correlate these activities with the phytochemical components, the bioactivity-guided fractionation of the DML extract allowed the isolation of an active fraction which was constituted of five compounds characterized as as luteolin-3'-O-(3''-O-E-p-coumaroyl)-α-L-rhamnopyranoside (1), luteolin-3'-O-(2''-O-E-p-coumaroyl)-α-L-rhamnopyranoside (2), a-amyrin (3), 3-epilupeol (4) and stigmasterol (5). Among the five isolated constituents, the triterpenes 3 and 4, and the sterol 5 have been already well known by their anti-inflammatory properties. Flavone 2 (Luteolin-3'-O-(2''-O-E-p-coumaroyl)-α-L-rhamnopyranoside)was responsible for the antiproliferative activity, showing in vitro cytotoxic activity against MCF-7 human cancer cell line with IC50 value of 13.9 µM. By the other hand flavone (1) exhibited COX-1 inhibition (IC50 = 93 mM). Flavone 1, together with the triterpenes 3 and 4 were the responsible for inhibiting TPA-induced inflammation by inhibit COX-1 enzyme. Therefore, these results support the traditional use of the infusion made with the leaves of B. copallifera as an anti-inflammatory agent.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: General Experimental Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antiproliferative and anti-inflammatory acyl glucosyl flavones from the leaves of Bursera copallifera

et al. 2019

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“…Indeed, α-amyrin and β-amyrin have been pointed as potent inhibitors of inflammation and hepatic oxidative stress [36][37][38]. Recently, both α-amyrin and β-amyrin were found to reduce NO production by RAW 264.7 macrophages stimulated with LPS without affecting their viability in vitro [39,40]. β-amyrin also inhibited the secretion of IL-6 by LPS-treated human peripheral blood mononuclear cells [41].…”

Section: Resultsmentioning

confidence: 99%

Punica granatum Leaf Lipophilic Fraction Favours Mortality by Attenuating Inflammation in Mice with Polymicrobial Sepsis

Sousa¹,

Figueiredo²,

Araújo³

et al. 2019

JPP

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Punica granatum L. possesses known antimicrobial and anti-inflammatory actions. Preparations of different parts of this plant have been commonly used in the folk medicine to prevent and treat infections; and studies have supported the use of P. granatum extracts for this purpose. However, little is known of the effects of P. granatum-derived fractions in severe infectious diseases such as sepsis. Here, we investigated the actions of the hexane fraction (HF), rich in lipophilic compounds, obtained from the leaves of this plant, in a murine model of polymicrobial sepsis. Oral pre-treatment with HF increased mortality in septic mice. The same animals presented with lower levels of interleukin-6, nitric oxide and hydrogen peroxide in their peritoneal lavage samples than vehicle mice. HF also increased polymorphonuclear cell accumulation in to the peritoneum of mice with sepsis. Macrophage-derived nitric oxide upon lipopolysaccharide stimuli was markedly reduced by incubation with HF. Diterpenes, triterpenes, phytosterols, vitamin E and ascorbyl palmitate were detected in the HF. These results indicate that P. granatum leaf lipophilic fractions may worsen sepsis outcome. This effect may be associated with its bioactive compounds which act synergistically or not, increasing sepsis mortality in vivo.

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Picking pithy plants: Pith selectivity by wild white‐faced capuchin monkeys, Cebus imitator

DePasquale,

Poirier,

Mah

et al. 2023

American J Primatol

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Understanding diet selectivity is a longstanding goal in primate ecology. Deciphering when and why primates consume different resources can provide insights into their nutritional ecology as well as adaptations to food scarcity. Plant pith, the spongy interior of plant stems, is occasionally eaten by primates, but the context is poorly understood. We examine the ecological, mechanical, chemical, and nutritional basis of plant pith selection by a wild, frugivorous‐omnivorous primate (Cebus imitator). We test the hypothesis that pith is a fallback food, that is, consumed when fruit is less abundant, and test for differences between plant species from which pith is eaten versus avoided. We collected 3.5 years of capuchin pith consumption data to document dietary species and analyzed “pith patch visits” in relation to fruit availability, visits to fruit patches, and climatic seasonality. We analyzed dietary and non‐dietary species for relative pith quantity, mechanical hardness, odor composition, and macronutrient concentrations. Capuchins ate pith from 11 of ~300 plant species common in the dry forest, most commonly Bursera simaruba. We find that pith consumption is not directly related to fruit availability or fruit foraging but occurs most frequently (84% of patch visits) during the months of seasonal transition. Relative to common non‐dietary species, dietary pith species have relatively higher pith quantity, have softer outer branches and pith, and contain more terpenoids, a class of bioactive compounds notable for their widespread medicinal properties. Our results suggest that greater pith quantity, lower hardness, and a more complex, terpenoid‐rich odor profile contribute to species selectivity; further, as pith is likely to be consistently available throughout the year, the seasonality of pith foraging may point to zoopharmacognosy, as seasonal transitions typically introduce new parasites or pathogens. Our study furthers our understanding of how climatic seasonality impacts primate behavior and sheds new light on food choice by an omnivorous primate.

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Anti-inflammatory and antioxidative effects of six pentacyclic triterpenes isolated from the Mexican copal resin of Bursera copallifera

Cited by 58 publications

References 48 publications

Antiproliferative and anti-inflammatory acyl glucosyl flavones from the leaves of Bursera copallifera

Antiproliferative and anti-inflammatory acyl glucosyl flavones from the leaves of Bursera copallifera

Punica granatum Leaf Lipophilic Fraction Favours Mortality by Attenuating Inflammation in Mice with Polymicrobial Sepsis

Picking pithy plants: Pith selectivity by wild white‐faced capuchin monkeys, Cebus imitator

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