Triterpene methyl ethers from palmae epicuticular waxes

doi:10.1016/0031-9422(95)00173-5

Phytochemistry

Volume 39, Issue 6, August 1995, Pages 1381-1382

https://doi.org/10.1016/0031-9422(95)00173-5 Get rights and content

Abstract

Cylindrin and lupeol methyl ether were isolated for the first time from Palmae leaf epicuticular waxes. Butia capitata and Orbignya spp. contain large amounts of ethers, but these are absent in Arecastrum romanzoffianum. A new triterpene methyl ether was isolated from O. phalerata wax. The new compound was characterized as 3-β-methoxy lupane.

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Bioactive compounds and health benefits of some palm species traditionally used in Africa and the Americas – A review
2018, Journal of Ethnopharmacology
Citation Excerpt :
Lupeol was detected in the epicuticular wax of A. speciosa and Butia capitata (Mart.) Becc. (jelly palm-do-Cerrado) (García et al., 1995), in the root of E. precatoria (Galotta and Boaventura, 2005) and additionally it was found in the mesocarp of the Asian Phoenix theophrasti Greuter (Liolios et al., 2009). Ursolic acid was reported in leaves of A. catechu (Peng et al., 2015) and in leaves of the medicinal C. tepejilote (Jiménez et al., 2005), in young shoots of medicinal Calamus leptospadix Griff. (
According to previous ethno-medicinal reviews, Cocos nucifera, Elaeis guineensis and Phoenix dactylifera are among the main palms which are often used on the American and African continents to treat infections, infestations and disorders in the digestive, respiratory, genito-urinary, dermal, endocrine, cardiovascular, muscular-skeletal, mental and neural systems, as well as neoplasms, dental issues and metabolic and nutritional disorders. In addition, one or more species of the wild genera Acrocomia, Areca, Astrocaryum, Attalea, Bactris, Borassus, Calamus, Chamaedorea, Chamaerops, Euterpe, Hyphaene, Mauritia, Oenocarpus and Syagrus have a high number of records of these ethno-medicinal uses. The most used parts of the palm tree are the fruits, followed by roots, seeds, leaves and flower sap.
This review discusses the phytochemical composition and the pharmacological properties of these important ethno-medicinal palms, aiming to provide a contribution to future research prospects.
Significant information was compiled from an electronic search in widely used international scientific databases (Google Scholar, Science Direct, SciFinder, Web of Science, PubMed, Wiley on line Library, Scielo, ACS Publications), and additional information was obtained from dissertations, theses, books and other relevant websites.
Palms, in general, are rich in oils, terpenoids and phenolic compounds. Fruits of many species are notable for their high content of healthy oils and fat-soluble bioactive compounds, mainly terpenoids, such as pigment carotenoids (and provitamin A), phytosterols, triterpene pentacyclics and tocols (and vitamin E), while other species stood out for their phenolic compounds derived from benzoic and cinnamic acids, along with flavan-3-ol, flavone, flavonol, and stilbene compounds or anthocyanin pigments. In addition to fruits, other parts of the plant such as seeds, leaves, palm heart, flowers and roots are also sources of many bioactive compounds. These compounds are linked to the ethno-medicinal use of many palms that improve human health against infections, infestations and disorders of human systems.
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Diversity of opportunistic black fungi on babassu coconut shells, a rich source of esters and hydrocarbons
2017, Fungal Biology
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Elucidation of ecological and evolutionary parameters is necessary to understand those factors of habitat choice that seem to enhance opportunism on the human host (Vicente et al. 2008; Döğen et al. 2013; Gümral et al. 2014). Babassu coconuts are rich in lipids, terpenes and other hydrocarbons (Garcia et al. 1995) and are a commodity for industrial purposes (Teixeira 2008; Santos et al. 2013). The shells provide a rather special environment recalcitrant to microbial decomposition.
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Butia spp. (Arecaceae): An overview
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Citation Excerpt :
Flavonoid sulfates, flavone c-glycosides, tricin, luteolin, quercetin, and proanthocianidins are distributed in flowers and fruits in members of the Arecaceae family (Barron et al., 1988; Harborne et al., 1974; Harborne, 1975; Williams and Harborne, 1973) and were utilized as chemotaxonomic markers for speciation (Williams et al., 1983). A lipid fraction rich in linear hydrocarbon waxes has also been utilized as a taxonomic identifier within the Arecaceae family (García et al., 1995; Paroul et al., 2009). In both studies, the apolar compounds were extracted from leaves and analyzed by GC-MS. García et al. (1995) found B. capitata and Orbignya spp. containing large amounts of ethers, which were absent from Arecastrum romanzoffianum.
Butia is a genus of palms (Arecaceae), autochthonous to South America with great potential for income generation. In order to better utilize and maintain the currently available genetic resources, it is necessary to pursue studies directed towards the taxonomic and systematic characterization (morphological, phenotypic, molecular, chemical, and reproductive) and conservation of Butia spp. Despite the long use of this plant, a limited number of scientific studies and publications are available on Butia spp., with a significant proportion of the literature written in Portuguese. This review intends to compile all the available information on the genus, covering several aspects of the plant and its potential applications.
Phytochemical and biological studies of Butia capitata Becc. leaves cultivated in Egypt
2014, Asian Pacific Journal of Tropical Biomedicine
Citation Excerpt :
Very few works were traced in the genus Butia. Some authors reported the presence of cylindrin and lupeol methyl ether in the epicuticular waxes of the leaf of B. capitata as well as tricin C-glycosyl flavones, luteolin, quercetin glycosides and kaempferol[3,4], while tricin 7-glucosides, isoorientin and caffeylshikimic acid were reported in the flowers[5]. The aim of this work is to study the anti-inflammatory and antioxidant activity of the different successive extracts of B. capitata leaves, not previously studied, as well as the isolation and identification of the biologically active constituents.
To study the antioxidant and anti-inflammatory activity of Butia capitata (B. capitata) leaf extracts along with phytochemical analysis of the proposed bioactive constituents.
Different successive extracts of B. capitata Becc. leaves were prepared with selective organic solvents and screened for their anti-inflammatory activities in tested animals and in-vitro antioxidant effect. An extensive phytochemical investigation of the bioactive extracts through paper chromatography, thin layer chromatography, column chromatography, gas-liquid chromatography (GLC), high pressure liquid chromatography and spectral analysis. GC-Mass, ultraviolet, hydrogen and carbon nuclear magnetic resonance, electron ionization-mass spectrometry, heteronuclear multiple bond correlation and heteronuclear multiple quantum correlation were carried out.
Results showed that different extracts possess promising antioxidant effect and significant anti-inflammatory activity with variable degrees. The results of the phytochemical investigation of the bioactive extracts revealed the presence of volatile substances, lipoidal matter, α-tocopherol, free sugars, polysaccharides and flavonoidal compounds.
B. capitata leaf extracts were shown to possess variable antioxidant effect, the most promising was methanol extract. Both polar and non polar extracts were proved to have anti-inflammatory activity, the non polar extract was superior in this respect. The bioactivity of the extracts was ascribed to the presence of flavonoids, sterols and α-tocopherol.
Effects of a nanocomposite containing Orbignya speciosa lipophilic extract on Benign Prostatic Hyperplasia
2011, Journal of Ethnopharmacology
Citation Excerpt :
Regarding the kernels, unlike the preparation of an infusion for drinking, people eat them entirely or freshly grounded. Some compounds have been isolated from Orbignya phalerata such as tannins, sugars, saponins, steroid compounds (Bandeira et al., 1986) and triterpenes (Garcia et al., 1995). The anti-inflammatory and analgesic properties of babassu mesocarp were confirmed experimentally using a chloroform extract of the dried fruits as shown by the inhibition of carrageenan-induced acute inflammation, cotton pellet granuloma and formalin-induced arthritis in rats (Maia and Rao, 1989; Silva and Parente, 2001).
Lower urinary tract symptoms (LUTS) are a common complaint among aging men and are usually caused by Benign Prostatic Hyperplasia (BPH). A number of medical treatments for LUTS/BPH exist, such as α-blockers, 5α-reductase inhibitors, phytotherapeutical drugs and combination therapies. Babassu is the common name of a Brazilian native palm tree called Orbignya speciosa, whose kernels are commonly used (eaten entirely or as a grounded powder), in parts of Brazil for the treatment of urinary disorders. This study investigates the effects of Orbignya speciosa nanoparticle extract, a newly developed phytotherapic formulation derived from the kernels of babassu, in the treatment of BPH.
Orbignya speciosa extract was obtained from the kernels, a nanoparticulate system was developed and acute toxicity test was performed. BPH primary stromal cell and tissue cultures were established and treated with 300 μg/mL Orbignya speciosa nanoparticle (NanoOse) extract in order to evaluate its effects on apoptosis induction, cytotoxicity, cell morphology and proliferation.
Our results indicated that NanoOSE shows no toxicity in animals and acts incisively by promoting morphological cell changes, reducing cell proliferation as well as inducing necrosis/apoptosis on BPH cells and tissues.
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Anti-thrombotic effect of chronic oral treatment with Orbignya phalerata Mart.
2007, Journal of Ethnopharmacology
Babassu is the popular name of Orbignya phalerata Mart. (Arecaceae). The mesocarp flour obtained from their fruits has been used in Brazil as medicine in the treatment of pains, constipation, obesity, leukemia, rheumatism, ulcerations, tumors, inflammations and venous diseases. The effect of the chronic oral treatment with aqueous extract of babassu mesocarp (500 mg/kg day) on the number of platelets, the prothrombin time (PT), the activated partial thromboplastin time (aPTT), the nitric oxide (NO) production and the carrageenin-induced thrombosis was evaluated, using C57Bl/6 mice. The chronic oral treatment with babassu mesocarp induced an anti-thrombotic effect. There was a 88.9% reduction in the necrosis of the tail. This effect seems to be related to an increase in the ability of the macrophage to produce NO and to a slow coagulation process associated to an increase of 12.0 and 13.9% in PT and aPTT, respectively. However, the anti-thrombotic effect seems to be not related to alterations in the number of platelets. It is possible to conclude that the oral treatment with babassu mesocarp has a significant anti-thrombotic effect, which could justify the popular use of babassu mesocarp in the treatment of venous diseases. Meanwhile, this study suggests a potential use of babassu mesocarp as a prophylactic agent to avoid thrombosis events.

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ChemotaxonomyTriterpene methyl ethers from palmae epicuticular waxes

Abstract

Phytochemistry

Phytochemistry

Phytochemistry

Tetrahedron

Chemotaxonomy
Triterpene methyl ethers from palmae epicuticular waxes