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1.
Phytother Res ; 37(7): 2741-2744, 2023 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-36597265

RESUMEN

Antibacterial activity of Xylopia pancheri Baill. (Annonaceae) leaf extract was investigated against susceptible Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) and extended-spectrum-ß-lactamase (ESBL)-producing Pseudomonas aeruginosa. Results showed that X. pancheri leaf extract displayed antibacterial activity against S. aureus with higher inhibitory effect on MRSA compared to control gentamycin antibiotic, and IC50 value of 36.97 µg/mL [95%CI:29.59-46.18] against MRSA.


Asunto(s)
Staphylococcus aureus Resistente a Meticilina , Infecciones Estafilocócicas , Xylopia , Staphylococcus aureus , Pruebas de Sensibilidad Microbiana , Antibacterianos/farmacología , Infecciones Estafilocócicas/microbiología , Extractos Vegetales/farmacología
2.
Mar Drugs ; 16(10)2018 Oct 11.
Artículo en Inglés | MEDLINE | ID: mdl-30314382

RESUMEN

Arsenicin A (C3H6As4O3) was isolated from the New Caledonian poecilosclerid sponge Echinochalina bargibanti, and described as the first natural organic polyarsenic compound. Further bioguided fractionation of the extracts of this sponge led us to isolate the first sulfur-containing organic polyarsenicals ever found in Nature. These metabolites, called arsenicin B and arsenicin C, are built on a noradamantane-type framework that is characterized by an unusual As⁻As bonding. Extensive NMR measurements, in combination with mass spectra, enabled the assignment of the structure for arsenicin B (C3H6As4S2) as 2. The scarcity of arsenicin C and its intrinsic chemical instability only allowed the collection of partial spectral data, which prevented the full structural definition. After the extensive computational testing of several putative structures, structure 3 was inferred for arsenicin C (C3H6As4OS) by comparing the experimental and density functional theory (DFT)-calculated ¹H and 13C NMR spectra. Finally, the absolute configurations of 2 and 3 were determined with a combined use of experimental and time-dependent (TD)-DFT calculated electronic circular dichroism (ECD) spectra and observed specific rotations. These findings pose great challenges for the investigation of the biosynthesis of these metabolites and the cycle of arsenic in Nature. Arsenicins B and C showed strong antimicrobial activities, especially against S. aureus, which is comparable to the reference compound gentamycin.


Asunto(s)
Arsenicales/farmacología , Poríferos/química , Azufre/farmacología , Animales , Antiinfecciosos/farmacología , Dicroismo Circular/métodos , Espectroscopía de Resonancia Magnética/métodos , Espectrometría de Masas/métodos , Staphylococcus aureus/efectos de los fármacos
3.
Molecules ; 23(6)2018 Jun 05.
Artículo en Inglés | MEDLINE | ID: mdl-29874780

RESUMEN

Volatile components of seven species of the Bazzanioideae sub-family (Lepidoziaceae) native to New Caledonia, including three endemic species (Bazzania marginata, Acromastigum caledonicum and A. tenax), were analyzed by GC-FID-MS in order to index these plants to known or new chemotypes. Detected volatile constituents in studied species were constituted mainly by sesquiterpene, as well as diterpene compounds. All so-established compositions cannot successfully index some of them to known chemotypes but afforded the discovery of new chemotypes such as cuparane/fusicoccane. The major component of B. francana was isolated and characterized as a new zierane-type sesquiterpene called ziera-12(13),10(14)-dien-5-ol (23). In addition, qualitative intraspecies variations of chemical composition were very important particularly for B. francana which possessed three clearly defined different compositions. We report here also the first phytochemical investigation of Acromastigum species. Moreover, crude diethyl ether extract of B. vitatta afforded a new bis(bibenzyl) called vittatin (51), for which a putative biosynthesis was suggested.


Asunto(s)
Biomarcadores/metabolismo , Hepatophyta/química , Hepatophyta/clasificación , Espectroscopía de Resonancia Magnética , Nueva Caledonia , Especificidad de la Especie
4.
Bioorg Med Chem ; 25(6): 1817-1829, 2017 03 15.
Artículo en Inglés | MEDLINE | ID: mdl-28214231

RESUMEN

22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2',3,4',6'-tetramethoxychalcone (FKd 19). FKd induced a G1/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24h-effect on Akt/mTor normal cells versus a 48h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents.


Asunto(s)
Chalcona/análogos & derivados , Flavonoides/farmacología , Espectroscopía de Resonancia Magnética con Carbono-13 , Línea Celular , Línea Celular Tumoral , Chalcona/química , Chalcona/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Flavonoides/química , Humanos , Espectroscopía de Protones por Resonancia Magnética , Espectrometría de Masa por Ionización de Electrospray , Relación Estructura-Actividad
5.
Chem Biodivers ; 12(12): 1848-61, 2015 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-26663838

RESUMEN

Plant secondary metabolites can be useful chemosystematic markers to distinguish species at different taxonomy levels. For example, sesquiterpenes and diterpenes show specific distribution patterns within conifers and so provide especially precious information about the diversity and evolutionary relationships of this group. The aim of the present study was to provide a first insight into the terpene diversity of endemic Podocarpaceae from New Caledonia. The leaf essential oils of Dacrydium araucarioides Brongn. & Gris, Dacrydium balansae Brongn. & Gris, Dacrydium guillauminii J.Buchholz, Dacrydium lycopodioides Brongn. & Gris, Falcatifolium taxoides (Brongn. & Gris) de Laub., and Acmopyle pancheri (Brongn. & Gris) Pilg. from New Caledonia were characterized by GC/FID and GC/MS analyses, and the chemotaxonomic relationships of these species were determined by comparison of their terpene compositions. Cluster analysis based on the biosynthetic origin of their volatile terpenes led to the description of three distinct groups of essential oils and showed close relationships between those of D. araucarioides and D. balansae as well as between those of A. pancheri and F. taxoides.


Asunto(s)
Aceites Volátiles/química , Hojas de la Planta/química , Tracheophyta/química , Estructura Molecular , Nueva Caledonia , Aceites Volátiles/aislamiento & purificación , Especificidad de la Especie , Terpenos/química , Tracheophyta/clasificación
6.
Planta Med ; 79(14): 1313-8, 2013 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-23929244

RESUMEN

Dengue virus is the world's most prevalent human pathogenic arbovirus. There is currently no treatment or vaccine, and solutions are urgently needed. We previously demonstrated that biflavonoids from Dacrydium balansae, an endemic gymnosperm from New Caledonia, are potent inhibitors of the Dengue virus NS5 RNA-dependent RNA polymerase. Herein we describe the structure-activity relationship study of 23 compounds: biflavonoids from D. balansae (1-4) and from D. araucarioides (5-10), hexamethyl-amentoflavone (11), cupressuflavone (12), and apigenin derivatives (13-23). We conclude that 1) over the four different biflavonoid skeletons tested, amentoflavone (1) and robustaflavone (5) are the most promising ones for antidengue drug development, 2) the number and position of methyl groups on the biflavonoid moiety modulate their inhibition of Dengue virus NS5 RNA-dependent RNA polymerase, and 3) the degree of oxygenation of flavonoid monomers influences their antidengue potential. Sotetsuflavone (8), with an IC50 = 0.16 µM, is the most active compound of this series and is the strongest inhibitor of the Dengue virus NS5 RNA-dependent RNA polymerase described in the literature.


Asunto(s)
Antivirales/farmacología , Virus del Dengue/efectos de los fármacos , Flavonoides/farmacología , Extractos Vegetales/farmacología , ARN Viral/efectos de los fármacos , ARN Polimerasa Dependiente del ARN/antagonistas & inhibidores , Tracheophyta/química , Antivirales/química , Virus del Dengue/enzimología , Virus del Dengue/genética , Flavonoides/química , Concentración 50 Inhibidora , Nueva Caledonia , Extractos Vegetales/química , ARN Viral/metabolismo , ARN Polimerasa Dependiente del ARN/genética , Relación Estructura-Actividad , Proteínas no Estructurales Virales/antagonistas & inhibidores , Proteínas no Estructurales Virales/genética
7.
Parasitol Res ; 112(4): 1379-84, 2013 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-23371495

RESUMEN

The aim of the present study was to demonstrate acaricidal activity on the cattle tick Rhipicephalus (Boophilus) microplus of essential oils from endemic conifers of New Caledonia in the context of the development of natural alternatives. Acaricidal activity of essential oils extracted from resin and heartwood of five endemic conifers of New Caledonia (Araucaria columnaris, Agathis moorei, Agathis ovata, Callitris sulcata, and Neocallitropsis pancheri) was evaluated on 14- to 21-day-old Rhipicephalus microplus tick larvae using the Larval Packal Test bioassay. A first screening with 5% dilute solution was carried out and the oils with 100% of mortality at this rate were diluted until no activity was shown. The heartwood oils of the two Cupressaceae were the most active with LC50 value of 0.65% for C. sulcata and 0.55% for N. pancheri while resin oil of A. columnaris (LC50=1.62%) was the most active of the Araucariaceae family. Negative control (ethanol) was not toxic to the larvae. The chemical composition of essential oil from resin of A. columnaris was analyzed by gas chromatography-mass spectrometry. The essential oil was characterized by high level of sesquiterpene hydrocarbons and oxygenated sesquiterpenes and was composed mainly of aromadendrene (23.1%) and bicyclogermacrene (16.0%). In order to compare different plant resources in a sustainable program of natural acaricide, an "essential oil efficiency EOE" can be measured as the ratio between the yield of extraction and LC50 value. This study shows that A. columnaris (EOE=2.36) and N. pancheri (EOE=3.51) could provide valuable and effective natural acaricides for control of the cattle tick R. microplus.


Asunto(s)
Acaricidas/farmacología , Aceites Volátiles/farmacología , Rhipicephalus/efectos de los fármacos , Tracheophyta/química , Acaricidas/química , Acaricidas/aislamiento & purificación , Animales , Bioensayo , Femenino , Cromatografía de Gases y Espectrometría de Masas , Larva/efectos de los fármacos , Nueva Caledonia , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Sesquiterpenos/análisis , Análisis de Supervivencia
8.
J Ethnobiol Ethnomed ; 19(1): 44, 2023 Oct 18.
Artículo en Inglés | MEDLINE | ID: mdl-37853377

RESUMEN

BACKGROUND: Traditional Polynesian medicine for children has been poorly documented, and few data are available on their efficacy and safety. In this context, the aim of this study was to identify traditional practices used for treating children and then assess the efficacy and safety of the most cited remedies by reviewing the literature. METHODS: In 2022, a semi-structured survey was carried out on five islands from the Society archipelago (Bora Bora, Huahine, Moorea, Raiatea, and Tahiti). A total of 86 participants were interviewed including 19 experts in herbalism. A thorough literature review was performed on the most cited plant species to gather the relevant ethnobotanical, pharmacological, and clinical data of each remedy. RESULTS: Participants mentioned using 469 remedies to treat 69 health disorders. The most represented health categories were digestive system, skin disorders, infectious diseases, and respiratory system. A total of 67 plant species (representing 731 use-reports) were mentioned and Annona muricata, Gardenia taitensis, and Hibiscus rosa-sinensis were the main plants reported. Regarding the safety of cited remedies, one plant (Microsorum grossum) showed high risk of toxicity, and its use should be avoided in infants and children. CONCLUSION: Our survey confirms the importance of traditional medical practices for children in the Society Islands. A lack of data in children for most cited remedies demonstrate the need for more pharmacological and toxicological research on Polynesian medicinal plants. Finally, the potential risk of toxicity for some cited plant species reported calls for a better information of traditional medicine users and healers.


Asunto(s)
Fitoterapia , Plantas Medicinales , Humanos , Niño , Etnobotánica , Medicina Tradicional , Polinesia , Conocimientos, Actitudes y Práctica en Salud
9.
Planta Med ; 78(7): 672-7, 2012 May.
Artículo en Inglés | MEDLINE | ID: mdl-22411725

RESUMEN

In order to find new molecules for antiviral drug design, we screened 102 ethyl acetate extracts from New-Caledonian flora for antiviral activity against the dengue 2 virus RNA-dependant RNA polymerase (DV-NS5 RdRp). The leaf extract of Dacrydium balansae, which strongly inhibited the DV-NS5, was submitted to bioguided fractionation. Four biflavonoids ( 1- 4), three sterols ( 5- 7), and two stilbene derivatives ( 8- 9) were identified and evaluated for their antiviral potential on the DV-NS5 RdRp. Biflavonoids appeared to be potent inhibitors of DV-NS5 RdRp with IC (50)s between 0.26 and 3.12 µM. Inhibitory activity evaluations against the RNA polymerase from other Flaviviridae viruses allowed us to conclude that these compounds are specific inhibitors of the DV RNA polymerase. The strongest inhibitions were observed with hinokiflavone ( 4), but podocarpusflavone A ( 2) is the strongest noncytotoxic inhibitor of the DV-NS5 and it also displayed polymerase inhibitory activity in a DV replicon. A preliminary structure-activity relationship study (SARs) revealed the necessity of the biflavonoid skeleton, the influence of number and position of methoxylations, and the importance of a free rotation of the linkage between the two apigenin monomers of the biflavonoids. To the best of our knowledge, podocarpusflavone A ( 2) is the strongest noncytotoxic non-nucleotide molecule exhibiting a specific inhibitory activity against the RNA polymerase domain of DV-NS5 and thus is promising for chemotherapy development against dengue fever.


Asunto(s)
Antivirales/farmacología , Biflavonoides/farmacología , ARN Polimerasas Dirigidas por ADN/antagonistas & inhibidores , Virus del Dengue/enzimología , Inhibidores Enzimáticos/farmacología , Fitoterapia , ARN Polimerasa Dependiente del ARN/antagonistas & inhibidores , Tracheophyta/química , Antivirales/química , Biflavonoides/química , ARN Polimerasas Dirigidas por ADN/química , Virus del Dengue/efectos de los fármacos , Nueva Caledonia , Corteza de la Planta/química , Hojas de la Planta/química , Relación Estructura-Actividad , Proteínas no Estructurales Virales/metabolismo
10.
Front Pharmacol ; 13: 1081310, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-36699063

RESUMEN

Introduction: Formerly named Plectranthus forsteri, Coleus forsteri (Benth.) A.J.Paton, 2019 is a Lamiaceae traditionally used to treat flu-like symptoms and shock-related ecchymosis, especially in the Pacific region. Few studies investigated chemical composition and anti-inflammatory potential of this plant. Method: Herein, we investigated anti-inflammatory potential of C. forsteri ethanolic (ePE) and cyclohexane (cPE) plant extract on LPS-induced human macrophages models and quantified cytokines and quinolinic acid (QUIN) as inflammatory markers. Results: Our results show that extract of ePE and cPE significantly inhibit inflammatory cytokine IL-6 and TNF-α induced by LPS on PMA-derived THP-1 macrophages. QUIN production is also diminished under ePE and cPE treatment in activated human monocyte-derived macrophages (MDMs). Seven abietane diterpenes were characterized from C. forsteri cPE including coleon U (1), coleon U-quinone (2), 8α,9α-epoxycoleon U-quinone (3), horminone or 7α-hydroxyroyleanone (4), 6ß,7α-dihydroxyroyleanone (5), 7α-acetoxy-6ß-hydroxyroyleanone (6) and 7α-formyloxy-6ß-hydroxyroyleanone (7). Discussion: We discussed potential contributions of these molecules from C. forsteri extracts for their anti-inflammatory activities.

11.
Pharm Biol ; 49(4): 369-76, 2011 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-21284535

RESUMEN

CONTEXT: With the emergence of strains multiresistant to antimalarial drugs, the search for new active molecules remains a priority. Ethnopharmacology appears to be a good method of selection in such investigations. OBJECTIVE: The aim of this research work is to select plants used in Melanesian traditional medicine, in New Caledonia and Vanuatu, which should be a promising source for the isolation of new antimalarial drugs. MATERIALS AND METHODS: Forty-seven plant extracts belonging to 12 families, traditionally used by the Melanesian people or belonging to an antimalarial known genus, were screened in vitro for antimalarial activity on Plasmodium falciparum chloroquine (CQ)-resistant (FcB1) and CQ-sensitive (HB3) strains. They were also tested for their inhibitory effects on a protein kinase (Pfnek) and their cytotoxicity on human breast adenocarcinoma (MCF7) cells. RESULTS: Among all extracts, four displayed strong in vitro activities against P. falciparum: Gardenia urvillei Montrouzier, Scleria polycarpa Boeckeler, Terminalia catappa L. and Acronychia laevis J.R. & J.G. Forster, the latter being also toxic on MCF7 cells. Except for the extracts of S. polycarpa, all others that were active on P. falciparum, also possess an inhibitory effect on Pfnek. DISCUSSION AND CONCLUSION: These results confirm that ethnopharmacology is an excellent approach for such investigations. The two countries considered clearly present advantages in the field. Indeed, local populations keep their traditional knowledge alive, and their flora is exceptionally rich. In New Caledonia, the high endemicity rate (74%) ranks the island as one of the world's biodiversity hotspots. As a consequence, chances to discover new active natural compounds are also high.


Asunto(s)
Antimaláricos/farmacología , Extractos Vegetales/farmacología , Plasmodium falciparum/efectos de los fármacos , Antimaláricos/aislamiento & purificación , Antineoplásicos/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Cloroquina/farmacología , Doxorrubicina/farmacología , Femenino , Humanos , Nueva Caledonia , Inhibidores de Proteínas Quinasas/farmacología , Vanuatu
12.
Nat Prod Res ; 35(12): 2099-2102, 2021 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-31441670

RESUMEN

The first chemotaxonomic study based on volatile components of Porella viridissima (Mitt.) Grolle is reported. The GC-MS analysis of ether extract was performed; ten santalane and five pinguisane-type sesquiterpenes were identified together with perrottetianal A as major diterpene. Most of detected santalane-type sesquiterpenes are reported for the first time in liverwort. P. viridissima was found to belong to the chemotype III (pinguisane/sacculatane) and shared chemical similarities with P. navicularis. Perrotettianal A was isolated and has shown strong cytotoxicity against ovarian cancer.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Hepatophyta/química , Hepatophyta/clasificación , Antineoplásicos Fitogénicos/química , Diterpenos/análisis , Diterpenos/química , Diterpenos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Cromatografía de Gases y Espectrometría de Masas , Humanos , Neoplasias Ováricas/tratamiento farmacológico , Neoplasias Ováricas/patología , Extractos Vegetales/análisis , Extractos Vegetales/química , Sesquiterpenos/análisis , Sesquiterpenos/química , Compuestos Orgánicos Volátiles/análisis
13.
PeerJ ; 7: e6896, 2019.
Artículo en Inglés | MEDLINE | ID: mdl-31198623

RESUMEN

BACKGROUND: Different parts of the tree Calophyllum inophyllum L. (nuts, leaves, roots, bark, fruits, nut oil and resin) are used as traditional medicines and cosmetics in most of the Pacific Islands. The oil efficiency as a natural cure and in traditional cosmetics has been largely described throughout the South Pacific, which led us to investigate C. inophyllum's chemical and genetic diversity. A correlative study of the nut resin and leaf DNA from three distinct archipelagos in the South Pacific was carried out in order to identify diversity patterns in C. inophyllum across the South Pacific. METHODS: Calophyllum inophyllum plants were sampled from French Polynesia, New Caledonia and Fiji. We extracted tamanu oil (nut oil) resin for chemo-diversity studies and sampled leaf tissues for genetic studies. We applied an analysis method designed for small quantities (at a microscale level), and used High Performance Liquid Chromatography (HPLC) to establish the chemo-diversity of tamanu oil resin. In-house standards were co-eluted for qualitative determination. Genetic diversity was assessed using chloroplast barcoding markers (the Acetyl-CoA carboxylase (accD) gene and the psaA-ycf3 intergenic spacer region). RESULTS: Our HPLC analysis revealed 11 previously known tamanu oil constituents, with variability among plant samples. We also isolated and characterized two new neoflavonoids from tamanu oil resin namely, tamanolide E1 and E2 which are diastereoisomers. Although genetic analysis revealed low genetic variation, our multivariate analysis (PCA) of the tamanu oil resin chemical profiles revealed differentiation among geographic regions. CONCLUSION: We showed here that chromatographic analysis using formalized in-house standards of oil resin compounds for co-elution studies against oil resin samples could identify patterns of variation among samples of C. inophyllum, and discriminate samples from different geographical origins.

14.
Nat Prod Commun ; 11(12): 1919-1922, 2016 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-30508365

RESUMEN

Essential oil from leaves of Neinuaron vieilardii (Baill.) Baill., a shrub used in the kanak pharmacopeia, was analyzed by gas chromatography and combined. gas chromatography-mass spectrometry. The main compounds identified were safrole (49.7%), linalool (8.0%), 5-cadinene (5.1%), caryophyllene oxide.(4%) and A-6opaene (2.4%). This chemical composition is consistent with leaf oils of the Atherospermataceae family and demonstrates the proximity of the two genera Nemnuaron and Atherosperma as regards to their essential oil compositions. The modified Larval Packet Test (LPT) was used to assess acaricidal effect of N. viefflardii essential oil on larvae of the cattle tick Rhipicephalus (Boophilus) microplus and LC(50) was then calculated to 14.67%. High content of safrole in this oil which is suspected of being a human carcinogen, poses the problem of the use of this oil in a perspective of development of alternative tick control strategy and in the traditional medicinal consumption of Nemuaron vieillardii.


Asunto(s)
Acaricidas , Magnoliopsida/química , Aceites Volátiles , Fitoquímicos , Rhipicephalus/efectos de los fármacos , Acaricidas/química , Acaricidas/farmacología , Animales , Larva/efectos de los fármacos , Aceites Volátiles/química , Aceites Volátiles/farmacología , Fitoquímicos/análisis , Fitoquímicos/farmacología , Hojas de la Planta/química
15.
Nat Prod Commun ; 11(8): 1161-1164, 2016 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-30725581

RESUMEN

Volatile components of seven Frullania species (Frullaniaceae) from New Caledonia, including five endemic species (F. bella, F. scalaris, F. mamnmillosa, F. cornita and F. falsicornuta), were analyzed by GC-MS in order to index these plants to known chemotypes. Constituents detected in these Frullania species were mainly sesquiterpenes, as well as the bibenzyl dihydrognetin, and the flavonoid naringinin-5,7,4'-trimethyl ether. These compositions allowed an indexation of Frullania species from New Caledonia to cyclocolorenone, sesquiterpene lactone and bibenzyl chemotypes. In addition, qualitative intraspecies variations of chemical composition were very important and made indexation to known chemotypes very tricky. Moreover, two of the endemic liverworts did not possess any biomarker that linked to a known chemotype.


Asunto(s)
Frullania/química , Compuestos Orgánicos Volátiles/química , Estructura Molecular , Nueva Caledonia
16.
Phytochemistry ; 66(2): 241-7, 2005 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-15652581

RESUMEN

Chemical study of Cunonia macrophylla, a New Caledonian Cunoniaceae, based on bioactive effects of a crude methanol extract of the leaves, detected bioactive tannins for the first time in this plant family. These ellagitannins have been identified as ellagic acid-4-O-beta-D-xylopyranoside (6), mallorepanin (3), mallotinic acid (1) along with corilagin (2), chebulagic acid (4), ellagic acid (5) and gallic acid (7) and have been shown to possess antimicrobial activity and to inhibit xanthine oxidase. Antimicrobial effects on bacterial human pathogens (Staphylococcus aureus, Corynebacterium accolans) and on a plant pathogen (Erwinia carotovora) as well as on a human pathogenic yeast (Candida albicans) were investigated. Activity is reported here for the first time for compounds 1, 3, 4 and 6. The inhibitory effects of all molecules against xanthine oxidase in relation to their structure was evaluated and compared. Compound 6 presented the best activity and seems to be of considerable interest for further studies.


Asunto(s)
Taninos Hidrolizables/química , Taninos Hidrolizables/farmacología , Magnoliopsida/química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Candida albicans/efectos de los fármacos , Corynebacterium/efectos de los fármacos , Erwinia/efectos de los fármacos , Taninos Hidrolizables/aislamiento & purificación , Estructura Molecular , Nueva Caledonia , Xantina Oxidasa/antagonistas & inhibidores
17.
PLoS One ; 10(9): e0138602, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-26406588

RESUMEN

BACKGROUND: Calophyllum inophyllum L. (Calophyllaceae) is an evergreen tree ethno-medically used along the seashores and islands of the Indian and Pacific Oceans, especially in Polynesia. Oil extracted from the seeds is traditionally used topically to treat a wide range of skin injuries from burn, scar and infected wounds to skin diseases such as dermatosis, urticaria and eczema. However, very few scientific studies reported and quantified the therapeutic properties of Calophyllum inophyllum oil (CIO). In this work, five CIO from Indonesia (CIO1), Tahiti (CIO2, 3), Fiji islands (CIO4) and New Caledonia (CIO5) were studied and their cytotoxic, wound healing, and antibacterial properties were presented in order to provide a scientific support to their traditional use and verify their safety. METHODS: The safety of the five CIO was ascertained using the Alamar blue assay on human keratinocyte cells. CIO wound healing properties were determined using the scratch test assay on human keratinocyte cells. CIO-stimulated antibacterial innate immune response was evaluated using ELISA by measuring ß defensin-2 release in human derivative macrophage cells. CIO antibacterial activity was tested using oilogramme against twenty aerobic Gram- bacteria species, twenty aerobic Gram+ bacteria species, including a multi-drug resistant Staphylococcus aureus strain and two anaerobic Gram+ bacteria species e.g. Propionibacterium acnes and Propionibacterium granulosum. To detect polarity profile of the components responsible of the antibacterial activity, we performed bioautography against a Staphylococcus aureus strain. RESULTS: Based on Alamar Blue assay, we showed that CIO can be safely used on keratinocyte cells between 2.7% and 11.2% depending on CIO origin. Concerning the healing activity, all the CIO tested accelerated in vitro wound closure, the healing factor being 1.3 to 2.1 higher compared to control when keratinocytes were incubated after scratch with CIO at 0.1%. Furthermore, our results showed that CIO exhibit two distinct antibacterial effects: one against Gram+ bacteria by direct inhibition of mitotic growth and another potent effect against Gram- bacteria due to increased release of ß-defensin 2 peptide by macrophages. Interestingly, the needed concentrations of CIO to inhibit bacteria growth and to promote wound healing are lower than concentrations exhibiting cytotoxic effects on keratinocyte cells. Finally, we performed bioautography assay against Staphylococcus aureus to determine polarity profile of the components responsible for CIO antibacterial activity. Our results showed for the five tested CIO that components responsible of the bacterial growth inhibition are the more polar one on the TLC chromatographic profile and are contained in the resinous fraction of the oil. CONCLUSIONS: This study was conducted to evaluate cytotoxicity, wound healing and antibacterial properties of five CIO traditionally used to treat infected wounds. Using cell and bacteria cultures, we confirmed the pharmacological effects of CIO as wound healing and antimicrobial agent. Moreover, we showed that concentration of CIO needed to exhibit therapeutic effects are lower than concentrations exhibiting cytotoxic effects in vitro. For the first time, this study provides support for traditional uses of CIO. These wound healing and antibiotic properties make CIO a valuable candidate to treat infected wounds especially in tropical areas.


Asunto(s)
Antibacterianos/farmacología , Calophyllum/química , Aceites de Plantas/farmacología , Cicatrización de Heridas/efectos de los fármacos , Células Cultivadas , Etnofarmacología , Regulación de la Expresión Génica/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Humanos , Queratinocitos/efectos de los fármacos , Macrófagos/efectos de los fármacos , Islas del Pacífico/etnología , Semillas/química , Infección de Heridas/tratamiento farmacológico , beta-Defensinas/metabolismo
18.
Nat Prod Commun ; 9(9): 1223-7, 2014 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-25918778

RESUMEN

The leaf, wood and bark oils of three species of Myodocarpus, M. viellardii Brongn. & Gris, M. fraxinifolius Brongn. & Gris and M. lanceolatus Dubard & R. Viguier have been examined. From the wood oil of M. viellardii the major components were α-pinene (22.4%) and a monoterpene methyl ester, methyl myodocarpate (methyl 3,7-dimethylbicyclo [4,1,0]hept-3-ene-7-carboxylate) (61%), based on the δ-3-carene skeleton. Also present in lesser amounts was the corresponding acid, myodocarpic acid (3,7-dimethylbicyclo[4,1,0]hept-3-ene-7-carboxilic acid) and the corresponding alcohol, myodocarpol (3,7- dimethylbicyclo[4,1,0]hept-3-en-7-yl) methanol), in lesser (< 3%) amounts. The bark oil contained ß-caryophyllene (13.8%) and a series of long chain fatty alcohols, dodecanol, tetradecanol, hexadecanol, octadecanol and octadec-9-en-1-ol in amounts of 1.4-15% (all but octadecanol > 11%). The leaf oil of this species produced a sesquiterpenic oil with the principal components being ß-caryophyllene (36%), α-humulene (11.1%) and bicyclogermacrene (10.6%). In M. fraxinifolius, both the wood and bark oils contained a series of long chain alcohols, tetradecanol (30-38%), hexadecanol (23-29%) and octadec-9-en-1-ol (12%) as principal components. In the leaf oil of this species the principal component was ß-caryophyllene (63%), with lesser amounts of humulene oxide II (2.9%), isocomene (2.8%) and viridiflorol (1.4%). In M. lanceolatus, the leaf oil was dominated by the monoterpene hydrocarbons α-pinene (22.9%) and δ-3-carene (32.6%). In the wood oil of this species the principal components were geraniol (7.4%), citronellol (4.7%), germacrene-B (7.1%), zingiberine (6.8%) and linalool (6.7%), while in the bark oil they were geraniol (12.4%), citronellol (2.6%), germacrene-B (5.8%), and linalool (6.5%).


Asunto(s)
Magnoliopsida/química , Corteza de la Planta/química , Extractos Vegetales/química , Aceites de Plantas/química , Madera/química , Estructura Molecular , Nueva Caledonia , Hojas de la Planta/química
19.
Nat Prod Commun ; 5(6): 949-56, 2010 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-20614833

RESUMEN

The volatile components obtained by hydrodistillation of leaves of C. neocaledonica Dummer, C. sulcata (Parlatore) Schlechter and N. pancheri (Carrière) de Laubenfels from New Caledonia were investigated for the first time by a combination of GC and GC-MS analysis, and compared with the heartwood oil compositions of the three species. The essential oils from C. sulcata and C. neocaledonica leaves contain a majority of monoterpenes while the leaf oil of N. pancheri is characterized by a high level of sesquiterpenoids. On the basis of the sesquiterpenoid composition of the wood- and leaf oils, N. pancheri is closely related to both New Caledonian Callitris spp. However, C. sulcata and C. neocaledonica oils remain distinct from N. pancheri and the Australian Callitris oils by the presence of compounds biosynthetically related to the bisabolyl cation, mainly barbatenes and thujopsene.


Asunto(s)
Cupressaceae/química , Aceites Volátiles/química , Aceites de Plantas/química , Árboles/química , Nueva Caledonia
20.
Phytother Res ; 21(4): 398-400, 2007 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-17236172

RESUMEN

An alkaloidal extract of the leaves of Melochia odorata exhibited antifungal activity against Candida albicans, Cryptococcus neoformans and Saccharomyces cerevisiae using a TLC bioautographic method. Bioassay-guided fractionation of this extract using separation by normal and reverse high-performance liquid chromatography (HPLC) resulted in the isolation of two active compounds identified as frangulanine, a cyclic peptide alkaloid, and waltherione-A, a quinolinone alkaloid.


Asunto(s)
Alcaloides/aislamiento & purificación , Antifúngicos/aislamiento & purificación , Malvaceae/química , Alcaloides/farmacología , Antifúngicos/farmacología , Candida albicans/efectos de los fármacos , Cryptococcus neoformans/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Hojas de la Planta/química , Saccharomyces cerevisiae/efectos de los fármacos
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