Limonoides isolados dos frutos de Carapa guianensis Aublet (Meliaceae)

Silva, Suniá Gomes; Nunomura, Rita de Cássia Saraiva; Nunomura, Sergio Massayoshi

doi:10.1590/s0100-40422012001000009

Cited by 7 publications

(4 citation statements)

References 13 publications

(15 reference statements)

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“…Isolated and semi-synthetic limonoids 1 - 5 were fully characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) one and two-dimensional spectrometric techniques. Comparison of the NMR spectral data with literature data and analysis of the 1D and 2D NMR data allowed for the positive identification and spectral assignment of isolated limonoids 1 [ 32 ], 2 [ 33 ], 3 [ 34 ] and 4 [ 35 ] (Figure 1 ). Di-deacetylation of 3 led to the formation of a product that exhibited HRMS, 1 H and 13 C NMR data consistent with 6α-hydroxydeacetylgedunin ( 5 ).…”

Section: Resultsmentioning

confidence: 99%

“…However, gedunin ( 6 ) was not isolated in the present work from RPSM. Interestingly, a recent study on the fruit from the same tree specimens from which fruit for the present study was collected described the isolation of 7-deacetyl gedunin ( 9 ), but not gedunin ( 6 ) [ 35 ]. Gedunin was considered to be an optimal structure for its high in vitro activity against different strains of P. falciparum and because structural modification of gedunin through semi-synthetic reactions yielded derivatives exhibiting decreased in vitro anti-plasmodial activity compared to gedunin [ 21 , 22 ].…”

Section: Discussionmentioning

confidence: 99%

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In vitro and in vivo anti-malarial activity of limonoids isolated from the residual seed biomass from Carapa guianensis (andiroba) oil production

Pereira

Silva

Amorim

et al. 2014

Malar J

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BackgroundCarapa guianensis is a cultivable tree used by traditional health practitioners in the Amazon region to treat several diseases and particularly symptoms related to malaria. Abundant residual pressed seed material (RPSM) results as a by-product of carapa or andiroba oil production. The objective of this study was to evaluate the in vitro and in vivo anti-malarial activity and cytotoxicity of limonoids isolated from C. guaianensis RPSM.Methods6α-acetoxyepoxyazadiradione (1), andirobin (2), 6α-acetoxygedunin (3) and 7-deacetoxy-7-oxogedunin (4) (all isolated from RPSM using extraction and chromatography techniques) and 6α-hydroxy-deacetylgedunin (5) (prepared from 3) were evaluated using the micro test on the multi-drug-resistant Plasmodium falciparum K1 strain. The efficacy of limonoids 3 and 4 was then evaluated orally and subcutaneously in BALB/c mice infected with chloroquine-sensitive Plasmodium berghei NK65 strain in the 4-day suppressive test.ResultsIn vitro, limonoids 1-5 exhibited median inhibition concentrations (IC50) of 20.7-5.0 μM, respectively. In general, these limonoids were not toxic to normal cells (MRC-5 human fibroblasts). In vivo, 3 was more active than 4. At oral doses of 50 and 100 mg/kg/day, 3 suppressed parasitaemia versus untreated controls by 40 and 66%, respectively, evidencing a clear dose–response.Conclusion6α-acetoxygedunin is an abundant natural product present in C. guianensis residual seed materials that exhibits significant in vivo anti-malarial properties.Electronic supplementary materialThe online version of this article (doi:10.1186/1475-2875-13-317) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

In vitro and in vivo anti-malarial activity of limonoids isolated from the residual seed biomass from Carapa guianensis (andiroba) oil production

Pereira

Silva

Amorim

et al. 2014

Malar J

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“…According to Ambrozin et al (2006) and Silva and Nunomura (2012), oils that are rich in fatty acids, such as oleic, palmitic, stearic and linoleic acids, have biological activity against arthropods. Research has identified the presence of limonoids in oils extracted from andiroba seeds, which have proven insecticidal and repellent abilities (Ambrozin et al, 2006).…”

Section: Discussionmentioning

confidence: 99%

Chemical composition and acaricidal activity of seed oils of the palms Mauritia flexuosa and Mauritiella armata in Rhipicephalus microplus (Ixodidae)

Santos

Morais-Costa

Figueiredo

et al. 2021

RSD

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Rhipicephalus microplus is responsible for considerable economic losses in tropical and subtropical regions. Plant compounds have been utilized as alternative to conventional acaricids. The objective in this study was to evaluate the effects of fixed oils extracted from seeds of Mauritia flexuosa and Mauritiella armata, palm trees typical of the Brazilian Cerrado on tick R. microplus.The fixed oils were used against engorged females and larvae by biocarrapaticidograms and larval mortality by larval pack tests (LPT). Chemical compositions of the oils were evaluated by gas chromatography using an electron impact ionization detector and showed the presence of the compounds: palmitoleic acid, linoleic acid, palmitic acid, and myristic acid. In the biocarrapaticidogram, the oil from M. flexuosa and M. armata at 5% and 10% concentrations showed efficacies > 80%. Regarding the effect of fixed oils from palm trees on R. microplus larvae, mortality above 80% was observed at all concentrations tested.These bioproducts are a promising alternative for controlling this tick and may be adapted into current integrated control methods for cattle farming.

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“…Andiroba seed oil extraction has been known for centuries (Aublet 1775). The oil is used for medicinal purposes (Silva et al 2012) and increasingly in the cosmetics industry in recent years (Boufleuer 2004;Shanley and Medina 2005;Mendonça and Ferraz 2007).…”

Section: Introductionmentioning

confidence: 99%

Do polyembryonic seeds of Carapa surinamensis (Meliaceae) have advantages for seedling development?

2019

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Polyembryony is the differentiation and development of multiple embryos in a single seed. This characteristic can provide advantages, as more than one embryo is produced with the same amount of resources, and the probability of establishment of at least one seedling increases. However, sibling seedlings may also increase competition, affecting development and survival. In the present study, the possible advantages and disadvantages of polyembryony were analyzed in the initial establishment of seedlings of Carapa surinamensis (Meliaceae), a tree species that produces monoembryonic or polyembryonic seeds. In this regard, the development of single seedlings was compared with a pair of seedlings emerging from polyembryonic seeds. We compared the development of seedlings attached to or detached from each other and to the seed resources. We observed two levels of competition: (a) for the seed reserves during germination and initial development, as multiple embryos of C. surinamensis share the same reserves, and (b) for external factors, mostly space for root and shoot development, and also for light. Reducing the competition for external factors by separating the siblings was not enough to reduce the effects of competition for seed reserves in the first six months of development. Nevertheless, viable seedlings were produced in all treatments. Thus, depending on sprout management in the nursery, the number of seedlings per seed can be significantly increased by detaching the seedlings, or more vigorous seedlings can be obtained when only one seedling is maintained. Sementes poliembriônicas de Carapa surinamensis (Meliaceae) tem vantagens para o desenvolvimento das plântulas?RESUMO Poliembrionia é a diferenciação e o desenvolvimento de múltiplos embriões em uma única semente. Esta característica pode proporcionar diversas vantagens, como aumentar o número de embriões produzidos com a mesma quantidade de recursos, e aumentar a probabilidade de estabelecimento de pelo menos uma plântula de uma única semente. Por outro lado, a competição entre plântulas pode aumentar, afetando seu desenvolvimento e sobrevivência. Neste estudo, foram analisadas as possíveis vantagens e desvantagens da poliembrionia em sementes de andiroba, Carapa surinamensis (Meliaceae), uma espécie arbórea que produz sementes monoembriônicas ou poliembriônicas. Comparamos o desenvolvimento de plântulas únicas com o de pares de plântulas provenientes de sementes poliembriônicas. As plântulas foram mantidas unidas ou separadas entre si e ligadas à ou destacadas da semente. Os resultados revelaram dois níveis de competição: (a) pelas reservas da semente durante a germinação e desenvolvimento inicial da plântula, quando embriões múltiplos de C. surinamensis compartilham as mesmas reservas, e (b) por fatores externos, principalmente espaço para o desenvolvimento da raiz e da parte aérea, e luz. A redução da competição por fatores externos, através da separação das plântulas, não foi suficiente para reduzir os efeitos da competição pelas reservas das sementes no...

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Limonoides isolados dos frutos de Carapa guianensis Aublet (Meliaceae)

Cited by 7 publications

References 13 publications

In vitro and in vivo anti-malarial activity of limonoids isolated from the residual seed biomass from Carapa guianensis (andiroba) oil production

In vitro and in vivo anti-malarial activity of limonoids isolated from the residual seed biomass from Carapa guianensis (andiroba) oil production

Chemical composition and acaricidal activity of seed oils of the palms Mauritia flexuosa and Mauritiella armata in Rhipicephalus microplus (Ixodidae)

Do polyembryonic seeds of Carapa surinamensis (Meliaceae) have advantages for seedling development?

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