Carapanolides T–X from Carapa guianensis (Andiroba) Seeds

Miyake, Teppei; Ishimoto, Sari; Ishimatsu, Naoko; Higuchi, Keiichiro; Minoura, Katsuhiko; Kikuchi, Takashi; Yamada, Takeshi; Muraoka, Osamu; Tanaka, Reiko

doi:10.3390/molecules201119737

Cited by 23 publications

(19 citation statements)

References 21 publications

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“…Extracts of the bark, flowers, and seeds have been used for centuries by the Amazonian people and exhibit various effects: anti-bacterial [ 4 ], anti-cancerous [ 5 ], anti-tumor [ 6 ], anti-fungal [ 6 ], insect repellent [ 7 ], analgesic [ 8 ], anti-malarial [ 9 ], anti-inflammatory [ 10 ], antiallergic [ 11 ], and anti-plasmoidal effects [ 12 ], as well as acute and subacute toxicity [ 13 ]. In the course of our studies on the chemical constituents from C. guianensis ( Carapa guianensis ) [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ], we have isolated several limonoids, including andirolides A–Y from the flower oil [ 14 , 15 , 16 , 17 ], carapanolides A–X [ 18 , 19 , 20 , 21 , 22 ], and guianolides A and B [ 23 ] from the seed oil. We have also reported that several limonoids from C. guianensis showed cytotoxic [ 14 , 16 , 18 , 19 , 23 ], antimalarial [ 15 ], anti-inflammatory [ 17 , 20 , 22 ], and triglyceride metabolism-promoting activities [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Hepatoprotective Limonoids from Andiroba (Carapa guianensis)

Ninomiya

Miyazawa

Ozeki

et al. 2016

IJMS

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Three gedunin-type limonoids, gedunin (1), 6α-acetoxygedunin (2), and 7-deacetoxy-7-oxogedunin (3), which were isolated from the seed and flower oils of andiroba (Carapa guianensis Aublet, Meliaceae), exhibited hepatoprotective effects at doses of 25 mg/kg, p.o. against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. To characterize the mechanisms of action of 1–3 and clarify the structural requirements for their hepatoprotective effects, 17 related limonoids (1–17) isolated from the seed and/or flower oils of C. guianensis were examined in in vitro studies assessing their effects on (i) d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes, (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages, and (iii) tumor necrosis factor-α (TNF-α)-induced cytotoxicity in L929 cells. The mechanisms of action of 1–3 are likely to involve the inhibition of LPS-induced macrophage activation and reduced sensitivity of hepatocytes to TNF-α; however, these compounds did not decrease the cytotoxicity caused by d-GalN. In addition, the structural requirements of limonoids (1–17) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-α-induced cytotoxicity in L929 cells were evaluated.

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Section: Introductionmentioning

confidence: 99%

Hepatoprotective Limonoids from Andiroba (Carapa guianensis)

Ninomiya

Miyazawa

Ozeki

et al. 2016

IJMS

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“…No que tange suas propriedades antiparasíticas, o óleo da C. guianensis demostrou caráter protetivo a partir da presença de limonóides no seu óleo 9,10 . No que tange a sua bioquímica, tal classe de substância tem a sua efetividade anti-parasitária atribuída a presença de tetranortriterpenóides, de modo que os principais exemplos encontrados na andiroba são o 6α-acetoxygedunin, 7-deacetoxi-7-oxogedunin, andirobin, gedunin, metil-angolensate e caraponolideos C-I, T-U e V-X [11][12][13] .…”

Section: Introductionunclassified

Estudo em bases de patentes sobre a andiroba e suas propriedades anti-inflamatórias

Carvalho¹,

Carvalho²,

Sirqueira³

et al. 2022

PRMJ

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“…Among the limonoids found in C. guianensis seed oil are 6 α -acetoxygedunin, 7-deacetoxy-7-oxogedunin, andirobin, gedunin and methyl-angolensate [ 12 ], guianolides A and B, [ 13 ], carapanolides M–S [ 14 ], carapanolides C–I [ 15 ], carapanolides T-U, and carapanolides V-X [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Carapa guianensis Aublet (Andiroba) Seed Oil: Chemical Composition and Antileishmanial Activity of Limonoid-Rich Fractions

Oliveira

Tellis

Chagas

et al. 2018

BioMed Research International

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Leishmaniasis is a complex of diseases caused by protozoa of the genus Leishmania and affects millions of people around the world. Several species of plants are used by traditional communities for the treatment of this disease, among which is Carapa guianensis Aubl. (Meliaceae), popularly known as andiroba. The objective of the present work was to conduct a chemical study of C. guianensis seed oil and its limonoid-rich fractions, with the aim of identifying its secondary metabolites, particularly the limonoids, in addition to investigating its anti-Leishmania potential. The chemical analyses of the C. guianensis seed oil and fractions were obtained by electrospray ionization mass spectrometry (ESI-MS). The cytotoxic activity was tested against peritoneal macrophages, and antileishmanial activity was evaluated against promastigotes and intracellular amastigotes of Leishmania amazonensis. All the C. guianensis seed oil samples analyzed exhibited the same pattern of fatty acids, while the limonoids 7-deacetoxy-7-hydroxygedunin, deacetyldihydrogedunin, deoxygedunin, andirobin, gedunin, 11β-hydroxygedunin, 17-glycolyldeoxygedunin, 6α-acetoxygedunin, and 6α,11β-diacetoxygedunin were identified in the limonoid-rich fractions of the oil. The C. guianensis seed oil did not exhibit antileishmanial activity, and cytotoxicity was higher than 1000 μg/mL. Three limonoid-rich oil fractions demonstrated activity against promastigotes (IC50 of 10.53±0.050, 25.3±0.057, and 56.9±0.043μg/mL) and intracellular amastigotes (IC50 of 27.31±0.091, 78.42±0.086, and 352.2±0.145 μg/mL) of L. amazonensis, as well as cytotoxicity against peritoneal macrophages (CC50 of 78.55±1.406, 139.0±1.523, and 607.7±1.217 μg/mL). The anti-Leishmania activity of the limonoid-rich fractions of C. guianensis can be attributed to the limonoids 11β-hydroxygedunin and 6α,11β-diacetoxygedunin detected in the chemical analysis.

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Carapanolides T–X from Carapa guianensis (Andiroba) Seeds

Abstract: Abstract:Two new mexicanolide-type limonoids, carapanolides T-U (1-2), and three new phragmalin-type limonoids, carapanolides V-X (3-5), were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D-and 2D-NMR spectroscopy.

Cited by 23 publications

References 21 publications

Hepatoprotective Limonoids from Andiroba (Carapa guianensis)

Hepatoprotective Limonoids from Andiroba (Carapa guianensis)

Estudo em bases de patentes sobre a andiroba e suas propriedades anti-inflamatórias

Carapa guianensis Aublet (Andiroba) Seed Oil: Chemical Composition and Antileishmanial Activity of Limonoid-Rich Fractions

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