Biotransformation of 4-nerolidylcatechol by Heraclides brasiliensis (Lepidoptera: Papilionidae) reduces the toxicity of Piper umbellata (Piperaceae)

Ramos, Clécio S.; Souza, Luciano de J.; Kato, Massuo Jorge; Batista, Ronan

doi:10.1007/s00049-011-0096-0

Cited by 11 publications

(8 citation statements)

References 30 publications

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“…Our study demonstrated similar results when evaluating the cytotoxic effect in K562 cells, a multi-drug resistant cell, after treatment with compounds (1), (3) and (5). In contrast, Ramos et al (2011) produced a derivative of compound (1) using the biotransformation of Heraclides brasiliensis (Lepidoptera: Papilionidae) larvae. This derivative showed a reduction of cytotoxicity when compared to the lead compound (1).…”

Section: Discussionmentioning

confidence: 99%

4-Nerolidylcatechol analogues as promising anticancer agents

Cortez

Ávila

Cunha

et al. 2015

European Journal of Pharmacology

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4-Nerolidylcatechol (1) is an isolated compound from Pothomorphe umbellata L. (Piperaceae) with promising antitumor cells properties. However it presents lability under light and room temperatures. Many efforts have been directed towards discovering anticancer agents endowed with cytotoxic activities. Here, we evaluated cytotoxic effects of 4-NRC analogues (LQFMs 2-6) and the cell death pathways induced by these compounds in multidrug-resistant K562 cells. Compounds (2-6) exhibited cytotoxic activities in a concentration-dependent manner against leukaemic cells, specially the compounds (3) and (5). Additionally, compounds (1), (3) and (5) promoted marked alterations on the cell morphology, including nuclear changes as demonstrated by Hoescht 33342 staining. Moreover, these compounds promoted apoptosis induction in K562 cells by phosphatidylserine exposure, increase of sub-G1 cells and modulation of the caspases-3/7, -8 and -9 activation. In addition, the pancaspase inhibitor z-VAD-fmk partially reduced the apoptosis induced by the compounds (1) and (5)-induced, suggesting caspase-dependent and caspase-independent cell death pathways. Compounds (1) and (5) also modified the cell cycle progression by G0/G1 and S arrest, respectively. Furthermore, compounds (1), (3) and (5) promoted mitochondrial dysfunction associated to accumulation of cytosolic cytochrome c and modulated the NF-ĸB activation. In addition, unlike their analogues, 4-NRC (1) also promoted a significant cyclin D1 inhibition. Together, these data suggest that the mechanism of cell death of 4-NRC and its analogues (3) and (5) occurs by apoptosis through mitochondrial mechanisms. Considering that LQFMs are biocompatible synthetic analogues produced by molecular simplification of (1) without the chiral centre, which is associated with the instability found in compound (1), we suggest that these compounds are promising candidates for further pre-clinical studies.

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Section: Discussionmentioning

confidence: 99%

4-Nerolidylcatechol analogues as promising anticancer agents

Cortez

Ávila

Cunha

et al. 2015

European Journal of Pharmacology

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“…In summary, amides are generally associated to the chemical defense strategy in plants because of their potent insecticidal or repellent action against a broad range of insect species but, despite the variety of activities, their metabolic fate in insects is virtually unknown. Thus, as part of the study of metabolism of plant secondary compounds by insects, [19][20][21][22][23][24] herein we describe the metabolism of the major amides from leaves of P. tuberculatum by the insects Heraclides hectorides (Lepidoptera: Papilionidae) and Naupactus bipes (Coleoptera: Curculionidae), which are observed as herbivores of P. tuberculatum leaves in the field. For comparison purposes, four generalist herbivores Elaeochora trilineata (Orthoptera: Romaleidae), Chromacris speciosa (Orthoptera: Romaleidae), Tropidacris collaris (Orthoptera: Romaleidae) and Xyleus discoideus (Orthoptera: Romaleidae) were also offered leaves of P. tuberculatum to test the hypothesis that specialization on Piper hosts correlates with biotransformation of their toxic amides as a mechanism to circumvent toxicity.…”

Section: Introductionmentioning

confidence: 99%

Metabolization of Insecticidal Amides from Leaves of Piper tuberculatum by Heraclydes hectorides and Naupactus bipes

Ramos

Silva

Moraes

et al. 2020

J. Braz. Chem. Soc.

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Amides have been recognized as potent insecticidal natural products but, despite their variety of targets and mechanisms of action, their metabolic fate in insects is virtually unknown. The currently accepted hypothesis is that specialist herbivores are capable of biotransforming xenobiotics rendering them more polar and excretable while generalist insects do not have comparable capacity. The leaves from Piper tuberculatum, rich in insecticide amides, were offered to two insect species found on Piper leaves under natural conditions and also to four generalist grasshoppers in order to compare their capacity of biotransforming xenobiotics. The amides 1-7 were identified in the P. tuberculatum leaves and their corresponding carboxylic acids 8-13 were detected in frass samples of two host insects suggesting that these species promote the amides hydrolysis. The four generalist grasshoppers when offered P. tuberculatum leaves, starved to death after 72 h, indicating a strong antifeedant activity of P. tuberculatum leaves.

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“…Some phenolic compounds are sequestered and reused by larvae, e.g., as wing pigments of adult butterflies (Burghardt et al 1997(Burghardt et al , 2001. Certain phenolic compounds proceed intact through the digestive tract of lepidopterans, while others are chemically modified by the larvae (Ferreres et al 2008;Ramos et al 2012;Salminen et al 2004).…”

Section: Introductionmentioning

confidence: 99%

Phenolic Compounds and Their Fates In Tropical Lepidopteran Larvae: Modifications In Alkaline Conditions

et al. 2015

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Lepidopteran larvae encounter a variety of phenolic compounds while consuming their host plants. Some phenolics may oxidize under alkaline conditions prevailing in the larval guts, and the oxidation products may cause oxidative stress to the larvae. In this study, we aimed to find new ways to predict how phenolic compounds may be modified in the guts of herbivorous larvae. To do so, we studied the ease of oxidation of phenolic compounds from 12 tropical tree species. The leaf extracts were incubated in vitro in alkaline conditions, and the loss of total phenolics during incubation was used to estimate the oxidizability of extracts. The phenolic profiles of the leaf extracts before and after incubation were compared, revealing that some phenolic compounds were depleted during incubation. The leaves of the 12 tree species were each fed to 12 species of lepidopteran larvae that naturally feed on these trees. The phenolic profiles of larval frass were compared to those of in vitro incubated leaf extracts. These comparisons showed that the phenolic profiles of alkali-treated samples and frass samples were similar in many cases. This suggested that certain phenolics, such as ellagitannins, proanthocyanidins, and galloylquinic acid derivatives were modified by the alkaline pH of the larval gut. In other cases, the chromatographic profiles of frass and in vitro incubated leaf extracts were not similar, and new modifications of phenolics were detected in the frass. We conclude that the actual fates of phenolics in vivo are often more complicated than can be predicted by a simple in vitro method.

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Biotransformation of 4-nerolidylcatechol by Heraclides brasiliensis (Lepidoptera: Papilionidae) reduces the toxicity of Piper umbellata (Piperaceae)

Cited by 11 publications

References 30 publications

4-Nerolidylcatechol analogues as promising anticancer agents

4-Nerolidylcatechol analogues as promising anticancer agents

Metabolization of Insecticidal Amides from Leaves of Piper tuberculatum by Heraclydes hectorides and Naupactus bipes

Phenolic Compounds and Their Fates In Tropical Lepidopteran Larvae: Modifications In Alkaline Conditions

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