Schistosomicidal Activity of Alkyl-phenols from the Cashew <i>Anacardium occidentale</i> against <i>Schistosoma mansoni</i> Adult Worms

Alvarenga, Tavane A.; Oliveira, Pollyanna Francielli de; Souza, Júlia Medeiros; Tavares, Denise Crispim; Silva, Márcio Luís Andrade e; Cunha, Wilson Roberto; Groppo, Milton; Januário, Ana Helena; Magalhães, Lizandra G.; Pauletti, Patrícia Mendonça

doi:10.1021/acs.jafc.6b04200

Cited by 24 publications

(15 citation statements)

References 33 publications

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“…3A–C ). The cytoprotective effect of cardol triene was also reported in normal human lung fibroblast cell line, GM07492A, with the 192.6 ± 6.0 µM 34 . Cardol monoene, however, was reported with a cytotoxicity against the SW620 (CC 50 of 14.18 ± 0.76 µM), KATO-III (CC 50 of 19.06 ± 0.39 µM), HepG2 (CC 50 of 2.23 ± 0.22 µM), Chago I (CC 50 of 2.55 ± 0.18 µM) and BT474 (CC 50 of 13.46 ± 0.14 µM) cell lines 16 , 18 , 35 .…”

Section: Discussionmentioning

confidence: 64%

Cardol triene inhibits dengue infectivity by targeting kl loops and preventing envelope fusion

Kanyaboon

Saelee

Suroengrit

et al. 2018

Sci Rep

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Dengue virus causes a global burden that specific chemotherapy has not been established. A previous report suggested that anacardic acid inhibited hepatitis C virus infection. Here, we explored structure activity relationship of anacardic acid, cardanol, and cardol homologues with anti-DENV cellular infectivities. Cardol triene showed the highest therapeutic index at 29.07 with the CC50 and EC50 of 207.30 ± 5.24 and 7.13 ± 0.72 µM, respectively. Moreover, we observed that the more unsaturated the hydrocarbon tail, the higher the CC50s in all head groups. High CC50s were also found in HepG-2, THP-1, and HEK-293 cell lines where cardol triene CC50s were 140.27 ± 8.44, 129.77 ± 12.08, and 92.80 ± 3.93 µM, respectively. Cardol triene expressed pan-dengue inhibition with the EC50s of 5.35 to 8.89 µM and kl loops of dengue envelope proteins were major targets. The strong binding energy at T48, E49, A50, P53, K128, V130, L135, M196, L198, Q200, W206, L207, I270, and L277 prevented cellular pH-dependent fusion. Zika virus kl loops were aligned in the closed position preventing cardol triene to bind and inhibit fusion and infectivity. This study showed for the first time that cardol triene had a potential for further development as anti-dengue inhibitors.

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Section: Discussionmentioning

confidence: 64%

Cardol triene inhibits dengue infectivity by targeting kl loops and preventing envelope fusion

Kanyaboon

Saelee

Suroengrit

et al. 2018

Sci Rep

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“…The NMR analysis of the isolated compounds (supporting information) was compared to the literature and confirmed the structure of the compounds as cardol triene [5-(8 Z ,11 Z )-8,11,14-Pentadecatrien-1-yl-1,3-benzenediol] ( 1 ) [29], cardol diene [5-(8 Z ,11 Z )-8,11-Pentadecadien-1-yl-1,3-benzenediol] ( 2 ) [29,30], cardanol triene [3-(8 Z ,11 Z )-8,11,14-Pentadecatrien-1-ylphenol] ( 3 ) [30], cardanol monoene [3-(8Z)-8-Pentadecen-1-ylphenol] ( 4 ) [30], anacardic acid diene [2-Hydroxy-6-(8Z,11Z)-8,11-pentadecadien-1-ylbenzoic acid] ( 5 ) [31], and anacardic acid monoene [2-Hydroxy-6-(8Z)-8-pentadecenylbenzoic acid] ( 6 ) [31] (Figure 1).…”

Section: Resultsmentioning

confidence: 76%

Chemical Constituents of Anacardium occidentale as Inhibitors of Trypanosoma cruzi Sirtuins

et al. 2019

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Benznidazole and nifurtimox, the only drugs available for the treatment of Chagas disease, have limited efficacy and have been associated with severe adverse side effects. Thus, there is an urgent need to find new biotargets for the identification of novel bioactive compounds against the parasite and with low toxicity. Silent information regulator 2 (Sir2) enzymes, or sirtuins, have emerged as attractive targets for the development of novel antitrypanosomatid agents. In the present work, we evaluated the inhibitory effect of natural compounds isolated from cashew nut (Anacardium occidentale, L. Anacardiaceae) against the target enzymes TcSir2rp1 and TcSir2rp3 as well as the parasite. Two derivates of cardol (1, 2), cardanol (3, 4), and anacardic acid (5, 6) were investigated. The two anacardic acids (5, 6) inhibited both TcSir2rp1 and TcSir2rp3, while the cardol compound (2) inhibited only TcSir2rp1. The most potent sirtuin inhibitor active against the parasite was the cardol compound (2), with an EC50 value of 12.25 µM, similar to that of benznidazole. Additionally, compounds (1, 4), which were inactive against the sirtuin targets, presented anti-T. cruzi effects. In conclusion, our results showed the potential of Anacardium occidentale compounds for the development of potential sirtuin inhibitors and anti-Trypanosoma cruzi agents.

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“…Further elution with the same solvent yielded a fraction rich (> 95%) in 5‐(8 Z ,11 Z )‐8,11,14‐pentadecatrienyl resorcinol (10.5 g). Spectroscopic data ( 1 H‐NMR and 13 C‐NMR) of this fraction agreed with those previously reported for this compound (Alvarenga et al ., ).…”

Section: Methodsmentioning

confidence: 97%

A cytochrome P450 CYP71 enzyme expressed in Sorghum bicolor root hair cells participates in the biosynthesis of the benzoquinone allelochemical sorgoleone

et al. 2018

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Summary Sorgoleone, a major component of the hydrophobic root exudates of Sorghum spp., is probably responsible for many of the allelopathic properties attributed to members of this genus. Much of the biosynthetic pathway for this compound has been elucidated, with the exception of the enzyme responsible for the catalysis of the addition of two hydroxyl groups to the resorcinol ring.A library prepared from isolated Sorghum bicolor root hair cells was first mined for P450‐like sequences, which were then analyzed by quantitative reverse transcription‐polymerase chain reaction (RT‐qPCR) to identify those preferentially expressed in root hairs. Full‐length open reading frames for each candidate were generated, and then analyzed biochemically using both a yeast expression system and transient expression in Nicotiana benthamiana leaves. RNA interference (RNAi)‐mediated repression in transgenic S. bicolor was used to confirm the roles of these candidates in the biosynthesis of sorgoleone in planta.A P450 enzyme, designated CYP71AM1, was found to be capable of catalyzing the formation of dihydrosorgoleone using 5‐pentadecatrienyl resorcinol‐3‐methyl ether as substrate, as determined by gas chromatography‐mass spectroscopy (GC‐MS). RNAi‐mediated repression of CYP71AM1 in S. bicolor resulted in decreased sorgoleone contents in multiple independent transformant events.Our results strongly suggest that CYP71AM1 participates in the biosynthetic pathway of the allelochemical sorgoleone.

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Schistosomicidal Activity of Alkyl-phenols from the Cashew Anacardium occidentale against Schistosoma mansoni Adult Worms

Cited by 24 publications

References 33 publications

Cardol triene inhibits dengue infectivity by targeting kl loops and preventing envelope fusion

Cardol triene inhibits dengue infectivity by targeting kl loops and preventing envelope fusion

Chemical Constituents of Anacardium occidentale as Inhibitors of Trypanosoma cruzi Sirtuins

A cytochrome P450 CYP71 enzyme expressed in Sorghum bicolor root hair cells participates in the biosynthesis of the benzoquinone allelochemical sorgoleone

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