A novel 1-indanone isolated from <i>Uvaria afzelii</i> roots

Timothée, Okpekon Aboua; Millot, Marion; Champy, Pierre; Gleye, Christophe; Yolou, S; Bories, Christian; Loiseau, Philippe M.; Laurens, A.; Hocquemiller, Reynald

doi:10.1080/14786410802497240

Cited by 35 publications

(26 citation statements)

References 16 publications

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“…Spodoptera larval frass, which deters oviposition in conspecific females, contains 1-indanone (Klein et al, 1990;Anderson et al, 1993), but we were unable to corroborate presence of 1-indanone or any other indane in frass collections of S. littoralis reared on several diets (data not shown). Indanone is found in roots of tropical plants (Okpekon et al, 2009), decaying wood fungi (Rukachaisirikul et al, 2013), and filamentous marine cyanobacteria (Nagle et al, 2000), which are probably not relevant for S. littoralis or C. pomonella. However, our results indicate that one or several indanone analogs are ligands for CpomOR19 and SlitOR19, but the source of these compounds and their behavioral and ecological roles are yet to be elucidated.…”

Section: The Ecological Role Of Indanes Is Yet Unknownmentioning

confidence: 99%

A Conserved Odorant Receptor Detects the Same 1-Indanone Analogs in a Tortricid and a Noctuid Moth

et al. 2015

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Odorant receptors (ORs) interface animals with airborne chemical signals. They are under strong selection pressure and are therefore highly divergent in different taxa. Yet, some OR orthologs are highly conserved. These ORs may be tuned to odorants of broad importance, across species boundaries. Two widely distributed lepidopteran herbivores, codling moth Cydia pomonella (Tortricidae) feeding in apples and pears, and the African cotton leafworm Spodoptera littoralis (Noctuidae), a moth feeding on foliage of a wide range of herbaceous plants, both express a receptor ortholog, OR19, which shares 58% amino acid identity and 69% amino acid similarity. Following heterologous expression in the empty neuron system of Drosophila melanogaster, we show by single sensillum recordings that CpomOR19 and SlitOR19 show similar affinity to several substituted indanes. Tests with a series of compounds structurally related to 1-indanone show that 2-methyl-1-indanone, 2-ethyl-1-indanone, 3-methyl-1-indanone, and 1-indanone elicit a strong response from both ORs. A keto group in position 1 is essential for biological activity and so are both rings of the indane skeleton. However, there is an important difference in steric complementary of the indane rings and the receptor. Methyl substituents on the benzene ring largely suppressed the response. On the other hand, alkyl substituents at position 2 and 3 of the five-membered ring increased the response indicating a higher complementarity with the receptor cavity, in both CpomOR19 and SlitOR19. Our results demonstrate a conserved function of an odorant receptor in two moths that are phylogenetically and ecologically distant. It is conceivable that a conserved OR is tuned to signals that are relevant for both species, although their ecological roles are yet unknown. Our finding demonstrates that functional characterization of ORs leads to the discovery of novel semiochemicals that have not yet been found through chemical analysis of odorants from insects and their associated host plants.

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Section: The Ecological Role Of Indanes Is Yet Unknownmentioning

confidence: 99%

A Conserved Odorant Receptor Detects the Same 1-Indanone Analogs in a Tortricid and a Noctuid Moth

et al. 2015

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“…In this study, it was reported that the methanolic extracts of the root of Uvaria afzelii, at doses of 125 mg/kg, 250 mg/kg and 500 mg/kg, significantly reduced the serum hepatic enzymes, total and un-conjugated bilirubin. Phytochemical studies of this plant has shown the presence of syncarpic acid, dimethoxym atteucinol, emorydone, 2-hydroxydemethoxym at-teucinol, uvafzelic acid, syncarpurea, afzeliindanone, flavonoids, triterpenoids and phenols [76][77][78]. Some of these compounds have also been credited for their antiparasitic and antioxidant activities [79].…”

Section: Uvaria Afzeliimentioning

confidence: 99%

African natural products with potential antioxidants and hepatoprotectives properties: a review

et al. 2016

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Free radicals are highly reactive molecules generated during oxidation reactions which in turn initiate chain reactions resulting to cellular damage. There is substantial evidence implicating free radicals especially reactive oxygen species (ROS) in the etiology of more than one hundred degenerative disorders in humans including, arthritis, atherosclerosis, ischemia and reperfusion injury of many tissues, gastritis, diabetics, central nervous system injury, acquired immunodeficiency syndrome (AIDS) and cancer. Scientific evidence postulates that bioactive compounds especially from natural products are capable of providing protection against free radicals. Consequently, few decades have witnessed a surfeit of research geared towards validating the antioxidant and hepatoprotective potential of the natural products. In this review, African natural products whose antioxidants activities were scientifically validated either in their crude extracts and/or derived products have been discussed. A total 1076 plants species representing 287 family, 132 isolated compounds and 7 insect/mollusk secreation were found. The plant species from the following families; Fababceae, Asteraceae, Lamiaceae, Moraceae, Euphorbiaceae, Combretaceae and Malvaceae have received more scientific attention than others. Analysis of the reports revealed that Combretum apiculatum, Telfaria occidentalis, Acalypha racemosa, Garcinia lucida were the most active plant extracts from African flora. The most active ROS-detoxifying phytochemicals were moracin T, U, S and R (84-87), oleanolic acid (54), 5,7,4′-trihydroxy-3,8,3′,5′-tetramethoxyflavone (89), 5,7,3′-trihydroxy-3,8,4′,5′-trimethoxyflavone (88), luteolin (3′,4′,5,7-tetrahydroxy flavone) (117) and genistein (4′,5,7-trihydroxyisoflavone) (116). The significant antioxidant potential demonstrated by some crude extracts and their constituent compounds render them good candidates for the development of new drugs. Although, the study of the mechanisms of actions as well as clinical validation of some of these isolated compounds is lacking. It is hoped that pertinent scientist and stakeholders will look further into some of these compounds for detailed authentification and subsequent commercialization.

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“…These compounds are renowned for their “non-host” origins (Klein et al, 1990; Anderson et al, 1993; Nagle et al, 2000; Okpekon et al, 2009; Rukachaisirikul et al, 2013). CpomOR19 binding to indanes represented the first deorphanization of a receptor of the codling moth to compounds emitted by non-hosts.…”

Section: Functional Characterization Of Cpomor19mentioning

confidence: 99%

Current Status on the Functional Characterization of Chemosensory Receptors of Cydia pomonella (Lepidoptera: Tortricidae)

Cattaneo

2018

Front. Behav. Neurosci.

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Cydia pomonella (Lepidoptera: Tortricidae) is a major pest of apple, pear and walnuts. For its control, alternative strategies targeting the olfactory system, like mating disruption, have been combined with insecticide applications. The efficacy of these strategies headed the direction of efforts for the functional characterization of codling moth chemosensory receptors to implement further control methods based on chemical sensing. With the advent of transcriptomic analysis, partial and full-length coding sequences of chemosensory receptors have been identified in antennal transcriptomes of C. pomonella. Extension of partial coding sequences to full-length by polymerase chain reaction (PCR)-based techniques and heterologous expression in empty neurons of Drosophila melanogaster and in Human Embryonic Kidney cells allowed functional studies to investigate receptor activation and ligand binding modalities (deorphanization). Among different classes of antennal receptors, several odorant receptors of C. pomonella (CpomORs) have been characterized as binding kairomones (CpomOR3), pheromones (CpomOR6a) and compounds emitted by non-host plants (CpomOR19). Physiological and pharmacological studies of these receptors demonstrated their ionotropic properties, by forming functional channels with the co-receptor subunit of CpomOrco. Further investigations reported a novel insect transient receptor potential (TRPA5) expressed in antennae and other body parts of C. pomonella as a complex pattern of ribonucleic acid (RNA) splice-forms, with a possible involvement in sensing chemical stimuli and temperature. Investigation on chemosensory mechanisms in the codling moth has practical outcomes for the development of control strategies and it inspired novel trends to control this pest by integrating alternative methods to interfere with insect chemosensory communication.

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A novel 1-indanone isolated from Uvaria afzelii roots

Cited by 35 publications

References 16 publications

A Conserved Odorant Receptor Detects the Same 1-Indanone Analogs in a Tortricid and a Noctuid Moth

A Conserved Odorant Receptor Detects the Same 1-Indanone Analogs in a Tortricid and a Noctuid Moth

African natural products with potential antioxidants and hepatoprotectives properties: a review

Current Status on the Functional Characterization of Chemosensory Receptors of Cydia pomonella (Lepidoptera: Tortricidae)

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