Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway

Rocha, Daniele F. O.; Wouters, Felipe C.; Zampieri, Dávila; Brocksom, Timothy J.; Machado, Glauco; Marsaioli, Anita J.

doi:10.3390/molecules180911429

Cited by 31 publications

(56 citation statements)

References 44 publications

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“…This suggests that these compounds might not be especially useful for distinguishing phylogenetic relationships among taxa in Gonyleptidae. The composition of the defensive secretion of D. pectinifemur is congruent with those already described for the clade that includes Discocyrtus ("Pachylinae 4" in Hara et al 2005), also corroborated by Rocha et al 2013. Use of 2,3-dimethyl-1,4-benzoquinone is particularly widespread in Gonyleptidae Hara et al 2005), and it often co-occurs with 2,3-dimethyl-1,4-hydroquinone (Gnaspini and Hara 2007;Wouters 2011), as for D. pectinifemur.…”

Section: Discussionsupporting

confidence: 81%

“…Although the compounds in the defensive secretions of D. pectinifemur and D. oliverioi ) are similar, these compounds also are found in various cosmetids and gonyleptids (Gnaspini and Hara 2007;Rocha et al 2011Rocha et al , 2013. This suggests that these compounds might not be especially useful for distinguishing phylogenetic relationships among taxa in Gonyleptidae.…”

Section: Discussionmentioning

confidence: 99%

“…Use of 2,3-dimethyl-1,4-benzoquinone is particularly widespread in Gonyleptidae Hara et al 2005), and it often co-occurs with 2,3-dimethyl-1,4-hydroquinone (Gnaspini and Hara 2007;Wouters 2011), as for D. pectinifemur. According to Wouters (2011) and Rocha et al (2013), the co-occurrence of both compounds might be due to 2,3-dimethyl-1,4-hydroquinone being a precursor of 2,3-dimethyl-1,4-benzoquinone. Therefore, we propose that hydroquinones and their respective benzoquinones should be considered synonymous, if used for phylogenetic purposes.…”

Section: Discussionmentioning

confidence: 99%

“…However, Rocha et al (2013) obtained different RI values for these same compounds by using a linear regression. In order to compare our data with those of Rocha et al (2013), we also ran a linear regression for the three major compounds, 2,3-dimethyl-1,4-benzoquinone, 2-ethyl-3-methyl-1,4-benzoquinone, and 2,3,5-trimethyl-1,4-benzoquinone. This gave the equation y-1124=37.344(x-8.986), allowing recalculation of RIs for 2,3-dimethyl-1,4-hydroquinone (1445) and 2-ethyl-3-methyl-1,4-hydroquinone (1496).…”

Section: Chemical Analysesmentioning

confidence: 99%

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The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

et al. 2015

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Harvestmen have a pair of scent glands that open through ozopores. The literature suggests a link between the morphology of the ozopore area and the emission of a defensive secretion. A previous study on a species that aggregates in open areas, where individuals are probably more easily spotted by predators, showed that this defensive secretion causes conspecifics to flee. However, it is unknown whether this behavior occurs in species that aggregate in sheltered areas, where prey are harder to find. Herein, we describe the morphology of the ozopore area, the mode of emission of the defensive secretion, and its chemical composition in the harvestman Discocyrtus pectinifemur. We also tested if the defensive secretion is used as an alarm pheromone. We found that D. pectinifemur releases the defensive secretion in different ways, one of them being as a jet. Emission as a jet contrasts with that known for all congeners previously studied, and is in accord with the expected morphology of the ozopore. We found that the defensive secretion of D. pectinifemur does not function as an alarm pheromone. The composition of the defensive secretion, a mixture of quinones, is congruent with those already described for the clade that includes Discocyrtus. Our results support the link between the morphology of the scent glands area and the emission behavior of the defensive secretion, and they suggest that the alarm pheromone function in harvestmen may be dependent on ecological factors.

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Section: Discussionsupporting

confidence: 81%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Chemical Analysesmentioning

confidence: 99%

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The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

et al. 2015

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“…cavicollis was toxic to all of the organisms tested. Rocha et al [37] noted that most species with a quinonic chemoprofile live in the soil, where they are in direct contact with many pathogenic microorganisms. The same authors indicated that MIC values for benzoquinones are low and asserted that these chemicals are very effective at deterring microorganisms.…”

Section: Resultsmentioning

confidence: 99%

Chemical Defence in a Millipede: Evaluation and Characterization of Antimicrobial Activity of the Defensive Secretion from Pachyiulus hungaricus (Karsch, 1881) (Diplopoda, Julida, Julidae)

et al. 2016

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The chemical defence of the millipede Pachyiulus hungaricus is reported in the present paper, in which a chemical characterization is given and antimicrobial activity is determined. In total, independently of sex, 44 compounds were identified. All compounds belong to two groups: quinones and pentyl and hexyl esters of long-chain fatty acids. The relative abundances of quinones and non-quinones were 94.7% vs. 5.3% (males) and 87.3% vs. 12.7% (females), respectively. The two dominant quinones in both sexes were 2-methyl-1,4,-benzoquinone and 2-methoxy-3-methyl-1,4-benzoquinone. Antibacterial and antifungal activity of the defensive secretion was evaluated in vitro against seven bacterial strains and eight fungal species. With the aid of a dilution technique, the antimicrobial potential of the secretion and high sensitivity of all tested strains were confirmed. The lowest minimum concentrations of these compounds (0.20–0.25 mg/mL) were sufficient for inhibition of Aeromonas hydrophila, Listeria monocytogenes and Methicillin resistant Staphylococcus aureus (MRSA). The growth of eight tested fungal species was inhibited by slightly lower concentrations of the secretion, with Fusarium equiseti as the most sensitive fungus and Aspergillus flavus as the most resistant. Values of MIC and MFC in the employed microdilution assay ranged from 0.10 to above 0.35 mg/mL. The given extract contains antimicrobial components potentially useful as therapeutic agents in the pharmaceutical and agricultural industries.

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Nuptial gift chemistry reveals convergent evolution correlated with antagonism in mating systems of harvestmen (Arachnida, Opiliones)

Kahn

Cao

Burns

et al. 2018

Ecology and Evolution

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Nuptial gifts are material donations given from male to female before or during copulation and are subject to sexual selection in a wide variety of taxa. The harvestman genus Leiobunum has emerged as a model system for understanding the evolution of reproductive morphology and behavior, as transitions between solicitous and antagonistic modes of courtship have occurred multiple times within the lineage and are correlated with convergence in genital morphology. We analyzed the free amino acid content of nuptial gift secretions from five species of Leiobunum using gas chromatography–mass spectrometry. Multivariate analysis of the free amino acid profiles revealed that, rather than clustering based on phylogenetic relationships, nuptial gift chemical composition was better predicted by genital morphology and behavior, suggesting that convergent evolution has acted on the chemical composition of the nuptial gift. In addition, we found that, species with solicitous courtship produce gifts consisting of a 19% larger proportion of essential amino acids as compared to those with more antagonistic courtship interactions. This work represents the first comparative study of nuptial gift chemistry within a phylogenetic framework in any animal group and as such contributes to our understanding of the evolution of reproductive diversity and the participant role of nuptial gift chemistry in mating system transitions.

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Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway

Cited by 31 publications

References 44 publications

The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

The Scent Glands of the Neotropical Harvestman Discocyrtus pectnifemur: Morphology, Behavior and Chemistry

Chemical Defence in a Millipede: Evaluation and Characterization of Antimicrobial Activity of the Defensive Secretion from Pachyiulus hungaricus (Karsch, 1881) (Diplopoda, Julida, Julidae)

Nuptial gift chemistry reveals convergent evolution correlated with antagonism in mating systems of harvestmen (Arachnida, Opiliones)

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