Quinones and phenols in the defensive secretions of neotropical opilionids

Eisner, Thomas; Jones, Tappey H.; Hicks, Karen; Silberglied, Robert E.; Meinwald, Jerrold

doi:10.1007/bf00988447

Cited by 40 publications

(40 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The occurrence of alkylated 1,4-benzoquinones in G. longipes is chemotaxonomically in agreement with the constitution of the defensive secretions previously reported for other Gonyleptidae (Estable et al, 1955;Fieser and Ardao, 1956;Roach et al, 1980;Acosta et al, 1993;Eisner et al, 2004), including congeneric species, such as Goniosoma spelaeum (Gnaspini and Cavalheiro, 1998). The derivative 2,3-dimethyl-1,4-benzoquinone has been already identified in other harvestman species belonging to the families Cosmetidae, Gonyleptidae, and Manaosbiidae (Estable et al, 1955;Fieser and Ardao, 1956;Eisner et al, 1977Eisner et al, , 2004Roach et al, 1980;Acosta et al, 1993), but this is the first report of 2-ethyl-3-methyl-1,4-benzoquinone as a natural product. Moreover, the use of bidimensional nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry is reported for the first time for chemical characterization of substances from harvestmen, providing additional protocols for studies of scent secretions in the group.…”

Section: Discussionmentioning

confidence: 80%

Chemical Defense in Harvestmen (Arachnida, Opiliones): Do Benzoquinone Secretions Deter Invertebrate and Vertebrate Predators?

et al. 2005

View full text Add to dashboard Cite

Abstract-Two alkylated 1,4-benzoquinones were identified from the defensive secretion produced by the neotropical harvestman Goniosoma longipes (Gonyleptidae). They were characterized as 2,3-dimethyl-1,4-benzoquinone and 2-ethyl-3-methyl-1,4-benzoquinone. We tested the effectiveness of these benzoquinone secretions against several predator types, including invertebrates and vertebrates. Different predators were exposed to the harvestmen's gland secretion or to distilled water in laboratory bioassays. Our results indicate that secretions containing the 1,4-benzoquinones released by G. longipes can be an effective defense against predation, and that the effectiveness of the secretion is dependent on the predator type. The scent gland secretion repelled seven ant species, two species of large wandering spiders, and one frog species, but was not an effective defense against an opossum. Our study also demonstrates that the scent gland secretion of G. longipes can work as a chemical shield preventing the approach of three large predatory ants for at least 10 min. The chemical shield may protect the harvestman against successive attacks of the same ant worker and also allow the harvestman to flee before massive ant recruitment. Our data support the suggestion that chemical defenses may increase survival with some but not all potential predators. This variation in defense effectiveness may result from many interacting factors, including the attack strategy, size, learning ability, and physiology of the predators, as well as the chemical nature of the defensive compounds, type of emission, and amount of effluent released by the prey.

show abstract

Section: Discussionmentioning

confidence: 80%

Chemical Defense in Harvestmen (Arachnida, Opiliones): Do Benzoquinone Secretions Deter Invertebrate and Vertebrate Predators?

et al. 2005

View full text Add to dashboard Cite

show abstract

“…The third extender unit loses its labelled carbon, leaving only the non-labelled carbon at C-3. The unexpected enrichment at C-2 is consistent with the incorporation of a propionate unit and the conversion of [1][2][3][4][5][6][7][8][9][10][11][12][13] C]acetate into [1][2][3][4][5][6][7][8][9][10][11][12][13] C]propionate via succinyl-CoA with a methylmalonyl-CoA mutase, as reported for the harvestman I. pustulosa [24]. However, the C 3 label scrambling observed in I. pustulosa was not present in biosynthetic pathway of 7 for Ma.…”

mentioning

confidence: 70%

“…Alkyl phenols are also found in species belonging to other families, such as Cynorta astora (Cosmetidae), which produces 19 and 21 [6], and Hoplobunus mexicanus (Stygnopsidae), which produces 18 and 21 [10]. Phenol 18 has lower biological activity than benzoquinones 6 and 8 against all tested microorganisms, except for R. glutinis.…”

Section: Phenols Identificationmentioning

confidence: 99%

“…Gonyleptid scent gland exudates are mainly composed of vinyl ketones and their hetero-Diels-Alder adducts [3][4][5], alkyl phenols [3,[6][7][8][9][10] and benzoquinones [3,6,[11][12][13][14].…”

Section: Open Accessmentioning

confidence: 99%

“…striatus (Scheme 2). Eisner and co-workers reported that benzoquinone 9 and phenol 21 from Zygopachylus albimarginis (Manaosbiidae) [6] had the same biosynthetic origin for both components. The production of benzoquinones, hydroquinones and phenols by the forked fungus beetle Bolitotherus cornutus also suggests that the alkyl benzoquinones and alkyl phenols might share a similar biosynthetic origin [36].…”

mentioning

confidence: 99%

See 2 more Smart Citations

Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway

et al. 2013

View full text Add to dashboard Cite

Abstract:Benzoquinones are usually present in arthropod defence exudates. Here, we describe the chemical profiles of 12 harvestman species belonging to the neotropical family Gonyleptidae. Nine of the studied species produced benzoquinones, while three produced alkyl phenols. Two benzoquinones and one phenol exhibited biological activity against bacteria and fungi. We also studied the biosynthesis of 2-ethyl-1,4-benzoquinone by feeding Magnispina neptunus individuals with 13 C-labelled precursors; the benzoquinones were biosynthesised through a polyketide pathway using acetate and propionate building blocks.

show abstract

Interspecific, ontogenetic, and sexual variation in ozopore morphology among cosmetid harvestmen (Arachnida, Opiliones, Laniatores)

Townsend

Teevan‐Kamhawi²,

Calpo³

2019

Journal of Morphology

View full text Add to dashboard Cite

The ozopores of cosmetid harvestmen rest upon lateral projections of the carapace, have simple or highly reduced channels, and are partially obscured by enlarged dorsal processes associated with coxae I and II. Rather than use scent gland secretions to form a chemical shield on the dorsum, the cosmetid harvestman exhibits a unique defensive behavior known as “leg dabbing” in which the distal tip of tarsus I or II is dipped into fluid that accumulate at the base of coxa II and the droplet on the tarsus is pointed toward the predator. Relatively little is known about interspecific variation in ozopore morphology among cosmetid harvestmen. In this study, we used scanning electron microscopy to examine the ozopores of males and females of nine species as well as those of antepenultimate nymphs for two species. Among adults, we found differences between species in the shapes of the ozopores (round or subtriangular), the morphology of the dorsal and lateral channels (if present), and the relative size, shape and armature of the dorsal posterior process (dpp) of coxa I and the dorsal anterior process (dap) of coxa II. Our observations suggest that the morphology of dpp I and dap II could be sources for systematic characters in future phylogenetic studies of the Cosmetidae. We observed ontogenetic differences but relatively little intersexual variation in the morphology of the ozopore. The ozopores of nymphs are generally more oval than those of adults and the opening of the ozopore of the nymph is less obstructed, if at all, by the dorsal coxal processes of legs I–II. These morphological differences suggest that nymphs may use scent gland secretions in a manner different from that of adults.

show abstract

Quinones and phenols in the defensive secretions of neotropical opilionids

Cited by 40 publications

References 12 publications

Chemical Defense in Harvestmen (Arachnida, Opiliones): Do Benzoquinone Secretions Deter Invertebrate and Vertebrate Predators?

Chemical Defense in Harvestmen (Arachnida, Opiliones): Do Benzoquinone Secretions Deter Invertebrate and Vertebrate Predators?

Harvestman Phenols and Benzoquinones: Characterisation and Biosynthetic Pathway

Interspecific, ontogenetic, and sexual variation in ozopore morphology among cosmetid harvestmen (Arachnida, Opiliones, Laniatores)

Contact Info

Product

Resources

About