1980
DOI: 10.1007/bf01402927
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Defensive substances of opilionids

Abstract: Abstract--Two quinones (2,3-dimethyl-l,4-benzoquinone and 2,3,5-trimethyl-l,4-benzoquinone) and three phenols (2,3-dimethylphenol, 2-methyl-5-ethylphenol, and 2,3,4-trimethylphenol) were isolated from the defensive secretions of opilionids (Laniatores) from the Panama Canal Zone. The trimethylphenol was not previously reported as a natural product.

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Cited by 30 publications
(25 citation statements)
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“…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: Discussionsupporting
confidence: 89%
See 1 more Smart Citation
“…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: Discussionsupporting
confidence: 89%
“…To date, nearly 30 species have had their secretions chemically characterized, and a phylogenetic pattern may be observed. Species belonging to the suborder Eupnoi produce a variety of acyclic compounds, such as short-chain ketones and alcohols among the sclerosomatids and naphthoquinones among the phalangiids (references in Roach et al, 1980). In the suborder Laniatores, species of the superfamily Travunioidea produce mainly terpenoids, whereas among the Gonyleptoidea, the secretion is composed of phenols and alkylated 1,4-benzoquinones (references in Eisner et al, 1978;Acosta et al, 1993;Gnaspini and Cavalheiro, 1998).…”
Section: Introductionmentioning
confidence: 99%
“…Their presence in opilionids appears to be restricted to species of the families Gonyleptidae (to which A. aculeatus belongs) and Cosmetidae, both members of the suborder Laniatores Roach et al, 1980;Holmberg, 1986;Acosta et al, 1993). However, 1,4-benzoquinones are not the exclusive defensive compounds of the Laniatores.…”
Section: Discussionmentioning
confidence: 99%
“…Laniatores, de forma geral, produzem quinonas metiladas (Estable et al, 1955;Fieser & Ardao, 1956;Eisner et al, 1971Eisner et al, , 2004Acosta et al, 1993;Gnaspini & Cavalheiro, 1998) e, eventualmente alguns tipos de fenóis Roach et al, 1980;Duffield et al, 1981). Ekpa et al (1984) registraram em Sclerobunus robustus, espécie da família Triaenonychidae, a ocorrência de substâncias que divergem do que se sabe que muitos outros opiliões produzem, tais como bornil-propionato, bornil-acetato, feniltilamina, nicotina e traços de limoneno e canfeno.…”
Section: Travunioidea E Triaenonychoidea Representam Os Insidiatoresunclassified
“…Há inclusive algumas substâncias como 4,6-dimetil-6-noneno-3-ona (Jones et al, 1976), 2-metil-5-etilfenol ) e 2,3,4-trimetilfenol (Roach et al, 1980), dentre outras, que nunca haviam sido encontradas na natureza.…”
Section: Travunioidea E Triaenonychoidea Representam Os Insidiatoresunclassified