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First biosynthetic pathway of 1-hepten-3-one in Iporangaia pustulosa (Opiliones).

Rocha DF, Wouters FC, Machado G, Marsaioli AJ - Sci Rep (2013)

Bottom Line: Our analysis also indicates the presence of methylmalonyl-CoA mutase, converting acetate into propionyl-CoA via succinyl-CoA, together with other C₃ unit routes.This is the first biosynthetic study of alkyl vinyl ketones in arthropods.Our results shed light on the origin and diversification of chemical compounds in a major arthropod group.

View Article: PubMed Central - PubMed

Affiliation: Chemistry Institute, State University of Campinas, POB 6154, 13083-970 Campinas, SP, Brazil.

ABSTRACT
Arthropods produce a great variety of natural compounds, many of which have unexplored biosynthesis. Among the armored harvestmen (Arachnida: Opiliones) of the suborder Laniatores, the defensive gland exudates contain vinyl ketones and other constituents of supposed polyketide origin. We have studied the biosynthesis of 1-hepten-3-one in the Neotropical harvestman Iporangaia pustulosa by feeding individuals with ¹³C-labeled precursors, demonstrating its mixed acetate/propionate origin. ¹³C NMR spectroscopy showed an unusual labeling pattern suggesting different propionate sources for starting and extender units. Our analysis also indicates the presence of methylmalonyl-CoA mutase, converting acetate into propionyl-CoA via succinyl-CoA, together with other C₃ unit routes. This is the first biosynthetic study of alkyl vinyl ketones in arthropods. Our results shed light on the origin and diversification of chemical compounds in a major arthropod group.

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Female of the harvestman Iporangaia pustulosa releasing two white droplets of scent gland exudate in the lateral margins of the carapace.The photo was taken by Prof. Glauco Machado.
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f1: Female of the harvestman Iporangaia pustulosa releasing two white droplets of scent gland exudate in the lateral margins of the carapace.The photo was taken by Prof. Glauco Machado.

Mentions: Arthropods produce a great variety of natural compounds that are used in inter- and intra-species chemical communication. Although the identity of these info-chemicals have been intensively explored over the last 60 years1, their biosynthesis remains vastly unexplored when compared to plants and microorganisms2. Moreover, most biosynthetic studies with arthropods focus on insects, and only a few on other major arthropod groups such as arachnids, whose species may produce venoms, repellent exudates, and pheromones1. Arachnids of the order Opiliones, for instance, have a pair of exocrine glands that release a great variety of odorous compounds3 (Fig. 1) used as alarm pheromones4 and defense against predators567. However, their biosynthetic pathways have never been investigated.


First biosynthetic pathway of 1-hepten-3-one in Iporangaia pustulosa (Opiliones).

Rocha DF, Wouters FC, Machado G, Marsaioli AJ - Sci Rep (2013)

Female of the harvestman Iporangaia pustulosa releasing two white droplets of scent gland exudate in the lateral margins of the carapace.The photo was taken by Prof. Glauco Machado.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3818658&req=5

f1: Female of the harvestman Iporangaia pustulosa releasing two white droplets of scent gland exudate in the lateral margins of the carapace.The photo was taken by Prof. Glauco Machado.
Mentions: Arthropods produce a great variety of natural compounds that are used in inter- and intra-species chemical communication. Although the identity of these info-chemicals have been intensively explored over the last 60 years1, their biosynthesis remains vastly unexplored when compared to plants and microorganisms2. Moreover, most biosynthetic studies with arthropods focus on insects, and only a few on other major arthropod groups such as arachnids, whose species may produce venoms, repellent exudates, and pheromones1. Arachnids of the order Opiliones, for instance, have a pair of exocrine glands that release a great variety of odorous compounds3 (Fig. 1) used as alarm pheromones4 and defense against predators567. However, their biosynthetic pathways have never been investigated.

Bottom Line: Our analysis also indicates the presence of methylmalonyl-CoA mutase, converting acetate into propionyl-CoA via succinyl-CoA, together with other C₃ unit routes.This is the first biosynthetic study of alkyl vinyl ketones in arthropods.Our results shed light on the origin and diversification of chemical compounds in a major arthropod group.

View Article: PubMed Central - PubMed

Affiliation: Chemistry Institute, State University of Campinas, POB 6154, 13083-970 Campinas, SP, Brazil.

ABSTRACT
Arthropods produce a great variety of natural compounds, many of which have unexplored biosynthesis. Among the armored harvestmen (Arachnida: Opiliones) of the suborder Laniatores, the defensive gland exudates contain vinyl ketones and other constituents of supposed polyketide origin. We have studied the biosynthesis of 1-hepten-3-one in the Neotropical harvestman Iporangaia pustulosa by feeding individuals with ¹³C-labeled precursors, demonstrating its mixed acetate/propionate origin. ¹³C NMR spectroscopy showed an unusual labeling pattern suggesting different propionate sources for starting and extender units. Our analysis also indicates the presence of methylmalonyl-CoA mutase, converting acetate into propionyl-CoA via succinyl-CoA, together with other C₃ unit routes. This is the first biosynthetic study of alkyl vinyl ketones in arthropods. Our results shed light on the origin and diversification of chemical compounds in a major arthropod group.

Show MeSH