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1.
J Nat Prod ; 76(9): 1559-64, 2013 Sep 27.
Article in English | MEDLINE | ID: mdl-23978079

ABSTRACT

Four species of gonyleptid harvestmen, Acanthogonyleptes pulcher, Gonyleptes saprophilus (Gonyleptinae), Sodreana barbiellini, and Sodreana leprevosti (Sodreaninae), were examined by GC-MS and ¹³H NMR. All of these species release vinyl ketones, and three of them produce the corresponding pyranyl ketones, which are presumed hetero-Diels-Alder (HDA) dimers. The vinyl ketones 5-methyl-1-hexen-3-one, rac-4-methyl-1-hexen-3-one, and (S)-4-methyl-1-hexen-3-one were synthesized. Natural 4-methyl-1-hexen-3-one is present as a single stereoisomer and has the R-configuration. Vinyl ketone dimers (HDA dimers) were also observed in the scent gland exudate and characterized by HRMS, ¹³C NMR, and ¹H NMR chemical shifts of the pyranyl moiety.


Subject(s)
Arachnida/chemistry , Ketones/chemistry , Pyrans/chemistry , Scent Glands/chemistry , Vinyl Compounds/chemistry , Animals , Arachnida/classification , Arachnida/genetics , Gas Chromatography-Mass Spectrometry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Scent Glands/metabolism , Stereoisomerism
2.
J Nat Prod ; 74(4): 658-63, 2011 Apr 25.
Article in English | MEDLINE | ID: mdl-21361365

ABSTRACT

The defensive secretions of five neotropical species of harvestmen (Opiliones: Gonyleptidae) from the Brazilian Atlantic Forest were analyzed and chemically characterized by GC-MS and NMR methods. Three of the species, Cobania picea, Roweria virescens, and Serracutisoma proximum, secrete a mixture of 2,3-dimethyl-1,4-benzoquinone and 2-ethyl-3-methyl-1,4-benzoquinone. The secretions produced by the other two species, Iporangaia pustulosa and Neosadocus maximus, contain 1-hepten-3-one, 5-methyl-1-hexen-3-one, and 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone (1) as major components, as well as 2,3-dimethyl-1,4-benzoquinone and 2-ethyl-3-methyl-1,4-benzoquinone as minor constituents. The dihydropyran 1-(6-butyl-3,4-dihydro-2H-pyran-2-yl)pentanone (1) is a new natural product, composed of two 1-hepten-3-one subunits formally linked in a hetero-Diels-Alder reaction. The natural product was proven to be racemic, and its biogenetic origin is discussed.


Subject(s)
Arachnida/chemistry , Pyrans/isolation & purification , Animals , Brazil , Gas Chromatography-Mass Spectrometry , Male , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Pentanones , Pyrans/chemistry , Pyrans/pharmacology , Scent Glands/metabolism , Stereoisomerism
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