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Article: Eclectic chemisociality of the honeybee : A wealth of behaviors, pheromones, and exocrine glands.

Blum, M S / Fales, H M

2013 Volume 14, Issue 11, Page(s) 2099–2107

Abstract: A dazzling variety of honeybee behaviors are triggered by pheromones produced by disparate exocrine glands. A multiplicity of chemical releasers of social behavior has been demonstrated to regulate a diversity of societal interactions, and many of these ... ...

Abstract	A dazzling variety of honeybee behaviors are triggered by pheromones produced by disparate exocrine glands. A multiplicity of chemical releasers of social behavior has been demonstrated to regulate a diversity of societal interactions, and many of these compounds are synthesized with great caste specificity. Recent investigations have resulted in the identification of a host of new compounds that are products of either worker or queen honeybees. This report fractionates these newly identified exocrine products according to their glandular proveniences and focuses on both the structural and behavioral eclecticism that characterizes these chemical signaling agents.
Language	English
Publishing date	2013-11-26
Publishing country	United States
Document type	Journal Article
ZDB-ID	800130-3
ISSN	1573-1561 ; 0098-0331
ISSN (online)	1573-1561
ISSN	0098-0331
DOI	10.1007/BF01014252
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Article: Iron carboxylate oxygen-centered-triangle complexes detected during electrospray use of organic acid modifiers with a comment on the finnigan TSQ-700 electrospray inlet system.

Ijames, C F / Dutky, R C / Fales, H M

Journal of the American Society for Mass Spectrometry

2013 Volume 6, Issue 12, Page(s) 1226–1231

Abstract: Use of infusion methods rather than high-performance liquid chromatography allowed us to confirm the observation that solutions of propionic acid-isopropanol restore sensitivity lost due to trifluoroacetic acid in electrospray mass spectra of basic ... ...

Abstract	Use of infusion methods rather than high-performance liquid chromatography allowed us to confirm the observation that solutions of propionic acid-isopropanol restore sensitivity lost due to trifluoroacetic acid in electrospray mass spectra of basic substances, particularly peptides. In this work, when propionic acid-isopropanol was used, we detected an abundant ion with m/z 622 that shifted to m/z 538 when we substituted acetic acid-methanol for the propionic acid-isopropanol. Via accurate mass measurement and tandem mass spectrometry the origin of the ion was identified as the complex Fe3O(O2CR)6(L)0-3, where L is one of several ligands from solvent or water. The grounding arrangement of the Finnigan TSQ-700 electrospray source produces electrolytic currents that may accentuate the abundance of this complex and specifically produces observable gas bubbles that adversely affect the spray stability.
Language	English
Publishing date	2013-11-10
Publishing country	United States
Document type	Journal Article
ZDB-ID	1073671-2
ISSN	1044-0305
ISSN	1044-0305
DOI	10.1016/1044-0305(95)00579-X
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Zs.A 4618: Show issues			Location: Je nach Verfügbarkeit (siehe Angabe bei Bestand) bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular Jg. 1995 - 2021: Lesesall (2.OG) ab Jg. 2022: Lesesaal (EG)
Zs.MO 241: Show issues

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Article: (5Z,9Z)-3-alkyl-5-methylindolizidines fromSolenopsis (Diplorhoptrum) species.

Jones, T H / Highet, R J / Blum, M S / Fales, H M

Journal of chemical ecology

2013 Volume 10, Issue 8, Page(s) 1233–1249

Abstract: The alkaloidal venom components of two species of thief ants,Solenopsis (Diplorhoptrum) species AA andS. (Diplorhoptrum)conjurata have been found to contain (5Z,9Z)-3-hexyl-5-methylindolizidine and a mixture of (5Z,9Z)-3-ethyl-5-methylindolizidine andcis- ...

Abstract	The alkaloidal venom components of two species of thief ants,Solenopsis (Diplorhoptrum) species AA andS. (Diplorhoptrum)conjurata have been found to contain (5Z,9Z)-3-hexyl-5-methylindolizidine and a mixture of (5Z,9Z)-3-ethyl-5-methylindolizidine andcis-2-methyl-6-nonyl-piperidine,trans-2-methyl-6-nonylpiperidine,cis-2-methyl-6-undecylpiperidine, and hexadecanoic acid.Monomorium pharaonis was similarly investigated and found to contain the indolizidine and pyrrolidines previously described (Ritter et al., 1977b). Both indolizidines were synthesized along with their stereoisomers and separated by preparative gas chromatography. Spectral studies revealed the stereochemistry to be 5Z,9Z in both cases. The stereochemistry of 2-butyl-5-pentylpyrrolidine inM. phaeronis has also been established. Biosynthetic relationships are discussed.
Language	English
Publishing date	2013-12-10
Publishing country	United States
Document type	Journal Article
ZDB-ID	800130-3
ISSN	1573-1561 ; 0098-0331
ISSN (online)	1573-1561
ISSN	0098-0331
DOI	10.1007/BF00988551
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Article: The uropygiols: identification of the unsaponifiable constituent of a diester wax from chicken preen glands.

Haahti, E O / Fales, H M

Journal of lipid research

2003 Volume 8, Issue 2, Page(s) 131–137

Abstract: The chief lipid fraction in the uropygial gland excretion of the domestic hen is a diester wax. The saponifiable fraction of this wax consists of saturated normal C(10)-C(20) fatty acids. The unsaponifiable fraction consists of a series of three ... ...

Abstract	The chief lipid fraction in the uropygial gland excretion of the domestic hen is a diester wax. The saponifiable fraction of this wax consists of saturated normal C(10)-C(20) fatty acids. The unsaponifiable fraction consists of a series of three homologous compounds, which have been named the uropygiols and identified by mass spectrometry, gas-liquid chromatography, and periodate cleavage as 2,3-n-alkanediols containing 22-24 carbon atoms. The native diols were shown to consist of about equal amounts of the threo and erythro isomers. Records of analyses of the natural products as well as related synthetic compounds are shown.
MeSH term(s)	Animals ; Chickens ; Chromatography, Gas ; Exocrine Glands/chemistry ; Fatty Alcohols/chemistry ; Female ; Grooming ; Mass Spectrometry ; Molecular Structure ; Waxes/chemistry
Chemical Substances	Fatty Alcohols ; Waxes
Language	English
Publishing date	2003-10-16
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	80154-9
ISSN	1539-7262 ; 0022-2275
ISSN (online)	1539-7262
ISSN	0022-2275
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Article: Chemistry of venom alkaloids in the ant genusMegalomyrmex.

Jones, T H / Blum, M S / Fales, H M / Brandão, C R / Lattke, J

Journal of chemical ecology

2013 Volume 17, Issue 9, Page(s) 1897–1908

Abstract: Chemical analyses of three species in the Neotropical ant genusMegalomyrmex have identified this taxon as the third myrmicine genus to produce alkaloids as major venom products. Workers ofM. leoninus and workers and ergatoids ofM. goeldii produce one or ... ...

Abstract	Chemical analyses of three species in the Neotropical ant genusMegalomyrmex have identified this taxon as the third myrmicine genus to produce alkaloids as major venom products. Workers ofM. leoninus and workers and ergatoids ofM. goeldii produce one or more of fourtrans-2,5-dialkylpyrrolidines previously identified in other myrmicine genera.M. modestus, on the other hand, is distinctive in producing the novel alkaloid (5E,8E)-3-butyl-5-hexylpyrrolizidine (5d), whose structure was established using a micro-Hofmann degradation sequence. The relationship ofMegalomyrmex to other alkaloid-producing ant genera is discussed along with the possible chemotaxonomic significance of the analyzed species when viewed in terms of the recognized species groups in this genus.
Language	English
Publishing date	2013-11-21
Publishing country	United States
Document type	Journal Article
ZDB-ID	800130-3
ISSN	1573-1561 ; 0098-0331
ISSN (online)	1573-1561
ISSN	0098-0331
DOI	10.1007/BF00993736
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Article: Characterization, synthesis, and behavioral responses to sex attractiveness pheromones of red-sided garter snakes (Thamnophis sirtalis parietalis).

Mason, R T / Jones, T H / Fales, H M / Pannell, L K / Crews, D

Journal of chemical ecology

2013 Volume 16, Issue 7, Page(s) 2353–2369

Abstract: The sex attractiveness pheromone of the red-sided garter snake,Thamnophis sirtalis parietalis, has been characterized as a mixture of 13 long-chain (C29-C37) saturated and monounsaturated methyl ketones. Samples of the major unsaturated ketones in the ... ...

Abstract	The sex attractiveness pheromone of the red-sided garter snake,Thamnophis sirtalis parietalis, has been characterized as a mixture of 13 long-chain (C29-C37) saturated and monounsaturated methyl ketones. Samples of the major unsaturated ketones in the mixture, (Z)-24-tritriaconten-2-one (7) and (Z)-26-pentatriaconten-2-one (10), and their saturated analogs, 2-tritriacontanone (8) and 2-pentatriacontanone (11) were prepared by unambiguous synthesis. In field bioassay tests, male garter snakes were presented with natural and synthetic pheromone components both individually and as a mixture. Males exhibited courtship behavior to the synthetic compounds approximating the natural blend.
Language	English
Publishing date	2013-11-22
Publishing country	United States
Document type	Journal Article
ZDB-ID	800130-3
ISSN	1573-1561 ; 0098-0331
ISSN (online)	1573-1561
ISSN	0098-0331
DOI	10.1007/BF01026943
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Article: Novel 2-ethyl-5-alkylpyrrolidines in the venom of an australian ant of the genusMonomorium.

Jones, T H / Blum, M S / Andersen, A N / Fales, H M / Escoubas, P

Journal of chemical ecology

2013 Volume 14, Issue 1, Page(s) 35–45

Abstract: Novel 2-ethyl-5-alkylpyrrolidines and their corresponding 1-pyrrolines have been identified as poison gland products from an unidentified Australian species ofMonomorium. The major alkaloids present in the venom of this ant aretrans-2-ethyl-5- ... ...

Abstract	Novel 2-ethyl-5-alkylpyrrolidines and their corresponding 1-pyrrolines have been identified as poison gland products from an unidentified Australian species ofMonomorium. The major alkaloids present in the venom of this ant aretrans-2-ethyl-5-undecylpyrrolidine andtrans-2-ethyl-5-(12-tridecen-1-yl)pyrrolidine. The position of the double bond in the latter was established from its dimethyl-disulfide adduct after the amine function had been protected, and the stereochemistry of the alkyl groups was determined by direct comparison with synthetic compounds. The corresponding 1-pyrrolines were also detected in varying amounts in this venom. The pyrrolidines and 1-pyrrolines possess considerable insecticidal activity when evaluated against termite workers. The alkaloidal venoms ofMonomorium appear to be an important factor contributing to the success of these small ants both as competitors and as predators.
Language	English
Publishing date	2013-11-26
Publishing country	United States
Document type	Journal Article
ZDB-ID	800130-3
ISSN	1573-1561 ; 0098-0331
ISSN (online)	1573-1561
ISSN	0098-0331
DOI	10.1007/BF01022529
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Article: Phenylalkenals in ponerine(Leptogenys sp.) and myrmicine (Pogonomyrmex sp.) ants.

Fales, H M / Jones, T H / Jaouni, T / Blum, M S / Schmidt, J O

Journal of chemical ecology

2013 Volume 18, Issue 6, Page(s) 847–854

Abstract: Cephalic extracts of two unrelated species of ants,Leptogenys processionalis andPogonomyrmex rugosus, have been found to contain 2-phenylpropenal and 2-phenyl-2-butenal, while two other species related to the first,L. chinensis andL. kitteli, lacked ... ...

Abstract	Cephalic extracts of two unrelated species of ants,Leptogenys processionalis andPogonomyrmex rugosus, have been found to contain 2-phenylpropenal and 2-phenyl-2-butenal, while two other species related to the first,L. chinensis andL. kitteli, lacked either.L. kitteli also produced a tetrasubstituted pyrazine found previously only in two New Zealand ants in the genusMesoponera. The chemical reactivity of the phenylalkenals suggests their function in repelling attack by predators.
Language	English
Publishing date	2013-11-20
Publishing country	United States
Document type	Journal Article
ZDB-ID	800130-3
ISSN	1573-1561 ; 0098-0331
ISSN (online)	1573-1561
ISSN	0098-0331
DOI	10.1007/BF00988325
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Article: Volatile compounds from ponerine ants in the genusMesoponera.

Fales, H M / Blum, M S / Bian, Z / Jones, T H / Don, A W

Journal of chemical ecology

2013 Volume 10, Issue 4, Page(s) 651–665

Abstract: Volatile constituents have been characterized from two species of ponerine ants in the genusMesoponera. 2,5-Dimethyl-3-isopentyl-pyrazine has been identified from cephalic extracts ofM. castanea andM. castaneicolor, by gas chromatography-mass ... ...

Abstract	Volatile constituents have been characterized from two species of ponerine ants in the genusMesoponera. 2,5-Dimethyl-3-isopentyl-pyrazine has been identified from cephalic extracts ofM. castanea andM. castaneicolor, by gas chromatography-mass spectrometry. Combined gasters and thoraces of both species are also characterized by the presence of nonanal, nonanoic acid, isovaleric acid, phenylacetic acid, and undecanal, as well as a series of aliphatic amines and amides.N-Isoamylnonylamine was a major constituent that was accompanied byN-isoamylnonenylamine,N,N-diisoamylnonylamine,N-acetyl nonylamine,N-formyl isoamylnonylamine,N-isovaleroyl nonylamine, and several other secondary and tertiary amines. The possible significance of the amines and amides as idiosyncratic natural products ofMesoponera species is discussed.
Language	English
Publishing date	2013-12-07
Publishing country	United States
Document type	Journal Article
ZDB-ID	800130-3
ISSN	1573-1561 ; 0098-0331
ISSN (online)	1573-1561
ISSN	0098-0331
DOI	10.1007/BF00994226
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Article: Overalkylation of a protein digest with iodoacetamide.

Boja, E S / Fales, H M

Analytical chemistry

2001 Volume 73, Issue 15, Page(s) 3576–3582

Abstract: Cystine linkages in proteins are often opened with reducing agents, sometimes to improve their digestion, often to eliminate disulfide linkages from complicating analysis of the digest. After reduction, the sulfhydryls are usually reacted with ... ...

Abstract	Cystine linkages in proteins are often opened with reducing agents, sometimes to improve their digestion, often to eliminate disulfide linkages from complicating analysis of the digest. After reduction, the sulfhydryls are usually reacted with iodoacetamide (IAM), iodoacetic acid (IAA), or another electrophile to prevent reformation of disulfide linkages in a random manner. When the amount of protein may be reliably estimated, side reactions from excess IAM or IAA can be avoided. When this is not so, removal of excess iodoalkane can be accomplished by HPLC, by dialysis, or simply by allowing a reducing thiol to consume any excess. In mass spectrometric analysis of proteins isolated by 1D or 2D gels, removal of the excess iodoalkane is often accomplished simply by washing the gel prior to proteolytic digestion. During a recent study of the glutathionylation site mapping of actin, IAM was used to block any residual sulfhydryl groups remaining on the protein so that they would not displace glutathione from its initial site. In addition, to avoid losses due to actin polymerization during dialysis, the IAM was allowed to remain during the digestion. This further ensured that any sulfhydryl groups liberated during the digestion would be similarly blocked by the IAM. Under these conditions, we observed the peptides to undergo N- as well as S-carbamidomethylation. In examining a series of other peptides alkylated with IAM in this way, we have found N-alkylation to be the rule rather than the exception and even O-alkylation was detected. The main sites to which the carbamidomethyl group attaches to the peptides have been located with LC-MS2 using an ion trap mass spectrometer and found to be the N-terminal amino group. A simple expedient to prevent such reactions when an excess of reducing agent must be avoided is to run the alkylation in the presence of a thioether such as 2,2'-thiodiethanol rather than a thiol.
MeSH term(s)	Actins/chemistry ; Alkylation ; Animals ; Cattle ; Chromatography, Liquid ; Cysteine/chemistry ; Hydrolysis ; Iodoacetamide/chemistry ; Iodoacetic Acid/chemistry ; Mass Spectrometry ; Oxidation-Reduction ; Peptides/analysis ; Peptides/chemistry ; Proteins/chemistry ; Sulfhydryl Reagents/chemistry
Chemical Substances	Actins ; Peptides ; Proteins ; Sulfhydryl Reagents ; Cysteine (K848JZ4886) ; Iodoacetic Acid (WF5188V710) ; Iodoacetamide (ZRH8M27S79)
Language	English
Publishing date	2001-08-01
Publishing country	United States
Document type	Journal Article
ZDB-ID	1508-8
ISSN	1520-6882 ; 0003-2700
ISSN (online)	1520-6882
ISSN	0003-2700
DOI	10.1021/ac0103423
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