Unusual Fatty Acid Isomers of Triacylglycerols and Polar Lipids in Female Limpet Gonads of <Emphasis Type="Italic">Cellana grata</Emphasis>

To investigate the occurrence of positional isomers of unsaturated fatty acids (FA) in triacylglycerols (TAG) and polar lipids (PL) in the female gonads of a dominant limpet, Cellana grata, fatty acid methyl esters (FAME) were fractionated according to the degree of their unsaturation by argentation thin-layer chromatography. Their structures were elucidated by gas chromatography-mass spectrometry of a combination of their FAME and picolinyl esters. A total of 125 different FA ranging from 12 to 24 carbon atoms were identified, and 105 unsaturated FA, including 34 nonmethylene-interrupted FA as minor components, were recognized. Although the major FA 16:0 and 18:1n-7, which accounted for more than 20 and 10%, respectively, of total FA, were present in TAG and PL, higher amounts of 20:4n-6 and 20:5n-3 were present in PL. Unsaturated FA consisting of more than five different positional isomers were 17:1, 19:1, 18:2, 19:2, 20:2, 21:2, 22:2, 20:3, and 22:3, most of which were present in TAG. Furthermore, a larger variety of nonmethylene-interrupted FA was found in TAG than in PL. This limpet gonad had a diverse assortment of unsaturated FA that comprised a wide range of unusual positional isomers with one to five double bonds.     

Novel Non-methylene-Interrupted Dienoic and Trienoic Fatty Acids with a Terminal Double Bond in Ovaries of the Limpet Cellana toreuma

In this study, to obtain further information on the structural diversity of non-methylene-interrupted (NMI) fatty acids (FA) in the gonads of the limpet Cellana toreuma, previously unreported minor NMI FA, fractionated by argentation thin-layer chromatography (TLC), in the ovaries were characterized by gas chromatography–mass spectrometry (GC–MS) analysis of their 3-pyridylcarbinol derivatives. As a result, five novel NMI FA were identified as 5,14-pentadecadienoic acid (15: 2Δ5,14), 5,9,18-nonadecatrienoic acid (19:3Δ5,9,18), 5,9,20-heneicosatrienoic acid (21:3Δ5,9,20), 7,13,20-heneicosatrienoic acid (21:3Δ7,13,20), and 5,9,22-tricosatrienoic acid (23:3Δ5,9,22). Possible biosynthetic pathways for these FA are also discussed in relation to structural variations of NMI FA regioisomers. This study clearly reinforces the findings of our previous works with structurally diverse NMI FA with a terminal double bond.     

Attraction of Female and Male Bactrocera papayae to Conspecific Males Fed with Methyl Eugenol and Attraction of Females to Male Sex Pheromone Components

The attraction of female and male Bactrocera papayae to conspecific males fed with methyl eugenol (ME) and female attraction to male synthetic sex pheromone, trans-coniferyl alcohol (CF), were evaluated in a wind tunnel. Earlier and greater attraction were exhibited by both females and males to ME-fed than to non-ME-fed males as dusk approaches. Males increased their precopulatory behavior (i.e., wing fanning and mounting) during the period of higher attractancy. These data confirm that the consumption of ME enhances the mating competitiveness of males and suggest that ME also functions as a precursor to the male sex and aggregation pheromones. Three phenylpropanoid compounds biosynthesized from ME, coniferyl alcohol, 2-allyl-4,5-dimethoxyphenol, and 3,4-dimethoxycinnamyl alcohol, were detected in male rectal gland along with an endogenous rectal compound, N-(3-methylbutyl) acetamide. When offered singly to the females, coniferyl alcohol was found to be most attractive.     

Electrophysiological Responses of Female and Male Hypsipyla grandella (Zeller) to Swietenia macrophylla Essential Oils

The mahogany shoot borer, Hypsipyla grandella, is one of the most economically important Neotropical forest pest insects because it attacks valuable timber of the Meliaceae. Despite detailed information on the life cycle of H. grandella, factors influencing attack by the shoot borer are not well known. Electroantennogram studies of borer antennae indicate that both female and male moths elicited significant antennal responses to essential oil of the terminal shoots, mature and senescent leaves, in three concentrations. -Himachalene, germacrene D, germacrene A, cadina-1,4-diene, hexadecanoic acid, and ethyl hexadecanoate appeared in all essential oils from Swietenia macrophylla. Germacrene-D and -himachalene were also present in the active essential oil of Cedrela odorata and Toona ciliata. These findings suggest that these compounds play a role in attracting H. grandella to oviposit on the leaves of these plants. The GC-EAD of essential oil from S. macrophylla mature leaves to female H. grandella antennae led to the identification of -caryophyllene as the main constituent responsible for the antennae response.     

Task-Related Differences in the Cuticular Hydrocarbon Composition of Harvester Ants, Pogonomyrmex barbatus

Colonies of the harvester ant, Pogonomyrmex barbatus, perform a variety of tasks. The behavior of an individual worker appears to depend on its recent history of brief contacts with ants of the same and other task groups. The purpose of this study was to determine whether task groups differ in cuticular hydrocarbon composition. We compared the cuticular hydrocarbon composition of ants collected under natural conditions as they performed one of three tasks: patrolling (locating food sources), foraging, or nest maintenance. Task groups differed significantly in the relative proportions of classes of hydrocarbon compounds, as well as in individual compounds. Relative to nest maintenance workers, foragers and patrollers had a higher proportion of straight-chain alkanes relative to monomethylalkanes, dimethylalkanes, and alkenes. There was no significant difference in the chain length of n-alkanes among the task groups. Foragers did not differ in hydrocarbon composition from patrollers. Colonies differed significantly from one another in hydrocarbon composition, but task groups differed in consistent ways from colony to colony, suggesting that the mechanism responsible for task-related hydrocarbon composition was the same in all colonies. P. barbatus workers switch tasks during their lifetimes, suggesting that cuticular hydrocarbon composition changes during adulthood as well. Nest maintenance workers are probably younger than foragers and patrollers and perform very little of their work outside of the nest. Task-related hydrocarbon differences detected here may be associated with worker age, and/or the abiotic characteristics (temperature, humidity, and ultraviolet light) of the interior and exterior work environments.     

Comparison of Oligosaccharide Compositions in Male Nuptial Secretions of Three Cockroach Species of the Genus Blattella

Male cockroaches of the genus Blattella secrete courtshippheromones from abdominal tergal glands. Conspecific females mount courting males and feed on their tergal exudates. In the German cockroach, B. germanica, a complex mixture of oligosaccharides was previously identified as the major phagostimulants in the male tergal secretion. We compared the oligosaccharide compositions of three Blattella species from different habitats, B. germanica (house), B. lituricollis (field), and B. nipponica (forest), by gas chromatographic (GC) analysis of their trifluoroacetylated derivatives. The three possessed a series of maltooligosaccharides and oligoglucosyl trehaloses with 14 and 11 linkages in common. However, B. germanica was conspicuous for its accumulation of a oligoglucosyl trehalose with a 16 linkage [O--D-glucopyranosyl-(16)--D-glucopyranosyl -D-glucopyranoside] as the most prominent component of the secretion. Such diversification of the male pheromonal compositions within the genus might be reflected by biosynthetic systems in males and chemosensory properties in females suited for their natural habitat.     

Fate of the Dietary Terpene, P-Cymene, in the Male Koala

The fate of the dietary terpene, p-cymene, is reported in a specialist Eucalyptus leaf folivore, the koala (Phascolarctos cinereus). Six male koalas were given two single oral doses of p-cymene (0.37 mmol/kg and 1.49 mmol/kg). Urine and feces were collected for two 24-hr periods after each dose and analyzed for metabolites by extraction, gas chromatography, and mass spectrometry. A total of six metabolites were detected in the urine. A novel, extensively oxidized metabolite, 4-(1,2-dihydroxy-1-methylethyl)-benzoic acid, was identified and its structure elucidated by high resolution and chemical ionization mass spectrometry. Minor amounts of two glycine conjugated metabolites were also detected. Five metabolites were present in sufficient amounts to quantify, using isolated urinary metabolites as reference standards. The mean fractional recovery of administered p-cymene was 0.77 ± 0.09 and 0.84 ± 0.12 for the low and high dose, respectively. The major metabolite excreted was the novel carboxy diol compound. No fecal metabolites were found. Thus, the koala employs a strategy in the metabolism of p-cymene that promotes the production of extensively oxidized metabolites that consequently have increased polarity and enhanced renal excretion. This strategy is compared with that employed by other Eucalyptus leaf folivores.     

Rhizopus and Fusarium are Selected as Dominant Fungal Genera in Rhizospheres of Brassicaceae

We isolated several strains of Rhizopus and Fusarium spp. as dominant fungi in the rhizospheres of Brassicaceae plants. The Fusarium isolates showed a higher tolerance of the antifungal constituents of "mustard oil," which originates from the glucosinolates that are characteristic secondary metabolites of the Brassicaceae, than other Fusarium isolates from non-Brassicaceae plants. In contrast, the Rhizopus isolates showed a high tolerance regardless of their source. Myrosinase activity was found in Bn-R-1-1 (Rhizopus sp.) isolated from the rhizoplane of Brassica napus and Ls-F-in-4-1 (Fusarium sp.) isolated from a surface-disinfected root of Lepidium sativum (Brassicaceae). Ls-F-in-4-1 was the Fusarium most tolerant of the Brassicaceae antifungal constituents. These results suggest that fungi in the rhizospheres of Brassicaceae plants may be selected because of secondary metabolites exuded from the roots of host plants.     

Pheromonal Discrimination of Sex by Male and Female Leopard Geckos (Eublepharis macularius)

The ability of male and female Eublepharis macularius to discriminate among pheromones of males and females and a blank control was investigated. Stimuli were presented on ceramic tiles in the animal's home cages. Males tongue-flicked at significantly lower rates in response to male stimuli than to female and control stimuli. Males also performed aggressive behaviors toward male, but not female or control, stimuli, and tail vibrations toward female, but not male or control, stimuli. Mean tongue-flick rates by females did not differ significantly among conditions. Discrimination of male pheromones by females was demonstrated by greater performance of labial-licking and chin-rubbing in response to male stimuli than to either female or control stimuli.     

Fatty Acid Composition and Oil Yield in Fruits of Five <Emphasis Type="Italic">Arecaceae</Emphasis> Species Grown in Cuba

The present study targeted the whole-fruit oil yield and fatty acid composition from five of the most abundant Arecaceae species grown in Cuba. The oil yields (% dry weight), determined by the Soxhlet extraction technique with hexane, were 25.5, 5.3, 6.9, 5.4, and 6.4% for Roystonea regia, Colpothrinax wrightii, Sabal maritima, Sabal palmetto and Thrinax radiata, respectively. The free fatty acid (FFA) content varied from 2.7 to 6.8%. Fatty acid (FA) profiles of the oils indicated that lauric acid (13.7–44.4%), myristic acid (9.4–22.4%) and palmitic acid (9.2–17.1%) as major saturated FA; whereas oleic acid (9.6–42.7%) and linoleic acid (9.3–17.0%) as major unsaturated FA. R. regia fruit seemed the most promising among Arecaceae grown in Cuba because of its high oil yield and low oil FFA content.     

Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season

Enantiomer separation of (6Z,9Z)-cis-3,4-epoxynonadecadiene and (3Z,9Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3Z,9Z)-(6R,7S)-Epoxynonadecadiene was identified from ovipositor extracts ofColotois pen-Naria, while inErannis defoliaria the 6S,7R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3Z,6Z,9Z)-Nonadecatriene was found in both species, while the presence of (3Z,6Z,9Z)-heneicosatriene was indicated inC. Pennaria only. A 10103 blend of (3Z,9Z)-(6R,7S)-epoxynonadecadiene, (3Z,6Z,9Z)-heneicosatriene, and (3Z,6Z,9Z)-nonadecatriene was found to be optimal for catchingC. Pennaria, whileE. Defoliaria males were optimally caught by a 11 mixture of (3Z,9Z)-(6S,7R)-epoxynonadecadiene and (3Z,6Z,9Z)-nona-decatriene. (6Z,9Z)-(3S,4R)-Epoxynonadecadiene was identified from ovipositor extracts ofAgriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flyingA. Aurantiaria and the late winter/early spring flyingA. Leucophearia. Males ofAgriopis marginaria, which fly in late winter/early spring, were attracted to (3Z,9Z)-(6S,7R)-epoxynonadecadiene. The addition of (3Z,6Z,9Z)-nonadecatriene to theS,R-enantiomer increased captures. Optimal catches were recorded with a 103 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.     

Seasonal Variation of the Chemical Content and Fatty Acid Composition of Mantle and Tentacle of Male and Female Sepia officinalis

The goal of this study was to evaluate the chemical composition and the fatty acid profile of mantle and tentacle of male and female Sepia officinalis, sampled at four seasons from the Mediterranean sea of Tunisia. S. officinalis were found to be rich in glycogen, protein and oil, and significant differences were observed between samples. The level of saturated fatty acid and unsaturated fatty acid showed significant variability among sex and during seasons. DHA and EPA, as polyunsaturated fatty acids, were the most abundant in all samples (14.8–27.8 % and 10.4–18.3 %, respectively). Oleic acid was the most abundant monounsaturated fatty acids (1.63–4.52 %). Σn3 and Σn6 was remarkably different between seasons and among sex. This study could be suitable for the development of reliable guide of fatty acid accumulation in cephalopod.     

Distance Communication of Sexual Status in the Crayfish <Emphasis Type="Italic">Orconectes quinebaugensis</Emphasis>: Female Sexual History Mediates Male and Female Behavior

Chemical communication plays an important role in mediating social interactions of many taxa, particularly arthropods. Many individuals communicate information about their reproductive status to potential mates through distance and/or contact pheromones, an ability that may be advantageous to both signalers and receivers. In this paper, we describe tests of two hypotheses on the role of distance communication in the reproductive behaviors of crayfish (Orconectes quinebaugensis). First, we hypothesized that male crayfish would show stronger attraction towards virgin females (females with no viable sperm) than towards non-virgin females because of the fitness costs (to males) associated with sperm competition. Second, we hypothesized that female crayfish should show differential responses to mature male signals depending on their own sexual history: virgin females should be more strongly attracted to male signals than should non-virgin females because they must mate at least once to be able to fertilize eggs in the spring. Data from two Y-maze experiments yielded support for both hypotheses: males were attracted to signals from virgin females, but not to signals from non-virgins. Likewise, virgin females were attracted to signals from males, but non-virgin females were not. We discuss our data in the context of the potential costs and benefits of mate searching and suggest that distance chemical communication of sexual status may be particularly advantageous when the costs of mate searching are high.     

Evaluation of the Major Female Eurytoma amygdali Sex Pheromone Components, (Z,Z)-6,9-Tricosadiene and (Z,Z)-6,9-Pentacosadiene for Male Attraction in Field Tests

We evaluated the attraction of male almond seed wasp Eurytoma amygdali to the synthetic alkadienes (Z,Z)-6,9-tricosadiene and (Z,Z)-6,9-pentacosadiene and their blend in almond orchards using baited rubber septa attached to cardboard rectangular adhesive traps. The two alkadienes were recently isolated from virgin female whole body extracts and SPME collected volatiles. The alkenes (Z)-9-tricosene, (Z)-9-pentacosene, and (Z)-9-heptacosene, present in female extracts, were also added to the blend of the alkadienes and tested. The alkadienes tested individually attracted males when the traps were baited with doses ranging from 10 to 30 mg/trap. The maximum number of males was attracted to traps baited with 10 mg of a (Z,Z)-6,9-C(23:2):(Z,Z)-6,9-C(25:2) blend at a ratio of 7:3. Results with the three alkenes added to the blend were inconclusive because of low populations. The present study on E. amygdali is the first one reporting attraction of males to synthetic sex pheromone components in field trials for a Eurytomidae species. The synthetic alkadienes blend offers the potential to develop an effective system for monitoring populations of the almond seed wasp in almond orchards.     

Sour-Taste Tolerance in Four Species of Nonhuman Primates

The taste of most fruits is characterized by a mixture of sensations termed sweet and sour by humans, and the food selection behavior of primates suggests that they may use the relative salience of sweetness and sourness to assess palatability of potential food items. Therefore, taste responses of six squirrel monkeys, five pigtail macaques, four olive baboons, and four spider monkeys to sweet-sour taste mixtures were assessed in two-bottle preference tests of brief duration (2 min). Monkeys were given the choice between a reference solution of 50 mM sucrose and mixtures containing 10, 30, or 50 mM citric acid plus 10, 20, 50, 100, 200, 400, 800, or 1000 mM sucrose. We found that the four species differed markedly in their acceptance of physiological concentrations of sour-tasting citric acid. Whereas olive baboons showed the highest degree of sour-taste tolerance and actually preferred most of the sweet-sour taste mixtures over sweet-tasting reference solutions, squirrel monkeys showed the lowest degree of sour-taste tolerance and rejected most of the sweet-sour taste mixtures even when they contained considerably more sucrose than the reference solutions. Additional tests demonstrated that the preference for sweet-sour taste mixtures was not based on masking effects. Rather, the animals perceived both the sweetness and the sourness of the taste mixtures and made a trade-off between the attractive and aversive properties of the two taste qualities. The results of this study suggest that the proximate reason for the marked differences in acceptance of sweet-sour taste mixtures are differences among species in the hedonic evaluation of the sour taste of citric acid. Possible ultimate reasons, which do not necessarily exclude, but may complement each other, include evolutionary adaptation to dietary specialization, avoidance of competition pressure, and phylogenetic relatedness.     

Attraction of Male European Tarnished Plant Bug, <Emphasis Type="Italic">Lygus rugulipennis</Emphasis> to Components of the Female Sex Pheromone in the Field

Previous work showed that females of the European tarnished plant bug, Lygus rugulipennis Poppius (Heteroptera: Miridae), produced three chemicals, hexyl butyrate, (E)-2-hexenyl butyrate, and (E)-4-oxo-2-hexenal, and that these were suspected to be components of the female sex pheromone. In field experiments, traps baited with blends of these chemicals dispensed from polyethylene vials and sachets failed to catch significant numbers of males. Here, we report more recent field experiments in which the chemicals were released from glass microcapillary tubes. A blend of hexyl butyrate and (E)-4-oxo-2-hexenal was significantly attractive to male L. rugulipennis. In addition, whereas the mixture of all three components attracted fewer L. rugulipennis males, this tertiary blend captured significantly greater numbers of males of the congeneric species Lygus pratensis than the binary mixture. The possible reasons for the success of the microcapillaries compared with other dispensers are discussed.     

Fatty Acid Composition of Turkish <Emphasis Type="Italic">Rhododendron</Emphasis> Species

This study describes work aimed at the rapid evaluation of the fatty acid (FA) composition of Turkish Rhododendron species, particularly the leaves and the flowers of the toxic plants, R. ponticum and R. luteum. The FA profiles of the available parts of three other nonpoisonous Rhododendron species were also investigated. Subtotal extracts obtained (using n-hexane, chloroform and methanol) from total chloroform:methanol (1:1) extracts were analyzed and compared to each other. Palmitic acid was found to be the most abundant FA in almost all Rhododendron extracts, and the majority of leaf and flower extracts contained significant portions of C18 unsaturated FAs (18:1n-9, 18:2n-6, 18:3n-3). The n-hexane extracts of R. ponticum leaves and R. luteum flowers were unique, as they contained an unusual series of even-chain iso FAs (C16–C24). Especially the n-hexane extracts were found to comprise uncommon FAs with odd-numbered carbons (C13–C29). Overall, n-hexane proved to be the best solvent by representing the richest FA profile, whereas chloroform or methanol appeared less suitable for FA analyses. Appreciable intra-species variations in FA compositions among the leaves as well as other anatomical parts examined were observed. This study highlights the chemotaxonomical importance of the FAs for the genus Rhododendron.     

Photoprotection Differences between Dominant Tree Species at Mid- and Late-Successional Stages in Subtropical Forests in Different Seasonal Environments

Plants growing in subtropical regions are often affected by high temperature and high light in summer and low temperature and high light in winter. However, few studies have compared the photoprotection mechanism of tree species at different successional stages in these two environments, although such studies would be helpful in understanding the succession of forest communities in subtropical forests. In order to explore the strategies used by dominant species at different successional stages to cope with these two environmental conditions, we selected two dominant species in the mid-successional stage, Schima superba and Castanopsis chinensis, and two dominant species in the late-successional stage, Machilus chinensis and Cryptocarya chinensis. The cell membrane permeability, chlorophyll fluorescence, chlorophyll content, and a few light-protective substances of these dominant species were measured in summer and winter. The results show that in summer, the young leaves of dominant species in the mid-successional stage showed higher anthocyanin content and superoxide dismutase (SOD) activity, while those in the late-successional stage showed higher flavonoid and total phenolic content, total antioxidant activity, non-photochemical quenching (NPQ), and carotenoid/chlorophyll (Car/Chl) ratio. In winter, young leaves of dominant species in the mid-successional stage were superior to those in the late-successional stage only in terms of catalase (CAT) activity and NPQ, while the anthocyanin, flavonoids, and total phenol content, total antioxidant capacity, and Car/Chl ratio were significantly lower compared to the late-successional stage. Our results show that the dominant species in different successional stages adapted to environmental changes in different seasons through the alterations in their photoprotection strategies. In summer, the dominant species in the mid-successional stage mainly achieved photoprotection through light shielding and reactive-oxygen-species scavenging by SOD, while the antioxidant capacity of trees in the late-successional stage mainly came from an increased antioxidative compounds and heat dissipation. In winter, the dominant species in the mid-successional stage maintained their photoprotective ability mainly through the scavenging of reactive oxygen species by CAT and the heat dissipation provided by NPQ, while those in the late-successional stage were mainly protected by a combination of processes, including light shielding, heat dissipation, and antioxidant effects provided by enzymatic and non-enzymatic antioxidant systems. In conclusion, our study partially explains the mechanism of community succession in subtropical forests.     

Chemical Composition and Oxidative Stability of Kernel Oils from Two Current Subspecies of Pistacia atlantica in Iran

Pistacia atlantica subsp. mutica (PAM) and kurdica (PAK) kernel oils showed significantly lower unsaturated to saturated fatty acid ratios (6.39, 6.33, respectively) and calculated oxidizability (Cox) values (3.99, 4.13, respectively) than those of the P. vera L. cv. Ohadi (PVO) kernel oil (8.91, 4.41) samples. The highest peroxide value was observed for the PAK oil (4.07 mequiv kg⁻¹) (PAM, 1.94; PVO, 0.37) samples. Iodine values for the PAM, PAK, and PVO oils were 104.26, 104.77, and 110.66, respectively. The saponification number of the PVO oil was significantly greater than the PAM and PAK oils, which were statistically not different. The unsaponifiable contents, which were composed mainly of sterols, ranged from 5.63 to 6.14%. Statistically the total tocopherols contents of the PAM (818.58 mg α-tocopherol kg⁻¹) and PVO (815.90 mg α-tocopherol kg⁻¹) oils were significantly higher than that of the PAK oil (499.91 mg α-tocopherol kg⁻¹). Total phenolics contents differed significantly, the greatest concentration was for the PAM oil (81.12 mg gallic acid kg⁻¹), followed by the PVO (62.84 mg gallic acid kg⁻¹) and PAK (56.51 mg gallic acid kg⁻¹) oil samples. The wax contents of the oil samples were statistically in the same range, namely 5.67–6.48%. Oxidative stability data indicated that the PAM oil is the most resistant to the formation of lipid oxidation products, followed by the PAK and PVO oil samples.     

Gustatory Responsiveness to Six Bitter Tastants in Three Species of Nonhuman Primates

Gustatory responsiveness of six adult squirrel monkeys, four spider monkeys, and five pigtail macaques to six bitter tastants was assessed in two-bottle preference tests of brief duration (2 min). Animals were given the choice between a 30-mM sucrose solution and defined concentrations of a bitter tastant dissolved in a 30-mM sucrose solution. With this procedure, Saimiri sciureus, Ateles geoffroyi, and Macaca nemestrina were found to significantly discriminate concentrations as low as 0.2, 0.05, and 0.1 mM quinine hydrochloride; 1, 1, and 0.05 mM caffeine; 20, 5, and 1 mM naringin; 5, 2, and 1 mM salicin; 0.01, 0.001, and 0.02 mM sucrose octaacetate; and 0.05, 0.01, and 0.5 mM denatonium benzoate, from the alternative stimulus. With the exception of naringin in the pigtail macaques, all three species rejected all suprathreshold concentrations of all bitter tastants tested. The spider monkeys and the pigtail macaques displayed the lowest taste avoidance thresholds with three of the six tastants each; in contrast, the squirrel monkeys displayed the highest taste avoidance thresholds with four of the six tastants. The across-tastant patterns of taste avoidance thresholds were identical in spider monkeys and squirrel monkeys; both species displayed the following order of sensitivity: sucrose octaacetate > denatonium benzoate > quinine hydrochloride > caffeine > salicin > naringin. All three primate species were more sensitive to the two artificial tastants (sucrose octaacetate and denatonium benzoate) compared to the four naturally occurring tastants. However, the concentrations detected by all three primate species with the four naturally occurring tastants are well below those reported in plants or arthropods consumed by these species suggesting that they may use bitterness as a criterion for food selection.