2,3-Dihydrofarnesoic acid, a unique terpene from trichomes ofLycopersicon hirsutum, repels spider mites.

Abstract:

:Lycopersicon hirsutum, a wild relative of the tomato, is highly resistant to arthropod herbivores. Both botanic forms ofL. hirsutum, L. hirsutum f.glabratum (C.H. Mull.) andL. hirsutum f.typicum (Humb. & Bonpl.), are resistant to two-spotted spider mites,Tetranychus urticae Koch. However, leaves and trichome secretions from f.typicum repel mites more so than those from f.glabratum. We have previously demonstrated that trichome secretions from LA 1363 and LA 1927, accessions of f.typicum, repelled mites. In this paper we report the identification of the primary component of trichome secretions responsible for repellency. Leaflet washes having compositions similar to trichome secretions were collected and separated into neutral and acid fractions; repellency was mainly associated with the acid fraction, which, when applied to nonrepellent leaflets of f.glabratum, rendered them repellent. Separation of leaflet washes by HPLC allowed purification and subsequent identification by gas chromatography-mass spectrometry and nuclear magnetic resonance of 2,3-dihydrofamesoic acid (3,7,11-trimethyl-6, 10-dodecadienoic acid) as the primary chemical component responsible for repellency. Application of this acid to leaflets ofL. esculentum rendered them repellent. Other volatile compounds present in minor amounts in the acid fractions were farnesoic acid and 16∶0, 16∶3, 18∶0, 18∶2, and 18∶3 fatty acids. This is the first report of the natural occurrence of 2,3-dihydrofarnesoic acid.

journal_name

J Chem Ecol

authors

Snyder JC,Guo Z,Thacker R,Goodman JP,Pyrek JS

doi

10.1007/BF00980597

subject

Has Abstract

pub_date

1993-12-01 00:00:00

pages

2981-97

issue

12

eissn

0098-0331

issn

1573-1561

journal_volume

19

pub_type

杂志文章
  • Prothoracic gland semiochemicals of green lacewings.

    abstract::Adult chrysopids have paired prothoracic glands (PG) that are thought to produce defensive secretions (allomones). We analyzed PG extracts of the following green lacewings from North and South America, Australia, and China: Ceraeochrysa cubana (Brazil); Chrysopa (= Co.) oculata, Co. nigricornis, Co. incompleta, Co. qu...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-009-9701-x

    authors: Aldrich JR,Le TC,Zhang QH,Torres J,Winterton SL,Han B,Miller GL,Chauhan KR

    更新日期:2009-10-01 00:00:00

  • Chemistry of fruit flies: Nature of glandular secretion and volatile emission ofBactrocera (bactrocera) cacuminatus (Héring).

    abstract::The major component of the rectal glandular extract and volatile emission of maleBactrocera cacuminatus is racemic 1,7-dioxaspiro[5.5]undecane. l-Hydroxy-5-nonanone as its open chain form, together with 6-n-butyl-3,4-dihydro-2H-pyran are minor components. 1,7-Dioxaspiro[5.5]undecan-4-ol is present at a low level and i...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00994347

    authors: Krohn S,Fletcher MT,Kitching W,Drew RA,Moore CJ,Francke W

    更新日期:1991-02-01 00:00:00

  • 2,2'-OXO-1,1'-azobenzene: Selective toxicity of rye (Secale cereale L.) allelochemicals to weed and crop species: II.

    abstract::Three allelochemicals from rye or its breakdown products were evaluated for activity on garden cress (Lepidum sativum L.), barnyardgrass [Echinochloa crus-galli (L.) Beauv.], cucumber (Cucumis sativus L.), and snap bean (Phaseolus vulgaris L.). 2,4-Dihydroxy-1,4(2H)-benzoxazin-3-one (DIBOA), 2(3H)-benzoxazolinone (BOA...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00994418

    authors: Chase WR,Nair MG,Putnam AR

    更新日期:1991-01-01 00:00:00

  • Ethanol and (-)-alpha-Pinene: attractant kairomones for bark and ambrosia beetles in the southeastern US.

    abstract::In 2002-2004, we examined the flight responses of 49 species of native and exotic bark and ambrosia beetles (Coleoptera: Scolytidae and Platypodidae) to traps baited with ethanol and/or (-)-alpha-pinene in the southeastern US. Eight field trials were conducted in mature pine stands in Alabama, Florida, Georgia, North ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-009-9613-9

    authors: Miller DR,Rabaglia RJ

    更新日期:2009-04-01 00:00:00

  • Factors accounting for the variability in the behavioral response of the onion fly (Delia antiqua) to n-dipropyl disulfide.

    abstract::The onion fly Delia antiqua is a specialist herbivore attacking only onions and closely related Allium species. n-Dipropyl disulfide (Pr2S2) has long been known to be attractive to onion flies in the laboratory and in the field. However, the insect's response is highly variable. Using behavioral bioassays we found tha...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1025642703888

    authors: Romeis J,Ebbinghaus D,Scherkenbeck J

    更新日期:2003-09-01 00:00:00

  • Lespedeza phenolics and Penstemon alkaloids: Effects on digestion efficiencies and growth of voles.

    abstract::Lespedeza cuneata contains high levels of phenolics and is a common food plant of the meadow vole (Microtus pennsylvanicus);Penstemon digitalis contains substantial quantities of alkaloids and is a common food plant of meadow voles and prairie voles (M. ochrogaster). We investigated the palatability of these plants an...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01012104

    authors: Lindroth RL,Batzli GO,Avildsen SI

    更新日期:1986-03-01 00:00:00

  • Identification of a New Blend of Host Fruit Volatiles from Red Downy Hawthorn, Crataegus mollis, Attractive to Rhagoletis pomonella Flies from the Northeastern United States.

    abstract::A new blend of volatiles was identified for the fruit of downy red hawthorn, Crataegus mollis, that is attractive to Rhagoletis pomonella flies infesting this host in the northeastern USA. The new blend was as attractive as the previously identified mixture but is more complex in the number of odorants (six in the old...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-018-0977-6

    authors: Cha DH,Powell THQ,Feder JL,Linn CE Jr

    更新日期:2018-08-01 00:00:00

  • Structural significance of the geminal-dimethyl group of (+)-trans-verbenyl acetate, sex pheromone mimic of the American cockroach.

    abstract::The significance of the geminal dimethyl group at C-6 of (+)-trans-veibenyl acetate (Ib), a sex pheromone mimic of the American cockroach, was investigated. Our interest was first directed to eliminating either methyl group of the geminal dimethyl group. Consequently, alcohols (IIIa and IVa) possessing a monomethyl gr...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00990225

    authors: Manabe S,Takayanagi H,Nishino C

    更新日期:1983-04-01 00:00:00

  • Chemical ecological characteristics of herbivory of Siparuna guianensis seeds by buffy-headed marmosets (Callithrix flaviceps) in the Atlantic Forest of southeastern Brazil.

    abstract::The buffy-headed marmoset (Callithrix flaviceps) is apparently the only predispersal herbivore of the seeds of Siparuna guianensis at the Caratinga Biological Station in southeastern Brazil. Both the fruit receptacles and the frutioles (seeds) of S. guianensis are relatively rich in nutrients such as carbohydrates, pr...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1023/a:1005672017673

    authors: Simas NK,Ferrari SF,Pereira SN,Leitão GG

    更新日期:2001-01-01 00:00:00

  • Mite predator responses to prey and predator-emitted stimuli.

    abstract::We found that the searching behavior of two acarine predators,Amblyseius fallacis andPhytoseiulus macropilis, for prey,Tetranychus urticae, is affected by the following stimuli: (1) prey silk and associated feces, whose combined physical and chemical properties elicit reduction in the rate of predator movements and lo...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00992387

    authors: Hislop RG,Prokopy RJ

    更新日期:1981-09-01 00:00:00

  • Effect of Male House Mouse Pheromone Components on Behavioral Responses of Mice in Laboratory and Field Experiments.

    abstract::Urine of male house mice, Mus musculus, is known to have primer pheromone effects on the reproductive physiology of female mice. Urine-mediated releaser pheromone effects that trigger certain behavioral responses are much less understood, and no field studies have investigated whether urine deposits by male or female ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-017-0819-y

    authors: Musso AE,Gries R,Zhai H,Takács S,Gries G

    更新日期:2017-03-01 00:00:00

  • Turnabout is fair play: Secondary roles for primary compounds.

    abstract::Chemically based resistance of plants to herbivorous insects is today essentially synonymous with allelochemically based resistance; the importance of plant secondary compounds in determining patterns of host-plant utilization has been established in a wide variety of insect-plant interactions. In contrast, primary me...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF02033799

    authors: Berenbaum MR

    更新日期:1995-07-01 00:00:00

  • Identification and field evaluation of non-host volatiles disturbing host location by the tea geometrid, Ectropis obliqua.

    abstract::Volatile organic compounds derived from non-host plants, Ocimum basilicum, Rosmarinus officinalis, Corymbia citriodora, and Ruta graveolens, can be used to mask host plant odors, and are repellent to the tea geometrid, Ectropis obliqua. Volatile compounds were collected by headspace absorption, and the components were...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-013-0344-6

    authors: Zhang ZQ,Sun XL,Xin ZJ,Luo ZX,Gao Y,Bian L,Chen ZM

    更新日期:2013-10-01 00:00:00

  • Differences in oxidase and esterase activities involved in pheromone biosynthesis in two species ofChoristoneura.

    abstract::The released pheromone and the glandular lipids, labeled with [(14)C]acetate, were analyzed fromChoristoneura orae andChoristoneura fumiferana budworm moths by thin-layer chromatography and autoradiography. Radiolabeled lipids in the gland appeared to be identical in the two moths with both insects containing high amo...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01014083

    authors: Morse D,Meighen EA

    更新日期:1990-05-01 00:00:00

  • Responses of freshwater prawn,Macrobrachium rosenbergii, to chemical attractants.

    abstract::Chemoreception in the adults of the freshwater prawnMacrobrachium rosenbergii was investigated under controlled laboratory conditions, using behavioral assays. Tests were carried out on groups, as well as on individuals, all at their intermolt stages of the molt cycle, and prestarved for three to four days. Of 28 diff...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01014678

    authors: Harpaz S,Kahan D,Galun R,Moore I

    更新日期:1987-09-01 00:00:00

  • Relative importance of infochemicals from first and second trophic level in long-range host location by the larval parasitoidCotesia glomerata.

    abstract::Recently parasitoids were hypothesized to encounter a reliability-detectability problem relating to chemical stimuli from the first and second trophic level, when searching for hosts. The relative role of infochemicals originating from the host,Pieris brassicae (second trophic level), and its food plant, cabbage (firs...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987470

    authors: Steinberg S,Dicke M,Vet LE

    更新日期:1993-01-01 00:00:00

  • Light-induced variation in phenolic levels in foliage of rain-forest plants : I. Chemical changes.

    abstract::Levels of phenolic secondary metabolites in the leaves of four west African rain-forest plants,Acacia pennata, Cynometra leonensis, Diopyros thomasii, andTrema guineensis, were correlated with incident light intensity at both the inter- and intraindividual level. Enhanced phenolic levels under high light intensity app...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01022527

    authors: Mole S,Ross JA,Waterman PG

    更新日期:1988-01-01 00:00:00

  • Sex pheromone biosynthesis of (E,E)-8,10-dodecadienol in codling mothCydia pomonella involvesE9 desaturation.

    abstract::Sex pheromone biosynthesis in the codling mothCydia pomonella (Lepidoptera; Tortricidae) was studied by topical application of deuterated fatty acids in DMSO to pheromone glands. The incorporation of deuterium label into fatty acids and alcohols in the pheromone gland was monitored by gas chromatography with flame ion...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01018782

    authors: Löfstedt C,Bengtsson M

    更新日期:1988-03-01 00:00:00

  • Potential allelochemicals from an invasive weed Mikania micrantha H.B.K.

    abstract::Phytotoxicity-directed extraction and fractionation of the aerial parts of Mikania micrantha H.B.K. led to the isolation and identification of three sesquiterpenoids: dihydromikanolide, deoxymikanolide, and 2,3-epoxy-1-hydroxy-4,9-germacradiene-12,8:15,6-diolide. These sesquiterpenoids inhibited both germination and s...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-005-5805-0

    authors: Shao H,Peng S,Wei X,Zhang D,Zhang C

    更新日期:2005-07-01 00:00:00

  • Naphthoquinones and anthraquinones from scent glands of a dyspnoid Harvestman, Paranemastoma quadripunctatum.

    abstract::Extracts of Paranemastoma quadripunctatum (Opiliones, Dyspnoi, Nemastomatidae) contained seven components, all of which likely originated from the secretion of well-developed prosomal scent glands. The two main components (together accounting for more than 90% of the secretion) were identified as 1,4-naphthoquinone an...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-010-9745-y

    authors: Raspotnig G,Leutgeb V,Schaider M,Komposch C

    更新日期:2010-02-01 00:00:00

  • Identification and synthesis of the sex pheromone of the Madeira mealybug, Phenacoccus madeirensis Green.

    abstract::Two components were identified from aeration extracts of the virgin female Madeira mealybug, Phenacoccus madeirensis as trans-(1R,3R)-chrysanthemyl (R)-2-methylbutanoate and (R)-lavandulyl (R)-2-methylbutanoate (with a ratio of 3:1) by a combination of gas chromatography retention time matches, mass spectrometry, and ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-009-9649-x

    authors: Ho HY,Su YT,Ko CH,Tsai MY

    更新日期:2009-06-01 00:00:00

  • Comparison of age-dependent quantitative changes in the male labial gland secretion of Bombus terrestris and Bombus lucorum.

    abstract::Age-related changes of antennal-active components of male labial gland extracts were studied in two closely related bumblebee species, Bombus terrestris and B. lucorum. In B. terrestris, compounds eliciting electroantennogram (EAG) responses of virgin queens were ethyl dodecanoate, 2,3-dihydrofarnesal, 2,3-dihydrofarn...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-009-9650-4

    authors: Zácek P,Kalinová B,Sobotník J,Hovorka O,Ptácek V,Coppée A,Verheggen F,Valterová I

    更新日期:2009-06-01 00:00:00

  • The chemical feeding ecology ofNeodiprion dubiosus schedl,N. rugifrons midd., andN. lecontei (Fitch) on jack pine (Pinus banksiana lamb.).

    abstract::Two monophagous sawflies,Neodiprion dubiosus andN. rugifrons, actively avoid feeding on the current season's needles of jack pine,Pinus banksiana, while the polyphagousN. lecontei feeds indiscriminately on foliage of all age classes. Bioassay studies with needle extracts indicate thatN. dubiosus andN. rugifrons larval...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987514

    authors: Schuh BA,Benjamin DM

    更新日期:1984-07-01 00:00:00

  • HPLC-MS Analysis of Lichen-Derived Metabolites in the Life Stages of Crambidia cephalica (Grote & Robinson).

    abstract::Tiger moths (Lepidoptera: Erebidae: Arctiinae: Arctiini) are notable for their specialized associations with hosts that produce toxic secondary compounds, and are thus an ideal study system for understanding insect-plant interactions and the evolution of antipredatory defense. Likewise, their sister lineage (Arctiinae...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-016-0799-3

    authors: Anderson TJ,Wagner DL,Cooper BR,McCarty ME,Zaspel JM

    更新日期:2017-01-01 00:00:00

  • Possible pheromonal regulation of reproduction in wild carnivores.

    abstract::Recent observations of social behavior and reproduction in wolves, coyotes, hunting dogs, mongooses, and lions suggest possible involvement of pheromones in the regulation of reproductive activity. Observed phenomena resemble the known pheromonal effects in mice such as suppression or synchronization of estrus, induct...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00988206

    authors: Hradecký P

    更新日期:1985-02-01 00:00:00

  • Different Responses of an Invasive Clonal Plant Wedelia trilobata and its Native Congener to Gibberellin: Implications for Biological Invasion.

    abstract::The invasive clonal plant Wedelia trilobata contains higher levels of ent-kaurane diterpenes, which are precursors of gibberellins (GAs), and higher rates of clonal growth than its native congener W. chinensis in invaded habitats. We hypothesized that the higher levels of endogenous GAs facilitate greater ramet growth...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-016-0670-6

    authors: Dai ZC,Fu W,Qi SS,Zhai DL,Chen SC,Wan LY,Huang P,Du DL

    更新日期:2016-02-01 00:00:00

  • Identification of female-produced sex pheromone of the honey locust gall midge, Dasineura gleditchiae.

    abstract::The honey locust gall midge, Dasineura gleditchiae Osten Sacken 1866 (Diptera: Cecidomyiidae) is the main pest of ornamental varieties of the honey locust tree, Gleditsia triacanthos L., in North America, and is now becoming a pest of concern in Europe. Female midges were observed to emerge in the early morning with t...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/s10886-009-9641-5

    authors: Molnár B,Kárpáti Z,Szocs G,Hall DR

    更新日期:2009-06-01 00:00:00

  • Disruption of male spruce budworm orientation to calling females in a wind tunnel by synthetic pheromone.

    abstract::Male spruce budworm [Chorisloneura fumiferana (Clem.)] moths were held for 3 hr in a wind tunnel and subjected to various concentrations of background synthetic pheromone. They were then exposed to calling females and their response was recorded. The background pheromone was presented either as discrete turbulent plum...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF00987797

    authors: Sanders CJ

    更新日期:1982-02-01 00:00:00

  • Evidence for (E,Z)-8,10-dodecadienyl acetate as the major component of the sex pheromone of the eastern pine seedworm,Cydia toreuta (Lepidoptera: Tortricidae).

    abstract::The sex pheromone ofCydia toreuta (Grote), the eastern pine seedworm, was investigated using electroantennogram (AG) measurements, gas chromatography (combined GC-FID-EAD) measurements, and field tests. (E,Z)-8,10-dodecadienyl acetate (E,Z8,10-12:Ac) and (E,E)-8,10-dodecadienyl actetate (E,E8,10-12: Ac) produced both ...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF01014702

    authors: Katovich SA,Swedenborg PD,Giblin M,Underhill EW

    更新日期:1989-02-01 00:00:00

  • Fecal volatiles as part of the aggregation pheromone complex of the desert locust,Schistocerca gregaria (Forskal) (Orthoptera: Acrididae).

    abstract::Olfactometric bioassays showed that nymphs of crowded desert locusts,Schistocerca gregaria, aggregated in response to volatiles derived from their feces and to volatiles emitted from the feces of young adults, but were indifferent to volatiles emitted by older adult feces. On the other hand, young and older adults wer...

    journal_title:Journal of chemical ecology

    pub_type: 杂志文章

    doi:10.1007/BF02066244

    authors: Obeng-Ofori D,Torto B,Njagi PG,Hassanali A,Amiani H

    更新日期:1994-08-01 00:00:00