The discovery of 2,5-dialkylcyclohexan-1,3-diones as a new class of natural products.

Abstract:

:Orchids employing sexual deceit attract males of their pollinator species through specific volatile signals that mimic female-released sex pheromones. One of these signals proved to be 2-ethyl-5-propylcyclohexan-1,3-dione (chiloglottone1), a new natural product that was shown to be most important in the relations between orchids of the genus Chiloglottis, native to Australia, and corresponding pollinator species. Systematic investigations on the mass spectrometric fragmentation pattern of 2,5-dialkylcyclohexan-1,3-diones identified key ions providing information about the structures of the substituents at positions 2 and 5. Results enabled us to identify 2-ethyl-5-pentylcyclohexan-1,3-dione (chiloglottone2) and 2-butyl-5-methylcyclohexan-1,3-dione (chiloglottone3) as new natural products that play a decisive role in the pollination syndrome of some Chiloglottis species. During field bioassays, pure synthetic samples of chiloglottone1-3 or mixtures thereof proved to be attractive to the corresponding orchid pollinators. Because of their likely biogenesis from ubiquitous fatty acid precursors, 2,5-dialkylcyclohexan-1,3-diones may represent a hitherto overlooked, widespread class of natural products.

authors

Franke S,Ibarra F,Schulz CM,Twele R,Poldy J,Barrow RA,Peakall R,Schiestl FP,Francke W

doi

10.1073/pnas.0900646106

subject

Has Abstract

pub_date

2009-06-02 00:00:00

pages

8877-82

issue

22

eissn

0027-8424

issn

1091-6490

pii

0900646106

journal_volume

106

pub_type

杂志文章
  • Functional identification of a neurocircuit regulating blood glucose.

    abstract::Previous studies implicate the hypothalamic ventromedial nucleus (VMN) in glycemic control. Here, we report that selective inhibition of the subset of VMN neurons that express the transcription factor steroidogenic-factor 1 (VMN(SF1) neurons) blocks recovery from insulin-induced hypoglycemia whereas, conversely, activ...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1521160113

    authors: Meek TH,Nelson JT,Matsen ME,Dorfman MD,Guyenet SJ,Damian V,Allison MB,Scarlett JM,Nguyen HT,Thaler JP,Olson DP,Myers MG Jr,Schwartz MW,Morton GJ

    更新日期:2016-04-05 00:00:00

  • Role of type 2 deiodinase in response to acute lung injury (ALI) in mice.

    abstract::Thyroid hormone (TH) metabolism, mediated by deiodinase types 1, 2, and 3 (D1, D2, and D3) is profoundly affected by acute illness. We examined the role of TH metabolism during ventilator-induced lung injury (VILI) in mice. Mice exposed to VILI recapitulated the serum TH findings of acute illness, namely a decrease in...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1109926108

    authors: Barca-Mayo O,Liao XH,DiCosmo C,Dumitrescu A,Moreno-Vinasco L,Wade MS,Sammani S,Mirzapoiazova T,Garcia JG,Refetoff S,Weiss RE

    更新日期:2011-12-06 00:00:00

  • Uncovering modern paint forgeries by radiocarbon dating.

    abstract::Art forgeries have existed since antiquity, but with the recent rapidly expanding commercialization of art, the approach to art authentication has demanded increasingly sophisticated detection schemes. So far, the most conclusive criterion in the field of counterfeit detection is the scientific proof of material anach...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1901540116

    authors: Hendriks L,Hajdas I,Ferreira ESB,Scherrer NC,Zumbühl S,Smith GD,Welte C,Wacker L,Synal HA,Günther D

    更新日期:2019-07-02 00:00:00

  • Biologically templated organic polymers with nanoscale order.

    abstract::Methods for the construction of ordered nanoscale arrays have been implicated in fields ranging from separation technologies to microelectronics. Yet, despite the plethora of nanoscale structures assembled in nature that use a templating strategy, chemists have been unable to replicate this success. A technology is re...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.0711308105

    authors: Willis B,Eubanks LM,Wood MR,Janda KD,Dickerson TJ,Lerner RA

    更新日期:2008-02-05 00:00:00

  • Slab melting versus slab dehydration in subduction-zone magmatism.

    abstract::The second critical endpoint in the basalt-H(2)O system was directly determined by a high-pressure and high-temperature X-ray radiography technique. We found that the second critical endpoint occurs at around 3.4 GPa and 770 °C (corresponding to a depth of approximately 100 km in a subducting slab), which is much shal...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1010968108

    authors: Mibe K,Kawamoto T,Matsukage KN,Fei Y,Ono S

    更新日期:2011-05-17 00:00:00

  • Scientists' incentives and attitudes toward public communication.

    abstract::In an era of large-scale science-related challenges and rapid advancements in groundbreaking science with major societal implications, communicating about science is critical. The profile of science communication has increased over the last few decades, with multiple sectors calling for such activities. As scientists ...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1916740117

    authors: Rose KM,Markowitz EM,Brossard D

    更新日期:2020-01-21 00:00:00

  • Quest for life-long protection by vaccination.

    abstract::Life-long protection from disease through immunization can be accomplished through individual or community protection. Individual protection is the goal for vaccination against diseases that have inanimate or animal reservoirs or that pose risks for certain populations. Community protection is the goal for vaccination...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章,评审

    doi:10.1073/pnas.91.7.2464

    authors: Dowdle WR,Orenstein WA

    更新日期:1994-03-29 00:00:00

  • Hypothalamic ventromedial COUP-TFII protects against hypoglycemia-associated autonomic failure.

    abstract::The nuclear receptor Chicken Ovalbumin Upstream Promoter-Transcription Factor II (COUP-TFII) is an important coordinator of glucose homeostasis through its function in different organs such as the endocrine pancreas, adipose tissue, skeletal muscle, and liver. Recently we have demonstrated that COUP-TFII expression in...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1219262110

    authors: Sabra-Makke L,Maritan M,Planchais J,Boutant M,Pégorier JP,Even PC,Vasseur-Cognet M,Bossard P

    更新日期:2013-03-12 00:00:00

  • Gene expression patterns in visual cortex during the critical period: synaptic stabilization and reversal by visual deprivation.

    abstract::The mapping of eye-specific, geniculocortical inputs to primary visual cortex (V1) is highly sensitive to the balance of correlated activity between the two eyes during a restricted postnatal critical period for ocular dominance plasticity. This critical period is likely to have amplified expression of genes and prote...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.0710172105

    authors: Lyckman AW,Horng S,Leamey CA,Tropea D,Watakabe A,Van Wart A,McCurry C,Yamamori T,Sur M

    更新日期:2008-07-08 00:00:00

  • Two distinct adenosine-sensitive sites on adenylate cyclase.

    abstract::The effects of adenosine and adenosine analogs on adenylate cyclases from several tissues have been examined. Two adenosine-reactive sites have been identified: (i) the "R" site, occupancy of which usually leads to activation of cyclase and which requires integrity of the ribose ring for activity, and (ii) the "P" sit...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.74.12.5482

    authors: Londos C,Wolff J

    更新日期:1977-12-01 00:00:00

  • Side-chain repacking calculations for predicting structures and stabilities of heterodimeric coiled coils.

    abstract::An important goal in biology is to predict from sequence data the high-resolution structures of proteins and the interactions that occur between them. In this paper, we describe a computational approach that can make these types of predictions for a series of coiled-coil dimers. Our method comprises a dual strategy th...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.261563398

    authors: Keating AE,Malashkevich VN,Tidor B,Kim PS

    更新日期:2001-12-18 00:00:00

  • The animal model of human amnesia: long-term memory impaired and short-term memory intact.

    abstract::Normal monkeys and monkeys with lesions of the hippocampal formation and adjacent cortex (the H+ lesion) were trained on the delayed nonmatching to sample (DNMS) task with a delay of 0.5 s between the sample and the choice. The animals with H+ lesions learned the task normally at this short delay and also exhibited th...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.91.12.5637

    authors: Alvarez P,Zola-Morgan S,Squire LR

    更新日期:1994-06-07 00:00:00

  • High levels of the Mps1 checkpoint protein are protective of aneuploidy in breast cancer cells.

    abstract::Most human cancers are aneuploid and have chromosomal instability, which contrasts to the inability of human cells to normally tolerate aneuploidy. Noting that aneuploidy in human breast cancer correlates with increased expression levels of the Mps1 checkpoint gene, we investigated whether these high levels of Mps1 co...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1007645108

    authors: Daniel J,Coulter J,Woo JH,Wilsbach K,Gabrielson E

    更新日期:2011-03-29 00:00:00

  • Glucocorticoids regulate proopiomelanocortin gene expression in vivo at the levels of transcription and secretion.

    abstract::After adrenalectomy, the plasma levels of adrenocorticotropic hormone (corticotropin, ACTH)/endorphin peptides in rats rise dramatically in the first 4 hr while pituitary peptide levels fall sharply. Eight hours after adrenalectomy, plasma levels are near control values again but they then increase continuously over t...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.80.22.6982

    authors: Birnberg NC,Lissitzky JC,Hinman M,Herbert E

    更新日期:1983-11-01 00:00:00

  • Subsystem organization of axonal connections within and between the right and left cerebral cortex and cerebral nuclei (endbrain).

    abstract::The endbrain (telencephalon) is at the rostral end of the central nervous system and is primarily responsible for supporting cognition and affect. Structurally, it consists of right and left cerebral hemispheres, each parceled into multiple cortical and nuclear gray matter regions. The global network organization of a...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1807255115

    authors: Swanson LW,Hahn JD,Jeub LGS,Fortunato S,Sporns O

    更新日期:2018-07-17 00:00:00

  • Predominance of hemodynamic rather than metabolic factors in the pathogenesis of diabetic glomerulopathy.

    abstract::Six groups of Munich-Wistar rats underwent micropuncture study 2-10 weeks and morphologic studies 11-13 months after induction of streptozotocin diabetes or after sham treatment. Diabetic rats received diets containing 6% (group D6), 12% (D12), or 50% protein (D50) and were maintained under similar conditions of moder...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.82.17.5963

    authors: Zatz R,Meyer TW,Rennke HG,Brenner BM

    更新日期:1985-09-01 00:00:00

  • Exon shuffling mimicked in cell culture.

    abstract::Undesired side products of DNA transfections are usually discarded. However, here, we show that such products may provide insight into mutational events that are also a major driving force in protein evolution. While studying the small heat-shock protein alphaA-crystallin, we transfected the hamster alphaA-crystallin ...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.96.14.8074

    authors: van Rijk AA,de Jong WW,Bloemendal H

    更新日期:1999-07-06 00:00:00

  • Sleep transforms the cerebral trace of declarative memories.

    abstract::After encoding, memory traces are initially fragile and have to be reinforced to become permanent. The initial steps of this process occur at a cellular level within minutes or hours. Besides this rapid synaptic consolidation, systems consolidation occurs within a time frame of days to years. For declarative memory, t...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.0705454104

    authors: Gais S,Albouy G,Boly M,Dang-Vu TT,Darsaud A,Desseilles M,Rauchs G,Schabus M,Sterpenich V,Vandewalle G,Maquet P,Peigneux P

    更新日期:2007-11-20 00:00:00

  • Range of cell-wall alterations enhance saccharification in Brachypodium distachyon mutants.

    abstract::Lignocellulosic plant biomass is an attractive feedstock for the production of sustainable biofuels, but the commercialization of such products is hampered by the high costs of processing this material into fermentable sugars (saccharification). One approach to lowering these costs is to produce crops with cell walls ...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1414020111

    authors: Marriott PE,Sibout R,Lapierre C,Fangel JU,Willats WG,Hofte H,Gómez LD,McQueen-Mason SJ

    更新日期:2014-10-07 00:00:00

  • The virulence factor AvrXa7 of Xanthomonas oryzae pv. oryzae is a type III secretion pathway-dependent nuclear-localized double-stranded DNA-binding protein.

    abstract::AvrXa7 is a member of the avrBs3 avirulence gene family, which encodes proteins targeted to plant cells by a type III secretion apparatus. AvrXa7, the product of avrXa7, is also a virulence factor in strain PXO86 of Xanthomonas oryzae pv. oryzae. Avirulence and virulence specificities are associated with the central r...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.170286897

    authors: Yang B,Zhu W,Johnson LB,White FF

    更新日期:2000-08-15 00:00:00

  • Endogenous sources of variation in language acquisition.

    abstract::A fundamental question in the study of human language acquisition centers around apportioning explanatory force between the experience of the learner and the core knowledge that allows learners to represent that experience. We provide a previously unidentified kind of data identifying children's contribution to langua...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1517094113

    authors: Han CH,Musolino J,Lidz J

    更新日期:2016-01-26 00:00:00

  • Localization of cardiac L-type Ca(2+) channels to a caveolar macromolecular signaling complex is required for beta(2)-adrenergic regulation.

    abstract::L-type Ca(2+) channels play a critical role in regulating Ca(2+)-dependent signaling in cardiac myocytes, including excitation-contraction coupling; however, the subcellular localization of cardiac L-type Ca(2+) channels and their regulation are incompletely understood. Caveolae are specialized microdomains of the pla...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.0503465103

    authors: Balijepalli RC,Foell JD,Hall DD,Hell JW,Kamp TJ

    更新日期:2006-05-09 00:00:00

  • New strategy for the synthesis of chemically modified RNA constructs exemplified by hairpin and hammerhead ribozymes.

    abstract::The CuAAC reaction (click chemistry) has been used in conjunction with solid-phase synthesis to produce catalytically active hairpin ribozymes around 100 nucleotides in length. Cross-strand ligation through neighboring nucleobases was successful in covalently linking presynthesized RNA strands with high efficiency (tr...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1006447107

    authors: El-Sagheer AH,Brown T

    更新日期:2010-08-31 00:00:00

  • Microbial battery for efficient energy recovery.

    abstract::By harnessing the oxidative power of microorganisms, energy can be recovered from reservoirs of less-concentrated organic matter, such as marine sediment, wastewater, and waste biomass. Left unmanaged, these reservoirs can become eutrophic dead zones and sites of greenhouse gas generation. Here, we introduce a unique ...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1307327110

    authors: Xie X,Ye M,Hsu PC,Liu N,Criddle CS,Cui Y

    更新日期:2013-10-01 00:00:00

  • The anti-HIV pentameric pseudopeptide HB-19 is preferentially taken up in vivo by lymphoid organs where it forms a complex with nucleolin.

    abstract::The HB-19 pseudopeptide 5[Kpsi(CH(2)N)PR]-TASP, psi(CH(2)N) for reduced peptide bond, is a specific inhibitor of HIV infection in different CD4(+) cell lines and in primary T-lymphocytes and macrophages. It blocks virus-particle attachment to permissive cells by binding and forming a stable complex with nucleolin expr...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.221467298

    authors: Krust B,Vienet R,Cardona A,Rougeot C,Jacotot E,Callebaut C,Guichard G,Briand JP,Grognet JM,Hovanessian AG,Edelman L

    更新日期:2001-11-20 00:00:00

  • Hybrid polarizing solids for pure hyperpolarized liquids through dissolution dynamic nuclear polarization.

    abstract::Hyperpolarization of substrates for magnetic resonance spectroscopy (MRS) and imaging (MRI) by dissolution dynamic nuclear polarization (D-DNP) usually involves saturating the ESR transitions of polarizing agents (PAs; e.g., persistent radicals embedded in frozen glassy matrices). This approach has shown enormous pote...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1407730111

    authors: Gajan D,Bornet A,Vuichoud B,Milani J,Melzi R,van Kalkeren HA,Veyre L,Thieuleux C,Conley MP,Grüning WR,Schwarzwälder M,Lesage A,Copéret C,Bodenhausen G,Emsley L,Jannin S

    更新日期:2014-10-14 00:00:00

  • Thy1+IL-7+ lymphatic endothelial cells in iBALT provide a survival niche for memory T-helper cells in allergic airway inflammation.

    abstract::Memory CD4(+) T helper (Th) cells are central to long-term protection against pathogens, but they can also be pathogenic and drive chronic inflammatory disorders. How these pathogenic memory Th cells are maintained, particularly at sites of local inflammation, remains unclear. We found that ectopic lymphoid-like struc...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.1512600113

    authors: Shinoda K,Hirahara K,Iinuma T,Ichikawa T,Suzuki AS,Sugaya K,Tumes DJ,Yamamoto H,Hara T,Tani-Ichi S,Ikuta K,Okamoto Y,Nakayama T

    更新日期:2016-05-17 00:00:00

  • Energetics of nanocrystalline TiO2.

    abstract::The energetics of the TiO(2) polymorphs (rutile, anatase, and brookite) were studied by high temperature oxide melt drop solution calorimetry. Relative to bulk rutile, bulk brookite is 0.71 +/- 0.38 kJ/mol (6) and bulk anatase is 2.61 +/- 0.41 kJ/mol higher in enthalpy. The surface enthalpies of rutile, brookite, and ...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.251534898

    authors: Ranade MR,Navrotsky A,Zhang HZ,Banfield JF,Elder SH,Zaban A,Borse PH,Kulkarni SK,Doran GS,Whitfield HJ

    更新日期:2002-04-30 00:00:00

  • A poxvirus-like type IB topoisomerase family in bacteria.

    abstract::We report that diverse species of bacteria encode a type IB DNA topoisomerase that resembles vaccinia virus topoisomerase. Deinococcus radiodurans topoisomerase IB (DraTopIB), an exemplary member of this family, relaxes supercoiled DNA in the absence of a divalent cation or ATP. DraTopIB has a compact size (346 aa) an...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.032613199

    authors: Krogh BO,Shuman S

    更新日期:2002-02-19 00:00:00

  • Capture of flanking DNA by a P element in Drosophila melanogaster: creation of a transposable element.

    abstract::A 6.1-kilobase insertion into the rudimentary (r) gene was cloned and partially sequenced. The insertion consists of a 703-base-pair (bp) P element next to a 5.4-kilobase single-copy sequence. The normal position of the single-copy sequence is near the tip of the X chromosome. Upon insertion into the r gene, this chim...

    journal_title:Proceedings of the National Academy of Sciences of the United States of America

    pub_type: 杂志文章

    doi:10.1073/pnas.88.3.693

    authors: Tsubota SI,Huong DV

    更新日期:1991-02-01 00:00:00