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Benjamin R Lichman, Mohamed O Kamileen, Gabriel R Titchiner, Gerhard Saalbach, Clare E M Stevenson, David M Lawson, Sarah E O'Connor
Terpene synthases typically form complex molecular scaffolds by concerted activation and cyclization of linear starting materials in a single enzyme active site. Here we show that iridoid synthase, an atypical reductive terpene synthase, catalyzes the activation of its substrate 8-oxogeranial into a reactive enol intermediate, but does not catalyze the subsequent cyclization into nepetalactol. This discovery led us to identify a class of nepetalactol-related short-chain dehydrogenase enzymes (NEPS) from catmint (Nepeta mussinii) that capture this reactive intermediate and catalyze the stereoselective cyclisation into distinct nepetalactol stereoisomers...
January 2019: Nature Chemical Biology
Sándor Koczor, Ferenc Szentkirályi, József Vuts, John C Caulfield, David M Withall, John A Pickett, Michael A Birkett, Miklós Tóth
Green lacewings (Chrysopidae) are predators of soft-bodied pest insects and are among the most important biological control agents in crop protection. Chrysopa spp. are of special importance since, unlike most green lacewing species, adults are also predatory. The current study was undertaken in search of Chrysopa formosa compounds with semiochemical activity. Using coupled gas chromatography-electroantennography (GC-EAG), head and thorax extracts of C. formosa elicited EAG responses to a compound subsequently identified by coupled GC/mass spectrometry, microchemistry, chemical synthesis and GC peak enhancement as (Z)-4-tridecene...
February 2018: Journal of Chemical Ecology
John M Billingsley, Anthony B DeNicola, Joyann S Barber, Man-Cheng Tang, Joe Horecka, Angela Chu, Neil K Garg, Yi Tang
Monoterpene indole alkaloids (MIAs) represent a structurally diverse, medicinally essential class of plant derived natural products. The universal MIA building block strictosidine was recently produced in the yeast Saccharomyces cerevisiae, setting the stage for optimization of microbial production. However, the irreversible reduction of pathway intermediates by yeast enzymes results in a non-recoverable loss of carbon, which has a strong negative impact on metabolic flux. In this study, we identified and engineered the determinants of biocatalytic selectivity which control flux towards the iridoid scaffold from which all MIAs are derived...
November 2017: Metabolic Engineering
Beibei Xiang, Xiaoxue Li, Yan Wang, Xiaoxuan Tian, Zhen Yang, Lin Ma, Xia Liu, Yong Wang
Swertia mussotii is an important medicinal plant found on the Qinghai Tibetan Plateau that has great economic and medicinal value. This plant has enjoyed a long history of use as a curative for hepatitis. The biological activity of secoiridoids, including gentiopicroside and swertiamarin, has been mainly tested for its anti-hepatitis effects. Here, we identify two candidate genes ( SmIS1 and SmIS2 ) that are homologues of iridoid synthase and that are components of the secoiridoid pathway in S. mussotii . Using sequencing and phylogenetic analyses, we confirm that SmIS1 and SmIS2 contain six conserved short-chain dehydrogenases/reductase (SDR) motifs and thus belong to the P5βRs group...
August 22, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Alex Campbell, Philippe Bauchart, Nicholas D Gold, Yun Zhu, Vincenzo De Luca, Vincent J J Martin
The monoterpene indole alkaloids (MIAs) are a valuable family of chemicals that include the anticancer drugs vinblastine and vincristine. These compounds are of global significance-appearing on the World Health Organization's list of model essential medicines-but remain exorbitantly priced due to low in planta levels. Chemical synthesis and genetic manipulation of MIA producing plants such as Catharanthus roseus have so far failed to find a solution to this problem. Synthetic biology holds a potential answer, by building the pathway into more tractable organisms such as Saccharomyces cerevisiae...
May 20, 2016: ACS Synthetic Biology
Jeffrey R Aldrich, Kamal Chauhan, Qing-He Zhang
Green lacewings (Neuroptera: Chrysopidae) are voracious predators of aphids and other small, soft-bodied insects and mites. Earlier, we identified (1R,2S,5R,8R)-iridodial from wild males of the goldeneyed lacewing, Chrysopa oculata Say, which is released from thousands of microscopic dermal glands on the abdominal sterna. Iridodial-baited traps attract C. oculata and other Chrysopa spp. males into traps, while females come to the vicinity of, but do not usually enter traps. Despite their healthy appearance and normal fertility, laboratory-reared C...
2016: PeerJ
Yumei Hu, Weidong Liu, Satish R Malwal, Yingying Zheng, Xinxin Feng, Tzu-Ping Ko, Chun-Chi Chen, Zhongxia Xu, Meixia Liu, Xu Han, Jian Gao, Eric Oldfield, Rey-Ting Guo
Structures of the iridoid synthase nepetalactol synthase in the presence of NAD(+) , NADPH or NAD(+) /10-oxogeranial were solved. The 10-oxogeranial substrate binds in a transoid-O1-C3 conformation and can be reduced by hydride addition to form the byproduct S-10-oxo-citronellal. Tyr178 Oζ is positioned 2.5 Å from the substrate O1 and provides the second proton required for reaction. Nepetalactol product formation requires rotation about C1-C2 to form the cisoid isomer, leading to formation of the cis-enolate, together with rotation about C4-C5, which enables cyclization and lactol production...
December 14, 2015: Angewandte Chemie
Shimaa A M Ebrahim, Hany K M Dweck, Johannes Stökl, John E Hofferberth, Federica Trona, Kerstin Weniger, Jürgen Rybak, Yoichi Seki, Marcus C Stensmyr, Silke Sachse, Bill S Hansson, Markus Knaden
Detecting danger is one of the foremost tasks for a neural system. Larval parasitoids constitute clear danger to Drosophila, as up to 80% of fly larvae become parasitized in nature. We show that Drosophila melanogaster larvae and adults avoid sites smelling of the main parasitoid enemies, Leptopilina wasps. This avoidance is mediated via a highly specific olfactory sensory neuron (OSN) type. While the larval OSN expresses the olfactory receptor Or49a and is tuned to the Leptopilina odor iridomyrmecin, the adult expresses both Or49a and Or85f and in addition detects the wasp odors actinidine and nepetalactol...
December 2015: PLoS Biology
Sándor Koczor, Ferenc Szentkirályi, John A Pickett, Michael A Birkett, Miklós Tóth
Common green lacewings (Chrysoperla carnea complex) form a group of generalist predators important for biological control. Several reports show attraction of these insects to plant volatiles, and a highly attractive ternary compound floral bait has been developed. With aphids being a preferred prey of larvae, one might expect these lacewings to be attracted to aphid semiochemicals, for instance, to aphid sex pheromones, as found for several other green lacewing species. However, in a previous study, we found that traps containing aphid sex pheromone compounds (1R,4aS,7S,7aR)-nepetalactol (NEPOH), (4aS,7S,7aR)-nepetalactone (NEPONE), and a ternary floral bait attracted fewer individuals than those containing the ternary floral bait alone...
June 2015: Journal of Chemical Ecology
Ramakrishnan Krithika, Prabhakar Lal Srivastava, Bajaj Rani, Swati P Kolet, Manojkumar Chopade, Mantri Soniya, Hirekodathakallu V Thulasiram
Catharanthus roseus [L.] is a major source of the monoterpene indole alkaloids (MIAs), which are of significant interest due to their therapeutic value. These molecules are formed through an intermediate, cis-trans-nepetalactol, a cyclized product of 10-oxogeranial. One of the key enzymes involved in the biosynthesis of MIAs is an NAD(P)(+) dependent oxidoreductase system, 10-hydroxygeraniol dehydrogenase (Cr10HGO), which catalyses the formation of 10-oxogeranial from 10-hydroxygeraniol via 10-oxogeraniol or 10-hydroxygeranial...
2015: Scientific Reports
Vonny Salim, Brent Wiens, Sayaka Masada-Atsumi, Fang Yu, Vincenzo De Luca
Iridoids are key intermediates required for the biosynthesis of monoterpenoid indole alkaloids (MIAs), as well as quinoline alkaloids. Although most iridoid biosynthetic genes have been identified, one remaining three step oxidation required to form the carboxyl group of 7-deoxyloganetic acid has yet to be characterized. Here, it is reported that virus-induced gene silencing of 7-deoxyloganetic acid synthase (7DLS, CYP76A26) in Catharanthus roseus greatly decreased levels of secologanin and the major MIAs, catharanthine and vindoline in silenced leaves...
May 2014: Phytochemistry
C A Campbell, G W Dawson, D C Griffiths, J Pettersson, J A Pickett, L J Wadhams, C M Woodcock
Behavioral studies using an olfactometer demonstrated that sexual females (oviparae) of the damson-hop aphid,Phorodon humuli, release a pheromone to which males respond. Volatiles produced by the oviparae were analyzed by coupled gas chromatography-single cell recording from the secondary rhinaria on the male antenna and showed the presence of one peak with major activity. Coupled gas chrornatography-mass spectrometry suggested a nepetalactol, which was shown to have the 4aR, 7S, 7aS stereochemistry by synthesis from the corresponding nepetalactone isolated from the labiate plantNepeta mussinii...
December 1990: Journal of Chemical Ecology
Emily J Symmes, Sarah Y Dewhirst, Michael A Birkett, Colin A M Campbell, Keith Chamberlain, John A Pickett, Frank G Zalom
Mealy plum, Hyalopterus pruni, and leaf-curl plum, Brachycaudus helichrysi, aphids are the primary arthropod pests in orchards that produce dried plums (i.e., prunes). The sexual stage of their respective lifecycles occurs on prune trees in the fall, during which time males respond to sex pheromones produced by oviparous females. Air-entrainment collections confirmed that oviparous H. pruni and B. helichrysi emitted combinations of (4aS, 7S, 7aR)-nepetalactone and (1R, 4aS, 7S, 7aR)-nepetalactol. The responses of H...
May 2012: Journal of Chemical Ecology
Sándor Koczor, Ferenc Szentkirályi, Michael A Birkett, John A Pickett, Erzsébet Voigt, Miklós Tóth
BACKGROUND: The deployment of synthetic attractants for the manipulation of lacewing populations as aphid predators is currently used in integrated pest management. This study investigates a synthetic bait comprising floral compounds previously found to attract the Chrysoperla carnea complex, and, for the first time, the aphid sex pheromone components (1R,4aS,7S,7aR)-nepetalactol and (4aS,7S,7aR)-nepetalactone, in field experiments in Hungary, for their ability to manipulate lacewing populations...
December 2010: Pest Management Science
Joel S Beckett, James D Beckett, John E Hofferberth
The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin, and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the individual antipodes of actinidine by a novel tandem cycloaddition/pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial.
April 2, 2010: Organic Letters
R W H M van Tol, H H M Helsen, F C Griepink, W J de Kogel
All aphid species studied so far share the same sex pheromone components, nepetalactol and nepetalactone. Variation by different enantiomers and blends of the two components released by different aphid species are limited and can only partially explain species-specific attraction of males to females. While some host-plant odours are known to enhance specific attraction of aphid species, herbivore-induced plant volatiles that synergise attractiveness to the sex pheromone are unknown. Here, we demonstrate that for the host-alternating rosy apple aphid (Dysaphis plantaginea (Passerini)) specificity of attraction of males to females is triggered by female-induced tree odours in combination with a 1:8 ratio of (4aS,7S,7aR)-nepetalactone and (1R,4aS,7S,7aR)-nepetalactol...
December 2009: Bulletin of Entomological Research
Sarah Y Dewhirst, Michael A Birkett, Jean D Fitzgerald, Alex Stewart-Jones, Lester J Wadhams, Christine M Woodcock, Jim Hardie, John A Pickett
The sex pheromones of many aphid species from the subfamily Aphididae comprise a mixture of the iridoids (cyclopentanoids) (1R,4aS,7S,7aR)-nepetalactol and (4aS,7S,7aR)-nepetalactone. In this paper, we investigate whether other chemicals, in addition to nepetalactol and nepetalactone, are released from Dysaphis plantaginea (rosy apple aphid) oviparae as part of their sex pheromone. Four compounds present in an air entrainment sample collected from D. plantaginea oviparae feeding on apple (Malus silvestris c...
December 2008: Journal of Chemical Ecology
Marie Pettersson, C Rikard Unelius, Irena Valterová, Anna-Karin Borg-Karlson
Volatiles released by seedlings of Norway spruce infested with the aphid Cinara pilicornis were analyzed using SPME-GC-MS. Among the stress-induced compounds released by the host plant, citronellol, cis-trans-nepetalactone and cis-trans-nepetalactol was found. These compounds originated from the aphids and they were assumed to be pheromone components for this aphid species. To determine the relative stereochemistry of the nepetalactone, a diagnostic method was developed. The method was based on multivariate analysis of tabulated relative intensities of mass fragments of the four nepetalactone diastereomers...
February 8, 2008: Journal of Chromatography. A
Alex Stewart-Jones, Sarah Y Dewhirst, Lisa Durrant, Jean D Fitzgerald, Jim Hardie, Antony M Hooper, John A Pickett, Guy M Poppy
Insect communication is primarily via chemicals. In Aphidinae aphids, the structure and ratio of iridoid (monoterpenoid) chemicals are known to be important components of the sex pheromone. However, for enhanced species specificity, it has been suggested that release of sex pheromone might be restricted to a narrow time period within the diel cycle. Here, we determine the structure, ratios and release patterns of iridoid chemicals produced by a serious global pest, the rosy apple aphid, Dysaphis plantaginea...
December 2007: Journal of Experimental Biology
Tom W Pope, Colin A M Campbell, Jim Hardie, John A Pickett, Lester J Wadhams
The bird cherry-oat aphid, Rhopalosiphum padi (L.), and the damson-hop aphid, Phorodon humuli (Schrank), migrate at the same time of year and colonize closely related Prunus spp. as primary hosts, but utilize (1R,4aS,7S,7aR)-nepetalactol and (1RS,4aR,7S,7aS)-nepetalactol, respectively, as sex pheromones. Interactions between these sex pheromones and benzaldehyde and methyl salicylate, plant volatiles common to primary hosts of both species, were investigated to assess whether they confer reproductive isolation between these species...
January 2007: Journal of Chemical Ecology
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