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Isolation and Bacterial Expression of a Sesquiterpene Synthase Cdna

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Isolation and Bacterial Expression of a Sesquiterpene Synthase Cdna Proc. Natl. Acad. Sci. USA Vol. 94, pp. 12833–12838, November 1997 Biochemistry Isolation and bacterial expression of a sesquiterpene synthase cDNA clone from peppermint (Mentha x piperita, L.) that produces the aphid alarm pheromone (E)-b-farnesene (insect pheromoneyplant-insect chemical communicationysynomone) JOHN CROCK,MARK WILDUNG, AND RODNEY CROTEAU* Institute of Biological Chemistry, and Department of Biochemistry and Biophysics, Washington State University, Pullman, WA 99164-6340 Contributed by Rodney Croteau, September 25, 1997 ABSTRACT (E)-b-Farnesene is a sesquiterpene semio- kairomonal oviposition stimulant to the European corn borer chemical that is used extensively by both plants and insects for (Ostrinia) (18). (E)-b-farnesene is the major component of communication. This acyclic olefin is found in the essential oil pollen odor in Lupinus and stimulates pollination behavior in of peppermint (Mentha x piperita) and can be synthesized from bumblebees (19). Feeding by larval lepidopterans, such as farnesyl diphosphate by a cell-free extract of peppermint Heliothis or Spodoptera (Noctuidae), increases the amount of secretory gland cells. A cDNA from peppermint encoding (E)-b-farnesene released by corn; the volatile olefin then is (E)-b-farnesene synthase was cloned by random sequencing of detected as a synomone by the parasitic wasp Cotesia margini- an oil gland library and was expressed in Escherichia coli. The ventris (HymenopterayBraconidae) for locating the lepidopt- corresponding synthase has a deduced size of 63.8 kDa and eran hosts (8). Circumstantial evidence also suggests the 21 ' m requires a divalent cation for catalysis (Km for Mg 150 M; lepidopteran induced production and emission of (E)-b- 21 ' m Km for Mn 7 M). The sesquiterpenoids produced by the farnesene from corn serves as a synomone for Cotesia kariyai recombinant enzyme, as determined by radio-GC and GC-MS, (20) and from cotton leaves as a synomone for C. marginiventris are (E)-b-farnesene (85%), (Z)-b-farnesene (8%), and d- (21, 22). cadinene (5%) with the native C15 substrate farnesyl diphos- Perhaps of greatest significance in plant-insect interactions ' m 5 21 phate (Km 0.6 M; Vrel 100) and Mg as cofactor, and is the use of (E)-b-farnesene by most aphid species as an alarm 1 (E)-b-farnesene (98%) and (Z)-b-farnesene (2%) with Mn2 pheromone (23, 24). Aphids exposed to (E)-b-farnesene be- 5 as cofactor (Vrel 80). With the C10 analog, GDP, as substrate come agitated and disperse from their host plant (25). Alate 5 m 5 21 (Km 1.5 M; Vrel 3 with Mg as cofactor), the monoter- aphids are usually more sensitive than are apterae species and penes limonene (48%), terpinolene (15%), and myrcene often will not colonize a host displaying (E)-b-farnesene. Ants (15%) are produced. that defend aphids are sensitive to host-emitted (E)-b- farnesene and, when exposed, will display aggressive behavior (E)-b-farnesene (Fig. 1) is an acyclic sesquiterpene olefin that (26). (E)-b-farnesene also mimics the action of juvenile hor- occurs in a wide range of both plant and animal taxa. More mone III in some insects (27), may play a role in control of than 600 papers have been published on the occurrence of this aphid morphological types, and is acutely toxic to aphids at a natural product and its deployment as an important courier in dose of 100 ngyaphid (28). (E)-b-farnesene vapor is also toxic chemical communication. The olefin is found in the essential to whiteflies (29). oil of hundreds of species of both gymnosperms, such as Efforts to control aphid behavior by topical application of Torreya taxifolia (Florida torreya) (1) and Larix leptolepis (E)-b-farnesene to crops have met with little success, because (larch) (2), and angiosperms, such as Robinia pseudoacacia of volatility and rapid oxidative inactivation in air (30). De- (black locust) (3), Medicago sativa (alfalfa) (4), Chamomilla rivatives of (E)-b-farnesene with reduced volatility, or in- recutita (chamomile) (5), Vitis vinifera (grapes) (6), Cannabis creased stability, have shown promise in reducing aphid- sativa (hemp) (7), Zea mays (corn) (8), Piper nigrum (black transmitted viruses, such as barley mosaic virus (30), potato pepper)†, Daucus carota (carrot)†, and Mentha x piperita virus Y (31), and beet mosaic virus (31). The wild potato (peppermint) (9). Solanum berthaultii, which produces (E)-b-farnesene in type A Although socially dominant male mice produce both a- trichomes, is more repellent to the green peach aphid than are farnesene and (E)-b-farnesene in their urine as pheromones commercial varieties of S. tuberosum that produce lower levels (10), it is in the insects and plants that the use of (E)-b- of the olefin (32, 33). In alfalfa, repellency to the blue alfalfa farnesene as a semiochemical is most extensive. (E)-b- aphid and the pea aphid is correlated with the leaf content of Farnesene is emitted by the Dufour’s gland of andrenid bees (E)-b-farnesene, but not with the amount of the co-occurring (11) and by several genera of ants (12–14), where it serves both sesquiterpene caryophyllene (34). as a defensive allomone and as a trail pheromone. This For plants that produce (E)-b-farnesene, breeding for in- sesquiterpene is synthesized de novo in the osmetrial glands of creased production has met with some success (34), but has larval Papilio (LepidopterayPapilionidae) as an allomone (15), been limited by genetic variation in these species. (E)-b- and it functions as a feeding stimulant to the sand fly Lutzomyia farnesene synthase has been purified from maritime pine longipalpis (DipterayPsychodidae), an important vector of the (Pinus pinaster) and characterized (35), but the gene has not yet blood disease leishmaniasis (16). Several species of predatory been isolated from any source. A cDNA clone for (E)-b- carabid beetles use (E)-b-farnesene as a prey-finding kairomone (17). When released by corn, this olefin is also a Abbreviations: FDP, farnesyl diphosphate; I, identity; S, similarity. Data deposition: The sequence reported in this paper has been The publication costs of this article were defrayed in part by page charge deposited in the GenBank database (accession no. AF024615). *To whom reprint requests should be addressed. e-mail: croteau@ payment. This article must therefore be hereby marked ‘‘advertisement’’ in mail.wsu.edu. accordance with 18 U.S.C. §1734 solely to indicate this fact. †Beckstrom-Sternberg, S. M. & Duke, J. A. (1994) The Phytochemical © 1997 by The National Academy of Sciences 0027-8424y97y9412833-6$2.00y0 Database, Version 4.3; http:yyprobe.nalusda.gov:8300ycgi-biny PNAS is available online at http:yywww.pnas.org. browseyphytochemdb. 12833 Downloaded by guest on September 23, 2021 12834 Biochemistry: Crock et al. Proc. Natl. Acad. Sci. USA 94 (1997) sodium ascorbate, 25 mM KCl, 10 mM DTT and 10% glycerol, and supplemented with 0.5% (wtyvol) polyvinylpolypyrroli- done and 1% (wtyvol) Amberlite XAD-4 polystyrene resin. The sonicate was centrifuged at 3,700 3 g for 15 min, and an aliquot of the supernatant then was placed in a 10-ml screw- capped glass test tube containing divalent metal ions (10 mM m 3 MgCl2 and 1 mM MnCl2) and substrate (7.3 M [1- H]FDP). The aqueous layer was overlaid with 1 ml of pentane, and the sealed tube was incubated at 30°C for 2 hr. The pentane overlay then was collected, and the aqueous layer was extracted twice (1 ml) with pentane. The combined pentane extracts were passed through an anhydrous MgSO4-silica gel column to obtain the labeled hydrocarbon fraction for GC-MS analysis, or for radio-GC analysis by using peppermint oil as an internal standard. Instrumental Analysis. Radio-GC was performed on a Gow-Mac 550P instrument (He carrier 40 mlymin, injector 220°C, detector 250°C and 150 mA) attached to a Packard 894 gas proportional counter. The column (3.18 mm i.d. by 3.66 m FIG. 1. The sesquiterpene synthase substrate, FDP, and sesquit- erpene olefins found in peppermint essential oil. stainless steel with 15% polyethylene glycol ester (AT1000 Alltech) on Gas Chrom Q was programmed from 150°C (5-min farnesene synthase would, by transgenic manipulation, provide hold) to 220°C at 5°Cymin. Thermal conductivity and radio- a valuable addition to the arsenal of natural compounds active activity outputs were monitored after calibration with an ' in host plant resistance. The substrate for (E)-b-farnesene external radiochemical standard, and 20,000 disintegrations synthase is farnesyl diphosphate (FDP), an ubiquitous isopre- per minute of tritiated product were injected with data analysis noid intermediate involved in cytoplasmic phytosterol biosyn- that used Turbochrome Navigator version 4.1 software (Per- thesis. Sesquiterpene synthases lack plastidial targeting se- kin–Elmer). Liquid scintillation counting was performed in y y quences and are localized to the cytoplasm (36). Therefore, toluene ethanol (70:30, vol vol) containing 0.4% Omnifluor (DuPontyNEN) by using a Packard 460 CD spectrometer (3H even in plants that do not normally produce sesquiterpenes, a ' recombinant (E)-b-farnesene synthase would be directed to efficiency 43%). GC-MS analysis used a Hewlett-Packard 6890–5972 system with a 5MS capillary column (0.25 mm i.d. the cytoplasm where substrate is supplied by the mevalonate m pathway and where production of (E)-b-farnesene should by 30 m with 0.25 m coating of 5% phenyl methyl siloxane). result. In this paper, we describe the isolation, sequencing, and Injections were made cool on-column at 40°C with oven programming from 40°C (50°Cymin) to 50°C (5-min hold), functional heterologous expression of a cDNA from pepper- y y mint that encodes (E)-b-farnesene synthase. then 10°C min to 250°C, then 50°C min to 300°C.
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