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Volatile Terpenoids and Tropolones in Heartwood Extracts of Yellow-Cedar, Monterey Cypress, and Their Hybrid Leyland Cypress Rick G

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Volatile Terpenoids and Tropolones in Heartwood Extracts of Yellow-Cedar, Monterey Cypress, and Their Hybrid Leyland Cypress Rick G Volatile terpenoids and tropolones in heartwood extracts of yellow-cedar, Monterey cypress, and their hybrid Leyland cypress Rick G. Kelsey, M. P. González-Hernández, Joe Karchesy, Sheeba Veluthoor To cite this version: Rick G. Kelsey, M. P. González-Hernández, Joe Karchesy, Sheeba Veluthoor. Volatile terpenoids and tropolones in heartwood extracts of yellow-cedar, Monterey cypress, and their hybrid Leyland cypress. Annals of Forest Science, Springer Nature (since 2011)/EDP Science (until 2010), 2015, 72 (3), pp.349-355. 10.1007/s13595-014-0429-6. hal-01284178 HAL Id: hal-01284178 https://hal.archives-ouvertes.fr/hal-01284178 Submitted on 7 Mar 2016 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Annals of Forest Science (2015) 72:349–355 DOI 10.1007/s13595-014-0429-6 ORIGINAL PAPER Volatile terpenoids and tropolones in heartwood extracts of yellow-cedar, Monterey cypress, and their hybrid Leyland cypress Rick G. Kelsey & M. P. González-Hernández & Joe Karchesy & Sheeba Veluthoor Received: 14 July 2014 /Accepted: 3 October 2014 /Published online: 17 October 2014 # INRA and Springer-Verlag France 2014 Abstract Monterrey cypress heartwoods are also active against various & Key message Leyland cypress, an intergeneric hybrid, fungi, bacteria, human insect pests, and plant pathogens, produces the same volatile heartwood compounds as its whereas Leyland cypress heartwood has never been thorough- parental taxa, yellow-cedar and Monterrey cypress. ly investigated. However, the proportion of total sesquiterpenes and some & Aims The first aim for this study was to examine the volatile of the individual components appear unique to their re- compounds in ethyl acetate extracts from the heartwood of all spective heartwoods. three tree species in Oregon. The second aim was to determine & Context Leyland cypress, xHesperotropsis leylandii is an the extent Leyland cypress differs from its parental species, intergeneric hybrid between yellow-cedar, Callitropsis and further investigate any of its novel compounds for bio- nootkatensis, and Monterey cypress, Hesperocyparis logical activity. macrocarpa. Their heartwoods are protected by bioactive & Methods Ethyl acetate extracts of fresh heartwood were compounds and rated very durable to durable for products prepared for three trees of each species and analyzed by gas used above ground. Several compounds in yellow-cedar and chromatography. & Results Thirty-three compounds were detected at 0.5 % or greater abundance across all species, and 23 were identified. Handling Editor: Jean-Michel Leban Carvacrol was the major monoterpene and nootkatin the most Contribution of the co-authors Kelsey contributed to designing the abundant tropolone in all three species. Valencene 11, 12-diol experiment, locating and sampling trees, lab analyses, and writing the and nootkatone topped the list of sesquiterpenes in yellow- paper. González-Hernández contributed to sampling trees, lab analyses, cedar and Leyland cypress, respectively, whereas no sesqui- and writing the paper. Karchesy and Veluthoor contributed to compound terpenes were detected in Monterrey cypress. This appears to identification and reviewing the paper. be the first report of tropolones hinokitiol, procerin, and R. G. Kelsey (*) nootkatin in Leyland cypress, α-thujaplicinol, pygmaein, USDA Forest Service, PNW Research Station, Corvallis, OR 97331, and procerin in Monterrey cypress, and hinokitiol in yellow- USA e-mail: [email protected] cedar. & Conclusions Leyland cypress heartwood does not M. P. González-Hernández biosynthesize structurally unique compounds from those pro- Department of Crop Production, Santiago de Compostela University, duced by its parental species, and is an unlikely source of 27002 Lugo, Spain e-mail: [email protected] novel biocides. However, the proportion of total sesquiter- penes and some of the individual components in Leyland J. Karchesy cypress heartwood may distinguish it from the heartwood of Wood Science and Engineering, Oregon State University, Corvallis, its parental species. OR 97331, USA e-mail: [email protected] S. Veluthoor Keywords Cupressaceae . Callitropsis nootkatensis . CoreValleys Herbal Technologies, Mini-Industrial Estate, Nallalam, Hesperocyparis macrocarpa . Hesperotropsis leylandii . Calicut 673027, Kerala, India x e-mail: [email protected] Monoterpenes . Sesquiterpenes 350 R.G. Kelsey et al. 1 Introduction considered sterile; it may be self-sterile, but can produce viable seeds when crossed with a compatible pollen donor Yellow-cedar (YC), Callitropsis nootkatensis (D. Don) Oerst. (Armitage 2011). The 15 cultivars of LC (Armitage 2011)are ex D.P. Little., also known as Alaska-cedar, Alaska yellow- propagated as clonal cuttings primarily for ornamental trees cedar, or Nootka cypress, has experienced numerous nomen- and shrubs, but it can be grown for timber (Nicholas 2014). clature changes in recent years, as reviewed by Garland and Like the parental species, LC heartwood is best for products Moore (2012). It is most abundant in the coastal forests of used above ground, and considered very durable to durable southeast Alaska and British Columbia with a southern exten- against brown-rot decay (Jones et al. 2013), but its chemical sion of its distribution primarily in the Cascade Range through composition has not been thoroughly investigated. Washington and Oregon to northern California, usually at Composition of the steam distilled essential oils, and ether elevations above 600 m (Harris 1990;Murray2010;Hennon extracts from one tree of each of the three taxa above have been et al. 2012). It is an ecologically and economically important examined (Liu 2009). However, oils collected after 6 h of tree that indigenous peoples have valued and used for centu- distillation had a substantially different composition from oils ries as a material resource (Stewart 1984;Hennonetal.2012). collected from 6 to 12 h. This may be due to various factors, Products made from its durable heartwood will last longer including nootkatin crystallization out of the essential oil (Liu when used above ground, compared to those having constant 2009) and thermal instability of some compounds during steam contact with the soil (DeGroot et al. 2000; Hennon et al. distillation. The objectives for this study were to examine the 2007). Above ground performance is demonstrated by dead- volatile compounds in ethyl acetate extracts from all three spe- standing YC trees that gradually lose their bark and sapwood, cies growing in Oregon to determine to what extent LC differs leaving predominately heartwood skeletons that can remain from its two parental species, and whether it contains any novel standing for up to a century after death with minimal loss in compounds worthy of investigating for biocidal activity. wood strength (McDonald et al. 1997). Heartwood durability is attributed to a mixture of various monoterpenes, sesquiter- penes, and tropolones (Carlsson et al. 1952;Duffetal.1954; Erdtman and Topliss 1957; Erdtman and Hirose 1962; Norin 2 Material and methods 1964; Kelsey et al. 2005; Khasawneh and Karchesy 2011; Khasawneh et al. 2011) that have proven biological activity 2.1 Plant material against various insects and microbes (Morales-Ramos et al. 2003;Arangoetal.2004; Panella et al. 1997, 2005; Taylor Heartwood samples were collected from three trees of each et al. 2006;Manteretal.2006, 2007;Jordanetal.2012). species at the locations listed in Table 1. The geographic Monterey cypress (MC), Hesperocyparis macrocarpa (Hartw.) Bartel has also experienced numerous nomenclature Table 1 Tree diameters and locations in Oregon changes in recent years (Garland and Moore 2012)andis Species Tree Dbh (cm) Location; latitude, longitude endemic to small areas around Monterey Bay and the central coast of California. This tree has been cultivated in Hawaii YC 1 38.1 Corvallis, PA; 44.655793°, −123.234268° and elsewhere around the world for wind breaks or an orna- 239.9 mental with potential as an important timber species in New 337.6 Zealand (Little and Skolmen 1989; Nicholas 2014). MC MC 1 57.7 Newport, OCA; 44.616962°, −124.050060° heartwood, like YC is more durable for above ground prod- 2a 101.3 Newport, BHM; 44.631375°, −124.058188° ucts than those in contact with soil; it is rated very durable to 3a 64.5 Newport, PMHC; 44.632637°, −124.048309° durable against brown-rot decay (Jones et al. 2013). It is LC 1 35.3 Dillard; 43.080601°, −123.409100° known to contain some of the same bioactive monoterpenes 236.1 andtropolonesasYC(CorbettandWright1953; Haluk and 333.5 Roussel 2000;Igrietal.1990; Zhang et al. 2012). – Hesperotropsis leylandii Trees were sampled 18 24 October, 2013. All YC trees and MC tree 1 Leyland cypress (LC), x (A. B. had multiple stems. The geographic origin of YC seeds was unavailable Jacks. & Dallim.) Garland and Gerry Moore has also experi- from the arboretum. LC was cultivar ‘Leighton Green’according to their enced nomenclature instability associated with phylogenetic owner. This cultivar is believed
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