Volatile compositions of two cactus species growing in the Sonoran Desert of southern Arizona

Transcription

1 2013; 1 (1): ISSN: AJEONP 2013; 1 (1): AkiNik Pulitions Reeived Aepted: Voltile ompositions of two tus speies growing in the Sonorn Desert of southern Arizon Cynthi R. Wright nd Willim N. Setzer Cynthi R. Wright Deprtment of Chemistry, University of Alm in Huntsville Huntsville, AL 35899, USA Willim N. Setzer Deprtment of Chemistry, University of Alm in Huntsville Huntsville, AL 35899, USA ABSTRACT The essentil oils of Opunti nthorp vr. mjor nd Opunti phenth vr. dist (Ctee) growing wild in the Orgn Pipe Ctus Ntionl Monument, Ajo, Arizon, nd the Arizon-Sonor Desert Museum, Tuson, Arizon, were otined y hydrodistilltion nd nlyzed y gs hromtogrphy mss spetrometry. The voltile oil yields nd ompositions of eh tus speies growing in the two lotions were signifintly different. The differenes my e ttriuted to rinfll differenes s well s differenes in soil omposition etween the two sites. Orgn Pipe Ctus Ntionl Monument is drier hitt thn the Arizon-Sonor Desert museum. The soil of the Orgn Pipe Ctus Ntionl Monument is rih with lime while soil t the Arizon-Sonorn Desert Museum is dominted y lihe. O. nthorp vr. mjor nd O. nthorp vr. dist growing in the drier, limey soil of the Orgn Pipe Ctus Ntionl Monument hd essentil oils dominted y lkne hydrorons, while O. nthorp vr. mjor from the Arizon-Sonor Desert Museum ws rih in hromenes, nd p-vinylguiol dominted the omposition of O. nthorp vr. dist growing in the lihe-rih soil of the Arizon-Sonor Desert Museum. Keywords: Opunti nthorp vr. mjor, Opunti phenth vr. dist, lime, lihe, euptoriohromene, homoslte, p-vinylguiol. Correspondene: Willim N. Setzer Deprtment of Chemistry, University of Alm in Huntsville Huntsville, AL 35899, USA E-Mil: wsetzer@hemistry.uh.edu 1. Introdution The Sonorn Desert, whih is onsidered to e sutropil desert, is loted in southestern Cliforni, southwestern Arizon, nd northern Mexio. Although the Sonorn Desert is one of the hottest nd driest deserts in North Ameri, it hs lrge diversity of speies, nd is home to t lest 60 speies of mmmls, more thn 350 ird speies, 20 mphiins, 100 reptiles, pproximtely 30 speies of ntive fish, nd more thn 2,000 speies of plnts [1]. The portion of the Sonorn Desert lying within the United Sttes is topogrphilly divided into lower, western setion tht inludes the Orgn Pipe Ctus Ntionl Monument, nd higher, wetter estern setion tht inludes Tuson nd the Arizon-Sonor Desert Museum [2]. The srity nd unertin distriution of rinfll within the Sonorn Desert is the single most importnt limti ftor influening the survivl nd distriution of plnt speies [3]. The verge rinfll for Tuson, Arizon nd Ajo, Arizon is 318 nd 213 mm per yer, respetively [4]. The Sonorn Desert lies in the Bsin nd Rnge geologi re wherein desert nd grsslnd vlleys re rimmed y prllel mountins extending north from Mexio [5]. These mountins re elieved to e formed y tive volnoes million yers go. The Sonorn Desert hs differing soils tht ffet vegettion. Soil omposition in the desert sins my e grvelly, sndy, or mde up of lys, whih my e humus poor nd gry in olor or rih in lime nd reddish in olor [6]. Soil of the Orgn Pipe Ctus Ntionl Monument is rih in lime [7]. Soil t the Arizon-Sonor Desert Museum is rih with unique minerl deposit lled lihe tht forms within grnite roks nd soils [6]. Clihe is reddish-rown lyer of deposit formed when minerl-rih wter flows through soil [6]. The wter leves ehind lium ronte preipitte tht hrdens s it forms lyers within the soil [6]. Atmospheri lium ontined in dust nd preipittion hs een shown to ontriute to the formtion of lihe soil [8]. ~ 41 ~

2 This study investigtes whether there re differenes in the essentil oil omposition of two tus speies ommonly found in the Sonorn Desert, Opunti nthorp vr. mjor (Engelm. & J.M. Bigelow) L.D. Benson nd Opunti phenth vr. dist (Griffiths) L.D. Benson & Wlk., growing in the lime-sed soil of the Orgn Pipe Ctus Ntionl Monument nd the lihe soil found t the Arizon-Sonor Desert Museum. O. nthorp is ylindro-opunti ntive to the sndy soils of flts nd wshes in the desert t 300 to 1,000 m elevtion from Sonor, Mexio, Riverside County, Cliforni, nd the Southern Counties of Arizon [9], inluding oth the Orgn Pipe Ctus Ntionl Monument nd the Arizon-Sonor Desert Museum. O. nthorp vr. mjor (ommonly known s ukhorn holl) is shru, roresent plnt, or smll tree with trunk of 10 to 15 m in dimeter nd height of 1 to 2 m [9]. The 2- to 5-m tuerles re presented on joints of 15 to 30 m long (Benson, 1969). The Pim Indins of Southern Arizon stemed the flower uds in pits nd utilized them for food [9]. O. nthorp vr. dist (syn. Opunti engelmnnii vr. engelmnnii) is prikly per tus distriuted in sndy soils of plins nd grsslnds t 500 up to 1500 m elevtion [9]. The rnge of O. nthorp vr. dist extends from Sonor nd Chihuhu, Mexio, through the Cliforni mountins ordering the deserts estwrd to Uth nd Texs [9]. The flt, jointed pds of O. nthorp vr. dist re oriulte to ellipti with length of 20 to 40 m long nd 18 to 23 m wide [9]. In Mexio, ttle, deer, nd other nimls onsume O. nthorp s forge [10]. In ft, opuntis suh s O. nthorp n e the prinipl omponent of desert niml s diet [10]. White-til deer hve een found to hve diet omposed of 21% opunti fodder [10]. The ntive O odhm people utilized prikly per tus pds s food soure [6]. Additionlly, the O odhm split nd heted the tus pds nd pplied to joints of the ody to tret rthritis nd rheumtism [6]. Smples for this study olleted from the Orgn Pipe Ctus Ntionl Monument were otined from very grvelly, limy soil [7]. The surfe lyer is light rown, very grvelly lom out 5 m thik [7]. The susoil is pink, very grvelly lom out 20 m thik nd the sustrtum is white nd pinkish gry, very grvelly lom nd wekly emented with lime to 1.5 m nd more [7]. This soil is omposed of younger intermedite lluvil fn nd terre deposits of poorly sorted oles, peles, nd snd, with lesser mounts of silt, ly nd oulders [11]. The Arizon-Sonor Desert Museum is loted in the Tuson Mountin rnge loted in Tuson, Arizon. Soil in the Tuson Mountin rnge lks rgilli horizons nd hs wek struturl development hrterized y modertely to highly emented li horizons t depths in exess of m [12]. Petroli horizons hve een found throughout the upper 10 m of lluvium omprising the lnd surfe within the Tuson Mountin rnge [12]. 2. Mterils nd Methods 2.1 Plnt Mteril Ctus speimens were identified nd olleted from the Orgn Pipe Ctus Ntionl Monument y Tim Tiits of the Ntionl Prk Servie, U.S. Deprtment of the Interior. Speimens of tus were lso olleted y Julie Wiens of the Arizon-Sonor Desert Museum. Smples were hopped nd frozen t -20 C until studied. The plnt smples were hydrodistilled using Likens- Nikerson pprtus with ontinuous extrtion with hloroform for four-hour period. The hloroform ws evported from the distilltes to give the essentil oils (Tle 1). The distilltes were stored t 4 C until nlysis. Tle 1: Essentil oil yields of Arizon Opunti speies. Smple Colletion site Mss of plnt mteril Oil yield nd desription O. nthorp vr. mjor Orgn Pipe Ctus Ntionl Monument g 40.0 mg olorless oil O. nthorp vr. mjor Arizon-Sonor Desert Museum 58.3 g 42.3 mg yellow oil O. nthorp vr. dist Orgn Pipe Ctus Ntionl Monument g 34.0 mg olorless oil O. nthorp vr. dist Arizon-Sonor Desert Museum mg olorless oil 2.2 Gs Chromtogrphy Mss Spetrometry The tus essentil oils of O. nthorp vr. mjor nd O. nthorp vr. dist were sujeted to gs hromtogrphi mss spetrl nlysis on n Agilent system onsisting of Model 6890 gs hromtogrph, Model 5973 mss seletive detetor [MSD, operted in EI mode (eletron energy = 70ev), sn rnge = mu, nd sn rte = 3.99 sns/se], nd n HP-5ms fused sili pillry with (5% phenyl)-poly-methylsiloxne sttionry phse, film thikness of 0.25 µm, length of 30 m, nd n internl dimeter of 0.25 mm. The rrier gs ws helium with olumn hed pressure of 48.7 kp nd flow rte of 1.0 ml/min. inlet temperture ws 200 ºC nd interfe temperture ws 280 ºC. The GC oven temperture progrm ws used s follows: 60 ºC initil temperture, hold for 5 mins; inresed t 3ºC/min to 280 ºC; inresed t 3ºC/min. A 1% w/v solution of the smple in CH 2Cl 2 ws prepred nd injeted using 10:1 split rtio. Identifition of the oil omponents ws sed on their retention indies determined y referene to homologous series of n- lknes, nd y omprison of their mss spetrl frgmenttion ptterns with those reported in the literture [13] nd stored on the MS lirry [NIST dtse (G1036A, revision D.01.00)/Chem Sttion dt system (G1701CA, version C )]. The perentges of eh omponent re reported s rw perentges sed on totl ion urrent without stndrdiztion. The essentil oil ompositions of O. nthorp vr. mjor re summrized in Tles 2 nd 3. Tles 4 nd 5 list the essentil oil omponents of O. nthorp vr. dist. ~ 42 ~

3 Tle 2: Chemil omposition of the essentil oil of Opunti nthorp vr. mjor from Orgn Pipe Ctus Ntionl Monument. RI Compound % RI Compound % 801 Hexnl tr Methylpentdene Hexnol Dodenoi id Furfurl Hexdene Methyl-2-hexnone tr 1615 Tetrdenl n-hexnol ,6,10-Trimethylpentdene (= Norpristne) Heptnone Heptdene Heptnol tr ,6,10,14-Tetrmethylpentdene (= Pristne) Heptnl ,6,10,14-Tetrmethylhexdene (= Phytne) Butyl propnote Nondeene Prenyl ette Eiosne Benzldehyde Isopropyl plmitte Dimethyl trisulfide Heneiosene Pentylfurn Heneiosne Unidentified d Doosene Benzeneetldehyde Doosne is-linlool oxide (furnoid) Triosne trns-linlool oxide (furnoid) Tetrosene Denl Tetrosne α-cmpholenl Unidentified e Cmphenone Unidentified f Otnoi id Pentosene Vitispirne Pentosne Nonnoi id Hexosene Tridene Hexosne Denoi id Heptosne Tetrdene Otosene Dodenl Otosne ,6,10-Trimethyltridene Squlene Pentdene Nonosne Nonylylohexne 0.7 Totl Identified (56) 96.9 The perentges of eh omponent re reported s rw perentges sed on totl ion urrent without stndrdiztion. tr = tre (< 0.05%). d MS, m/z(%): 139(9), 137(14), 119(21), 117(64), 112(70), 110(100), 77(27), 75(38), 71(61), 65(13), 63(13), 55(16), 43(93). e MS, m/z(%): 280(14), 279(54), 163(18), 137(14), 123(21), 111(20), 109(29), 105(23), 97(27), 95(50), 85(25), 83(27), 81(54), 71(27), 69(100), 67(57), 57(39), 55(48), 43(30), 41(45). f MS, m/z(%): 280(7), 263(15), 245(7), 179(8), 165(10), 163(11), 151(11), 137(11), 125(18), 111(30), 109(18), 105(18), 97(46), 95(23), 85(26), 83(46), 81(22), 71(33), 69(100), 67(25), 57(50), 55(46), 43(36), 41(39). Tle 3: Chemil omposition of the essentil oil of Opunti nthorp vr. mjor from Arizon-Sonor Desert Museum. RI Compound % RI Compound % 1190 α-terpineol tr 1715 Pentdenl Denl tr 1766 Euptoriohromene Tridene Otdene α-copene tr Ethylhexyl sliylte Elemene Unidentified e Dodenl ,10,14-Trimethylpentden-2-one (E)-Cryophyllene Enelin Aromdendrene Homoslte 0.7 ~ 43 ~

4 1478 γ-muuolene Unidentified f r-curumene Nondene Vlenene Unidentified g Pentdene Unidentified h Bisolene Eiosne γ-cdinene Isopropyl hexdenote δ-cdinene Otdenol Elemol Heneiosne (E)-Nerolidol (E)-Phytol (3Z)-Hexenyl enzote Doosne Spthulenol (9Z)-Triosene (= Muslure) Cryophyllene oxide Triosne Hexdene Tetrosne Unidentified d Methyltetrosne γ-eudesmol Pentosne Demethoxyenelin Hexosne Selin-11-en-4α-ol Heptosne Androenelinol Nonosne Heptdene 1.4 Totl Identified (48) 91.5 The perentges of eh omponent re reported s rw perentges sed on totl ion urrent without stndrdiztion. tr = tre (< 0.05%). d MS, m/z(%): 206(19), 162(100), 147(59), 134(20), 133(21), 121(24), 120(41), 119(27), 108(31), 107(50), 106(56), 105(52), 95(30), 93(58), 91(68), 81(56), 79(56), 77(33), 67(41), 55(34), 53(21), 43(13). e MS, m/z(%): 234(14), 220(14), 219(100), 203(20), 201(40), 187(21), 159(9), 115(9), 91(12), 79(9), 77(9), 69(11), 55(12), 43(25), 41(13). f MS, m/z(%): 216(81), 201(100), 173(21), 138(6), 121(7), 115(21), 109(13), 97(17), 95(13), 91(16), 83(23), 69(38), 57(21), 55(31), 43(44). g MS, m/z(%): 218(54), 203(100), 185(5), 147(8), 133(6), 105(6), 77(7), 69(10), 55(10), 43(31), 41(8). h MS, m/z(%): 219(3), 187(5), 159(4), 147(5), 135(16), 134(29), 121(12), 119(18), 107(38), 93(53), 91(12), 81(21), 79(20), 71(36), 67(31), 55(26), 43(100), 41(18). Tle 4: Chemil omposition of the essentil oil of Opunti phenth vr. dist from Orgn Pipe Ctus Ntionl Monument. RI Compound % RI Compound % Methyl-2-pentnol tr 1900 Nondene Furfurl tr 1932 Methyl plmitte Phenyletldehyde tr Heptdenol Aetophenone Plmiti id is-linlool oxide (furnoid) Eiosne trns-linlool oxide (furnoid) Isopropyl plmitte Linlool Methyleiosne p-cymen-8-ol Methyl linolete Otnoi id tr 2100 Heneiosne α-terpineol Linolei id p-vinylguiol Olei id (2E,4E)-Dedienl Doosene Benzletone Doosne Denoi id (2Z)-Doosene 0.4 ~ 44 ~

5 1429 (E)-β-Fmesene (9Z)-Triosene (= Muslure) Amyl-α-pyrone Triosne Mssoiltone Tetrosene Mltyl isoutyrte Tetrosne α-zingierene Pentosene Pentdene Pentosne (E,E)-α-Frnesene Methylpentosne Luri id Hexosene Hexdene Hexosne Methylhexdene tr Methylhexosne Heptdene Heptosne Myristi id Methyl lignoerte Otdene Otosne Butyl sliylte utyl ether Hexosnl Triutyrin Nonosne Homosolte ,7-Dimethylotosne 1.4 Totl Identified (60) The perentges of eh omponent re reported s rw perentges sed on totl ion urrent without stndrdiztion. tr = tre (< 0.05%). Tle 5: Chemil omposition of the essentil oil of Opunti phenth vr. dist from Arizon-Sonor Desert Museum. RI Compound % RI Compound % 1072 is-linlool oxide (furnoid) Methyleiosne trns-linlool oxide (furnoid) Otdenol Linlool Heneiosne α-terpineol (E)-Phytol Otnoi id tr Methyldoosne Gerniol (9Z)-Triosene (= Muslure) Nonnoi id Triosene Undenl Triosne p-vinylguiol Pentosne Denoi id Hexdeyl otnote Dodenl Unidentified d Pentdene Hexosne Tridenl Heptosne Luri id Otosne tr 1677 Tridenoi id Nonosne Myristi id Triontene Triutyrin Triontne Hexdenol Untriontne Nondene Dotriontne (2Z)-Nondeene Methyltriontne Plmiti id Hextriontne Isopropyl plmitte 1.1 Totl Identified (42) 96.1 The perentges of eh omponent re reported s rw perentges sed on totl ion urrent without stndrdiztion. tr = tre (< 0.05%). d MS, m/z(%): 299(20), 298(100), 283(3), 251(3), 233(4), 223(5), 195(3), 165(5), 151(4), 137(3), 115(3), 89(3), 77(3), 51(1). ~ 45 ~

6 3. Results nd Disussion Fifty-six ompounds were identified in O. nthorp vr. mjor growing wild in the Orgn Pipe Ctus Ntionl Monument. The primry omponents of the O. nthorp oil from the Orgn Pipe Ctus Ntionl Monument inluded otnoi id (12.3%), triosne (10.8%), denoi id (10.0%), nd 2-hexnol (8.6%). Alknes mde up 37.7% of the totl oil omposition, ftty ids nd ftty-id derivtives omprised 28.4%, with only 8.2% terpenoids. Interestingly, the oil lso ontined 0.5% dimethyl trisulfide. Although dimethyl trisulfide n e hrmful if onsumed or inhled y humns, it hs een identified in severl foods, inluding grli [14, 15], ruiferous vegetles [16,17], nd white truffle [18], s well s rewed offee [19], ged eers [20], nd ske [21]. A totl of 48 ompounds were identified in the essentil oil of O. nthorp vr. mjor growing wild in the Arizon-Sonor Desert Museum. Chromene ompounds omposed 71.5% of the totl essentil oil omposition. Euptoriohromene (66.6%) dominted the oil omposition of the tus growing in the liherih soil. Euptoriohromene is n undnt phytohemil onstituent of Euptorium speies [22], s well s Hemizoni fithii [23], n nnul her ntive to Cliforni, Centure solstitilis, the yellow strthistle [24], nd the rittleush, Eneli frinos [25]. Additionl hromenes lso identified in O. nthorp from the Arizon-Sonor Desert Museum inlude demethoxyeneelin (3.0%), enelin (1.6%), nd ndroenelinol (0.3%). O. nthorp vr. dist growing wild t the Orgn Pipe Ctus Ntionl Monument ontined 60 identifile ompounds. The mjor omponents of the oil inluded triosne (15.5%), plmiti id (7.0%), pentosne (6.3%), is-linlool oxide (5.1%), trns-linlool oxide (4.8%), nd luri id (4.5%). Alkne hydrorons mde up 45.8% of the totl oil, with 25.7% ftty ids nd derivtives, nd only 12.8% terpenoids. O. nthorp from the Orgn Pipe Ctus Ntionl Monument lso ontined 2.1% homoslte (3,3,5-trimethylylohexyl sliylte). Homoslte, nturlly ourring sunsreen tht my protet DNA from ultrviolet rdition, hs een identified s n emission of oth the sguro tus (Crnegie gignte) nd yu (Yu t) growing in the Ls Vegs, Nevd desert re [26]. Homoslte nd 2-ethylhexyl sliylte were lso deteted in O. nthorp from the Arizon-Sonor Desert Museum (Tle 3). Forty-two ompounds were identified in the oil of O. nthorp vr. dist growing wild t the Arizon-Sonor Desert Museum. The mjor omponents identified in the oil inlude p-vinylguiol (16.2%), triutyrin (7.8%), 1-otdenol (6.8%), nd 1- hexdenol (6.6%). The essentil oil ontined 33.2% ftty ids nd ftty-id derivtives nd 17.8% lknes. The mjor omponent, p-vinylguiol, is phenoli ompound tht hs een found in severl tropil fruits, inluding in ppy [27], str pple [28], nd mngo [29]. The essentil oil omposition of O. nthorp growing in the drier, lime soil of the Orgn Pipe Ctus Ntionl Monument differed signifintly from tht growing in the wetter, lihe soil of the Arizon-Sonor Desert Museum. O. nthorp from the Arizon-Sonor Desert Museum ontined 66.2% euptoriohromene nd onsisted of totl hromene onentrtion of 71.1%, while O. nthorp from the Orgn Pipe Ctus Ntionl Monument ws devoid of ny hromenes. There were 12 n-lknes ommon to O. nthorp from oth soil types s well s two ftty ldehydes (denl nd dodenl), nd isopropyl plmitte. Similrly, O. nthorp growing in the limey, drier soil of the Orgn Pipe Ctus Ntionl Monument differed signifintly from tht growing in the lihe-rih, wetter soil of the Arizon-Sonor Desert Museum. Notle differenes were the reltively undnt onentrtions of p-vinylquiol, triutyrin, hexdenol, nd phytol in the smple from the Arizon-Sonor Desert Museum site tht were either sent or in smll onentrtions in the Orgn Pipe Ctus Ntionl Monument smple. Additionlly, high-moleulrweight lknes ( C30) were present in the Arizon-Sonor Desert Museum smple, ut sent from the Orgn Pipe Ctus Ntionl Monument smple. Conversely, homoslte nd isopropyl plmitte were reltively onentrted in the Orgn Pipe Ctus Ntionl Monument smple, while the Arizon-Sonor Desert Museum smple hd only tre mount of isopropyl plmitte nd no homoslte. On the other hnd, there were severl ompounds ommon to the two smples, inluding the monoterpenoids, is- nd trns-linlool oxide, linlool, nd α- terpineol, the ftty ids denoi id, luri id, myristi id, nd plmiti id, nd numer of n-lknes. The voltile oil yields for oth O. nthorp nd O. nthorp were lower for the smples olleted from the Orgn Pipe Ctus Ntionl Monument (0.030% nd 0.023%, respetively), thn those olleted from the Arizon-Sonor Desert Museum (0.073% nd 0.081%, respetively). Additionlly, oth O. nthorp nd O. nthorp oils from Orgn Pipe Ctus Ntionl Monument hd greter onentrtions of lknes thn those from the Arizon-Sonor Desert Museum, nd ftty ids were more undnt in O. nthorp from Orgn Pipe Ctus Ntionl Monument. For O. nthorp, ftty id nd terpenoid onentrtions were similr for the two olletion sites. 4. Conlusions Two tus speies, Opunti nthorp vr. mjor nd O. nthorp vr. dist, were olleted from two different sites in southern Arizon, the Orgn Pipe Ctus Ntionl Monument nd the Arizon-Sonor Desert Museum. The essentil oils from eh of the tus speies were signifintly different in oil yields nd hemil ompositions. The differenes n e ttriuted to the different hitts of the two sites; the limey, drier soil of the Orgn Pipe Ctus Ntionl Monument, ompred to the liherih, wetter soil of the Arizon-Sonor Desert Museum. 5. Aknowledgments We re very grteful to the dministrtion nd stff of the Orgn Pipe Ctus Ntionl Monument nd the Arizon-Sonor Desert Museum for permission to rry out this projet. We re espeilly grteful to Tim Tiits of the Ntionl Prk Servie (Orgn Pipe Ctus Ntionl Monument) nd Julie Wiens of the Arizon- Sonor Desert Museum for plnt identifition nd olletion. 6. Referene: 1 Ntionl Prk Servie. Sonorn Desert Eosystem. Retrieved 17 August Strittholt JR, Brye SA, Wrd BC, Bhelet DM. Sonorn Desert Rpid Eoregionl Assessment Report. Prepred for the U.S. Deprtment of the Interior, Bureu of Lnd Mngement, Denver, Colordo, Mllery TD. Rinfll reords for the Sonorn Desert. Eology, 1936; 17: ~ 46 ~

7 4 Western Regionl Climte Center, Retrieved 17 August Srorough R. The geologi origin of the Sonorn Desert. Retrieved 17 August Ntionl Prk Servie. The Sonorn Desert. views/kcs/sonorndesert/html/et_02_chpter2.htm. Retrieved 17 August United Sttes Deprtment of Agriulture, Soil Conservtion Servie. Soil Survey: Orgn Pipe Ctus Ntionl Monument Gile LH, Peterson FF, Grossmn RB. Morphologil nd geneti sequenes of ronte umultion in desert soils. Soil Siene, 1966; 101: Benson LD. The Cti of Arizon, 3rd Ed. University of Arizon Press, Tuson, Noel PS. Remrkle Agves nd Cti. Oxford University Press, Perthree PA, Youerg A, Young, JJ. Geologi Mp of the Tillotson Pek 7 ½' Qudrngle nd prt of the Mount Ajo 7 ½' Qudrngle, Orgn Pipe Ctus Ntionl Monument, Pim County, Arizon. Arizon Geologil Survey DGM-73, one mp sheet, 1:24,000 mp sle, MAuliffe JR. Lndspe evolution, soil formtion, nd eologil ptterns nd proesses in Sonorn Desert jds. Eologil Monogrphs, 1994; 64: Adms RP. Identifition of Essentil Oil Components y Gs Chromtogrphy / Mss Spetrometry, 4th Ed. Allured Pulishing, Crol Strem, Illinois, USA, Rpior S, Breheret S, Tlou T, Bessière JM. Voltile flvor onstituents of fresh Mrsmius llieus (grli Mrsmius). Journl of Agriulturl nd Food Chemistry 1997; 45: Kimris AC, Sitis NG, Dferer DJ, Trntilis PA, Ppps CS, Polissiou MG. Comprison of distilltion nd ultrsound-ssisted extrtion methods for the isoltion of sensitive rom ompounds from grli (Allium stivum). Ultrsonis Sonohemistry, 2006; 13: Mruym FT. Identifition of dimethyl trisulfide s mjor rom omponent of ooked ssieous vegetles. Journl of Food Siene 1970; 35: Vlette L, Fernndez X, Poulin S, Loiseu AM, Lizzni- Cuvelier L, Levieil R, Restier L. Voltile onstituents from Romnso uliflower. Food Chemistry 2003; 80: Bellesi F, Pinetti A, Binhi A, Tirillini B. Voltile ompounds of the white truffle (Tuer mgntum Pio) from middle Itly. Flvour nd Frgrne Journl 1996; 11: Chin ST, Eyres GT, Mrriott PJ. Identifition of potent odournts in wine nd rewed offee using gs hromtogrphyolftometry nd omprehensive two-dimensionl gs hromtogrphy. Journl of Chromtogrphy A 2011; 1218: Gijs L, Perpète P, Timmermns A, Collin S. 3- Methylthiopropionldehyde s preursor of dimethyl trisulfide in ged eers. Journl of Agriulturl nd Food Chemistry 2000; 48: Isogi A, Utsunomiy H, Knd R, Iwt H. Chnges in the rom ompounds of ske during ging. Journl of Agriulturl nd Food Chemistry 2005; 53: Anthonsen T. New hromenes from Euptorium speies. At Chemi Sndinvi 1969; 23: Kloke JA, Blndrin MF, Adms RP, Kingsford E. Insetiidl hromenes from the voltile oil of Hemizoni fithii. Journl of Chemil Eology 1985; 11: Merrill GB. Euptoriohromene nd enelin, plnt growth regultors from yellow strthistle (Centure solstitilis L.) Journl of Chemil Eology 1989; 15: Wright C, Chhetri BK, Setzer WN. Chemil omposition nd phytotoxiity of the essentil oil of Eneli frinos growing in the Sonorn Desert. Amerin Journl of Essentil Oils nd Nturl Produts 2013; 1: Mtsung SN, Guenther AB, Potosnk MJ, Apel EC. Emission of sunsreen sliyli esters from desert vegettion nd their ontriution to erosol formtion. Atmospheri Chemistry nd Physis 2008; 8: Pino JA, Almor K, Mrot R. Voltile omponents of ppy (Cri ppy L., Mrdol vriety) fruit. Flvour nd Frgrne Journl 2003; 18: Pino JA, Mrot R, Rosdo A. Voltile onstituents of str pple (Chrysophyllum inito L.) from Cu. Flvour nd Frgrne Journl 2002; 17: Pino JA, Mes J, Muñoz Y, Mrtí MP, Mrot R. Voltile omponents from mngo (Mngifer indi L.) ultivrs. Journl of Agriulturl nd Food Chemistry 2005; 53: ~ 47 ~