Geochimica a Cosmorhimico mA .clVpol. detnirP55, pp. 2555-2577 0016-7037/91/$3,00+ .I0 thgirypoC 0 1991 Pergamon Press in .A.S.U yratnemideS dipil yrtsimehcoegoib of na cihportuerepyh enilakla noogal J. 0. GRIMALT,' I. YRUELA,* .C SAIZ-JIMENEZ,’ J. TOJA,~ J. W. DE ~,WUEEL dna J. ALBAIG~S’ ‘Department of Environmental Chemistry ,)CISC-DIC( idroJ anoriG 18,08034-Barcelona, niapS etutitsn12 fo Natural secruoseR dna ygoloiborgA ,)CISC( OP xoB 1052, 4 ,alliveS-0801 niapS ytisrevinU‘ fo ,alliveS ytlucaF fo ,ygoloiB tnemtrapeD fo lategeV ygoloiB dna ,ygolocE OP xoB 1095, ,alliveS-08014 niapS tfleD4 ytisrevinU fo ,ygolonhceT ytlucaF fo lacimehC gnireenignE dna slairetaM ,ecneicS cinagrO yrtsimehcoeG .tinU De seirV nav neostnalptsyeH 2, 2628 ZR ,tfleD ehT sdnalrehteN ;0991 1 .I (Received February 14, accepted in revisedjhn June I99 I) A-tcartsbA deliated yduts of the dipil noitisopmoc of yratnemides dna water etalucitrap selpmas of a etulid enilakla ekal atnaS( allalO ,noogaL riviuqladauG ,atleD nretsewhtuos )niapS has dewolla the -nedi noitacifit dna noitatitnauq of tuoba 300 sdnuopmoc gnitcelfer tnanimoderp stupni of cinagro rettam dna yrev ylrae citenegaid processes. esehT ,sdipil detanimod yb yttaf sdica ,)%68-O@ tnuocca for pu ot 0.25% wt. of yrd tnemides hcihw si tnetsisnoc htiw the hgih cihportue snoitidnoc of the noogal dna stseggus a good noitavreserp of the yllanigiro decudorp cinagro .rettam ,revewoH the yramirp dipil ,sdnuopmoc ylniam morf lairetcabonayc ,nigiro are ylgnorts .deifidom ehT ,23C-03C ,1 -3I dna l,1 sloid-S etutitsnoc the ylno rojam puorg that nac eb detubirtta yltcerid ot these .smsinagro ehT tnanimoderp ,sdipil gnidulcni the yttaf ,sdica are evitacidni of esnetni laiborcim ,gnikrower yleman snoitubirtnoc morf evitisop-marg dna evitagen-marg airetcabue dna .snegonahtem ,ylesrevnoC the rehgih tnalp sdipil are retteb devreserp dna etanimod the citahpila nobracordyh .noitcarf noitanegordyH dna noitardyhed are two rojam noitamrofsnart processes ni the yratnemides metsys gnieb detcelfer ni the noitamrofsnart fo slorets otni -)H(a5 dna slonats-)H(3/5 dna ,senerets dna 10-22-napoh-)H(3/12,)H(3/71 otni .enetpolpid noitadixO ni the water nmuloc smees ot evlovni the laitrap noitamrofsnart of slorets otni diorets ,senotek lotyhp otni cionacedartetlyhtemirt-31,9,5 dica dna two ciremosi ,sedilonacedaxeh-71-lyhtemartet-51,11,7,3 ,dna ,ylbissop lonamyhartet otni .eno-3-recammag enotnaidA dna cionapohomohsib dica ylbaborp tluser morf the laitrap noitadyxo of dednetxe -yhylop senapohyxord or the 33C-03C senapohyxordyh dnuof ni the noogal waters. INTRODUCTION nI muidos hcir-etahplus ,stnemnorivne ytinilakla yam etanigiro morf the ytivitca of gnicuder-etahplus airetcab that EHT REPPU TIMIL FO cinotknalp citehtnysotohp ytivitca si mrof etanobracib morf nobra ccinagro .secruos ehT -necnoc dnuof ni enilakla sekal GNILLAT( et ,.la 1973). yramirP -orp noitart of the devlossid stlas yb noitaropave yam osla evig noitcud ni lartuen cihportue sekal dna eniram gnillewpu areas esir ot noitamrof of gniniatnoc-etanobrac ,senirb dedivorp yllausu segnar neewteb 1,000 dna 2,000 gm 2m/C - ,yad that on tnacifingis stnuoma of muiclac or muisengam are gnihcae.I pu ot 10,000 gm 2m/C - yad ni niatrec gnillewpu tneserp KELAM-LE-DBA( dna ,KZIR ,b,a3691 dna c). snoiger et ,.la 197 1). enilaklA sekal yllareneg tibihxe (RYTHER ehT smsinagro gnivil ni these stnemnorivne tsum eb -ilakla noitcudorp seulav neewteb 10,000 dna 15,000 gm .*m/C yad tnarelot dna cilihpolah hcihw ylereves setatimil the ytisrevid et ,.la 1973) dna yam tnuoma ot erom naht 20,000 (TALLING of citoyrakorp dna citoyrakue .seiceps ,airetcabonayC yleman gm *m/C * yad ,STLEK( 1988). esehT stnemnorivne etutitsnoc aniluripS spp., yltnerruc etanimoderp TNARG( dna ,GNOL the s’dlrow tsom evitcudorp smetsys ,KCALEM( 198 1) dna 1985). nI the ecneserp of ruhplus ,seiceps hgih snoitartnecnoc yam evah del ot the noitareneg of nobracordyh ecruos rocks SNAVE( dna ,DNALKRIK 1988). of cihportotohp ruhplus ,airetcab ..e.i Ectothiorhodosphira ehT hgih pH of these sekal si a ecneuqesnoc of the hgih spp., are dnuof ,LLADNIT( 1988). noitartnecnoc of devlossid muidos etanobrac hcihw yam -er ,ylgnisirpruS the noitaziretcarahc of the cinagro rettam tlus morf retawdnuorg wash tuo of yratnemides snoitamrof tneserp ni these ekal smetsys has ylno neeb ni a detelped ni muiclac dna .muisengam rednU eseht ,snoitidnoc yrev detimil rebmun of seiduts SNEGED( et ,.la 1973, 1984), larenim gnihcael yb noi egnahcxe dna noitartnecnoc yb dna on noitamrofni si elbaliava no the ralucelom noitisopmoc noitaropave yam dael ot a tfihs ni the nobrac -racibledixoid of the yratnemides record. htiW siht ni ,dnim we kootrednu etanobrac/etanob muirbiliuqe towards etanobrac ,LLADNIT( a yduts of the noitisopmoc of yratnemides sdipil of the atnaS 1988). esehT smetsys act as a trap for cirehpsomta nobrac allalO ,noogaL na enilakla cihportuerepyh metsys detacol ni edixoid FFOHMI( et ,.la 1979). ehT devlossid etanobrac si the a riviuqladauG ,atleD anaiioD lanoitaN Park, nretsewhtuos evreser of cinagroni nobrac for sisehtnysotohp that affords niapSa (see .giF 1). oT the tseb of ruo ,egdelwonk siht si the regral ssamoib naht ni the gnidnopserroc lartuen cihportue tsrif yduts denrecnoc htiw a deliated evitatilauq dna -nauq sekal GNILLAT( et ,.la 1973). ,eromrehtruF the hgih pH -ne evitatit sisylana of the yratnemides sdipil of na enilakla -al secnah the ytilibulos of suorohpsohp hcihw osla stluser n einirtsuc .tnemnorivne Data are dessucsid ni smret of -erp rehgih ytivitcudorp (TALLING dna ,GNILLAT 1965). tnanimod tupni secruos dna ylrae citenegaid processes. 2555 2556 .J 0. tlamirG te .la - ANAROD LANOITAN KRAP -‘- SEEVEL N .GIF 1. paM fo atnaS Olalla noogaL dna gnidnuorrus .aera gnilpmaS setis era detacidni sa ni elbaT .1 SLAIRETAM DNA SDOHTEM hguorht 250 .mp stouqilA fo eht stnemides detaert htiw 0.2 N lCH rof eht lavomer fo etanobrac erew dezylana rof cinagro nobrac gnisu retaW sisylanA a olraC abrE tnemurtsni ledoM 1106. retaW selpmas erew detcelloc ,ylhtnom morf rebotcO 1985 ot -oN rebmev 1987, at eht retnec fo eht .noogal Hp nosirC( Hp )retem dna ytivitcudnoc ISY( )retemivitcudnoc erew derusaem gnirud .gnilpmas dipiL noitcartxE dna noitanoitcarF retaW selpmas rof lacimehc sisylana erew derots at .C°4 ehT gniwollof sdohtem erew :desu ytinilakla ;cirtemulov( NAMRETLOG dna ,OMYLC raluceloM dipil sisylana saw demrofrep yb telhxoS noitcartxe fo 1969), edirolhc ,cirtemulov( SONgA ;noitatipicerp ,AHPA 1980), dezinegomoh stnemides (30 )g htiw 150 Lm fo -enahtemorolhcid etahplus ;cirtemirolac( ,REIDOR 1975), muiclac dna muisengam lonahtem (2:l) rof 36 .h ehT tcartxe saw muucav detaropave ot 2 ;cirtemoxelpmoc( ,AHPA 1980), etartin noitcuder( ot etirtin hguorht Lm dna dezylordyh thginrevo htiw 35 Lm fo 6% .HOeM/HOK ehT a uC-dC ;nmuloc DNALKCIRTS dna ,SNOSRAP 1972), etirtin -roloc( gnidnopserroc lartuen dna cidica snoitcarf erew ylevisseccus derevocer ;cirtemi DNALKCIRTS dna ,SNOSRAP 1972), muinomma -irelssen( htiw enaxeh-n (3 X 30 ,)Lm eht rettal retfa noitacifidica Hp( 2) htiw noitaz retfa ;noitatipicerp ,REIDOR 1975), dna evitcaer elbulos -sohp .qa 6 N .lCH ehT cidica ,snoitcarf ylsuoiverp decuder ot 0.5 ,Lm suorohp ;cirtemirolac( YHPRUM dna ,YELIR 1962). erew deifiretse thginrevo htiw 15 Lm fo 10% .HGeM/JFB ehT -norob citehtnysotohP stnemgip erew denimreted yb noitartlif hguorht lonahtem xelpmoc saw deyortsed htiw 15 Lm fo retaw dna eht yttaf namtahW C/FG ssalg erbif sretlif fo llams retaw semulov i( 100 .)Lm sdica derevocer sa lyhtem sretse yb noitcartxe htiw 3 X 30 Lm fo ehT lanimon erop ezis fo eseht sretlif (1.2 )mp saw etauqeda esuaceb .enaxeh-n ehT lartuen sdipil erew detanoitcarf yb nmuloc -amorhc on citehtnysotohp smsinagro rellams naht 1.2 mp dluoc eb devresbo yhpargot gnisu a nmuloc dellif htiw 8 g fo hcae 5% retaw detavitcaed yb cipocsorcim .sdohtem retfA thginrevo noitcartxe ni dloc )C°4( animula (70-230 ,hsem )kcreM )pot( dna acilis (70-230 ,hsem )kcreM ,lonahtem eht ecnabrosba fo eht degufirtnec stcartxe saw derusaem .)mottob( ehT gniwollof snoitcarf erew :detcelloc (I) 20 Lm fo yllacirtemotohportceps at 665 dna 750 .mn ehT detcerroc ecnabrosba ,enaxeh-n (II) 20 Lm fo 10% enahtemorolhcid ni ,enaxeh-n (III) 40 at 665 mn saw desu ot etaluclac eht yllacitpo tnelaviuqe noitartnecnoc Lm fo 20% enahtemorolhcid ni ,enaxeh-n )VI( 40 Lm fo 25% -n fo u-llyhporolhc yb eht TALLING dna REVIRD (1963) dna -NELLOV enaxeh ni ,enahtemorolhcid )V( 20 Lm fo 5% lonahtem ni -olhcid REDIEW (1969) sdohtem hcihw dnopserroc ot eht tnemerusaem fo ,enahtemor dna )IV( 40 Lm fo 10% lonahtem ni .enahtemorolhcid eht a-llyhporolhc sulp eht .a-edibrohpoeahp noitcarF V dna IV erew dezitavired roirp ot latnemurtsni sisylana selpmaS rof eht yduts fo notknalpotyhp seiceps erew ylraluger dexif yb noitalylis ,edimatecaoroulfirt)lylislyhtemi@sib( 100 ,Lp C°08 htiw lug01 gnirud retaw .noitcelloc seicepS noitacifitnedi dna gnitnuoc 30 .)nim erew dehsilpmocca ni ssel naht 24 h retfa gnilpmas htiw na detrevni lacitpo epocsorcim ,nokiN( )trofaiD gniwollof eht euqinhcet fo -HTU HLOMRE .)8591( nI emos sesac ni aviv ro dexif-lomrof selpmas erew noitazitavireD fo detarutasnU stnenopmoC denimaxe ni noitidda ot eht lug01 .snoitaraperp larutcurtS noitanimreted fo elbuod dnob snoitisop dna eht -eg Sediment gnilpmaS dna kluB sesylanA yrtemo fo detarutasnu selucelom saw demrofrep yb noitazitavired fo stouqila fo detceles dipil ,snoitcarf yleman ,snobracordyh yttaf ,sdica stnemideS erew nekat yb ytivarg gniroc dna derots at .C°02- erofeB dna .slohocla sdohteM rof eht noitamrof fo sedixope dna lyhtemid sisylana yeht erew tuc otni 3 mc ,snoitces ,deird-ezeerf dna deveis edihplusid )SDMD( stcudda erew desu sa .swollof dipiL yrtsimehcoegoib fo na enilakla noogal 2557 noitatitnauQ Formation of epoxides ehT snoitcarf erew devlossid ni enahtemorolhcid (50 )Lr dna noitatitnauQ saw demrofrep morf eht GC .secart nI eht esac fo detaert htiw 05I LP fo cioznebreporolhc-m dica noitulos (0.26 M ni eht niahc-dim detutitsbus ,slohocla-n eht noitubirtnoc fo hcae -isop .)enahtemorolhcid ehT noitcaer saw deitc tuo ni a 2 Lm laiv desolc lanoit remosi ot eht GC kaep fo eht gnidnopserroc golomoh saw htiw a denil-nolfeT .pac ehT erutxim saw derrits ni na cinosartlu denimreted yb ssam yhpargotnemgarf gnisu cificeps .snoi htab rof 10 nim dna dewolla ot tcaer thginrevo ni eht dark. ehT nA lanretxe dradnats gniniatnoc ,enacedartet-n ,enasocod-n -odn gnitluser noitulos saw detartnecnoc rednu a maerts fo negortin dna ,enatnocairt dna enatnocairtaxeh-n saw yllareneg .desu A dradnats dettimbus ot latnemurtsni .sisylana fo 5a(H)- dna eno-3-natselohc-)H(@S saw desu rof eht .senonats -lA slohoc dna slorets erew detatitnauq gnisu a dradnats fo ,lonasocodn ,183-natselohc-)H(@S ,10-3j3-natselohc-)H(aS dna -tselohclyhte-42 Formation of DMDS adducts .10-83-ne-5 ehT snoitartnecnoc fo yttaf sdica erew denimreted yb ehT snoitcarf ( l-300 )gm erew devlossid ni nobrac edihplusid ( 1 nosirapmoc htiw a dradnats fo cionacedatpeh-n dna cionasocieneh-n )Lm dna detaert htiw I Lm fo SDMD dna 100 LP fo enidoi noitulos lyhtem .sretse selpmaS dna sdradnats erew yldetaeper detcejni litnu (58 gm fo I2 ni 1 Lm fo lyhteid .)rehte ehT noitcaer saw deirrac tuo ssel naht 5% noisrepsid saw devresbo ni eht derusaem .saera ni 5 Lm sebut desolc htiw a denil-nolfeT pac dna tpek at C°06 rof 24 .h retfA ,noitcaer 2 Lm fo enaxeh-n erew added dna the excess of enidoi saw detanimile htiw 90zSzaN noitulos (5% ni dellitsid .)retaw STLUSER DNA NOISSUCSID ehT erutxim saw ylsuorogiv nekahs litnu .noitaroloced ehT cinagro atnaS allalO noogaL sgnoleb ot the dnop metsys detacol reyal saw devomer htiw a ruetsaP ettepip dna eht suoeuqa esahp saw detcartxe rehtruf htiw enaxeh-n (2 X 1 .)Lm ehT eerht cinagro raen the senud of the W-E eniltsaoc of the riviuqladauG stcartxe erew denibmoc dna detartnecnoc ot 100 Lp rednu a maerts atleD .giF( 1). sihT noogal si of enecoloH nigiro SODANARG( fo .negortin et ,.la 1988), dna sti cigolordyh emiger sdneped no tcerid ,llafniar ,ffo-nur dna water elbat .snoitallicso ehT egareva latnemurtsnI sisylanA water level segnahc morf 1.9 m )gnirps( ot 0.2 m .)llaf( sihT saG yhpargotamorhc (CC) saw demrofrep htiw a olraC abrE VTF wollahs water nmuloc denibmoc htiw dniw noitca stneverp 4 160 CC tnemurtsni deppiuqe htiw a emalf noitazinoi rotceted dna ytisned noitacifitarts dna secnahne tnemides .noisnepsuser a sseltilps .rotcejni A 25 m X 0.25 mm .d.i nmuloc detaoc htiw -PC Repeated negyxo snoitanimreted evah nwohs that tsom of Si18 BC )kcapmorhC( saw desu mlif( ssenkciht 0.13 .)mp negordyH the water nmuloc si ,cixo htiw a tnenamrep cixona water saw eht reirrac sag (50 .)‘-semc ehT nevo erutarepmet saw -orp demmarg morf 60 ot 300°C at .‘-nim*C”6 rotcejnI dna rotceted reyal of 5-4 mc detautis evoba the gniylrednu .tnemides serutarepmet ,erew ,ylevitcepser 300 dna 330°C. ehT noitcejni saw ehT nigiro of atnaS allalO waters si .latnenitnoc citamilC ni eht sseltilps edom ,tnevlos( ,enatco-osi toh eldeen )euqinhcet peek dna cihpargopot factors etomorp the tropsnart of elbulos stlas gni eht tilps evlav desolc rof 35 .s dna stneirtun morf the gnidnuorrus lios otni the noogal where CC delpuoc ot ssam yrtemortccps )SM-CC( saw demrofrep htiw yeht emoceb .detartnecnoc ehT wol muiclac dna muisengam a drakcaP-ttelweH 5995 tnemurtsni deppiuqe htiw na PH 300 data .metsys A nmuloc fo 25 m X 0.2 mm .di detaoc htiw 5-PH -ttelweH( ni the area sdael ot a tfihs towards etanobrac noitalumucca )drakcaP saw desu mlif( ssenkciht 0.11 .)mp muileH saw used sa ni the water ,nmuloc gnivlovni na esaercni of devlossid -ni reirrac .sag ehT nevo erutarepmet saw demmargorp morf 60 ot 300°C cinagro nobrac dna pH. ehT llarevo process stluser ni a -em at .‘-nim*C”4 noitcejnI snoitidnoc (300°C) erew eht emas sa -ed enilahos cihportuerepyh enilakla noogal ,STLBK( 1988) erehw debircs .evoba SM serutarepmet :erew refsnart enil 3OO”C, noi ecruos 200°C dna rezylana 230°C. Data erew deriuqca ni eht nortcele tcapmi eht hgih pH seulav egareva( 9.3, sd 0.74) are detaler ot -ohp edom (70 ,)Ve gninnacs neewteb 50-650 at I s rep .edaced citehtnysot noitcudorp (see .giF 2). tolllluHC ,,qem - I C-l/qcmAWWATE lLAluA flATM 1)1@. IA I,!Knr -- CAWOkW meq,, - CALCIW meq/l - MAOS3lOM mew I .GIF 2. niaM devlossid ,snoi ,Hp ,ytivitcudorp dna rojam notknalpotyhp spuorg ni eht sretaw fo atnaS Olalla .noogaL 2558 J. 0. tlamirG et .la sA ni other enilakla ~ihportuer~yh sekal GNILLAT( et ,.la elbaT .1 kluB sretemarap fo eht cinagro rettam ;3791 IMHOFF et ,.la 1979), esned snoitalupop of -cabonayc morf atnaS allalO .selpmas airet are dnuof ( 1 -60 10’ ,)lm/sllec yllausu gnitneserper 99% I aRETAW aSTNEMIDES 1 of the latot notknalpotyhp ssamoib (see .giF 2). Spirufina platensis setutitsnoc the tnanimod ;seiceps at pH > 10 siht msinagro si dnuof as na tsomla erup .erutluc a~il~ip~ spp. are osla the tnanimoderp sezisehtnysotohp ni ynam other enilakla sekal TNARG( dna ,GNOL 1985). Other airetcabonayc I detarutas 501 076 0041 0041 1486 deifitnedi ni the atnaS allalO noogaL edulcni Anabaenopsis detarutasnu 001 023 046 017 053 slohoclA 51 031 072 033 002 circularis, A. tanganyikae, Aphanothece clathrata, Coelos- cilcyca 01 26 031 002 021 phaerium kuetzingianum, dna Microcystis aeruginosa. tsoM sterols 8.4 66 041 431 57 of these seiceps evah osla neeb deifitnedi ni other enilakla snobracordyH 81 65 08 85 76 detarutas 11 03 44 33 45 sekal ,LLADNIT( 1988). detarutasnu 8.5 42 43 42 31 nI cidosipe cases, gnorts llafniar yam esuac na tnatropmi citamora 08.0 09.0 6.0 84.0 tlas ,noitulid gnitluser ni a decrease of cinotknalp ytivitcudorp senapretirtyxohteM 8.2 9.4 0.5 1.3 dna pH seulav (see the doirep neewteb yraunaJ 1986 dna senoteK 84.0 44.0 08.0 36.0 94.0 senehpoihT 24.0 06.0 55.0 ,60.0 lirpA 1986 ni .giF 2). nI these cases, other ,srezisehtnysotohp ,atyhporolhc or atyhponelgue (Trachelomon~ spp.) yam )a gnilpmaS setis are detacidni ni .giF .1 ,A B dna grow ni noitidda ot the tnanimo~p .a~e~abonayc No -bus ,lC ecafrus ;stnemides ,2C 61-41 cm core ;noitces desrem setyhporcam are dnuof ni atnaS allalO ,stnemides ,WC retaw .setalucitrap )b detaluclaC morf latot CG devloser skaep hguohtla emos suotnemalif eagla (Cladophora sp., Oedogon- ium sp., dna Spirogyra varians) evah yllacidarops neeb -bo devres ni noitcennoc htiw these noitulid sedosipe AJOT( et dica serutxim ssapmocne htob the free dna deifiretse -moc ,.la 1991). .stnenop yehT are detanimod yb BIC-& cionakla-n dna cionekla-n sdica htiw neve revo odd nobrac rebmun -referp cinagrO kluB noitisopmoC of stnemideS .secne yttaF sdica morf airetcabonayc yllausu niatnoc -atco dna retaW setalucitraP cioneidaced ro/dna cioneirtacedatco ”,‘,6A( or )s‘,2‘,pA sdica ehT egareva ygolohtil of atnaS allalO stnemides -erroc ni a noitroporp pu ot 40% %52-02-m( ni .S platensis; RE- ZANKA et ,.la 1983). nI atnaS allalO stnemides on traces of sdnops ot kcalb dnas (74%), tlis (22%), dna a wol noitroporp detarutasnuirt cionecedatco sdica evah neeb ,dnuof dna ylno of yalc (4%), the renif slairetam gnieb erom tnadnuba at the llams stnuoma of cioneid~~ sdica evah neeb dezingocer lartnec part of the noogal where stnemides emoceb -ydnas ;%7.0-( see elbaT 2). ,revewoH htob water setalucitrap dna .ytlis ehT latot cinagro nobrac )COT( segnar neewteb 3.5 dna stnemides tibihxe a hgih noitroporp of cionecedaxeh dna -co 9%, gniwohs a lacihpargoeg noitubirtsid that slellarap the cionecedat .sdica ,suhT the 0:61/1:61 dna :81 0:61/l soitar ezis-niarg ,ygolohtil e.g., mumixam seulav towards the .retnec are ni the order of 2.l-l ni the stnemides dna 5.0- ni the esehT hgih COT ,stnetnoc dna yltneuqesnoc hgih noitroporp etalucitrap ,rettam whereas ni airetcabonayc yeht yllareneg of yratnemides dipil ,lairetam are osla tnetsisnoc htiw the hgih rate of citeht~sotohp noitcudorp of the gniylrevo waters. egnar neewteb 0.2 dna 0.3 ni( .S ~~ate~sis, 3.0-2.0 dna -f.O 0.2 for :61 1 f O&l dna :81 l/l ,0:6 .)ylevitcepser snoitairaV ni enO water etalucitrap elpmas dna ruof tnemides core -ces tneirtun ylppus do ton yltnacifingis retla the detarutasnu yttaf ,snoit three gnidnopserroc ot ecafrus slevel setis( ,A ,B ;C .giF dica noitisopmoc of airetcabonayc KCERROIP( dna POHL, 1) dna eno ot a depth of -41 16 mc etis( C), evah neeb detceles ;4891 KCERROIP et ,.la 19841, so that the secnereffid neewteb for dipil sisylana elbaT( 1). ehT tsom evitcnitsid erutaef of atnaS allalO selpmas dna the demuserp lairetcabonayc -erp these selpmas si the hgih egatnecrep of free dna deifiretse STOSTUC tsum tcelfer other secruos or processes. yttaf ,sdica gnitneserper tuoba %68-97 of the latot sdipil ehT yttaf dica noitisopmoc of ynam eagla sniatnoc egral elbanema ot CG .sisylana eerF dna deifiretse ,slohocla the stnuoma of cione-)Z(9-cedaxeh-n dna cione-)Z(9-cedatco-n dnoces noitcarf ni smret of ,ecnadnuba tneserper ,%71-6 sdica SACEUHC( dna ,YELIR 1969). ,revewoH ni the atnaS elihw the snobracordyh tnuoma ot ylno .%7-2 nI ,elpicnirp allalO ,noogaL the detarutasnu cionecedatco sdica are -erp the hgih noitroporp of yratnemides yttaf ,sdica ,.e.i( yttaf detanimod yb 1-cedatco-n cione-)Z(l ,dica na remosi -rahc lorets:dica oitar of :OI 1) stseggus a good noitavreserp of the citsiretca of ynam evit~en-nru airetcabue REVILO( dna lanigiro cinegoib stupni DAEHR( et ,.la 1977). ,eromrehtruF ,LLEWLOC 1973). sihT dnuopmoc si dezisehtnys yb ,C -nole the hgih noitartnecnoc of these yttaf sdica si tnetsisnoc htiw noitag of shorter niahc detarutasnuonom sdica -REUEHCS( the hgih ytivitcudorp of the noogal SENRAB( dna ,SENRAB 1978). TDNARB dna BLOCH, ;2691 DOOW et ,.la 1965). ,suhT the hgih tnetnoc of cione-)Z(9-cedaxeh-n dica ni these selpmas cilcycA dionerposI-noN sdnuopmoC si ylekil detaicossa htiw the laiborcim noitcudorp of -cedatco-n 1 cione-)Z(l .dica cione-)Z(9-cedatcO-n dica yam eb a edis Fatty acids tcudorp of siht citehtnys yawhtap TDN~BREUEH~( dna evitatneserpeR smargotamorhc of the yttaf dica -opmoc BLOCH, 1962). ,revewoH airetcab yam osla ecudorp siht noitis of stnemides dna water setalucitrap morf the atnaS dnuopmoc dna other 9A detarutasnuonom yttaf sdica yb -ed allalO noogaL are deyalpsid ni .giF 3. Peak snoitacifitnedi noitarutas of the gnidnopserroc cionakla-n sdica OCLUF( et dna noitartnecnoc segnar are nevig ni elbaT 2. esehT yttaf ,.la 1964). sediseB the tnanimoderp cis elbuod dnob ,yrtemoeg dipiL yrtsimehcoegoib fo na enilakla noogal 2559 0 A 0 B _jJjJ 2 , .GIF 3. evitatneserpeR smargotamorhc fo eht yttaf dica snoitcarf fo atnaS Olalla retaw setalucitrap )A( dna stnemides .)B( kaeP snoitacifitnedi era ni elbaT 2. eht ecnerrucco fo llams stnuoma fo tram cionekla-n sdica osla tneserper a ecruos fo tram detarutasnuonom yttaf sdica yam tcelfer snoitubirtnoc morf rehtie ciborea marg evitagen (EYSSEN dna ,TSLUHREV 1984). ,yllaniF the ecneserp of airetcabue NALLIG( et ,.la 1983) or enahtem or lonahtem -cedaxeh-n cione-ol dica yam eb evitacidni of snoitubirtnoc gnizilitu airetcab ,ALUKAM( ;8791 NALLIG dna ,MORTSDNAS morf Mycobacteria TDNARBREUEHCS( dna BLOCH, ;2691 1985). laiborciM noitanegordyh of detarutasnuylop sdica nac GNUH dna ,REKLAW 1970). 5 6 3 1 3 4 4 6 3 8 3 - 7 C2 !58 90 12 30 18 1s 60 XJ 20 4.5 3.5 3.5 2.4 1-s 0.2 3.4 0.9 0.5 0.04 Cl 14 16 120 9 190 15 7 5 90 7 3 7.5 8 6 45 1 8 35 7 6 90 9 55 3.5 30 2 10 4 1.3 _- 10 0.25 ue/o B 16 14 8 12 6 4 85 6 2 7 8 5 42 7 30 8 96 10 50 3 35 9 _- 13 100 180 0.9 8.5 1.1 3.5 1.1 0.2 4 4 3 3 5 2 7 2 _ 6 A 50 80 10 36 20 12 46 26 18 6.6 7.4 2.8 1.2 3.2 1.6 0.4 3.2 3.6 3.6 0.8 0.4 0.02 SAMPLES= _ CW 18 16 12 0.3 0.2 7.0 1.1 7.5 0.7 6.5 0.8 0.7 0.8 4.0 2.5 5.5 0.6 3.5 3.5 2.5 2.4 4.8 2.8 0.3 4.6 Wl acid .~~..___. IXXIIIJ . acid acid acid derivatives. acid acid acid acid acid acid acid acid acid acid ester acid acid acid acid acid acid acid acid acid acid acid acid acid acid acid Lagoon. acid ll(B)-enoic acid methyl as CONPOUNDS Olalla n-octadecadienoic ;hytanoic n-octadec-9(Z)-enoic kctadec-9(E)-enoic kctadec-ll(Z)-enoic kctadec koctadec-12-enoic kctadec-13-enoic &octadacanoic fkmethyloctadecanoic lO-m&hyloctadecenoic phytenoic c-nonadecanoic n_cos-ll-enoic n_cosanoic 2-methylco~anoic g-heneicosanoic n_docosanoic 2,6,10.14,18-pentamethylnonadecanoic n-tricoeanoic n-tetraco6anoic z-pentacoeanoic phExECO66IIOiC n-heptaco6anoic n-octaco6anoic E-nonaco6anoic &triacontanoic n_dotriacontanoic %7o(H),21g(H)-bi6homohopanOiC 176(H).216(H)-homohopanoic 176(HJ,21~(HJ-bi6homohopMOic 32. 33. 34. 35. 36. 37. 38. 39. 40. 41. 42. 43. 44. 46. 46. 47. 48. 49. 50. 51. 52. 53. 54. 55. 58. 57. 58. 59. 60. 61. 162. Santa C2 12 4 16 49 4 60 55 23 25 10 13 10 12 8 6 IS 8 9 10 12 analyzed 3.5 4.5 3.6 0.6 2.5 120 140 2.2 1.6 7.5 6.5 8 9 9 4 the Cl 25 10 25 90 42 33 23 24 16 28 17 17 16 25 27 28 20 28 28 7.5 100 110 0.8 3.3 220 320 3.7 acids in UP/P 9 9 8 B 26 30 38 30 27 20 18 30 15 15 17 30 25 26 15 28 30 7.5 8.5 110 102 3.4 200 300 3.6 3.9 92.5 0.85 A 4 10 4 3.6 3.4 14 44 3.8 64 SO 0.4 1.4 18 14 12 100 10 8 20 10 150 1.6 1.8 7 8 14 10 11 6 13 14 fatty SAMPLESa R ESR)IHENTS CW 14 10 33 1 b) 0.6 2.1 0.5 0.1 0.9 2.7 0.7 5.6 4.5 0.1 0.6 7.0 2.0 0.5 1.1 3.2 2.3 0.9 1.5 1.8 1.1 0.6 3.8 0.2 WAT w/l identified 1. (I) (I) Table lactones acid in acid as and acid acid acid acid acid acid acid acid acid acid acid acid acid acid acid acid acid acid acid acids acidb acid acid acid acid acid acid acid description Fatty 2. COUPOUND iso-dodecanoic ccdecanoic iso-tridecanoic zeiso-tridecanoic n_tridecanoic iso-tetradecanoic zatradecanoic a.8,12-trimethyltridecanoic iso-pentadecanoic zeiso-pentadecanoic c-pentadec4-enoic c-pentadec-9-enoic s-pentadecanoic 5.9.13-trimethyltetradecanoic &-hexadecanoic g-hexadec-9(Z)-enoic n-hexadec-9(E)-enoic n-hexadec-lo-enoic n_hexadec-ll(Z)-enoic g-hexadec-11(E)-cnoic n-hexadecanoic 2-methylhaxadecanoic &-heptadec-9anoic 3.7.11,15-tetramethyl-17-haxndecanolide . lO-methylhexadecanoic . iso-heptadecanoic zeiso-heptadecanoic fi-heptadec-9(Z)-enoic n_heptadec-ll(Z)-enoic g-heptadecanoic ~,7,II,I5-tetramethyl-17-hcxadecanolide sample Table * I. 2. 3. 4. 5. 6. 7. 8. 9. 0. 1. 2. 3. 4. 5. 6. 7. 8. 9. 3. 1. 2. 3. a55. 7. 3. 3. 3. 1. ) dipiL yrtsimehcoegoib fo na enilakla noogal 2561 m NOTGNIRRAF( dna ,NNIUQ 1973). ehT ecneserp of rehgih tnalp sdipil si a lareneg erutaef of enirtsucal stnemides morf etarepmet snoiger hcihw si devresbo evitcepserri of the -ed lanoitisop .snoitidnoc Hydrocarbons evitatneserpeR smargotamorhc of the snobracordyh -serp tne ni the tnemides dna water etalucitrap extracts are -sid deyalp ni .sgiF 4 dna 5. Peak snoitacifitnedi dna noitartnecnoc segnar are nevig ni selbaT 3 dna 4. enacedatpeH-n si the tnanimod nobracordyh ni htob -des n ) tnemi dna water ,setalucitrap a dnuopmoc that yllausu -per stneser lagla snoitubirtnoc KRALC( dna ,REMULB 1967; NAH et ,.la 1968). rehtonA tnatropmi tnenopmoc ni the stnemides si ,enacedatco-n the tsom tnadnuba nobracordyh ni ynam 1 tsaey dna lairetcab seiceps NAH( dna ,NIVLAC ;9691 DRIB dna LYNCH, ;4791 NAH et ,.la 1968). sediseB these two lo.2 I9 ,senakla-n a rebmun of snobracordyh are osla evitacidni of suonohthcotua .stupni ,suhT the raenil dna dehcnarb -,,C 1 Czo detarutasnuonom snifelo are nommoc ni eagla dna -yc airetcabona NAH( dna ,NIVLAC ;9691 IPLEG et ,.la 1968) dna 1 F2 : - - 3 .GIF 4. evitatneserpeR smargotamorhc fo eht lF nobracordyh snoitcarf fo atnaS Olalla retaw setalucitrap )A( dna stnemides .)B( kaeP snoitacifitnedi era ni elbaT 3. ehT tnanimoderp lairetcab nigiro of atnaS allalO yttaf dica snoitubirtsid si osla detcelfer ni the hgih noitroporp of iso- dna cionacedatnep-osietna sdica dna rehto dehcnarb -oh ,seugolom yleman iso- dna cionacedirt-osietna ,sdica dna iso- ,cionacedod ,cionacedartet dna cionacedaxeh ,sdica that are ylnommoc dnuof ni evitisop-marg airetcabue (CHO dna -LAS ,NOT ;6691 ,ADENAK 1967). Other dehcnarb-lyhtem yttaf -ca sdi deifitnedi ni siht noogal are osla citsiretcarahc of laiborcim 25 ,secruos yleman 1 lyhtem-O cionacedaxeh dna cionacedatco sdica :ignuf( OILLAB dna ,ANOLLECRAB 197 ;1 AILGINREC dna F3 ,YRREP ;4791 dna Mycobacteria: KALUJ et ,.la 1980), dna lyhtem-2 detutitsbus cionakla sdica (Mycobacteria: KALUJ te ,.la 1980). ehT hgih noitroporp fo iso- dna -atnep-osietna cionaced sdica dna I-cedatco-n cione-)Z(l dica edivorp na tnedive laiborcim ,erutangis ylralucitrap llew denifed ni the stnemides .giF( 3). ,revewoH the etalucitrap yttaf sdica are osla far resolc ot the noitisopmoc reported for enirtsucal -im laiborc serutxim ADUSTAM( dna ,AMAYOK 1977) naht ot the evoba detacidni lairetcabonayc yttaf dica .snoitubirtsid A elbaredisnoc degree of laiborcim gnikrower has ylsuoivbo -co derruc ni the water .nmuloc 146 rehtonA puorg of niahc-thgiarts yttaf sdica tneserp ni atnaS =#%I'46 allalO stnemides dna water setalucitrap stsisnoc of a -irtsid noitub of neve nobrac derebmun &+,,C detarutas .sgolomoh esehT are stneutitsnoc of ralucituc waxes of rehgih stnalp .GIF 5. evitatneserpeR smargotamorhc of the nobracordyh -carf ,YDUKUTTALOK( 1970), dna rieht ecnerrucco ni citauqa -ne snoit 2F dna 3F of atnaS allalO .stnemides Peak snoitacifitnedi are stnemnoriv si yllausu detaicossa htiw lairtserret snoitubirtnoc ni elbaT 4. 2562 J. 0. Grimalt et .la elbaT 3. snobracordyH deifitnedi ni noitcarf lF of atnaS allalO elpmas extracts. COMPOUND SAUPLESa CONPWND SANPLE? ow l/w uo/l no/P CU A B 'Cl c2 CW A B Cl Ci 83. D-tetradacane 0.8 12 37 50 10 .49 ptricoaane 10 1900 2800 1900 3OOC 64. kpantadccane 1.2 100 180 300 120 95. D-tetracos-l-one 0.7 70 180 200 15c 65. &hexadecane 2.3 300 400 850 350 96. ii-tetracoaane 3.2 360 690 700 800 66. keptadec-3(Z)-ena 20 30 40 15 97. &pentacos-l-eneb 9.5 3000 4700 1850 1000 67. g-heptadec-J(E)-ene 7 10 10 5 98. E-pentacoeane 9.2 1500 2900 1750 3000 68. br_heptadec-l-ene 5 7 10 4 99. n_hexacos-l-ens 0.9 100 230 300 100 69. +eptadcc-1-ene 5 7 12 4 1W. J+exacoeana 3.2 400 760 700 Boo 70. n_heptadecane 15 MOO 7900 6000 8500 101. n_heptacos-lane 6.5 15W 3700 1000 700 71. 7-eethylheptadecane 50 60 100 40 102. n_heptacoaane 8.7 2000 3700 1800 3200 72. 6-eethylheptadacane 57 80 80 50 103. cholesta-3,5-dieneb(XVIIal 560 1200 750 600 73. 2-eethylheptadecane 220 240 270 200 104. methylbranched hydrocarbon 320 800 760 150 74. 3-eethylhe tadecane 260 300 240 200 105. methylbranched hydrocarbon 50 120 100 60 75. phyt-14ne g 110 170 160 100 106. en41-eocatoo_n 2.4 100 270 250 150 76. E-octadecane 2.7 700 1200 1500 1600 107. n_octacosane 2.0 440 920 900 4060 77. phytane 1.3 200 290 400 300 108. cholest-2-ena (XVIal 0.8 560 1100 800 600 78. phyt-2(201-e& 200 340 320 120 109. 22,29,30-trienorhop-17(2l)-ene (XXIIIal 0.7 360 500 450 200 79. phyt-24ne 100 160 140 60 110. g-nonacoa-14ne 5.2 500 920 400 600 80. phytadiene 100 170 150 80 111. ;-nonacoeane 8.9 2600 5300 2000 6000 81. n-nonadec-3(Z)-ene 10 15 14 7 112. Zd-ethylcholesta-N,22-dieneb(XVIIIc) 440 610 550 700 82. n_nonadec-J(E)-ene 7 10 12 5 113. c-triacont-l-one 2.2 loo 190 150 130 83. n_nonadec-l-ene 0.6 25 50 45 20 114. +riacontane 1 .l 360 1200 1000 400 64. n_nonadecane 2.6 380 550 700 606 115. 24athylcholest-2-ene (XVIc) 240 260 280 300 85. l+aethylnonadecane 88 160 140 90 116. c-hentriacont-I-ene 4.0 200 300 400 350 86. n_cos-1-ene 0.1 23 62 50 40 117. fi-hentriacontana 9.5 4000 77w 3300 7500 87. n_COSanC 2.0 70 150 300 250 118. J+otriacontane 1.8 360 740 550 4OD 88. 2-methylcoaanc 5 10 12 10 119. 178(Hl.218(H1-hopane (XXVI) 0.4 440 900 750 600 89. 2,6.1O.14-tetramethyl-7-~3-cnethylpent-O_cnl~-pentadec-2-anab 7.8 800 1300 1200 1500 90. n-heneicosene 4.2 320 700 1200 1400 120. diploptene (XXV) 0.8 5800 8500 7500 4000 91. pdocos-l-em 0.8 31 89 200 100 121. n-tritriacontane 8.7 2000 3000 3300 8000 . 92. n_docoaane 2.8 140 310 4W 400 122. ptetratriacontane 1.8 150 250 230 180 1 93. n-tricos-14neo 9.5 lb00 2300 1700 1000 123. n-pentatriacontane 2.2 400 700 570 9001 a) elpmas noitpircsed as ni elbaT 1. )b dnuopmoc tneserp ni snoitcarf lF dna .2F c) evitatnet .noitacifitnedi the senacedatpehlyhtem are cificeps lairetcabonayc srotacidni of the snoitubirtsid of senekla-n dnuof ni enirtsucal -norivne ,.la ;8691 et ,.la 1970). .stnem (HAN et GELPI A tnacifingis noitroporp of the snobracordyh tneserp ni ehT ,3C&C senekla-n tneserp ni the atnaS allalO noogaL atnaS allalO stnemides dna water setalucitrap si detaler ot are tnerrucnoc htiw other suonegirret stnenopmoc hcus as the gnidnuorrus .noitategev ehT suonohthcolla sdnuopmoc the &&C ,senakla-n 23C&C cionakla-n ,sdica dna -ylop tneserp ni rehgih noitartnecnoc etutitsnoc a noitubirtsid of cilcyc rehgih tnalp srekram that lliw eb dessucsid .retal -eroM &+2C ,senakla-n htiw a mumixam at 33C-,3C dna na odd ,revo these senakla-n tibihxe a noitubirtsid that si yrev esolc nobrac rebmun .ecnereferp esehT snoitubirtsid are evitacidni ot enekla-n serutxim dnuof ni other enirtsucal stnemnorivne of snoitubirtnoc morf rehgih stnalp NOTNILGE( dna -MAH detanimod yb snoitubirtnoc morf lairtserret noitategev (AL- ,NOTLI 1967). yltnerrucnoC htiw these detarutas -racordyh et ,.la .)b4891 riehT nigiro si therefore ylekil detaler BAIGBS ,snob there si osla a noitubirtsid of ,3C-3ZC odd nobrac -mun ot suonegirret .secruos ehT ecneserp of these sdnuopmoc htob dereb senekla-n htiw a mumixam at .5ZC lyhtemiD edihplusid ni the water nmuloc setalucitrap dna stnemides si tnetsisnoc noitazitavired showed that the noitarutasnu si detacol at the htiw the gnorts ytiralimis ni the dipil noitisopmoc of these lanimret noitisop ni lla sgolomoh ALEURY( et ,.la 1990). two sepyt of selpmas dna stcelfer na tnatropmi degree of -des esehT -kla-n 1 ene- snoitubirtsid evah osla neeb devresbo ni tnemi .noisnepsuser other enirtsucal stnemnorivne et ,.la ;0891 (GIGER CARDOSO et ,.la ;3891 et ,.la ,b4891 et ,.la 1987). ALBAIG~S CRANWELL Ketones ,2C-,2C odd derebmun senekla-n evah neeb deifitnedi ni eno ,muiretcabonayc Anacystis montana et ,.la 1970) ehT ,srehte-yxohtem ,senotek dna slohocla were detcelloc (GELPI ,hcihw ni the ecnesba of elbavresbo rehgih tnalp ,secruos has ni snoitcarf ,VI V, dna .IV evitatneserpeR smargotamorhc del ot na noitpmussa of lairetcabonayc nigiro for the -rucco of these nmuloc yhpargotamorhc snoitcarf are deyalpsid ni ecner of &&iC snifelo ni citcratnA slios et .sgiF 6 dna 7. Peak snoitacifitnedi dna noitartnecnoc segnar (MATSUMOTO ,.la 1990). ,revewoH hgih stnuoma of thgiarts niahc senekla-n are nevig ni selbaT 5 dna 6. evah neeb reported ni stnalp hcus as ragus enac (SORM et ,.la ehT enonakla serutxim of atnaS allalO stnemides are 1964), roses et ,.la 1983), dna snref et desopmoc of enoZ-nacedatpeh-n dna na ladominu -irtsid (MLADENOVA (LYTLE ,.la 1976). ehT citehtnysoib msinahcem sevlovni yttaf dica noitub of 33&2C seno-2-nakla-n htiw na odd revo neve -rac noitalyxobraced dna 1989) hcihw si -noc nob rebmun ecnereferp gnizimixam at the 5ZC or 7ZC -oh (GORGEN BOLAND, tnetsis htiw the odd ot neve nobrac rebmun ecnanimoderp sgolom (see .giF SF-6 dna elbaT 5). ehT ytiralimis of these dipiL yrtsimehcoegoib of na enilakla noogal 2563 elbaT 4. snobracordyH deifitnedi ni snoitcarf 2F dna 3F of atnaS allalO elpmas extracts. DNUOPMOC SAMPLES ug/l n&P Cy A B Cl C2 ‘124. 3-methenyl-7.11,15-trimethylhexadcc-l-ene 30 70 60 27J 125. ncthylcyclohexenyltridacan; 50 120 80 so 126. enacedirtlynexeholcyc 22 s5 04 52 127. anerhtnanehponetnepolcyc&,7-lyporpo6ilyhtem-1 02 05 06 03 126. 2,6,10,14-tetramethyl-7-~3-methylp~ntyl~pentadecatrienc 10 30 35 10 129. 3-methyl-2-(3.7,11-trimethyldodecyl)thiophene (IV) 200 370 350 50 130. 3-(4,8.12-trimethyltridecyl)thiophene (V) 160 220 200 10 131. 2,6,10.15,19,23-hexamethyltctracoaa-G~E~,lO(E~,14~E~,16~E)-tctraene 240 360 340 100 132. cholesta-N.22-diene (XVIIIa) 50 90 100 50 133. tetrahydrosqualene 50 90 100 40 134. tetrahydrosqualenc 001 002 061 120 135. 24-ethylcholestatriens 002 024 004 160 136. 24_methylcholesta-5,24(26) eneid- )XIX( 52 06 07 30 137. 24-methylcholestatetraene 52 06 07 35 136. 24-ethylcholesta-3,5-diene )CIIVX( 03 07 07 25 .931 24-ethylcholestatriene 022 003 062 200 140. fern-7-ene (XMIIa) 06 061 041 90 141. hop-17(21)-ene (Xxv) 01 51 31 10 142. 24-ethylcholestatriene 7 02 22 9 143. enepoh 065 006 057 005 144. OOC cilcyconom dionerposi 09 002 061 06 145. etillenomisron-71 (xXx111) 04 07 09 05 146. enesyrhclyhtemirt 011 002 061 001 147. enesyrhcordyhatco-a21,21,11,a4,4.3,2,1-lyhtemartet-a21,7,4.3 (XXXIVa) 20 50 45 25 146. 3.3.7.12a-tetramethyl-l,2.3.4,4a.11,12,12a-octahydrochrysene (XXXIVb) 40 110 100 45 149. 3,3,7-trimethyl-1,2,3.4-tetrahydrochrysene (XXXV) 70 150 140 90 .051 2,6,10,15,19.23-hexamethyltetracosa-2~E~,6~E~.10~E~,14~E~,16~E~-pentaene 70 150 140 80 .151 dihydrosqualene isomer 80 170 160 90 152. squalsne (II) 0.46 2000 3750 3600 2100 153. 2.5,7,6-tetra . methyl-2-~4,6,l2-trimethyltridecyl~chroman (VII) 30 60 50 35 .45.u O4C _QuuiQw 04 41 a) elpmas noitpircsed as ni elbaT 1. seliforp htiw those of the senakla-n stseggus that these senotek dehcnarb sdnuopmoc ,si ,revewoh devresbo ni the lohocla etanigiro morf the noitadixo ofthese snobracordyh .snoitubirtsid esehT dehcnarb lyhtem slohocla evah neeb -ta (ALBAI& et ,.la 1984a), a process that ylekil srucco ni the water .nmuloc detubirt ot lairetcab stupni (CRANWELL, 1980; ED LEEUW et 1985). yehT evah neeb dnuof ni tnacifingis noitartnecnoc al., Alcohols ni the lohocla noitcarf of esrevid lairetcabonayc stam ED( ehT cilcyca slohocla tsisnoc of xelpmoc serutxim -mocne LEEUW et al., 1985). nI cases where the tam cinagro extracts gnissap ,thgiarts ,dehcnarb dna dionerposi I-nakla s10- dna were ton ,deifinopas yeht evah neeb deifitnedi ni the lohocla s10-2-nakla as llew as niahc-dim slohocla (see .sgiF 6 dna 7, yteiom of the yratnemides wax esters NOSB~D( et ,.la 1988). dna selbaT 5 dna 6). ralimiS ot the yttaf ,sdica the snoitcarf ehT lairetcab erutangis of the lohocla noitcarf yam osla eb deiduts here edulcni htob the free stnenopmoc dna the -se dezingocer yb the ecneserp of s10-2-nakla-n (CRANWELL, deifiret lohocla .seiteiom 1980). These compounds have been identified ni the llec sllaw ehT rojam sessalc tibihxe ladomib snoitubirtsid of neve of airetcab hcus as Escherichia coli (NACCARATO et al., 1972). nobrac rebmun detanimoderp 43C-41C .s10-1-nakla-n ehT In this respect, the simple distribution of n-alkan-2-01s found rewol edom 81C-41C( )egnar sezimixam at ,10-l-nacedaxeh-n in Santa Olalla sediments, encompassing only the C,,, Cl*, the tsom tnadnuba lohocla ni the ,noogal hcihw si yltnerruc and Czo homologs (see Table 6), is in correspondence with detaicossa htiw lagla 1976) or lairetcab Mycobacterium (WEETE, (ALBRO, the wax composition of certain bacteria (i.e., 1976) inputs. The dnoces edom &+C( )egnar selbmeser phlei; ASSELINEAU, 1966). the -nakla-n 10-l snoitubirtsid dnuof ni rehgih tnalp waxes Other contributions are also represented by the secondary (EGLINTON and HAMILTON, 1967). alcohols. This is the case of a complex distribution of Cz3- nI noitidda ot these ,slohocla lareves detarutasnu dna Cj, mid-chain-substituted alcohols with odd carbon number lyhtem dehcnarb seiceps evah neeb .deifitnedi A etinifed -ni ni the .stnemides Each golomoh stibihxe lareves preference noitaterpret of rieht ecnacifingis si tluciffid eud ot the detimil lanoitisop ,sremosi the lartnec dna neve nobrac rebmun of rebmun of seiduts no lohocla snoitisopmoc of .smsinagro the citahpila niahc gnieb the preferred setis for ,noitutitsbus morF a evitatilauq tniop of ,weiv the dehcnarb dna -utasnu ,.e.i 41-C for .slonasocanon esehT sepyt snoitubirtsidfo evah rated 10-l-nakla-n stnenopmoc lellarap the yttaf dica -irtsid neeb deifitnedi ni the tnevlos extracts of lareves rehgih stnalp snoitub debircsed :evoba the emas iso- dna sgolomoh-osietna (NETTING and MACEY, 1971; CHIBNALL et al., 1931), and are ,dnuof dna the rojam slonekla-n are detarutasnu at the their occurrence in lacustrine environments is indicative of emas 9A dna ”A .snoitisop A rehgih noitroporp of lyhtem terrestrial organic matter inputs. 2564 J. .0 tlamirG te .la LLEWNARC( et ,.la 1987). ,revewoH ot date these sloidenakla evah ylno neeb deifitnedi ni dleif snoitalupop of eno fresh/ hsikcarb water ,muiretcabonayc Aphanizomenon jlos aquae (MORRIS dna ,LLESSARB 1988), tub yeht evah ton neeb dnuof ni the gnidnopserroc derutluc seiceps (DE ,WUEEL pers. -moc .).num More noitamrofni si therefore dedeen for a retteb ecruos .tnemngissa ,ylralucitraP erom lairetcabonayc seiceps dluohs eb ,detagitsevni A. jlos aquae si ton dedulcni ni the neetriht seiceps of airetcabonayc deifitnedi ni atnaS .allalO dionerposI sdnuopmoC ylraE sisenegaid of sllyhporolhc sdael ot the noitareneg of egral stnuoma lotyhpfo (JOHNS et ,.la ;6691 xoC et ,.la 1972) hcihw si yltneuqesbus demrofsnart ot other dionerposi -dorp .stcu ehT detaler-lotyhp stnenopmoc dnuof ni atnaS allalO noogaL are dezirammus ni .giF 8. Alcohols ehT snoitartnecnoc fo eerf dna deifiretse 72-( lotyhp Jgp g ni eht ;stnemides 3.1 pg/L ni the water )setalucitrap 51 0 A .GIF 6. evitatneserpeR smargotamorhc fo eht F4 dna F5 lartuen detanegyxo snoitcarf fo atnaS Olalla .stnemides kaeP snoitacifitnedi era ni elbaT 5. ehT suonegirret snoitubirtnoc are therefore detneserper yb a puorg of cilcyca sdipil that si detanimod yb the 23C-02C neve nobrac derebmun yttaf-n sdica 053-071( &g) dna osla sedulcni the snoitubirtsid of &&C odd nobrac derebmun senakla-n (15-40 &g), 43C-,& neve nobrac rebmun -erp detanimod -nakla-n s10-1 04-02( Leg/g), dna ,3C-3ZC -dim detutitsbus-niahc slohocla 9.0-1.0( &g). nI noitidda ot the yradnoces ,slohocla lareves 23C-03C 1,13 0 dna 1,15 sloidenakla evah neeb deifitnedi (see dnuopmoc B Nos. 293, 294, 299, dna 304 ni elbaT 6). sihT erutxim si detanimod yb loid51,1-enatnocairtodn that si dnuof at a ralimis noitartnecnoc as the rojam slorets or emos .slonapoh esehT sloidenakla evah osla neeb reported ni eniram -ides stnem (DE WUEEL et ,.la ;1891 HTIMS et ,.la ;3891 NET NEVAH et ,.la 1987). setallegalfoniD dna sdiropohtiloccoc were -ini yllait detseggus as elbissop srosrucerp HTIMS( et ,.la 1983) tub erom tnecer seiduts evah detniop ot Eustigmatophyceae NAMKLOV( et ,.la 1989) or airetcabonayc SIRROM( dna ,LLESSARB 1988). nI the atnaS allalO ,noogaL on -gitsuE eaecyhpotam eagla evah neeb dnuof ,AJOT( pers. ,).nummoc gnitniop ot the tnadnuba airetcabonayc as the ylekil -rucerp sors. nI rehtona ylhgih evitcudorp ,noogal after a deliated yduts .GIF 7. evitatneserpeR smargotamorhc of the lohocla ,snoitcarf of laitnetop rosrucerp ,smsinagro the ecnerrucco of these ,6F of atnaS allalO water setalucitrap )A( dna stnemides (B). Peak sdnuopmoc has osla neeb detubirtta ot airetcabonayc snoitacifitnedi are ni elbaT 6.
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