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Abstract
A significant number of halogenated low molecular weight metabolites have exhibited an impressive array of biological properties ranging from antimicrobial to insecticidal activities. Studies on the natural products chemistry of the red seaweeds were recently stimulated by the discovery of the acyclic monoterpene halomon, which exhibits selective antitumor activity in the National Cancer Institute’s human tumor and disease oriented in vitro screen.
The present review is a taxonomy based compilation of the available literature on the halogenated volatile metabolites (C1–C10) produced by red seaweeds, with a short description of the reported ecological and pharmaceutical activities. The review begins with a presentation of simple halogenated hydrocarbons and phenols, showing their wide occurrence in rhodophyta, along with a description of simple halogenated lipids in some of the most frequently investigated red algae species and finally focuses on the chemical composition of individual red algae species.
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K Abrahamsson A Ekdahl M Pedersen J Collen (1995)ArticleTitleMarine algae–a source of trichloroethylene and perchloroethyleneLimnol. Oceanogr40IssueID7 1321–1326
PM Abreu JM Galindro (1996)ArticleTitlePolyhalogenated monoterpenes from Plocamium cartilagineum from the Portuguese coastJ. Nat. Prod59 1159–1162
PM Abreu JM Galindro (1998)ArticleTitleA new polyhalogenated epoxymonoterpene from Plocamium cartilagineumIndian J. Chem. Sect. B37 610–611
V Argandona Pozo T Del A San-Martin J Ravirosa (2000)ArticleTitleInsecticidal activity of Plocamium cartilagineum monoterpenesBol. Soc. Chil. Quim45 371–376
JM Baker WT Sturges J Sugier G Sunnenberg AA Lovett CE Reeves PD Nightingale SA Penkett (2001)ArticleTitleEmissions of CH3Br, organochlorines and organoiodines from temperate macroalgaeChemosphere–Global Change Sci3 93–106
KD Barrow CA Temple (1985)ArticleTitleBiosynthesis of halogenated monoterpenes in Plocamium cartilagineumPhytochemistry24 1697–1704
P Bates JW Blunt MP Hartshorn AJ Jones MHG Munro WT Robinson SC Yorke (1979)ArticleTitleHalogenated metabolites of the red alga Plocamium cruciferumAust. J. Chem32 2545–2554
AJ Blackman DJ Matthews (1982)ArticleTitleHalogenated phloroglucinols from Rhabdonia verticillataPhytochemistry21 2141–2142
JW Blunt NJ Bowman MHG Munro MJ Parsons GJ Wright KK Yeow (1985)ArticleTitlePolyhalogenated monoterpenes of the New Zealand marine red alga Plocamium cartilagineumAust. J. Chem38 519–525
JW Blunt MP Hartshorn MHG Munro SC Yorke (1978)ArticleTitleA novel C8 dichlorodienol metabolite of the red alga Plocamium cruciferumTetrahedron Lett19 4417–4418
JW Blunt BR Copp MHG Munro PT Northcote MR Prinsep (2003)ArticleTitleMarine Natural ProductsNat. Prod. Rep20 1–48
MR Brennan KL Erickson (1978)ArticleTitlePolyhalogenated indoles from the marine alga Rhodophyllis membranacea harveyTetrahedron Lett19 1637–1640
BJ Burreson RE Moore P Roller (1975a)ArticleTitleHaloforms in the essential oil of the alga Asparagopsis taxiformis (Rhodophyta)Tetrahedron Lett16 473–476
BJ Burreson RE Moore PP Roller (1976)ArticleTitleVolatile Halogen Compounds in the Alga Asparagopsis taxiformis (Rhodophyta)J. Agric. Food Chem24 856–861
BJ Burreson FX Woolard RE Moore (1975b)ArticleTitleChondrocole A and B Two Halogenated Dimethylhexahydrobenzofurans from the red alga Chondrococcus hornemanni (Mertens) SchmitzTetrahedron Lett26 2155–2158
Burreson BJ, Woolard FX & Moore RE (1975c) Evidence for the biogenesis of halogenated myrcenes from the red alga; Chondrococcus hornemanni. Chem. Lett. 1111–1114.
MA Calvo FJ Cabañes L Abarca (1986)ArticleTitleAntifungal activity of some mediterranean algaeMycopathologia93IssueID1 61–63
RJ Capon LM Engelhardt EL Ghisalberti PR Jefferies VA Patrick AH White (1984)ArticleTitleStructural studies on polyhalogenated monoterpenes from Plocamium species Monocyclo compoundsAust. J. Chem37 537–544
L Castedo ML Garcia E Quinoa R Riguera (1984)ArticleTitleHalogenated monoterpenes from Plocamium coccineum of northwest SpainJ. Nat. Prod47 724–726
JM Chantraine G Combaut J Teste (1973)ArticleTitlePhenols bromes d’une algue rouge, Halopytis incurvus: acides carboxyliquesPhytochemistry12 1793–1796
AM Chevolot-Magueur A Cave P Potier J Teste A Chiaroni C Riche (1976)ArticleTitleComposes bromes de Rytiphlea tinctoria (Rhodophyceae)Phytochemistry15 767–771
JC Coll AD Wright (1989)ArticleTitleTropical Marine Algae VI New Monoterpenes from Several Collections of Chondrococcus hornemannii (Rhodophyta, Gigartinales, Rizophyllidaceae)Aust. J. Chem42 1983–1993
JC Coll AD Wright (1987)ArticleTitleTropical Marine Algae I New Halogenated Monoterpenes from Chondrococcus hornemannii (Rhodophyta, Gigartinales, Rizophyllidaceae)Aust. J. Chem40 1893–1900
JC Coll BW Skelton AH White AD Wright (1988)ArticleTitleTropical marine algae II The structure determination of new halogenated monoterpenes from Plocamium hamatum (Rhodophyta, Gigartinales, Plocamiaceae)Aust. J. Chem41 1743–1753
J Collen A Ekdahl K Abrahamsson M Pedersen (1994)ArticleTitleThe involvement of Hydrogen Peroxide in the production of Volatile Halogenated Compounds by Meristiella GelidiumPhytochemistry36IssueID5 1197–1202
G Combaut Y Bruneau J Teste L Codomier (1978)ArticleTitleComposes halogenes d’ une algue rouge, Falkenbergia rufolanosa tetrasporophyte d’ Asparagopsis armataPhytochemistry17 1661–1663
JS Craigie DE Gruenig (1967)ArticleTitleBromophenols from red algaeScience157 1058–1059
P Crews (1977)ArticleTitleMonoterpene halogenation by the red alga Plocamium oregonumJ. Org. Chem42 2634–2636
P Crews E Kho (1974)ArticleTitleCartilagineal An unusual monoterpene aldehyde from the red marine alga; Plocamium cartilagineumJ. Org. Chem39 3303–3304
P Crews E Kho-Wiseman (1977)ArticleTitleAcyclic polyhalogenated monoterpenes from the red alga Plocamium violaceumJ. Org. Chem42 2812–2815
P Crews L Campbell E Heron (1977)ArticleTitleDifferent chemical types of Plocamium violaceum (Rhodophyta) from the Monterey Bay region; CaliforniaJ. Phycol13 297–301
P Crews E Kho-Wiseman P Montana (1978)ArticleTitleHalogenated Alicyclic Monoterpenes from the red algae PlocamiumJ. Org. Chem43 116–120
P Crews BL Myers S Naylor EL Clason RS Jacobs GB Staal (1984a)ArticleTitleBio–active monoterpenes from red seaweedsPhytochemistry23 1449–1451
P Crews S Naylor FJ Hanke ER Hogue E Kho R Braslau (1984b)ArticleTitleHalogen regiochemistry and substituent stereochemistry determination in marine monoterpenes by13C NMRJ. Org. Chem49 1371–1377
P Crews P Ng E Kho-Wiseman C Pace (1976)ArticleTitleHalogenated monoterpenes of the red alga MicrocladiaPhytochemistry15 1707–1711
M Cueto J Darias (1996)ArticleTitleUncommon tetrahydrofuran monoterpenes from Antarctic Pantoneura plocamioidesTetrahedron52 5899–5906
M Cueto J Darias (1997)ArticleTitleNew acetyl derivatives from Antarctic Delisea fimbriataJ. Nat. Prod60 279–281
M Cueto J Darias J Rovirosa A San Martin (1998b)ArticleTitleUnusual polyoxygenated monoterpenes from the Antarctic alga Pantoneura plocamioidesJ. Nat. Prod61 17–21
M Cueto J Darias J Rovirosa A San-Martin (1998a)ArticleTitleTetrahydropyran monoterpenes from Plocamium cartilagineum and Pantoneura plocamioidesJ. Nat. Prod.61 1466–1468
M Cueto J Darias J Rovirosa A San-Martin (1998c)ArticleTitlePantoneurotriols: probable biogenic precursors of oxygenated monoterpenes from Antarctic Pantoneura plocamioidesTetrahedron54 3575–3580
J Darias J Rovirosa A San-Martin AR Diaz E Dorta M Cueto (2001)ArticleTitleFuroplocamioids A-C, novel polyhalogenated furanoid monoterpenes from Plocamium cartilagineumJ. Nat. Prod64 1383–1387
De Carvalho LR & Roque NF (2003) Correlations between primary and secondary metabolites in Ceramiales (Rhodophyta). Biochem. Systemat. and Ecol. In Press.
G NanteuilParticleDe P Mastagli (1981)ArticleTitleA bromophenol in the red alga Halopitys incurvusPhytochemistry20 1750–1751
R NysParticleDe JC Coll BF Bowden (1992)ArticleTitleDelisea pulchra (cf. fimbriata) revisited. The structural determination of two new metabolites from the red alga Delisea pulchraAust.J. Chem45 1625–1632
R NysParticleDe AD Wright GM König O Sticher (1993)ArticleTitleNew halogenated furanones from the marine alga Delisea pulchra (cf.fimbriata)Tetrahedron49 11213–11220
AR Diaz-Marrero M Cueto E Dorta J Rovirosa A San-Martin J Darias (2002a)ArticleTitleNew halogenated monoterpenes from the red alga Plocamium cartilagineumTetrahedron58 8539–8542
Diaz-Marrero AR, Dorta E, Cueto M, Rovirosa J, San-Martin A & Darias J (2003) New 1,2-bromochloro vinylic monoterpenes from the red algaPlocamium cartilagineum. In: Proceedings of International Symposium “Chemistry and Biology of Marine Organisms’’, Greece, Crete, p. 129.
AR Diaz-Marrero J Rovirosa J Darias A San-Mart’n M Cueto (2002b)ArticleTitlePlocamenols A-C, novel linear polyhalohydroxylated monoterpenes from Plocamium cartilagineumJ. Nat. Prod5 585–588
RW Dunlop PT Murphy RJ Wells (1979)ArticleTitleNew polyhalogenated monoterpene from the red alga Plocamium angustumAust. J. Chem32 2735–2739
SA Dworjanyn R NysParticleDe PD Steinberg (1999)ArticleTitleLocalisation and surface quantification of secondary metabolites in the red alga Delisea pulchraMar. Biol133 727–736
A Ekdahl M Pedersen KA Abrahamsson (1998)ArticleTitleStudy of the diurnal variation of biogenic volatile halocarbonsMar. Chem63 1–8
DJ Faulkner (2001)ArticleTitleMarine Natural ProductsNat Prod. Rep18 1–49
W Fenical (1974)ArticleTitlePolyhaloketones from the red seaweed Asparagopsis taxiformisTetrahedron Lett15 4463–4466
RW Fuller JH Cardellina J Jurek PJ Scheuer B Alvarado-Lindner M McGuire GN Gray JR Steiner J Clardy (1994)ArticleTitleIsolation and structure/activity features of halomon-related antitumor monoterpenes from the red alga Portieria hornemanniiJ. Med. Chem37 4407–4411
RW Fuller JH Cardellina Y Kato LS Brinen J Clardy KM Snader MR Boyd (1992)ArticleTitleA pentahalogenated monoterpene from the red alga Portieria hornemannii produces a novel cytoxicity profile against a diverse panel of human tumor cell linesJ. Med. Chem35 3007–3011
WH Gerwick (1984)ArticleTitle2-Chloro-1,6(S*),8-tribromo-3-(8)(Z)-ochtodene: a metabolite of the tropical red seaweed Ochtodes secundirameaPhytochemistry23 1323–1324
KW Glombitza H Stoffelen (1972)ArticleTitle2,3-dibrom-5-hydroxybenzyl-1, 4’-disulfat (dikaliumsalz) aus RhodomelaceenPlanta Med22IssueID4 391–394
AG Gonzalez JM Arteaga JD Martin ML Rodriguez J Fayos M Martinez-Ripolls (1978)ArticleTitleTwo new polyhalogenated monoterpenes from the red alga Plocamium cartilagineumPhytochemistry17 947–948
KD Goodwin WJ North ME Lidstrom (1997)ArticleTitleProduction of bromoform and dibromomethane by Giant Kelp: Factors affecting release and comparison to anthropogenic bromine sourcesLimnol. Oceanogr42IssueID8 1725–1734
PM Gschwend JK MacFarlane KA Newman (1985)ArticleTitleVolatile halogenated organic compounds released to seawater from temperate marine macroalgaeScience227 1033–1035
AAL Gunatilaka VJ Paul PU Park MP Puglisi AD Gitler DS Eggleston RC Haltiwanger DGI Kingston (1999)ArticleTitleApakaochtodenes A and B: Two tetrahalogenated monoterpenes from the red marine alga Portieria hornemanniJ. Nat. Prod62 1376–1378
MD Higgs DJ Vanderah DJ Faulkner (1977)ArticleTitlePolyhalogenated monoterpenes from Plocamium cartilagineum from the British CoastTetrahedron33 2775–2780
Ichikawa N, Naya Y & Enomoto S (1974) New halogenated monoterpenes fromDesmia (Chondrococcus) hornemanni. Chem. Lett. 1333–1336.
N Ichikawa Y Naya S Enomoto (1975)ArticleTitleHalogenated monoterpene derivatives from Desmia (Chondrococcus) japonicusProc. Japan Acad51 562–570
N Jacobsen JO Madsen (1978)ArticleTitleHalogenated metabolites including brominated 2-heptanols and 2-heptyl acetates from the tetrasporophyte of the red alga Bonnemaisonia hamiferaTetrahedron Lett19 3065–3068
CW Jefford D Jaggi J Boukouvalas (1989)ArticleTitleTotal synthesis of bromobeckerelideTetrahedron Lett30(10) 1237–1240
J Jongaramruong AJ Blackman (2000)ArticleTitlePolyhalogenated monoterpenes from a Tasmanian collection of the red seaweed Plocamium cartilagineumJ. Nat. Prod63 272–275
N Katsui Y Suzuki S Kitamura T Irie (1967)ArticleTitle5,6-Dibromoprotocatechualdehyde and 2,3-dibromo-4,5- dihydroxybenzyl methyl ether : New dibromophenols from Rhodomela larixTetrahedron23 1185–1188
R Kazlauskas RO Lidgard RJ Wells (1978)ArticleTitleNew polybrominated metabolites from the red alga Ptilonia australasicaTetrahedron Lett19 3165–3168
R Kazlauskas PT Murphy RJ Wells (1982)ArticleTitleA brominated metabolite from the red alga Vidalia spiralisAust. J. Chem35 219–220
R Kazlauskas PT Murphy RJ Quinn RJ Wells (1976)ArticleTitleTwo polyhalogenated monoterpenes from the red alga Plocamium costatumTetrahedron Lett17 4451–4454
R Kazlauskas PT Murphy RJ Quinn RJ Wells (1977)ArticleTitleA new class of halogenated lactones from the red alga Delisea fimbriata (Bonnemaisonaceae)Tetrahedron Lett18 37–40
Kladi M, Vagias C & Roussis V (2003) Halogenated volatile metabolites from the red algaAsparagopsis armata and the tetrasporophyte phaseFalkenbergia rufolanosa. In: Book of Abstracts of International Symposium “Chemistry and Biology of Marine Organisms”, Greece, Crete, p. 131.
GM König AD Wright G Bernardinelli (1995)ArticleTitleDetermination of the absolute configuration of a series of halogenated furanones from the marine alga Delisea pulchraHelv. Chim. Acta78 758–764
GM König AD Wright R NysParticleDe (1999a)ArticleTitleHalogenated monoterpenes from Plocamium costatum and their biological activityJ. Nat. Prod62 383–385
GM König AD Wright A Linden (1999b)ArticleTitlePlocamium hamatum and its monoterpenes: chemical and biological investigations of the tropical marine red algaPhytochemistry52 1047–1053
GM König AD Wright O Sticher (1990)ArticleTitleA new polyhalogenated monoterpene from the red alga Plocamium cartilagineumJ. Nat. Prod53 1615–1618
I Kubo M Ochi K Shibata FJ Hanke T Nakatsu K-S Tan M Taniguchi T Kamikawa Y Yamagiwa M Arizuka W Wood (1990)ArticleTitleEffect of a marine algal constituent on the growth of lettuce and rice seedlingsJ. Nat. Prod53 50–56
F Laturnus (1995)ArticleTitleRelease of volatile halogenated organic compounds by unialgal cultures of polar macroalgaeChemosphere31IssueID6 3387–3395
F Laturnus (1996)ArticleTitleVolatile halocarbons released from Arctic macroalgaeMar. Chem55 359–366
F Laturnus C Wiencke FC Adams (1998)ArticleTitleInfluence of light conditions on the release of volatile halocarbons by Antarctic macroalgaeMar. Environ. Res45IssueID3 285–294
F Laturnus C Wiencke H Kloser (1996)ArticleTitleAntarctic Macroalgae–Sources of volatile halogenated organic compoundsMar. Environ. Res41IssueID2 169–181
C Lim J Lee Y Cho (2000)ArticleTitleStructures and some properties of the antimicrobial compounds in the red alga Symphyocladia latiusculaHan’guk Susan Hakhoechi33 280–287
M Manefield M Welch M Givskov GPC Salmond S Kjelleberg (2001)ArticleTitleHalogenated furanones from the red alga, Delisea pulchra, inhibit carbapenem antibiotic synthesis and exoenzyme virulence factor production in the phytopathogen Erwinia carotovoraFEMS Microbiol. Lett205 131–138
SL Manley K Goodwin W North (1992)ArticleTitleLaboratory production of bromoform, methylene bromide and methyl iodide by macroalgae and distribution in nearshore southern California watersLimnol. Oceanogr37IssueID8 1652–1659
SL Manley DJ Chapman (1978)ArticleTitleFormation of 3-bromo-4-hydroxybenzaldehyde from L-tyrosine in cell-free homogenates of Odonthalia floccosa (Rhodophycea): a proposed biosynthetic pathway for brominated phenolsFebs Lett93IssueID1 97–101
Marinlit Database (2004). University of Canterbury, Christchurch, New Zealand.
R Marshall DB Harper WC McRoberts MJ Dring (1999)ArticleTitleVolatile bromocarbons produced by Falkenbergia stages of Asparagopsis sp (Rhodophyta) Limnol. Oceanogr44 1348–1352
JD McCombs JW Blunt MV Chambers MHG Munro WT Robinson (1988)ArticleTitleNovel2(5H)-furanones from the red marine alga Delisea elegans (Lamouroux)Tetrahedron44 1489–1502
OJ McConnell W Fenical (1977a)ArticleTitleHalogen chemistry of the red alga AsparagopsisPhytochemistry16 367–374
OJ McConnell W Fenical (1977b)ArticleTitlePolyhalogenated 1-octene-3-ones, antibacterial metabolites from the red seaweed Bonnemaisonia asparagoidesTetrahedron Lett18 1851–1854
OJ McConnell W Fenical (1978)ArticleTitleOchtodene and ochtodiol; novel polyhalogenated cyclic monoterpenes from the red seaweed Ochtodes secundirameaJ. Org. Chem43 4238–4241
OJ McConnell W Fenical (1980)ArticleTitleHalogen chemistry of the red alga BonnemaisoniaPhytochemistry19 233–249
JS Mynderse DJ Faulkner (1974)ArticleTitleViolacene; a polyhalogenated monocyclic monoterpene from the Red Alga Plocamium violaceumJ. Am. Chem. Soc96 6771–6772
JS Mynderse DJ Faulkner (1975)ArticleTitlePolyhalogenated monoterpenes from the red alga Plocamium cartilagineumTetrahedron31 1963–1967
JS Mynderse DJ Faulkner (1978)ArticleTitleVariations in the halogenated monoterpene metabolites of Plocamium cartilagineum and Pviolaceum. Phytochemistry17 237–240
JS Mynderse DJ Faulkner J Finer J Clardy (1975)ArticleTitle(1R; 2S; ;5R)-1-Bromo-trans-2-chlorovinyl-4-5-dichloro-1;5-dimethyl cyclohexane, A monoterpene skeletal type from the red Alga Plocamium violaceumTetrahedron Lett16 2175–2178
F Nicod F Tillequin J Vaquette (1987)ArticleTitleMetabolite halogene nouveau, substance majoritaire de ptilonia magellancia, algue RhodophyceeJ. Nat. Prod50 259–260
PD Nightingale G Malin PS Liss (1995)ArticleTitleProduction of chloroform and other low-molecular-weight halocarbons by some species of macroalgaeLimnol. Oceanogr40IssueID4 680–689
RS Norton RG Warren RJ Wells (1977)ArticleTitleThree new polyhalogenated monoterpenes from Plocamium speciesTetrahedron Lett18 3905–3908
N Ohsawa Y Ogata N Okada N Itoh (2001)ArticleTitlePhysiological function of bromoperoxidase in the red marine alga, Corallina pilulifera production of bromoform as an allelochemical and the simultaneous elimination of hydrogen peroxidePhytochemistry58 683–692
VJ Paul ME Hay JE Duffy W Fenical K Gustafson (1987)ArticleTitleChemical defense in the seaweed Ochtodes secundiramea (Montagne) Howe (Rhodophyta): effects of its monoterpenoid components upon coral reef herbivoresJ. Exp. Mar. Biol. Ecol114 249–260
VJ Paul OJ McConnell W Fenical (1980)ArticleTitleCyclic monoterpenoid feeding deterrents from the red marine alga Ochtodes crockeryJ. Org. Chem45 3401–3407
M Pedersen (1978)ArticleTitleBromochlorophenols and a brominated diphenylmethane in red algaePhytochemistry17 291–293
M Pedersen P Saenger L Fries (1974)ArticleTitleSimple brominated phenols in red algaePhytochemistry13 2273–2279
JA Pettus RM Wing JJ Sims (1977)ArticleTitleMarine natural products XII Isolation of a family of multihalogenated gamma-methylene lactones from the red seaweed Delisea fimbriataTetrahedron Lett18 41–44
JJ Polzin GL Rorrer DP Cheney (2003)ArticleTitleMetabolic flux analysis of halogenated monoterpene biosynthesis in microplantlets of the macrophytic red alga Ochtodes secundirameaBiomol. Eng20 205–215
AF Rose JA Pettus JJ Sims (1977)ArticleTitleMarine natural products XIII Isolation and synthesis of some halogenated ketones from the red seaweed Delisea fimbriataTetrahedron Lett22 1847–1850
A San-Martin R Negrete J Rovirosa (1991)ArticleTitleInsecticide and acaricide activities of polyhalogenated monoterpenes from Chilean Plocamium cartilagineumPhytochemistry30 2165–2169
JF Siuda GR VanBlaricom PD Shaw RD Johnson RH White LP Hager KL Rinehart (1975)ArticleTitle1-Iodo-3,3-dibromo-2-heptanone, 1,1,3,3-tetrabromo-2-heptanone and related compounds from the red alga Bonnemaisonia hamiferaJ. Am. Chem. Soc97 937–938
MO Stallard DJ Faulkner (1974)ArticleTitleChemical constituents of the digestive gland of the sea hare Aplysiacalifornica - 1. Importance of dietComp. Biochem. Physiol49 25–35
DB Stierle JJ Sims (1979)ArticleTitlePolyhalogenated cyclic monoterpenes from the red alga Plocamium cartilagineum of AntarcticaTetrahedron35 1261–1265
DB Stierle JJ Sims (1984)ArticleTitlePlocamenone, A unique halogenated monoterpene from the red alga PlocamiumTetrahedron Lett25 153–156
DB Stierle RM Wing JJ Sims (1979)ArticleTitleMarine natural products XVI Polyhalogenated acyclic monoterpenes from red alga Plocamium of AntarticaTetrahedron35 2855–2859
DB Stierle RW Wing JJ Sims (1976)ArticleTitleMarine natural products XI Costatone costatolide, new halogenated monoterpenes from the red seaweed Plocamium costatumTetrahedron Lett17 4455–4458
VH Stoffelen KW Glombitza U Murawski J Bielaczek H Egge (1972)ArticleTitleBromophenole aus Polysiphonia lanosa (L) TandyPlanta Med22IssueID4 396–401
M Sugano A Sato H Nagaki S Yoshioka T Shiraki H Horikoshi (1990)ArticleTitleAldose reductase inhibitors from the red alga Asparagopsis taxiformisTetrahedron Lett31 7015–7016
J Sundstrom J Collen K Abrahamsson M Pedersen (1996)ArticleTitleHalocarbon production and in vivo brominating activity of Eucheuma denticulatumPhytochemisty42IssueID6 1527–1530
J Tanaka T Higa G Bernardinelli C Jefford (1989)ArticleTitleSulfur-containing polybromoindoles from the red alga Laurencia brongniartiiTetrahedron45IssueID23 7301–7310
T Urhahn K Ballschmiter (1998)ArticleTitleChemistry of the biosynthesis of halogenated methanes: C1-organohalogens as pre-industrial chemical stressors in the environmentChemosphere37IssueID6 1017–1032
D EngenParticleVan J Clardy E Kho-Wiseman P Crews MD Higgs DJ Faulkner (1978)ArticleTitleViolacene; a reassignment of structureTetrahedron Lett19 29–32
K Watanabe M Miyakado N Ohno A Okada K Yanagi K Moriguchi (1989)ArticleTitleA polyhalogenated insecticidal monoterpene from the red agla Plocamiun telfairiaePhytochemistry28 77–78
B Weinstein TL Rold CE Harrell MW Burns III JR Waaland (1975)ArticleTitleReexamination of the bromophenols in the red alga Rhodomela larixPhytochemistry14 2667–2670
FB Whitfield F Helidoniotis KJ Shaw D Svoronos (1999)ArticleTitleDistribution of bromophenols in species of marine algae from eastern AustraliaJ. Agric. Food Chem47 2367–2373
PG Williard LA Grab (1984)ArticleTitleTotal synthesis of costatone: a monoterpene from the red seaweed: Plocamium costatumTetrahedron Lett25 5009–5012
ML Wise GL Rorrer JJ Polzin R Croteau (2002)ArticleTitleBiosynthesis of Marine Natural Products: Isolation and Characterization of a Myrcene Synthase from Cultured Tissues of the Marine Red Alga Ochtodes secundirameaArch. Biochem. Biophy400IssueID1 125–132
FX Woolard RE Moore (1978)ArticleTitleThe structure and absolute configuration of chondrocolactone, a halogenated monoterpene from the red alga Chondrococcus hornemanni and a revised structure for chondrocole ATetrahedron Lett27 2367–2370
FX Woolard RE Moore PP Roller (1976a)ArticleTitleHalogenated acetamides, but-3-en-2-ols, and isopropanols from Asparagopsis taxiformis (delile) trevTetrahedron32 2843–2846
FX Woolard RE Moore PP Roller (1979)ArticleTitleHalogenated acetic and acrylic acids from the red alga Asparagopsis taxiformisPhytochemistry18 617–620
FX Woolard RE Moore M Mahendran A Sivapalan (1976b)ArticleTitle(-)-3-bromomethyl-3-chloro-7-methyl-1,6-octadiene from Sri Lanka Chondrococcus hornemanniPhytochemistry15 1069–1070
AD Wright GM König O Sticher R NysParticleDe (1991)ArticleTitleFive new monoterpenes from the marine red alga Portieria hornemanniiTetrahedron47 5717–5724
J Zegarski BM Howard (1985)ArticleTitleSyntheses of marine ochtodane antifeedants via hydrolytic dehalogenationTetrahedron Lett26 1363–1366
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Department of Pharmacy, Division of Pharmacognosy, University of Athens, Chemistry of Natural Products, 157 71, Panepistimiopolis Zografou, Athens, Greece
Maria Kladi, Constantinos Vagias & Vassilios Roussis
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Dedicated to our late student Christos Varytimidis for his intuitive efforts on bioactive natural products
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Kladi, M., Vagias, C. & Roussis, V. Volatile halogenated metabolites from marine red algae.Phytochem Rev3, 337–366 (2004). https://doi.org/10.1007/s11101-004-4155-9
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