Natural products can structure relationships between organisms, affect resource allocation, influence competition, mediate species distributions, and select for traits leading to the potential diversification of species (e.g. see reviews by McClintock and Baker 2001; Potin et al. 2002; Pohnert 2004; Ianora et al. 2006). Although there have been numerous efforts to determine patterns of metabolite distribution in marine ecosystems, particularly in macroalgae, these efforts have focused primarily on a macroscale: global patterns, patterns within specific habitats (e.g. the intertidal zone), and patterns correlated with changes in biotic and abiotic factors. Work in terrestrial ecosystems has led to the development of ecological models that describe trade-offs, costs, and benefits, and have been applied to marine algal systems (e.g. Cronin 2001; Jormalainen et al. 2003; Honkanen and Jormalainen 2005; Dworjanyn et al. 2006b; Ianora et al. 2006). However, the response of algal secondary metabolites to stimuli is a complex process, and these models do not consistently predict patterns of macroalgal metabolite production.
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References
Agrawal AA, Fishbein M (2006) Plant defense syndromes. Ecology 87:S132–S149
Amsler CD, Fairhead VA (2006) Defensive and sensory chemical ecology of brown algae. Adv Bot Res 43:1–91
Amsler CD, Iken K, McClintock JB, Amsler MO, Peters KJ, Hubbard JM, Furrow FB, Baker BJ (2005) Comprehensive evaluation of the palatability and chemical defenses of subtidal macroalgae from the Antarctic Peninsula. Mar Ecol Prog Ser 294:141–159
Armbrust EV, Berges JA, Bowler C, et al. (2004) The genome of the diatom Thalassiosira pseudonana: ecology, evolution, and metabolism. Science 306:79–86
Arnold TM, Targett NM (2003) To grow and defend: lack of tradeoffs for brown algal phlorotannins. Oikos 100:406–408
Arnold TM, Targett NM, Tanner CE, Hatch WI, Ferrari KE (2001) Evidence for methyl jasmonate-induced phlorotannin production in Fucus vesiculosus (Phaeophyceae). J Phycol 37:1026–1029
Bernays EA, Chapman RF (1994) Host-plant selection by phytophagous insects. Chapman & Hall, New York
Berry JP, Reece KS, Rein KS, Baden DG, Haas LW, Ribeiro WL, Shields JD, Snyder RV, Vogelbein WK, Gawley RE (2002) Are Pfiesteria species toxicogenic? Evidence against production of ichthyotoxins by Pfiesteria shumwayae. Proc Natl Acad Sci USA 99:10970–10975
Bhakuni DS, Rawat DS (2005) Bioactive marine natural products. Springer, New York
Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2006) Marine natural products. Nat Prod Rep 23:26–78
Boettcher AA, Targett NM (1993) Role of polyphenolic molecular-size in reduction of assimilation efficiency in Xiphister mucosus. Ecology 74:891–903
Bolwell GP, Butt VS, Davies DR, Zimmerlin A (1995) The origin of the oxidative burst in plants. Free Radical Res 23:517–532
Boonprab K, Matsui K, Akakabe Y, Yotsukura N, Kajiwara T (2003) Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata. Phytochemistry 63:669–678
Borell EM, Foggo A, Coleman RA (2004) Induced resistance in intertidal macroalgae modifies feeding behaviour of herbivorous snails. Oecologia 140:328–334
Bouarab K, Adas F, Gaquerel E, Kloareg B, Salaun JP, Potin P (2004) The innate immunity of a marine red alga involves oxylipins from both the eicosanoid and octadecanoid pathways. Plant Physiol 135:1838–1848
Bouarab K, Potin P, Correa J, Kloareg B (1999) Sulfated oligosaccharides mediate the interaction between a marine red alga and its green algal pathogenic endophyte. Plant Cell 11:1635–1650
Bryant JP, Chapin FS, Klein DR (1983) Carbon/nutrient balance of boreal plants in relation to vertebrate herbivory. Oikos 40:357–368
Ceh J, Molis M, Dzeha TM, Wahl M (2005) Induction and reduction of anti-herbivore defenses in brown and red macroalgae off the Kenyan coast. J Phycol 41:726–731
Cetrulo GL, Hay ME (2000) Activated chemical defenses in tropical versus temperate seaweeds. Mar Ecol Prog Ser 207:243–253
Chikaraishi Y (2006) Carbon and hydrogen isotopic composition of sterols in natural marine brown and red macroalgae and associated shellfish. Org Geochem 37:428–436
Cimino G, Crispino A, Dimarzo V, Gavagnin M, Ros JD (1990) Oxytoxins, bioactive molecules produced by the marine opisthobranch mollusk Oxynoe olivacea from a diet-derived precursor. Experientia 46:767–770
Collén J, Herve C, Guisle-Marsollier I, Leger JJ, Boyen C (2006b) Expression profiling of Chondrus crispus (Rhodophyta) after exposure to methyl jasmonate. J Exp Bot 57:3869–3881
Collén J, Pedersen M (1994) A stress induced oxidative burst in Eucheuma platycladum (Rhodophyta). Physiol Plantarum 92:417–422
Collén J, Roeder V, Rousvoal S, Collin O, Kloareg B, Boyen C (2006a) An expressed sequence tag analysis of thallus and regenerating protoplasts of Chondrus crispus (Gigartinales, Rhodophyceae). J Phycol 42:104–112
Cronin G (2001) Resource allocation in seaweeds and marine invertebrates: chemical defense patterns in relation to defense theories. In: McClintock JB, Baker B (eds) Marine Chemical Ecology. CRC Press, New York, pp 325–354
Cronin G, Hay ME (1996a) Susceptibility to herbivores depends on recent history of both the plant and animal. Ecology 77:1531–1543
Cronin G, Hay ME (1996b) Within plant variation in seaweed palatability and chemical defenses: optimal defense theory versus the growth differentiation balance hypothesis. Oecologia 105:361–368
Cvejic JH, Rohmer M (2000) CO2 as main carbon source for isoprenoid biosynthesis via the mevalonate-independent methylerythritol 4-phosphate route in the marine diatoms Phaeodactylum tricornutum and Nitzschia ovalis. Phytochemistry 53:21–28
de Nys R, Steinberg PD, Willemsen P, Dworjanyn SA, Gabelish CL, King RJ (1995) Broad-spectrum effects of secondary metabolites from the red alga Delisea pulchra in antifouling assays. Biofouling 8:259–271
Dethier MN, Williams SL, Freeman A (2005) Seaweeds under stress: Manipulated stress and herbivory affect critical life-history functions. Ecol Monogr 75:403–418
Diaz E, Guldenzoph C, Molis M, McQuaid C, Wahl M (2006) Variability in grazer-mediated defensive responses of green and red macroalgae on the south coast of South Africa. Mar Biol 149:1301–1311
Disch A, Schwender J, Muller C, Lichtenthaler HK, Rohmer M (1998) Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathways for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis PCC 6714. Biochem J 333:381–388
Dittmann E, Wiegand C (2006) Cyanobacterial toxins–occurrence, biosynthesis and impact on human affairs. Mol Nutr Food Res 50:7–17
Dixon RA (2005a) Engineering of plant natural product pathways. Curr Opin Plant Biol 8:329–336
Dixon RA (2005b) Plant biotechnology kicks off into the 21st century. Trends Plant Sci 10:560–561
Dixon RA, Achnine L, Kota P, Liu CJ, Reddy MSS, Wang LJ (2002) The phenylpropanoid pathway and plant defence – a genomics perspective. Mol Plant Pathol 3:371–390
Dixon RA, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7:1085–1097
Douglas S, Zauner S, Fraunholz M, Beaton M, Penny S, Deng LT, Wu XN, Reith M, Cavalier-Smith T, Maier UG (2001) The highly reduced genome of an enslaved algal nucleus. Nature 410:1091–1096
Dring MJ (2006) Stress resistance and disease resistance in seaweeds: the role of reactive oxygen metabolism. Adv Bot Res 43:175–207
Duke MV, Paul RN, Elsohly HN, Sturtz G, Duke SO (1994) Localization of artemisinin and artemisitene in foliar tissues of glanded and glandless biotypes of Artemisia annua L. Int J Plant Sci 155:365–372
Dworjanyn SA, de Nys R, Steinberg PD (1999) Localisation and surface quantification of secondary metabolites in the red alga Delisea pulchra. Mar Biol 133:727–736
Dworjanyn SA, de Nys R, Steinberg PD (2006a) Chemically mediated antifouling in the red alga Delisea pulchra. Mar Ecol Prog Ser 318:153–163
Dworjanyn SA, Wright JT, Paul NA, de Nys R, Steinberg PD (2006b) Cost of chemical defence in the red alga Delisea pulchra. Oikos 113:13–22
Edwards KF, Pfister CA, Van Alstyne KL (2006) Nitrogen content in the brown alga Fucus gardneri and its relation to light, herbivory and wave exposure. J Exp Mar Biol Ecol 336:99–109
Fahn A (1988) Secretory tissues in vascular plants. New Phytol 108:229–257
Fairhead VA, Amsler CD, McClintock JB, Baker BJ (2005) Variation in phlorotannin content within two species of brown macroalgae (Desmarestia anceps and D. menziesii) from the Western Antarctic Peninsula. Polar Biol 28:680–686
Fairhead VA, Amsler CD, McClintock JB, Baker BJ (2006) Lack of defense or phlorotannin induction by UV radiation or mesograzers in Desmarestia anceps and D. menziesii (Phaeophyceae). J Phycol 42:1174–1183
Farmer EE, Almeras E, Krishnamurthy V (2003) Jasmonates and related oxylipins in plant responses to pathogenesis and herbivory. Curr Opin Plant Biol 6:372–378
Farmer EE, Johnson RR, Ryan CA (1992) Regulation of expression of proteinase-inhibitor genes by methyl jasmonate and jasmonic acid. Plant Physiol 98:995–1002
Fulcher RG, McCully ME (1971) Histological studies of the genus Fucus. V. An autoradiographic and electron microscopic study of the early stages of regeneration. Can J Bot 49:161–165
Gavagnin M, Marin A, Castelluccio F, Villani G, Cimino G (1994) Defensive relationships between Caulerpa prolifera and its shelled sacoglossan predators. J Exp Mar Biol Ecol 175:197–210
Gerwick WH (1999) Eicosanoids in nonmammals. In: Sankawa U, Barton DHR, Nakanishi K, Meth-Cohn O (eds) Comprehensive natural products chemistry. Elsevier, New York. pp 207–254
Gerwick WH, Fenical W, Norris JN (1985) Chemical variation in the tropical seaweed Stypopodium zonale (Dictyotaceae). Phytochemistry 24:1279–1283
Gerwick WH, Nagle DG, Proteau PJ (1993a) Oxylipins from marine invertebrates. Top Curr Chem 167:117–180
Gerwick WH, Proteau PJ, Nagle DG, Wise ML, Jiang ZD, Bernart MW, Hamberg M (1993b) Biologically active oxylipins from seaweeds. Hydrobiologia 261:653–665
Halliwell B, Gutteridge J (2007) Free radicals in biology and medicine. Oxford University Press, New York
Hammerstrom K, Dethier MN, Duggins DO (1998) Rapid phlorotannin induction and relaxation in five Washington kelps. Mar Ecol Prog Ser 165:293–305
Hay ME, Steinberg PD (1992) The chemical ecology of plant-herbivore interactions in marine versus terrestrial communities. In: Rosenthal GA, Berenbaum MR (eds) Herbivores: their interactions with secondary metabolites. Evolutionary and ecological perspectives. Academic, San Diego, CA, pp 371–413
Herms DA, Mattson WJ (1992) The dilemma of plants: to grow or defend. Q Rev Biol 67:283–335
Honkanen T, Jormalainen V (2005) Genotypic variation in tolerance and resistance to fouling in the brown alga Fucus vesiculosus. Oecologia 144:196–205
Ianora A, Boersma M, Casotti R, Fontana A, Harder J, Hoffmann F, Pavia H, Potin P, Poulet SA, Toth G (2006) New trends in marine chemical ecology. Estuaries and Coasts 29:531–551
Jormalainen V, Honkanen T (2004) Variation in natural selection for growth and phlorotannins in the brown alga Fucus vesiculosus. J Evol Biol 17:807–820
Jormalainen V, Honkanen T, Koivikko R, Eranen J (2003) Induction of phlorotannin production in a brown alga: defense or resource dynamics? Oikos 103:640–650
Jung V, Pohnert G (2001) Rapid wound-activated transformation of the green algal defensive metabolite caulerpenyne. Tetrahedron 57:7169–7172
Keeling PJ (2004) Diversity and evolutionary history of plastids and their hosts. Am J Bot 91:1481–1493
Keeling PJ, Burger G, Durnford DG, Lang BF, Lee RW, Pearlman RE, Roger AJ, Gray MW (2005) The tree of eukaryotes. Trends Ecol Evol 20:670–676
Kim D, Filtz MR, Proteau PJ (2004) The methylerythritol phosphate pathway contributes to carotenoid but not phytol biosynthesis in Euglena gracilis. J Nat Prod 67:1067–1069
Küpper FC, Gaquerel E, Boneberg EM, Morath S, Salaun JP, Potin P (2006) Early events in the perception of lipopolysaccharides in the brown alga Laminaria digitata include an oxidative burst and activation of fatty acid oxidation cascades. J Exp Bot 57:1991–1999
Küpper FC, Kloareg B, Guern J, Potin P (2001) Oligoguluronates elicit an oxidative burst in the brown algal kelp Laminaria digitata. Plant Physiol 125:278–291
Küpper FC, Muller DG, Peters AF, Kloareg B, Potin P (2002) Oligoalginate recognition and oxidative burst play a key role in natural and induced resistance of sporophytes of laminariales. J Chem Ecol 28:2057–2081
Lamb C, Dixon RA (1997) The oxidative burst in plant disease resistance. Annu Rev Plant Phys 48:251–275
Leimu R, Koricheva J (2006) A meta-analysis of tradeoffs between plant tolerance and resistance to herbivores: combining the evidence from ecological and agricultural studies. Oikos 112:1–9
Lesser MP (2006) Oxidative stress in marine environments: biochemistry and physiological ecology. Annu Rev Physiol 68:253–278
Lichtenthaler HK (1999) The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu Rev Plant Phys 50:47–65
Lichtenthaler HK, Rohmer M, Schwender J (1997) Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Physiol Plantarum 101:643–652
Liechti R, Farmer EE (2002) The jasmonate pathway. Science 296:1649–1650
Lion U, Wiesemeier T, Weinberger F, Beltran J, Flores V, Faugeron S, Correa J, Pohnert G (2006) Phospholipases and galactolipases trigger oxylipin-mediated wound-activated defence in the red alga Gracilaria chilensis against epiphytes. ChemBioChem 7:457–462
Liu QY, van der Meer JP, Reith ME (1994) Isolation and characterization of phase-specific complementary DNAs from sporophytes and gametophytes of Porphrya purpurea (Rhodophyta) using subtracted complementary DNA libraries. J Phycol 30:513–520
Loomis WE (1953) Growth and differentiation – an introduction and summary. In: Loomis WE (ed) Growth and differentiation in plants. Iowa State College Press, Ames, IA, pp 1–17
Lüder UH, Clayton MN (2004) Induction of phlorotannins in the brown macroalga Ecklonia radiata (Laminariales, Phaeophyta) in response to simulated herbivory – the first microscopic study. Planta 218:928–937
Macaya EC, Rothausler E, Thiel M, Molis M, Wahl M (2005) Induction of defenses and within-alga variation of palatability in two brown algae from the northern-central coast of Chile: effects of mesograzers and UV radiation. J Exp Mar Biol Ecol 325:214–227
Mahalingam R, Fedoroff N (2003) Stress response, cell death and signalling: the many faces of reactive oxygen species. Physiol Plantarum 119:56–68
Matsuzaki M, Misumi O, Shin-i T, et al. (2004) Genome sequence of the ultrasmall unicellular red alga Cyanidioschyzon merolae 10D. Nature 428:653–657
Maximilien R, de Nys R, Holmstrom C, Gram L, Givskov M, Crass K, Kjelleberg S, Steinberg PD (1998) Chemical mediation of bacterial surface colonisation by secondary metabolites from the red alga Delisea pulchra. Aquat Microb Ecol 15:233–246
Mayes SR, Chiesa MD, Zhang Z, Barber J (1993) The genes aroA and trnQ are located upstream of psbO in the chromosome of Synechocystis 6803. FEBS J 325:255–261
McClintock JB, Baker BJ (2001) Marine chemical ecology. CRC, New York, NY
McConnell O, Fenical W (1977) Halogen chemistry of red alga Asparagopsis. Phytochemistry 16:367–374
McKey D (1974) Adaptive patterns in alkaloid physiology. Am Nat 108:305–320
Molis M, Korner J, Ko YW, Kim JH, Wahl M (2006) Inducible responses in the brown seaweed Ecklonia cava: the role of grazer identity and season. J Ecol 94:243–249
Moore BS (2006) Biosynthesis of marine natural products: macroorganisms (Part B). Nat Prod Rep 23:615–629
Nicholas GM, Phillips AJ (2006) Marine natural products: synthetic aspects. Nat Prod Rep 23:79–99
Obrien ET, White S, Jacobs RS, Boder GB, Wilson L (1984) Pharmacological properties of a marine natural product, stypoldione, obtained from the brown alga Stypopodium zonale. Hydrobiologia 116:141–145
Ouborg NJ, Vriezen WH (2007) An ecologist’s guide to ecogenomics. J Ecol 95:8–16
Paffenhofer GA, Ianora A, Miralto A, et al. (2005) Colloquium on diatom-copepod interactions. Mar Ecol Prog Ser 286:293–305
Patron NJ, Rogers MB, Keeling PJ (2006) Comparative rates of evolution in endosymbiotic nuclear genomes. BMC Evol Biol 6:46
Paul NA, Cole L, de Nys R, Steinberg PD (2006a) Ultrastructure of the gland cells of the red alga Asparagopsis armata (Bonnemaisoniaceae). J Phycol 42:637–645
Paul NA, de Nys R, Steinberg PD (2006b) Chemical defence against bacteria in the red alga Asparagopsis armata: linking structure with function. Mar Ecol Prog Ser 306:87–101
Paul VJ, Van Alstyne KL (1992) Activation of chemical defenses in the tropical green algae Halimeda spp. J Exp Mar Biol Ecol 160:191–203
Pavia H, Åberg P (1996) Spatial variation in polyphenolic content of Ascophyllum nodosum (Fucales, Phaeophyta). Hydrobiologia 327:199–203
Pavia H, Cervin G, Lindgren A, Åberg P (1997) Effects of UV-B radiation and simulated herbivory on phlorotannins in the brown alga Ascophyllum nodosum. Mar Ecol Prog Ser 157:139–146
Pavia H, Toth GB (2000) Inducible chemical resistance to herbivory in the brown seaweed Ascophyllum nodosum. Ecology 81:3212–3225
Pearson G, Lago-Leston A, Valente M, Serrao E (2006) Simple and rapid RNA extraction from freeze-dried tissue of brown algae and seagrasses. Eur J Phycol 41:97–104
Pearson G, Serrao EA, Cancela ML (2001) Suppression subtractive hybridization for studying gene expression during aerial exposure and desiccation in fucoid algae. Eur J Phycol 36:359–366
Peckol P, Krane JM, Yates JL (1996) Interactive effects of inducible defense and resource availability on phlorotannins in the North Atlantic brown alga Fucus vesiculosus. Mar Ecol Prog Ser 138:209–217
Pennings SC, Zimmer M, Dias N, Sprung M, Dave N, Ho C-K, Kunza A, McFarlin C, Mews M, Pfauder A, Salgado CS (2007) Latitudinal variation in plant-herbivore interactions in European salt marshes. Oikos 116:543–549
Pereira RC, Soares AR, Teixeira VL, Villaca R, da Gama BAP (2004) Variation in chemical defenses against herbivory in southwestern Atlantic Stypopodium zonale (Phaeophyta). Bot Mar 47:202–208
Peters AF, Marie D, Scornet D, Kloareg B, Cock JM (2004) Proposal of Ectocarpus siliculosus (Ectocarpales, Phaeophyceae) as a model organism for brown algal genetics and genomics. J Phycol 40:1079–1088
Phillips N, Smith CM, Morden CW (2001) An effective DNA extraction protocol for brown algae. Phycol Res 49:97–102
Pohnert G (2004) Chemical defense strategies of marine organisms. In: The chemistry of pheromones and other semiochemicals I. Topics in current chemistry, vol 239. Springer, Berlin. pp 179–219
Pohnert G (2005) Diatom/copepod interactions in plankton: the indirect chemical defense of unicellular algae. ChemBioChem 6:946–959
Pohnert G, Boland W (2002) The oxylipin chemistry of attraction and defense in brown algae and diatoms. Nat Prod Rep 19:108–122
Pohnert G, Jung V (2003) Intracellular compartmentation in the biosynthesis of caulerpenyne: study on intact macroalgae using stable-isotope-labeled precursors. Org Lett 5:5091–5093
Potin P, Bouarab K, Salaun JP, Pohnert G, Kloareg B (2002) Biotic interactions of marine algae. Curr Opin Plant Biol 5:308–317
Ragan MA (1976) Physodes and the phenolic compounds of brown algae. Composition and significance of physodes in vivo. Bot Mar 19:145–154
Ragan MA, Glombitza K (1986) Phlorotannins, brown algal polyphenols. In: Round FE, Chapman DJ (eds) Progress in phycological research, vol 4. Biopress, Bristol, England, pp 130–241
Rein KS, Borrone J (1999) Polyketides from dinoflagellates: origins, pharmacology and biosynthesis. Comp Biochem Physiol B: Biochem Mol Biol 124:117–131
Rhoades DF (1979) Evolution of plant chemical defense against herbivores. In: Rosenthal GA, Janzen DH (eds) Herbivores: their interaction with plant secondary metabolites. Academic, New York, pp 1–55
Richards TA, Dacks JB, Campbell SA, Blanchard JL, Foster PG, McLeod R, Roberts CW (2006) Evolutionary origins of the eukaryotic shikimate pathway: gene fusions, horizontal gene transfer, and endosymbiotic replacements. Eukaryot Cell 5:1517–1531
Rogers MB, Gilson PR, Su V, McFadden GI, Keeling PJ (2007) The complete chloroplast genome of the chlorarachniophyte Bigelowiella natans: evidence for independent origins of chlorarachniophyte and euglenid secondary endosymbionts. Mol Biol Evol 24:54–62
Rohde S, Molis M, Wahl M (2004) Regulation of anti-herbivore defence by Fucus vesiculosus in response to various cues. J Ecol 92:1011–1018
Ross C, Küpper FC, Vreeland V, Waite JH, Jacobs RS (2005) Evidence of a latent oxidative burst in relation to wound repair in the giant unicellular chlorophyte Dasycladus vermicularis. J Phycol 41:531–541
Ross C, Van Alstyne KL (2007) Intraspecific variation in stress-induced hydrogen peroxide scavenging by the ulvoid macroalga Ulva lactuca. J Phycol 43(3):466–474
Salgado CS, Pennings SC (2005) Latitudinal variation in palatability of salt-marsh plants: are differences constitutive? Ecology 86:1571–1579
Schoenwaelder MEA (2002) Physode distribution and the effect of ‘thallus sunburn’ in Hormosira banksii (Fucales, Phaeophyceae). Bot Mar 45:262–266
Schoenwaelder MEA, Clayton MN (2000) Physode formation in embryos of Phyllospora comosa and Hormosira banksii (Phaeophyceae). Phycologia 39:1–9
Schwender J, Gemunden C, Lichtenthaler HK (2001) Chlorophyta exclusively use the 1-deoxyxylulose 5-phosphate/2-C-methylerythritol 4-phosphate pathway for the biosynthesis of isoprenoids. Planta 212:416–423
Schwender J, Zeidler J, Groner R, Muller C, Focke M, Braun S, Lichtenthaler FW, Lichtenthaler HK (1997) Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae. FEBS Lett 414:129–134
Shibata T, Hama Y, Miyasaki T, Ito M, Nakamura T (2006) Extracellular secretion of phenolic substances from living brown algae. J Appl Phycol 18:787–794
Shibata T, Kawaguchi S, Hama Y, Inagaki M, Yamaguchi K, Nakamura T (2004) Local and chemical distribution of phlorotannins in brown algae. J Appl Phycol 16:291–296
Shick JM, Dunlap WC (2002) Mycosporine-like amino acids and related gadusols: biosynthesis, accumulation, and UV-protective functions in aquatic organisms. Annu Rev Physiol 64:223–262
Shick JM, Romaine-Lioud S, Ferrier-Pages C, Gattuso JP (1999) Ultraviolet-B radiation stimulates shikimate pathway-dependent accumulation of mycosporine-like amino acids in the coral Stylophora pistillata despite decreases in its population of symbiotic dinoflagellates. Limnol Oceanogr 44:1667–1682
Shimizu Y (2003) Microalgal metabolites. Curr Opin Microbiol 6:236–243
Smit AJ (2004) Medicinal and pharmaceutical uses of seaweed natural products: a review. J Appl Phycol 16:245–262
Snyder RV, Gibbs PDL, Palacios A, Abiy L, Dickey R, Lopez JV, Rein KS (2003) Polyketide synthase genes from marine dinoflagellates. Mar Biotechnol 5:1–12
Sotka EE (2003) Genetic control of feeding preference in the herbivorous amphipod Ampithoe longimana. Mar Ecol Prog Ser 256:305–310
Sotka EE, Taylor RB, Hay ME (2002) Tissue-specific induction of resistance to herbivores in a brown seaweed: the importance of direct grazing versus waterborne signals from grazed neighbors. J Exp Mar Biol Ecol 277:1–12
Stafford HA (2000) The evolution of phenolics in plants. In: Romeo JT (ed) Evolution of metabolic pathways. Elsevier, New York, pp 25–47
Stamp N (2003) Out of the quagmire of plant defense hypotheses. Q Rev Biol 78:23–55
Steinberg PD (1988) Effects of quantitative and qualitative variation in phenolic compounds on feeding in 3 species of marine invertebrate herbivores. J Exp Mar Biol Ecol 120:221–237
Steinberg PD, de Nys R, Kjelleberg S (2002) Chemical cues for surface colonization. J Chem Ecol 28:1935–1951
Steinberg PD, Van Altena I (1992) Tolerance of marine invertebrate herbivores to brown algal phlorotannins in temperate Australasia. Ecol Monogr 62:189–222
Stern JL, Hagerman AE, Steinberg PD, Winter FC, Estes JA (1996) A new assay for quantifying brown algal phlorotannins and comparisons to previous methods. J Chem Ecol 22:1273–1293
Strauss SY, Rudgers JA, Lau JA, Irwin RE (2002) Direct and ecological costs of resistance to herbivory. Trends Ecol Evol 17:278–285
Swanson AK, Druehl LD (2002) Induction, exudation and the UV protective role of kelp phlorotannins. Aquat Bot 73:241–253
Targett NM, Coen LD, Boettcher AA, Tanner CE (1992) Biogeographic comparisons of marine algal polyphenolics – evidence against a latitudinal trend. Oecologia 89:464–470
Toth GB, Langhamer O, Pavia H (2005) Inducible and constitutive defenses of valuable seaweed tissues: consequences for herbivore fitness. Ecology 86:612–618
Toth GB, Pavia H (2000) Water-borne cues induce chemical defense in a marine alga (Ascophyllum nodosum). Proc Natl Acad Sci USA 97:14418–14420
Toth GB, Pavia H (2002) Lack of phlorotannin induction in the kelp Laminaria hyperborea in response to grazing by two gastropod herbivores. Mar Biol 140:403–409
Toth GB, Pavia H (2007) Induced herbivore resistance in seaweeds: a meta-analysis. J Ecol 95:425–434
Tuomi J, Niemela P, Chapin FS, Bryant JP, Siren S (1988) Defensive responses of trees in relation to their carbon/nutrient balance. In: Mattson JB (ed) Mechanisms of woody plant defense against insects: search for patterns. Springer, New York, pp 57–72
Van Alstyne KL (1988) Herbivore grazing increases polyphenolic defenses in the intertidal brown alga Fucus distichus. Ecology 69:655–663
Van Alstyne KL, Dethier MN, Duggins DO (2001a) Spatial patterns in macroalgal chemical defenses. In: McClintock JB, Baker B (eds) Marine chemical ecology. CRC, New York. pp 301–324
Van Alstyne KL, Paul VJ (1990) The biogeography of polyphenolic compounds in marine macroalgae–temperate brown algal defenses deter feeding by tropical herbivorous fishes. Oecologia 84:158–163
Van Alstyne KL, Wolfe GV, Freidenburg TL, Neill A, Hicken C (2001b) Activated defense systems in marine macroalgae: evidence for an ecological role for DMSP cleavage. Mar Ecol Prog Ser 213:53–65
Varela-Alvarez E, Andreakis N, Lago-Leston A, Pearson GA, Serrao EA (2006) Genomic DNA isolation from green and brown algae (Caulerpales and Fucales) for microsatellite library construction. J Phycol 42:741–745
Waaland JR, Stiller JW, Cheney DP (2004) Macroalgal candidates for genomics. J Phycol 40:26–33
Waller RF, Patron NJ, Keeling PJ (2006) Phylogenetic history of plastid-targeted proteins. in the peridinin-containing dinoflagellate Heterocapsa triquetra. Int J Syst Evol Micr 56:1439–1447
Wanke M, Skorupinska-Tudek K, Swiezewska E (2001) Isoprenoid biosynthesis via 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) pathway. Act Biochim Pol 48:663–672
Weidner K, Lages BG, da Gama BAP, Molis M, Wahl M, Pereira RC (2004) Effect of mesograzers and nutrient levels on induction of defenses in several Brazilian macroalgae. Mar Ecol Prog Ser 283:113–125
Weinberger F, Friedlander M (2000) Response of Gracilaria conferta (Rhodophyta) to oligoagars results in defense against agar-degrading epiphytes. J Phycol 36:1079–1086
White SJ, Jacobs RS (1983) Effect of stypoldione on cell-cycle progression, DNA and protein-synthesis, and cell-division in cultured sea urchin embryos. Mol Pharmacol 24:500–508
Wink M (1997) Compartmentation of secondary metabolites and xenobiotics in plant vacuoles. In: Leigh RA, Sanders D, Callow JA (eds) The plant vacuole: advances in botanical research, vol 25. Academic, London, pp 141–169
Wojtaszek P (1997) Oxidative burst: an early plant response to pathogen infection. Biochem J 322:681–692
Wright JT, de Nys R, Poore AGB, Steinberg PD (2004) Chemical defense in a marine alga: heritability and the potential for selection by herbivores. Ecology 85:2946–2959
Wright JT, de Nys R, Steinberg PD (2000) Geographic variation in halogenated furanones from the red alga Delisea pulchra and associated herbivores and epiphytes. Mar Ecol Prog Ser 207:227–241
Xie DY, Dixon RA (2005) Proanthocyanidin biosynthesis – still more questions than answers? Phytochemistry 66:2127–2144
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Pelletreau, K.N., Targett, N.M. (2008). New Perspectives for Addressing Patterns of Secondary Metabolites in Marine Macroalgae. In: Amsler, C.D. (eds) Algal Chemical Ecology. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-74181-7_6
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