Abstract
The evolutionary origin of land plants (embryophytes) from their green algal ancestors was a pivotal event in the history of life (388, 533). Morphological and genetic studies have identified two distinct lineages within the green algae, termed Chlorophyta and Charophyta (114, 466). There is a concept that land plants descended from ancestral charophycean algae, and currently this theory is supported by molecular, biochemical, and ultrastructural evidence (388, 533). Red algae (Fig. 9.1) seem to be the most anciently emerged group among the eukaryotes 9–32) (469). The red and green algae sisterhood has been recently supported by molecular analysis (551). Phylogenetic studies have also been shown that heterokont algae (brown and yellow-green algae) possess red-algal plastids (462). However, the brown algae, in comparison to the green algae, are considered evolutionarily to be very different from the green plants (green algae, bryophytes, vascular plants) and are not closely related to each other, according to modern phylogenetic results (111).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Aboutabl E, Afifi M, Ghanem N, Yokoyama R, Fukuyama Y, Asakawa Y (1999) Aromatic compounds from the egyptian moss Eucladium verticillatum (brid) B.S.G. J Hattori Bot Lab 86:175
Adio AM, Paul C, König WA, Muhle H (2002) Volatile components from european liverworts Marsupella emarginata, M. aquatica and M. alpina. Phytochemistry 61:79
Ageta H, Arai Y (1990) Chemotaxonomy of ferns, 3. Triterpenoids from Polypodium polypodioides. J Nat Prod 53:325
Anton H, Heinrichs J, Mues R, Gradstein SR (2000) Chemotaxonomical and Morphological Characterization of Plagiochila dusenii (Hepaticae), Most Closely Related to Plagiochila validissima. J Hattori Bot Lab 89:93
Aoki T, Ohro T, Hiraga Y, Suga T, Uno M, Ohta S (1997) Biologically Active Clerodane-type Diterpene Glycosides from the Root-stalks of Dicranopretis pedata. Phytochemistry 46:839
Arakawa Y, Toyota M, Nishizawa T, Soma G, Asakawa Y (2007) Bitter-Tasting Constituents of the Fern Onichium japonicum. 51st Symposium on Chemistry of Terpenes, Essential Oils and Aromatics. Nagahama, Japan, Symposium Papers, p 110
Aratani T, Okano M, Funaki Y, Mizui F (1981) Seasonal Variation of Sterol, Hydrocarbon, and Fatty Acid Fractions in Codium fragile (Sur.) Hariot. Bull J Soc Sci Fish 47:391
Asakawa Y (1982) Chemical Constituents of the Hepaticae. In: Herz W, Grisebach H, Kirby GW (eds) Progress in the Chemistry of Organic Natural Products, vol 42. Springer, Vienna, p 285
Asakawa Y (1995) Chemical Constituents of the Bryophytes. In: Herz W, Kirby GW, Moore RE, Steglich W, Tamm Ch (eds) Progress in the Chemistry of Organic Natural Products, vol 65. Springer, Vienna, p 618
Asakawa Y (2004) Chemosystematics of the Hepaticae. Phytochemistry 65:623
Asakawa Y, Toyota M, Taira Z, Takemoto T (1983) Riccardin A and Riccardin B, Two Novel Cyclic Bis(Bibenzyls) Possessing Cytotoxicity from the Liverwort Riccardia multifida (L.) S. Gray. J Org Chem 48:2164
Asakawa Y, Toyota M, Nakaishi E, Tada Y (1996) Distribution of Terpenoids and Aromatic Compounds in New Zealand Liverworts. J Hattori Bot Lab 80:271
Asakawa Y, Toyota M, Nakaishi E, Taka Y (1997) Distribution of Terpenoids and Aromatic Compounds in the Liverwort Isotachis species. J Hattori Bot Lab 83:257
Asakawa Y, Toyota M, Oiso Y, Braggins JE (2001) Occurrence of Polygodial and 1-(2,4,6-Trimethoxyphenyl)-but-2-en-1-one from Some Ferns and Liverworts: Role of Pungent Components in Bryophytes and Pteridophytes Evolution. Chem Pharm Bull 49:1380
Ayer WA, Law DA (1962) Lycopodium Alkaloids. IV. The Constitution and Stereochemistry of Lycoclavine, an Alkaloid of Lycopodium clavatum var. megastachyon. Can J Chem 40:2088
Ayyad S-EN, Abdel-Halim OB, Shier WT, Hoye TR (2003)) Cytotoxic Hydroazulene Diterpenoids from the Brown Alga Cystoseira myrica. Z Naturforsch 58c:33
Bardón A, Bovi Mitre G, Kamiya N, Toyota M, Asakawa Y (2002) Eremophilanolides and Other Constituents from the Argentine Liverwort Frullania brasiliensis. Phytochemistry 59:205
Ben Ali A, De Baere R, Van der Auwera G, De Wachter R, Van de Peer Y (2001) Phylogenetic Relationships among Algae Based on Complete Large-Subunit rRNA Sequences. Int J Syst Evol Microbiol 51:737
Bhattacharya D, Medlin L (1998) Algal Phylogeny and the Origin of Land Plants. Plant Physiol 116:9
Breitmaier E (2006) Terpenes: Flavors, Fragrances, Pharmaca. Pheromones, Wiley-VCH Verlag, Weinheim
Buchanan MS, Hashimoto T, Asakawa Y (1996) Phenyl Esters and Phaeophytins from the Hornwort Megaceros flagellaris. Phytochemistry 41:1373
Chakraborty K, Lipton AP, Raj RP, Vijayan KK (2010) Antibacterial Labdane Diterpenoids of Ulva fasciata Delile from Southern Coast of Indian Peninsula. Food Chem 119:1399
Chiu P-L, Patterson GW, Fenner GP (1985) Sterols of Bryophytes. Phytochemistry 24:263
Chiu P-L, Patterson GW, Salt TA (1988) Sterol Composition of Pteridophytes. Phytochemistry 27:819
Chopra RN, Kumra PK (2005) Biology of Bryophytes. New Age International Publishers, New Dehli, p 354
Cullmann F, Becker H (1998) Terpenoid and Phenolic Constituents of Sporophytes and Spores from the Liverwort Pellia epiphylla. J Hattori Bot Lab 84:285
Cullmann F, Becker H (1998) Terpenoid Constituents of Pellia epiphylla. Phytochemistry 47:237
De Napoli L, Magno S, Mayol L, Novellino E (1982) Sterol Composition of Some Mediterranean Green Algae. Phytochemistry 21:1993
De Rosa S, De Giulio A, Iodice C, Zavodink N (1994) Sesquiterpenes from the Brown Alga Taonia atomaria. Phytochemistry 37:1327
Dembitsky VM, Rezanka T, Bychek IA, Afonina OM (1993) Polar Lipid and Fatty Acid Composition of Some Bryophytes. Phytochemistry 33:1009
Dembitsky VM, Rezanka T, Bychek IA, Afonina OM (1993) Acetylenic Acids and Lipid Composition of Some Mosses from Russia. Phytochemistry 33:1021
Dembitsky VM, Rezanka T (1995) Distribution of Acetylenic Acids and Polar Lipids in Some Aquatic Bryophytes. Phytochemistry 40:93
Dembitsky VM, Tolstikov GA (2004) Natural Halogenated Sesquiterpenes from Marine Organisms. Chemistry for Sustainable Development 12:1
El Hattab M, Culioli G, Valls R, Richou M, Piovetti L (2008) Apo-fucoxanthinoids and Loliolide from the Brown Alga Cladostephus spongiosus f. verticillatus (Heteroconta, Sphacelaries). Biochem Syst Ecol 36:447
Enoki N, Furusaki A, Suehiro K, Ishida R, Matsumoto T (1983) Epoxydictymene, A New Diterpene from the Brown Alga Dictyota dichotoma. Tetrahedron Lett 24:4341
Fattorusso E, Magno S, Mayol L, Amico V, Oriente G, Piattelli M, Tringali C (1978) Isolation of (2S,8R)-Germacra-1(11),5(12), E6-trien-2-ol Acetate from the Brown Alga Dilophus fasciola. Tetrahedron Lett 43:4149
Fenical W, Sims JJ, Squatrito D, Wing RM, Radlick P (1973) Zonarol and Isozonarol, Fungitoxic Hydroquinones from the Brown Seaweed Dictyopteris zonarioides. J Org Chem 38:2383
Geiger H, Seeger T, Zinsmeister HD, Frahm J-P (1997) The Occurrence of Flavonoids in Arthrodontous Mosses – An Account of the Present Knowledge. J Hattori Bot Lab 83:273
González AG, Ciccio JF, Rivera AP, Martin JD (1985) New Halogenated Diterpenes from the Red Alga Laurencia perforata. J Org Chem 50:1261
Grammes C, Burkhardt G, Veith M, Huch V, Becker H (1997) Epi-neoverrucosane- and Epi-homoverrucosane-type Diterpenoids from Fossombronia alaskana. Phytochemistry 44:1495
Gribble GW (2010) Naturally Occurring Organohalogen Compounds – A Comprehensive Update. In: Kinghorn AD, Falk H, Kobayashi J (eds) Progress in the Chemistry of Organic Natural Products, vol 91. Springer-Verlag, Vienna, New York, p 616
Hackl T, König WA, Muhle H (2004) Isogermacrene A, a Proposed Intermediate in Sesquiterpene Biosynthesis. Phytochemistry 65:2261
Hall SS, Faulkner DJ, Fayos J, Clardy J (1973) Oppositol, a Brominated Sesquiterpene Alcohol of a New Skeletal Class from the Red Alga. Laurencia subopposita J Am Chem Soc 95:7187
Harinantenaina L, Asakawa Y (2004) Chemical Constituents of Malagasy Liverworts, Part II: Mastigophoric Acid Methyl Ester of Biogenetic Interest from Mastigophora diclados (Lepicoleaceae subf. Mastigophoraceae). Chem Pharm Bull 52:1382
Harinantenaina L, Asakawa Y (2004) Constituents of Isotachis aubertii (Isotachidiaceae) Collected in Madagascar. Biochem Syst Ecol 32:1073
Harinantenaina L, Kurata R, Asakawa Y (2005) Chemical Constituents of Malagasy Liverworts, Part III: Sesquiterpenoids from Bazzania decrescens and Bazzania madagassa. Chem Pharm Bull 53:515
Hashimoto T, Irita H, Yoshida M, Kikkawa A, Toyota M, Koyama H, Motoike Y, Asakawa Y (1998) Chemical Constituents od the Japanese Liverworts Odontoschisma denudatum, Porella japonica, P. acutifolia subsp. tosana and Frullania hamatiloba. J Hattori Bot Lab 84:309
Hashimoto T, Kikkawa A, Yoshida M, Tanaka M, Asakawa Y (1998) Two Novel Skeletal Diterpenoids, Neodenudatenones A and B, from the Liverwort Odontoschisma denudatum. Tetrahedron Lett 39:3791
Hashimoto T, Toyota M, Koyama H, Kikkawa A, Yoshida M, Tanaka M, Takaoka S, Asakawa Y (1998) Novel ent-Vibsane- and Dolabellane-type Diterpenoids from the Liverwort Odontoschisma denudatum. Tetrahedron Lett 39:579
Hashimoto T, Tanaka M, Asakawa Y (2006) New Diterpenoids from the Liverworts Plagiochila sciophila and Odontoschisma denudatum. 50th Symposium on Chemistry of Terpenes, Essential Oils and Aromatics. Yokohama, Japan, Symposium Papers, p 361
Hori H, Lim B-L, Osawa S (1985) Evolution of Green Plants as Deduced from 5S rRNA Sequences. Proc Natl Acad Sci USA 82:820
Hseu TH, Wang JL, Tang CP (1980) The Structure of Onychiol B, [1aS,3aS-(1β,1aα,3aβ,5α,5aα,6α,10aβ)]-1-[1-(Hydroxymethyl)vinyl]-3a,5a,8-trimethyl-2,3,3a,4,5,5a,9,10,10a,10b-decahydro-1H,6H-cyclohept[e]indene-5,6-diol: A Diterpene Alcohol from Onychium japonicum (Thumb.) Kunze. Acta Cryst 36B:2802
Huang X-P, Zhu X-B, Deng L-P, Deng Z-W, Lin W-H (2006) Cycloartane Triterpenes from Marine Green Alga Cladophora fascicularis. Chin J Oceanol Limnol 24:443
Iliopoulou D, Vagias C, Galanakis D, Argyropoulos D, Rousis V (2002) Brasilane-type Sesquiterpenoids from Laurencia obtusa. Org Lett 4:3263
Irita H, Hashimoto T, Fukuyama Y, Asakawa Y (2000) Herbertane-type Sesquiterpenoids from the Liverwort Herbertus sakuraii. Phytochemistry 55:247
Jamieson GR, Reid EH (1972) The Component Fatty Acids of Some Marine Algal Lipids. Phytochemistry 11:1423
Juagdan EG, Kalidindi R, Scheuer P (1997) Two New Chamigranes from a Hawaiian Red Alga. Laurencia cartilaginea Tetrahedron 53:521
Kajiwara T, Hatanaka A, Tanaka Y, Kawai T, Ishihara M, Tsuneya T, Fujimura T (1989) Volatile Constituents from Marine Brown Algae of Japanese Dictyopteris. Phytochemistry 28:636
Kamaya R, Tanaka Y, Hiyama R, Ageta H (1990) Fern Constituents: Triterpenoids Isolated from the Leaves of Cheiropleuria biscupis. Chem Pharm Bull 38:2130
Karol KG, McCourt RM, Comino MT, Delwiche CF (2001) The Closest Living Relatives of Land Plants. Science 294:2351
Karunen P (1990) The Acyl Lipids of Bryophytes. In: Zinsmeister HD, Mues R (eds) Bryophytes. Oxford, UK, Clarendon Press, Their Chemistry and Chemical Taxonomy, p 121
Kazlauskas R, Mulder J, Murphy PT, Wells RJ (1980) New Metabolites from the Brown Alga Caulocystis cephalornithos. Aust J Chem 33:2097
Kazlauskas R, Murphy PT, Wells RJ, Daly JJ, Oberhansli WE (1977) Heterocladol, a Halogenated Selinene Sesquiterpene of Biosynthetic Significance from the Red Alga Laurencia filiformis: Its Isolation, Crystal Structure and Absolute Configuration. Aust J Chem 30:2679
Kimura J, Maki N (2002) New Loliolide Derivatives from the Brown Alga Undaria pinnatifida. J Nat Prod 65:57
Kladi M, Xenaki H, Vagias C, Papazafiri P, Roussis V (2006) New Cytotoxic Sesquiterpenes from the Red Algae Laurencia obtusa and Laurencia microcladia. Tetrahedron 62:182
Kobayashi J, Ishibashi M (1999) Marine Natural Products and Marine Chemical Ecology. In: Barton D, Nakanishi K, Meth-Cohn O (eds) Comprehensive Natural Products Chemistry, vol 8. Elsevier, Amsterdam Lausanne New York Oxford Shannon Singapore Tokyo, p 420
König WA, Bülow N, Fricke C, Melching S, Rieck A, Muhle H (1996) The Sesquiterpene Constituents of the Liverwort Preissia quadrata. Phytochemistry 43:629
Kraut L, Mues R (1999) The First Biflavone Found in Liverworts and Other Phenolics and Terpenoids from Chandonanthus hirtellus ssp. giganteus and Plagiochila asplenoides. Z Naturforsch 54c:6
Kraut L, Klaus T, Mues R, Eicher T, Zinsmeister HD (1997) Isolation and Synthesis of Rufulamide, an Oligopeptide Analogue from Metzgeria rufula. Phytochemistry 45:1621
Kraut L, Mues R, Zinsmeister HD (1997) Prenylated Bibenzyl Derivatives from Lethocolea glossophylla and Radula voluta. Phytochemistry 45:1249
Kunz S, Burkhardt G, Becker H (1994) Riccionidins A and B, Anthocyanidins from the Cell Walls of the Liverwort Ricciocarpos natans. Phytochemistry 35:233
Labbé C, Faini F, Villagrn C, Coll J, Rycroft DS (2005) Antifungal and Insect Antifeedant 2-Phenylethanol Esters from the Liverwort Balantiopsis cancellata from Chile. J Agric Food Chem 53:247
Lahlou EH, Hashimoto T, Asakawa Y (2000) Highly Oxygenated Sesquiterpenes from the Liverwort Trocholejeunea sandvicensis. Phytochemistry 53:271
Le Corguillé G, Pearson G, Valente M, Viegas C, Gschloessl B, Corre E, Bailly X, Peters AF, Jubin C, Vacherie B, Cock JM, Leblanc C (2009) Plastid Genomes of Two Brown Algae, Ectocarpus siliculosus and Fucus vesiculosus: Further Insights on the Evolution of Red-Algal Derived Plastids. BMC Evolutionary Biol 9:253
Lewis LA, McCourt RM (2004) Green Algae and the Origin of Land Plants. Am J Bot 9:1535
Li X, Wurtele ES, LaMotte CE (1994) Abscisic Acid is Present in Liverworts. Phytochemistry 37:625
Lim B-L, Kawai H, Hori H, Osawa S (1986) Molecular Evolution of 5S Ribosomal RNA from Red and Brown Algae. Jpn J Genet 61:169
Ludwiczuk A, Asakawa Y (2010) Chemosystematics of Selected Liverworts Collected in Borneo. Tropical Bryology 31:33
Ludwiczuk A, Nagashima F, Gradstein SR, Asakawa Y (2008) Volatile Components from the Selected Mexican, Ecuadorian, Greek, German and Japanese Liverworts. Nat Prod Commun 3:133
Ludwiczuk A, Komala I, Pham A, Bianchini J-P, Raharivelomanana P, Asakawa Y (2009) Volatile Components from Selected Tahitian Liverworts. Nat Prod Commum 4:1387
Lyakhova EG, Kalinovcky AI, Kolensikova SA, Vaskovsky VE, Stonik VA (2004) Halogenated Diterpenoids from the Red Alga Laurencia nipponica. Phytochemistry 65:2527
Manske RHF, Marion L (1947) The Alkaloids of Lycopodium Species. IX. Lycopodium annotinum var. acrifolium Fern. and the Structure of Annotine. J Am Chem Soc 69:2126
Markham KR (1990) Bryophyte Flavonoids, Their Structures, Distribution, and Evolutionary Significance. In: Zinsmeister HD, Mues R (eds) Bryophytes. Oxford, UK, Clarendon Press, Their Chemistry and Chemical Taxonomy, p 143
Markham KR, Porter LJ (1977) Flavonoids in the Green Algae (Chlorophyta). Phytochemistry 8:1777
Markham KR, Porter LJ (1979) Flavonoids of the Primitive Liverwort Takakia and Their Taxonomic and Phylogenetic Signifficance. Phytochemistry 18:611
Matsuo A, Ono K, Hamasaki K, Nozaki H (1996) Phaeophytins from a Cell Suspension Culture of the Liverwort Plagiochila ovalifolia. Phytochemistry 42:427
Matsuo Y, Suzuki M, Masuda M, Iwaki T, Morimoto Y (2008) Squalene-Derived Triterpene Polyethers from the Red Alga Laurencia omaezakiana. Helv Chim Acta 91:1261
McCourt RM, Delwiche CF, Karol KG (2004) Charophyte Algae and Land Plants Origins. Trends Ecol Evol 19:661
Mekem Sonwa M, König WA (2003) Chemical Constituents of the Essential Oil of the Hornwort Anthoceros caucasicus. Flavour Frag J 18:286
Mendez J, Sanz-Cabanilles F (1979) Cinnamic Acid Esters in Anthoceros Species. Phytochemistry 18:1409
Moreira D, Le Guyager H, Phillipe H (2000) The Origin of Red Algae and the Evolution of Chloroplast. Nature 405:69
Nagashima F, Momosaki S, Watanabe Y, Toyota M, Huneck S, Asakawa Y (1996) Terpenoids and Aromatic Compounds from Six Liverworts. Phytochemistry 41:207
Nagashima F, Murakami Y, Asakawa Y (1999) A Novel Skeletal Diterpenoid from the German Liverwort Barbilophozia hatcheri (Evans) Loeske. Chem Pharm Bull 47:138
Nagashima F, Matsumura N, Ashigaki Y, Asakawa Y (2003) Chemical Constituents of the Liverworts Bryopteris filicina, Plagiochila asplenioides and Porella canariensis. J Hattori Bot Lab 94:197
Nagashima F, Sekiguchi T, Takaoka S, Asakawa Y (2004) Terpenoids and Aromatic Compounds from the New Zealand Liverwort Plagiochila, Schistochila and Heteroscyphus Species. Chem Pharm Bull 52:556
Nagashima F, Kuba Y, Asakawa Y (2006) Diterpenoids and Aromatic Compounds from the Three New Zealand Liverworts Jamesoniella kirkii, Balantiopsis rosea and Radula species. Chem Pharm Bull 54:902
Nozaki H, Hayashi K-I, Nishimura N, Kawaide H, Matsuo A, Takaoka D (2007) Momilactone A and B as Allelochemicals from Moss Hypnum plumaeforme: First Occurrence in Bryophytes. Biosci Biotechnol Biochem 71:3127
Oiso Y, Toyota M, Asakawa Y (1999) Occurrence of a Bisbibenzyl Derivative in the Japanese Fern Hymenophyllum barbatum: First Isolation and Identification of Perrittetin H from the Pteridophytes. Chem Pharm Bull 47:297
Omatsu I (2004) Phytochemical Studies on 14 New Zealand Liverworts. Tokushima Bunri University, Tokushima, Japan, Master’s Thesis
Patterson GW (1972) Sterols of Nitella flexilis and Chara vulgaris. Phytochemistry 11:3481
Patterson GW, Wolfe GR, Salt TA, Chiu P-L (1990) Sterols of Bryophytes with Emphasis on the Configuration at C-24. In: Zinsmeister HD, Mues R (eds) Bryophytes. Oxford, UK, Clarendon Press, Their Chemistry and Chemical Taxonomy, p 103
Pryce RJ (1972) The Occurrence of Lunularic and Abscisic Acids in Plants. Phytochemistry 11:1759
Puglisi MP, Tan LT, Jensen PR, Fenical W (2004) Capisterones A and B from the Tropical Green Alga Penicillus capitatus: Unexpected Anti-fungal Defenses Targeting the Marine Pathogen Lindra thallasiae. Tetrahedron 60:7053
Qiu Y-L, Li L, Wang B, Chen Z, Knoop V, Groth-Malonek M, Dombrovska O, Lee J, Kent L, Rest J, Estabrook GF, Hendry TA, Taylor DW, Testa CM, Ambros M, Crandall-Stotler B, Duff RJ, Stech M, Frey W, Quandt D, Davis CC (2006) The Deepest Divergences in Land Plants Inferred from Phylogenomic Evidence. Proc Natl Acad Sci USA 103:15511
Renzaglia KS, McFarland KD, Smith DK (1997) Anatomy and Ultrastructure of the Sporophyte of Takakia ceratophylla (Bryophyta). Am J Bot 84:1337
Rodríguez AD, González E, Ramírez C (1998) The Structural Chemistry, Reactivity, and Total Synthesis of Dolabellane Diterpenoids. Tetrahedron 54:11683
Roussis V, King RL, Fenical W (1993) Secondary Metabolite Chemistry of the Australian Brown Alga Encyothalia cliftonii: Evidence for Herbivore Chemical Defence. Phytochemistry 34:107
Rycroft DS, Cole WJ (2001) Hydroquinone Derivatives and Monoterpenoids from the Neotropical Liverwort Plagiochila rutilans. Phytochemistry 57:479
Salm RF, Zinsmeister HD, Eicher T (1998) Nitrogen-containing Compounds from the Moss Fontinalis squamosa. Phytochemistry 49:887
Sansom CE, Larsen L, Perry NB, Berridge MV, Chia EW, Harper JL, Webb VL (2007) An Antiproliferative Bis-prenylated Quinone from the New Zealand Brown Alga Perithalia capillaris. J Nat Prod 70:2042
Saritas Y, Mekem Sonwa M, Iznaguen H, König WA, Muhle H, Mues R (2001) Volatile Constituents in Mosses (Musci). Phytochemistry 57:443
Sassa T, Tajima N, Sato M, Takahashi A, Kato N (2002) Fisicoccins P and Q, and 3-Epifusicoccins H and Q, New Polar Fisicoccins from Isolate Niigata 2-A of Peach Fusicoccum Canker Fungus. Biosci Biotechnol Biochem 66:2356
Sewón P (1992) Fatty Acyl Composition of Monogalactosyldiacyl Glycerols in Bryophyta. Phytochemistry 31:3461
Sewón P, Hellevuo T, Schmidt A, Becker H (2000) Fatty Acid Composition of Monogalactosyldiacylglycerols in Anthoceros agrestis and Conocephalum conicum. J Hattori Bot Lab 89:283
Shen Y-C, Tsai PI, Fenical W, Hay ME (1993) Secondary Metabolite Chemistry of the Caribbean Marine Alga Sporochnus bolleanus: A Basis for Herbivore Chemical Defense. Phytochemistry 32:71
Shi DY, Han LJ, Sun J, Yang YC, Shi JG, Fan X (2005) Studies on the Chemical Constituents of the Green Alga Chaetomorpha basiretorsa. Zhongguo Zhong Yao Za Zhi 30:1162
Shi DY, Han LJ, Sun J, Yang YC, Fan X, Shi JG (2007) Sesquiterpenes and Their Derivatives from the Marine Green Alga Chaetomorpha basiretorsa. Zhongcaoyao 38:496
Shiojima K, Arai Y, Masuda K, Kamada T, Ageta H (1983) Fern Constituents: Polypodatetraenes, Novel Bicyclic Triterpenoids Isolated from Polypodiaceous and Aspidiaceous Plants. Tetrahedron Lett 24:5733
Shiojima K, Suzuki M, Aoki H, Ageta H (1995) Fern Constituents: Four New Diterpenoid Glycosides from Fresh Leaflets of Gleichenia japonica. Chem Pharm Bull 43:5
Siamopoulou P, Bimplakis A, Iliopoulou D, Vagias C, Cos P, Berghe DV, Roussis V (2004) Diterpenes from the Brown Algae Dictyota dichotoma and Dictyota linearis. Phytochemistry 65:2025
Siddiqui HL, Munesada K, Suga T (1991) Biologically Active Novel Clerodane-type Diterpene Glycosides from the Root-stalks of Gleichenia japonica. Chem Lett: 701
Siems K, Weigt F, Wollenweber E (1996) Drimanes from the Epicuticular Wax of the Fern Nephrolepis biserrata. Phytochemistry 41:1119
Socolsky C, Muruaga N, Bardón A (2005) Drimanes and Other Terpenoids from the Fern Thelypteris hispidata (Decne.) Reed. Chem Biodivers 2:1105
Suire C, Bourgeois G, Koponen T (2000) Some Chemical Constituents of Thirteen Mosses from the Traditional Mniaceae Family. J Hattori Bot Lab 89:233
Suzuki M, Kurosawa E (1978) New Aromatic Sesquiterpenoids from the Red Alga Laurencia okamurai. Tetrahedron Lett 28:2503
Suzuki M, Kowata N, Kurosawa E (1981) Epicubebol and Related Sesquiterpenoids from the Brown Alga Dictyopteris divaricata. Bull Chem Soc Jpn 54:2366
Suzuki M, Segawa M, Kikuchi H, Suzuki T, Kurosawa E (1985) (5S,7R,10R)-Selin-4(14)-en-5α-ol, a Sesquiterpene Alcohol from the Red Alga Laurencia nipponica. Phytochemistry 24:2011
Suzuki T, Suzuki M, Kurosawa E (1975) α-Bromocuparene and α-Isobromocuparene, New Bromo Compounds from Laurencia species. Tetrahedron Lett 16:3057
Takeda R, Hasegawa J, Shinozaki M (1990) The First Isolation of Lignans, Megacerotonic Acid and Anthocerotonic Acid, from Non-Vascular Plants, Anthocerotae (Hornworts). Tetrahedron Lett 31:4159
Talpir R, Rudi A, Kashman Y, Loya Y, Hizi A (1994) Three New Sesquiterpene Hydroquinones from Marine Origin. Tetrahedron 50:4179
Tanaka N, Maehashi H, Saito S, Murakami T, Saiki Y, Chen C-M, Iitaka Y (1980) Chemical and Chemotaxanomical Study of Ferns. XXXI. Chemical Studies on the Constituents of Arachinoides standishii Ohwi. Chem Pharm Bull 28:3070
Tanaka N, Wada H, Murakami T, Sahashi N, Ohmoto T (1986) Chemische und Chemotaxonomische Untersuchungen der Pterophyten. LXIV. Chenische Untersuchungen der Inhaltsstoffe von Sceptridium ternatum var. ternatum. Chem Pharm Bull 34:3727
Tazaki H, Hayashida T, Nakasuga I, Nabeta K (1999) Terpenoids from the Liverworts Bazzania yoshinagana and Porella fauriei. Res Bull Obihiro Univ 21:53
Tazaki H, Ito M, Miyosgi M, Kawabata J, Fukushi E, Fijita T, Motouri M, Furuki T, Nabeta K (2002) Subulatin, an Antioxidic Caffeic Acid Derivative Isolated from the in vitro Cultured Liverworts, Jungermannia subulata, Lophocolea heterophylla, and Scapania parvitexta. Biosci Biotechnol Biochem 66:255
Teixeira VL, Cavalcanti DN, Pereira RC (2001) Chemosystematic Study of the Diterpenes from the Brown Alga Dictyota. Biochem Syst Ecol 29:313
Thomas RJ (1975) Lipid Composition of Maturing and Elongate Liverwort Sporophytes. Phytochemistry 14:623
Tori M, Nakashima K, Seike M, Asakawa Y (1994) Revised Structure of a Brasilane-type Sesquiterpene Isolated from the Red Alga Laurencia implicata and its Absolute Configuration. Tetrahedron Lett 35:3105
Toyota M, Nagashima F, Asakawa Y (1989) Volatile Components and **uisane-type Sesquiterpenoids from the Liverwort Porella cordaeana. Phytochemistry 28:3383
Toyota M, Nakaishi E, Asakawa Y (1996) Terpenoid Constituents of the New Zealand Liverwort Jamesoniella tasmanica. Phytochemistry 43:1057
Toyota M, Koyama H, Asakawa Y (1997) Sesquiterpenoids from the Three Japanese Liverworts Lejeunea aquatica. L flava and L japonica Phytochemistry 46:145
Toyota M, Saito T, Matsunami J, Asakawa Y (1997) A Comparative Study on Three Chemo-types of the Liverwort Conocephalum conicum Using Volatile Constituents. Phytochemistry 44:1265
Toyota M, Yoshida T, Asakawa Y (1997) Chemical Constituents of 12 Selected Japanese Liverworts. J Hattori Bot Lab 81:249
Toyota M, Kimura K, Asakawa Y (1998) Occurrence of ent-Sesquiterpene in the Japanese Moss – Plagiomnium acutum: First Isolation and Identification of ent-Sesqui- and Dolabellane-type Diterpenoids from the Musci. Chem Pharm Bull 46:1488
Toyota M, Masuda K, Asakawa Y (1998) Triterpenoid Constituents of the Moss Floribundaria aurea subsp. nipponica. Phytochemistry 48:297
Toyota M, Omatsu I, Braggins J, Asakawa Y (2006) Lipid Constituents of the New Zealand Liverwort Plagiochila circinalis. J Oleo Sci 55:579
Toyota M, Omatsu I, Braggins J, Asakawa Y (2009) Pungent Aromatic Compounds from New Zealand Liverwort Hymenophyton flabellatum. Chem Pharm Bull 57:1015
Trennheuser F, Burkhardt G, Becker H (1994) Anthocerodiazonin, an Alkaloid from Anthoceros agrestis. Phytochemistry 37:899
Valcic S, Huch V, Veith M, Becker H (1995) 13-epi-Homoverrucosane Derivatives and Other Diterpenes from Plagiochila (Hepaticae). Phytochemistry 40:199
van Alstyne KL, Wolfe GV, Freidenburg TL, Neill A, Hicken C (2001) Activated Defense Systems in Marine Macroalgae: Evidence for an Ecological Role for DMSP Cleavage. Mar Ecol Prog Ser 213:53
Vogelsang K, Schneider B, Petersen M (2006) Production of Rosmarinic Acid and a New Rosmarinic Acid 3-′O-β-d-glucoside in Suspension Cultures of the Hornwort Anthoceros agrestis Paton. Planta 223:369
von Reuß SH (2009) Structure Elucidation and Synthesis of New Secondary Metabolites from Liverworts and Microorganisms and Investigation of their Biogenesis. Ph.D. thesis, University of Hamburg
von Reuβ SH, König WA (2005) Olefinic Isothiocyanates and Iminodithiocarbonates from the Liverwort Corsinia coriandrina. Eur J Org Chem: 1184
Wang X-N, Yu W-T, Lou H-X (2005) Antifungal Constituents from the Chinese Moss Homalia trichomanoides. Chem Biodivers 2:139
Wang Y, Harrison LJ, Tan BC (2009) Terpenoids from the Liverwort Chandonanthus hirtellus. Tetrahedron 65:4035
Warmers U, Wihstutz K, Bülow N, Fricke C, König WA (1998) Sesquiterpene Constituents of the Liverworts Calypogeia muelleriana. Phytochemistry 49:1723
Wellman CH, Osterloff PL, Mohluddln U (2003) Fragments of the Earliest Land Plants. Nature 425:282
Wollenweber E, Favre-Bonvin J (1979) Novel Dihydrostilbene from Fronds of Notholaena dealbata and Notholaena limitanea. Phytochemistry 18:1243
Wright AD, König GM, Sticher O (1991) New Sesquiterpenes and C15-Acetogenins from the Marine Red Alga Laurencia implicata. J Nat Prod 54:1025
Wu C, Gunatilaka AAL, McCabe FL, Johnson RK, Spjut RW, Kingston DGI (1997) Bioactive and Other Sesquiterpenes from Chiloscyphus rivularis. J Nat Prod 60:1281
Zhang W-H, Zhong H-M, Che C-T (2005) Cycloartanes from the Red Algae Galaxaura sp. J Asian Nat Prod Res 7:59
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2013 Springer-Verlag Wien
About this chapter
Cite this chapter
Asakawa, Y., Ludwiczuk, A., Nagashima, F. (2013). Chemical Relationships Between Algae, Bryophytes, and Pteridophytes. In: Chemical Constituents of Bryophytes. Progress in the Chemistry of Organic Natural Products, vol 95. Springer, Vienna. https://doi.org/10.1007/978-3-7091-1084-3_9
Download citation
DOI: https://doi.org/10.1007/978-3-7091-1084-3_9
Published:
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-1083-6
Online ISBN: 978-3-7091-1084-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)