Abstract
More than 14,000 species belonging to the Bryophyta (mosses) are known, but, only a small percentage of these taxa have been analyzed chemically (40). In particular, the distribution of flavonoids in the Bryophyta has been studied by a German group (250). The distribution of terpenoids, simple benzoic, cinnamic, and phthalic acid derivatives, coumarins, and some nitrogen-containing aromatic compounds, the benzonaphthoxanthenones, has been investigated from several species of the Bryophyta. One of the most interesting recent discoveries concerning the chemical constituents of the Bryophyta is that Plagiomnium acutum (Mniaceae), belonging to the Eubryales, produces enantiomers of sesqui- and diterpenoids of those found in higher plants (884).
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
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
Acharya SP, Brown HC (1970) Hydroboration of terpenes. VI Hydroboration of α- and β-cedrenes Configurational Assignments for the Related Cedrane Derivatives J Org Chem 35:196
Adio AM, Paul C, König WA, Muhle H (2002) Volatile components from european liverworts Marsupella emarginata, M. aquatica and M. alpina. Phytochemistry 61:79
Adio AM, von Reuβ SH, Paul C, Muhle H, König WA (2007) Sesquiterpenoid constituents of the liverwort Marsupella aquatica. Tetrahedron Asymm 18:1245
Allen JRF, Holmstedt BR (1980) The Simple β-Carboline Alkaloids. Phytochemistry 19:1573
Amico V, Currenti R, Oriente G, Piattelli M, Tringali C (1981) 18-Hydroxy-3,7-dolabelladiene from the Brown Alga. Dictyota dichotoma Phytochemistry 20:848
Anhut S, Seeger T, Zinsmeister HD, Geiger H (1989) New Dihydrobiflavones from the Moss Plagiomnium cuspidatum. Z Naturforsch 44c:189
Arai Y, Yamaide M, Yamazaki S, Ageta H (1991) Fern Constituents: Triterpenoids Isolated from Polypodium vulgare. P fauriei and P virginianum Phytochemistry 30:3369
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, Toyota M, Nakaishi E, Tada Y (1996) Distribution of Terpenoids and Aromatic Compounds in New Zealand Liverworts. J Hattori Bot Lab 80:271
Basile A, Giordano S, Lopez-Saez JA, Castaldo Cobianchi R (1999) Antibacterial Activity of Pure Flavonoids Isolated from Mosses. Phytochemistry 52:1479
Batta AK, Ragaswani S (1969) Chemical Constituents of Polyporus dryadeus var. brevisporus and Fomes allardii. Phytochemsitry 8:1309
Becker R, Mues R, Zinsmeister HD, Herzog F, Geiger H (1986) A New Biflavone and Further Flavonoids from the Moss Hylocomium splendens. Z Naturforsch 41c:507
Cross BE, Calt RHB, Hanson JR, Curtis PJ, Grove JF, Morrison A (1963) New Metabolites of Gibberella fujikuroi. Part II. The Isolation of Fourteen New Metabolites. J Chem Soc: 2837
Dembitsky VM, Rezanka T (1995) Distribution of Acetylenic Acids and Polar Lipids in Some Aquatic Bryophytes. Phytochemistry 40:93
Fenical W, Sims JJ, Wing RM, Radlick PC (1972) Zonarene, a Sesquiterpene from the Brown Seaweed Dictyopteris zonarioides. Phytochemistry 11:1161
Fu P, Lin S, Shan L, Shen Y-H, Tang J, Liu R-H, Zhang X, Zhu R-L, Zhang W-D (2009) Constituents of the Moss Polytrichum commune. J Nat Prod 72:1335
Geiger H, Seeger T, Hahn H, Zinsmeister HD, Markham KR, Wong H (1993) 1H-NMR Assignments in Biflavonoid Spectra by Proton-Detected C-H Correlation. Z Naturforsch 48c:821
Geiger H, Voigt A, Seeger T, Zinsmeister HD, Lopez-Saez J-A, Perez-Alonso M-J Velasco-Negeruela A (1995) Cyclobartramiatriluteolin, a Unique Triflavonoid from Bartramia stricta. Phytochemistry 39:465
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
Hahn H, Seeger T, Geiger H, Zinsmeister HD, Markham K, Wong H (1995) The First Biaurone, a Triflavone and Biflavonoids from Two Aulacomnium Species. Phytochemistry 40:573
Hayashi K, Kawaide H, Notomi M, Sakigi Y, Matsuo A, Nozaki H (2006) Identification and Functional Analysis of Bifunctional ent-Kaurene Synthase from the Moss Physcomitrella patens. FEBS Lett 580:6175
Huneck S, Yoshimura I (1996) Identification of Lichen Substances. Berlin, Springer, p 493
Jackovic N, Andrade PB, Valentao P, Sobovljevic M (2008) HPLC-DAD of Phenolics in Bryophytes Lunularia cruciata, Brachytheciastrum velutinum and Kindbergia praelonga. J Serb Chem Soc 73:1161
Jung M, Zinsmeister HD, Geiger H (1994) New Three- and Tetraoxygenated Coumarin Glucosides from the Mosses Atrichum undulatum and Polytrichum formosum. Z Naturforsch 49c:697
Jung M, Geiger H, Zinsmeister HD (1995) Tri- and Tetrahydroxycoumarin Derivatives from Tetraphis pellucida. Phytochemistry 39:379
Kamaya R, Tanaka Y, Hiyama R, Ageta H (1990) Fern Constituents: Triterpenoids Isolated from the Leaves of Cheiropleuria biscupis. Chem Pharm Bull 38:2130
Karawya SM, Abdel Wahab SM, El-Olemy MM, Farrag NM (1984) Diphenyl Amine as an Antihyperglycemic Agent from Onion and Tea. J Nat Prod 47:775
Kato T, Kabuto C, Sasaki N, Tsunagawa M, Aizawa H, Fujita K, Kato Y, Kitahara Y, Takahashi N (1973) Momilactones, Growth Inhibitors from Rice. Oryza sativa L Tetrahedron Lett 14:3861
Kim SJ, Park HR, Park E, Lee SC (2007) Cytotoxic and Antitumor Activity of Momilactone B from Rice Hulls. J Agric Food Chem 77:1702
König WA, Bülow N, Saritas Y (1999) Identification of Sesquiterpene Hydrocarbons by Gas Phase Analytical Methods. Flavour Fragr J 14:367
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
Markham KR, Andersen QM, Viotto ES (1988) Unique Biflavonoid Types from the Moss Dicranoloma robustum. Phytochemistry 27:1745
Morais R, Harrison LJ, Becker H (1988) (+)-Gymnomitr-8(12)-en-9α-ol and (R)-(-)-8,11-Dihydro-α-cuparenone, Two Novel Sesquiterpenoids from the Liverwort Reboulia hemisphaerica. J Chem Res (S): 380
Nagashima F, Kondoh M, Kawase M, Simizu S, Osada H, Fuji M, Watanabe Y, Sato M, Asakawa Y (2003) Apoptosis-inducing Properties of ent-Kaurene-type Diterpenoids from the Liverwort Jungermannia trunctata. Planta Med 69:377
Nose M, Nakatani Y, Yamanishi T (1971) Studied on Flavor of Green Tea. Part IX. Identification and Composition of Intermediate and High Boiling Constituents in Green Tea Flavor. Agric Biol Chem 35:261
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
Omatsu I (2004) Phytochemical Studies on 14 New Zealand Liverworts. Tokushima Bunri University, Tokushima, Japan, Master’s Thesis
Osterdahl B (1979) Chemical Studies on Bryophytes. 22. Flavonoid C-Glycosides of Mnium undulatum. Acta Chem Scand B 33:400
Otomo K, Kanno Y, Motegi A, Kenmoku H, Yamane H, Mitsuhashi W, Oikawa H, Toshima H, Itoh H, Mitsuoka M, Sasa T, Toyomasu T (2004) Diterpene Cyclases Responsible for the Biosynthesis of Phytoalexins, Momilactones A, B, and Oryzalexins A-F in Rice. Biosci Biotechnol Biochem 68:2001
Rampendahl C, Seeger T, Geiger H, Zinsmeister HD (1996) The Biflavonoids from Plagiomnium undulatum. Phytochemistry 41:1621
Salm RF, Zinsmeister HD, Eicher T (1998) Nitrogen-containing Compounds from the Moss Fontinalis squamosa. Phytochemistry 49:887
Saritas Y, Mekem Sonwa M, Iznaguen H, König WA, Muhle H, Mues R (2001) Volatile Constituents in Mosses (Musci). Phytochemistry 57:443
Seeger T, Geiger H, Zinsmeister HD (1992) Isolierung und Strukturaufklärung von Bartramia-Triluteolin, Bartramiasäure und einigen Biflavonoiden aus dem Laubmoos Bartramia pomiformis. Z Naturforsch 47c:527
Seeger T, Voigt A, Geiger H, Zinsmeister HD, Schilling G, Lopez-Saez J-A (1995) Isomeric Triluteolins from Bartramia stricta and Bartramia pomiformis. Phytochemistry 40:1531
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
Sievers H, Burkhardt G, Becker H, Zinsmeister HD (1992) Hypnogenols and Other Dihydroflavonols from the Moss Hypnum cupressiforme. Phytochemistry 31:3233
Sievers H, Burkhardt G, Becker H, Zinsmeister HD (1994) Further Biflavonoids and 3′-Phenylflavonoids from Hypnum cupressiforme. Phytochemistry 35:795
Suire C, Bourgeois G, Koponen T (2000) Some Chemical Constituents of Thirteen Mosses from the Traditional Mniaceae Family. J Hattori Bot Lab 89:233
Tanaka R, Ohmowi K, Mintura K, Matsunaga S (1996) Two New Epoxyserratanes from the Cuticle of Picea jezoensis. J Nat Prod 59:237
Tanaka R, Tsujimoto K, Matsunaga S (1999) Two Serratane Triterpenes from the Stem Bark of Picea jezoensis var. hondoensis. Phytochemistry 52:1581
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
Vasconcelos JMJ, Silva AMS, Cavaleiro JAS (1998) Chromones and Flavanones from Artemisia campestris subsp. maritima. Phytochemistry 49:1421
Wang X-N, Yu W-T, Lou H-X (2005) Antifungal Constituents from the Chinese Moss Homalia trichomanoides. Chem Biodivers 2:139
Wilderman PR, Xu M, Jin Y, Coates RM, Peter RJ (2004) Identification of syn-Pimara-7,15-diene Synthase Reveals Functional Clustering of Terpene Synthases Involved in Rice Phytoalexin/Allelochemicals Biosynthesis. Plant Physiol 135:2098
Wu C-L, Huang C-D, Shih T-L (1993) A Sesquiterpene Oxide of a Novel Skeleton from the Liverwort Plagiochila peculiaris. Tetrahedron Lett 34:4855
Zheng GQ, Chang CJ, Stout TJ, Clardy J, Cassady JM (1989) Ohioensin-A: A Novel Benzonaphthoxanthenone from Polytrichum ohioense. J Am Chem Soc 111:5500
Zheng GQ, Chang CJ, Stout TJ, Clardy J, Ho DK, Cassady JM (1993) Ohioensins: Novel Benzonaphthoxanthenones from Polytrichum ohioense. J Org Chem 58:366
Zheng GQ, Ho DK, Elder PJ, Stephens RE, Cottrell CE, Cassady JM (1994) Ohioensins and Pallidisetins: Novel Cytotoxic Agents from the Moss Polytrichum pallidisetum. J Nat Prod 57:32
Zinsmeister HD, Becker H, Eicher T (1991) Mosses, a Source of Biologically Active Natural Products. Angew Chem 103:134
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 Constituents of Bryophyta. 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_5
Download citation
DOI: https://doi.org/10.1007/978-3-7091-1084-3_5
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)