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Biologically Active Compounds of the Marchantiophyta and Bryophyta

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Chemical Constituents of Bryophytes

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 95))

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Abstract

In earlier reviews (39, 40), chemical constituents isolated from the liverworts (Marchantiophyta) were discussed, possessing characteristic fragrances, bitterness, pungency, and sweetness as well as allergenic contact dermatitis, cytotoxic, antimicrobial, antifungal, calmodulin inhibitory, cardiotonic, insect antifeedant, 5-lipoxygenase inhibitory, molluscicidal, muscle relaxant, neurotrophic, plant growth regulatory, superoxide release inhibitory, thromboxane synthase inhibitory, and vasopressin antagonist activities. Several reviews dealing with biologically active compounds from liverworts have been published more recently (42, 43, 46–50, 80, 85, 568, 290). In this chapter, further biologically active compounds found in liverworts are summarized.

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References

  1. Aalto-Korte K, Lauerma A, Alanko K (2005) Occupational allergic contact dermatitis from lichens in present-Day Finland. Contact Dermatis 52:36

    Google Scholar 

  2. Adams DR, Brochwicz-Lewinski M, Butler AR (1999) Nitric oxide: physiological roles, biosynthesis and medical uses. In: Herz W, Falk H, Kirby GW, Moore RE, Tamm Ch (eds) Progress in the chemistry of organic natural products, vol 76. Springer-Verlag, Vienna, New York, p 211

    Google Scholar 

  3. Ainge GD, Gerard PJ, Hinkley SFR, Lorimer SD, Weavers RT (2001) Hodgsonox, a New class of sesquiterpene from the liverwort Lepidoleana hodgsoniae. Isolation directed by insecticidal activity. J Org Chem 66:2818

    CAS  Google Scholar 

  4. 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

    Google Scholar 

  5. 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

    Google Scholar 

  6. Asakawa Y (1998) Biologically Active Compounds from Bryophytes. J Hattori Bot Lab 84:91

    Google Scholar 

  7. Asakawa Y (1999) Phytochemistry of Bryophytes: Biologically Active Terpenoids and Aromatic Compounds from Liverworts. In: Romeo J (ed) Phytochemicals in Human Health Protection, Nutrition, and Plant Defense. Kluwer Academic/Plenum Publishers, New York, p 319

    Google Scholar 

  8. Asakawa Y (2007) Biologically Active Compounds from Bryophytes. Chenia 9:73

    Google Scholar 

  9. Asakawa Y (2008) Liverworts - Potential Source of Medicinal Compounds. Curr Pharm Design 14:3067

    CAS  Google Scholar 

  10. Asakawa Y (2008) Marchantiophyta: A Good Source of Biologically Active Substances. Science and Culture 74:31

    Google Scholar 

  11. Asakawa Y (2008) Marchantiophyta: A Good Source of Biologically Active Compounds. In: Mohamed H, Baki BB, Nasrulhaq-Boyce A, Lee PKY (eds) Bryology in the New Millenium. University of Malaya, Kuala Lumpur, p 367

    Google Scholar 

  12. Asakawa Y (2008) Recent Advances of Biologically Active Substances from Marchantiophyta. Nat Prod Commun 3:77

    CAS  Google Scholar 

  13. Asakawa Y, Harrison LJ, Toyota M (1985) Occurrence of a Potent Piscicidal Diterpenedial in the Liverwort Riccardia lobata var. yakushimensis. Phytochemistry 24:261

    CAS  Google Scholar 

  14. 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

    Google Scholar 

  15. 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

    CAS  Google Scholar 

  16. Asakawa Y, Ludwiczuk A (2008a) Bryophytes – Chemical Diversity, Bioactivity and Chemosystematics. Part 1. Chemical Diversity and Bioactivity. Medicinal Plants in Poland and in the World (Rośliny Lecznicze w Polsce i na Świecie) 2:33

    Google Scholar 

  17. Asakawa Y, Toyota M, Nagashima F, Hashimoto T (2008) Chemical Constituents of Selected Japanese and New Zealand Liverworts. Nat Prod Commun 3:289

    CAS  Google Scholar 

  18. Asakawa Y, Ludwiczuk A, Nagashima F, Toyota M, Hashimoto T, Tori M, Fukuyama Y, Harinantenaina L (2009) Bryophtes: Bio- and Chemical Diversity. Bioactivity and Chemosystematics Heterocycles 77:99

    CAS  Google Scholar 

  19. Baek S-H, Perry NB, Lorimer S.D (2003) ent-Costunolide from the Liverwort Hepatostolonophora paucistipula. J Chem Res (S): 14

    Google Scholar 

  20. Baek S-H, Oh HJ, Lim JA, Chun HJ, Lee HO, Ahn JW, Perry NB, Kim HM (2004) Biological Activities of Methyl-4-[[(2E)-3,7-dimethyl-2,6-octadienyl]oxy]-3-hydroxybenzoate. Bull Korean Chem Soc 25:195

    CAS  Google Scholar 

  21. Baek S-H, Phipps RK, Perry NB (2004) Antimicrobial Chlorinated Bibenzyls from the Liverwort Riccardia marginata. J Nat Prod 67:718

    CAS  Google Scholar 

  22. Burden RS, Kemp MS (1983) (-)-7-Hydroxycalamenene, a Phytoalexin from Tilia europaea. Phytochemistry 22:1039

    CAS  Google Scholar 

  23. Burgess EJ, Larsen L, Perry NB (2000) A Cytotoxic Sesquiterpene Caffeate from the Liverwort Bazzania novae-zelandiae. J Nat Prod 63:537

    CAS  Google Scholar 

  24. Cullmann F, Becker H (1998) Terpenoid and Phenolic Constituents of Sporophytes and Spores from the Liverwort Pellia epiphylla. J Hattori Bot Lab 84:285

    Google Scholar 

  25. Figueiredo AC, Sim-Sim M, Barroso JG, Pedro LG, Santos PAG, Fontinha SS, Schripsema J, Deans SG, Scheffer JJC (2002) Composition of the Essential Oil from the Marchesinia mackaii (Hook.) S.F. Gray Grown in Portugal. J Essent Oil Res 14:439

    CAS  Google Scholar 

  26. 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

    CAS  Google Scholar 

  27. Fukuyama Y, Matsumoto K, Tonoi Y, Yokoyama R, Takahashi H, Minami H, Okazaki H, Mitsumoto Y (2001) Total Syntheses of Neuroprotective Mastigophorenes A and B. Tetrahedron 57:7127

    CAS  Google Scholar 

  28. Gauvin-Bialecki A, Ah-Peng C, Smadja J, Strasberg D (2010) Fragrant Volatile Compounds in the Liverwort Drepanolejeunea madagascariensis (Steph.) Grolle: Approach by HS-SPME Technique. Chem Biodivers 7:639

    CAS  Google Scholar 

  29. Geis W, Becker H (2001) Odoriferous Sesquiterpenoids from the Liverwort Gackstroemia decipiens. Flavour Fragr J 16:422

    CAS  Google Scholar 

  30. Gijsen HJ, Wijnberg JBPA, Stork GA, De Groot A, De Waard MA, Van Nistelrooy JGM (1992) The Synthesis of Mono- and Dihydroxy Aromadendrane Sesquiterpenes Starting from Natural (+)-Aromadendrene. Tetrahedron 48:2465

    CAS  Google Scholar 

  31. Guo D-X, Du Y, Wang Y-Y, Sun L-M, Qu J-B, Wang X-N, Lou H-X (2009) Secondary Metabolites from the Liverwort Ptilidium pulcherrimum. Nat Prod Commun 4:1319

    CAS  Google Scholar 

  32. Guo XL, Leng P, Yeng Y, Yu LG, Lou H (2008) Plagiochin E, a Botanic-derived Phenolic Compound, Reverses Fungal Resistance to Fluconazole Relating to the Efflux Pump. J Appl Microbiol 104:831

    CAS  Google Scholar 

  33. 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

    CAS  Google Scholar 

  34. Harinantenaina L, Asakawa Y (2007) Chemical Constituents of Malagasy Liverworts. 6. A Myltaylane Caffeate with Nitric Oxide Inhibitory Activity from Bazzania nitida. J Nat Prod 70:856

    CAS  Google Scholar 

  35. Harinantenaina L, Asakawa Y (2007) Malagasy Liverworts, Source of New and Biologically Active Compounds. Nat Prod Commun 2:701

    CAS  Google Scholar 

  36. Harinantenaina L, Luang DN, Nishizawa T, Hashimoto T, Kohchi C, Soma G-I, Asakawa Y (2005) Bis(bibenzyls) from Liverworts Inhibit Lipopolysaccharide-Induced Inducible NOS in RAW 264.7 Cells: A Study of Structure-Activity Relationships and Molecular Mechanism. J Nat Prod 68:1779

    CAS  Google Scholar 

  37. Harinantenaina L, Takahara Y, Nishizawa T, Kohchi C, Soma G-I, Asakawa Y (2006) Chemical Constituents of Malagasy Liverworts, Part V: Prenyl Bibenzyls and Clerodane Diterpenoids with Nitric Oxide Inhibitory Activity from Radula appressa and Thysananthus spathulistipus. Chem Pharm Bull 54:1046

    CAS  Google Scholar 

  38. Harinantenaina L, Kida S, Asakawa Y (2007a) Phytochemistry of Three Selected Liverworts: Conocephalum conicum, Plagiochila barteri and P. terebrans. ARKIVOC: 22

    Google Scholar 

  39. Harinantenaina L, Quang DN, Nishizawa T, Hashimoto T, Kohchi C, Soma G-I, Asakawa Y (2007) Bioactive Compounds from Liverworts: Inhibition of Lipopolysaccharide-Induced Inducible NOS mRNA in RAW 264.7 Cells by Herbertenoids and Cuparenoids. Phytomedicine 14:486

    CAS  Google Scholar 

  40. Hashimoto T, Okumura Y, Suzuki K, Takaoka S, Kan Y, Tori M, Asakawa Y (1995) The Absolute Structures of New 1β-Hydroxysacculatane-type Diterpenoids with Piscicidal Activity from the Liverwort Pellia endiviifolia. Chem Pharm Bull 43:2030

    CAS  Google Scholar 

  41. 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

    Google Scholar 

  42. Hioki H, Shima N, Kawaguchi K, Harada K, Kubo M, Esumi T, Nishimaki-Mogami T, Sawada J-I, Hashimoto T, Asakawa Y, Fukuyama Y (2009) Synthesis of Riccardin C and Its Seven Analogues. Part 1: The Role of Their Phenolic Hydroxy Groups as LXRα Agonists. Bioorg Med Chem Lett 19:738

    CAS  Google Scholar 

  43. Hsiao G, Teng C-M, Wu C-L, Ko F-N (1996) Marchantin H as a Natural Antioxidant and Free Radical Scavenger. Arch Biochem Biophys 334:18

    CAS  Google Scholar 

  44. Huang W-J, Wu C-L, Lin C-W, Chi L-L, Chen P-Y, Chiu C-J, Huang C-Y, Chen C-N (2010) Marchantin A, a Cyclic Bis(bibenzyl ether), Isolated from the Liverwort Marchantia emarginata subsp. tosana Induces Apoptosis in Human MCF-7 Breast Cancer Cells. Cancer Lett 291:108

    CAS  Google Scholar 

  45. Huopalathi R, Lahtinen R, Hiltunen R, Laakso I (1988) Studies on the Essential Oils of Dill Herb. Anethum graveolens L Flavour Fragr J 3:121

    Google Scholar 

  46. Iwai Y, Murakami K, Gomi Y, Hashimoto T, Asakawa Y, Okuno Y, Ishikawa T, Hatakeyama D, Echigo N, Kuzuhara T (2011) Anti-influenza Activity of Marchantins, Macrocyclic Bisbibenzyls Contained in Liverworts. PLoS One 6:e19825

    CAS  Google Scholar 

  47. Izumi S, Nishio Y, Takashima O, Hirata T (1997) Monoterpenoids, Potent Inducers of Apoptosis in the Cells of Marchantia polymorpha. Chem Lett: 837

    Google Scholar 

  48. Keseru GM, Nogradi M (1995) The Biological Activity of Cyclic Bis(bibenzyls): A Rotational Approach. Bioorg Med Chem 3:1511

    CAS  Google Scholar 

  49. Keseru GM, Nogradi M (1996) Molecular Similarity Analysis on Biologically Active Macrocyclic Bis(bibenzyls). J Mol Recogn 9:133

    CAS  Google Scholar 

  50. Kim YC, da Bolzani VS, Baj N, Gunatilaka AAL, Kingston DGI (1996) A DNA-damaging Sesquiterpene and Other Constituents from Frullania nisquallensis. Planta Med 62:61

    CAS  Google Scholar 

  51. Komala I, Ito T, Nagashima F, Yagi Y, Asakawa Y (2009) New Sesqui- and Diterpenoids from the Liverwort Chandonanthus hirtellus. 53rd Symposium on Chemistry of Terpenes, Essential Oils and Aromatics. Nara, Japan, Symposium Papers, p 266

    Google Scholar 

  52. Komala I, Ito T, Nagashima F, Yagi Y, Kawahata M, Yamaguchi K, Asakawa Y (2010) Zierane Sesquiterpene Lactone, Cembrane and Fusicoccane Diterpenoids, from the Tahithian Liverwort Chendonanthus hirtellus. Phytochemistry 71:1387

    CAS  Google Scholar 

  53. Komala I, Ito T, Nagashima F, Yagi Y, Asakawa Y (2010) Cytotoxic, Radical Scavenging and Antimicrobial Activities of Sesquiterpenoids from the Tahitian Liverwort Mastigophora diclados (Brid.) Nees (Mastigophoraceae). J Nat Med 64:417

    CAS  Google Scholar 

  54. Komala I, Ito T, Nagashima F, Yagi Y, Asakawa Y (2011) Cytotoxic Bibenzyls, Germcrane- and Pinguisane-type Sesquiterpenoids from the Indonesian, Tahitian and Japanese Liverworts. Nat Prod Commun 6:303

    CAS  Google Scholar 

  55. Kondoh M, Suzuki I, Sato M, Nagashima F, Simizu S, Harada M, Fiji M, Osada H, Asakawa Y, Watanabe Y (2004) Kaurene Diterpene Induces Apoptosis in Human Leukemia Cells Partly Through a Caspase-8-Dependent Pathway. J Pharmacol Exp Ther 311:115

    CAS  Google Scholar 

  56. Kondoh M, Nagashima F, Suzuki I, Harada M, Fuji M, Asakawa Y, Watanabe Y (2005) Induction of Apoptosis by New ent-Kaurene-type Diterpenoids Isolated from the New Zealand Liverwort Jungermannia species. Planta Med 71:1005

    CAS  Google Scholar 

  57. Kondoh M, Suzuki I, Harada M, Nagashima F, Fuji M, Asakawa Y, Watanabe Y (2005) Activation of p38 Mitogen-Activated Oritein Kinase During ent-11α-Hydroxy-16-kauren-15-one-induced Apoptosis in Human Leukemia HL-60 Cells. Planta Med 71:275

    CAS  Google Scholar 

  58. 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

    Google Scholar 

  59. Labbé C, Faini F, Villagran C, Coll J, Rycroft DS (2007) Bioactive Polychlorinated Bibenzyls from the Liverwort Riccardia polyclada. J Nat Prod 70:2019

    Google Scholar 

  60. Lin S-J, Wu C-L (1996) Isoplagiochilide from the Liverwort Plagiochila elegans. Phytochemistry 41:1439

    CAS  Google Scholar 

  61. Lorimer SD, Perry NB (1994) Antifungal Hydroxyacetophenones from the New Zealand Liverwort. Plagiochila fasciculata Planta Med 60:386

    CAS  Google Scholar 

  62. Lorimer SD, Perry NB, Foster LM, Burgess EJ, Douch PGS, Hamilton MC, Donaghy MJ, McGregor RA (1996) A Nematode Larval Motility Inhibition Assay for Screening Plant Extracts and Natural Products. J Agric Food Chem 44:2842

    CAS  Google Scholar 

  63. Lorimer SD, Perry NB, Burgess EJ, Foster LM (1997) 1-Hydroxyditerpenes from Two New Zealand Liverworts, Paraschistochila pinnatifolia and Trichocolea mollissima. J Nat Prod 60:421

    CAS  Google Scholar 

  64. Lu Z-Q, Fan P-H, Ji M, Lou H-X (2006) Terpenoids and Bisbibenzyls from Chinese Liverworts Conocephalum conicum and Dumortiera hirsuta. J Asian Nat Prod Res 8:187

    CAS  Google Scholar 

  65. Matsuo A, Ono K, Hamasaki K, Nozaki H (1996) Phaeophytins from a Cell Suspension Culture of the Liverwort Plagiochila ovalifolia. Phytochemistry 42:427

    CAS  Google Scholar 

  66. Morita H, Tomizawa Y, Tsuchiya T, Hirasawa Y, Hashimoto T, Asakawa Y (2009) Antimitotic Activity of Two Macrocyclic Bis(bibenzyls), Isoplagiochins A and B from the Liverwort Plagiochila fruticosa. Bioorg Med Chem Lett 19:493

    CAS  Google Scholar 

  67. Nagashima F, Asakawa Y (1998) Chemical Constituents of the Liverworts Jungermannioideae and Myliioideae (Jungermanniaceae). In: Pandalay SG (ed) Recent Research Developments in Phytochemistry, vol. 2, part II, Research Signpost, Tivandrum, India, p. 327

    Google Scholar 

  68. Nagashima F, Momosaki S, Watanabe Y, Toyota M, Huneck S, Asakawa Y (1996) Terpenoids and Aromatic Compounds from Six Liverworts. Phytochemistry 41:207

    CAS  Google Scholar 

  69. Nagashima F, Kondoh M, Uematsu T, Nishiyama A, Saito S, Sato M, Asakawa Y (2002) Cytotoxic and Apoptosis-Inducing ent-Kaurane-type Diterpenoids from the Japanese Liverwort Jungermannia trunctata Nees. Chem Pharm Bull 50:808

    CAS  Google Scholar 

  70. Nagashima F, Kasai W, Kondoh M, Fuji M, Watanabe Y, Braggins JE, Asakawa Y (2003) New ent-Kaurene-type Diterpenoids Possessing Cytotoxicity from the New Zealand Liverwort Jungermannia species. Chem Pharm Bull 51:1189

    CAS  Google Scholar 

  71. Nagashima F, Kondoh M, Fuji M, Takaoka S, Watanabe Y, Asakawa Y (2005) Novel Cytotoxic Kaurane-type Diterpenoids from the New Zealand Liverwort Jungermannia species. Tetrahedron 61:4531

    CAS  Google Scholar 

  72. Neves M, Morais R, Gafner S, Hostettmann K (1998) Three Triterpenoids and One Flavonoid from the Liverwort Asterella blumeana Grown in vitro. Phytother Res 12:S21

    CAS  Google Scholar 

  73. Neves M, Morais R, Gafner S, Stoeckli-Evans H, Hostettmann K (1999) New Sesquiterpene Lactones from the Portuguese Liverwort Targonia lorbeeriana. Phytochemistry 50:967

    CAS  Google Scholar 

  74. Nishiki M, Toyota M, Asakawa Y (2007) Chemical Constituents of the Liverwort, Radula Species and Distribution of α-Tocopherol in Liverworts. 51st Symposium on Chemistry of Terpenes, Essential Oils and Aromatics. Nagahama, Japan, Symposium Papers, p 260

    Google Scholar 

  75. Niu C, Qu J-B, Lou H-X (2006) Antifungal Bis(bibenzyls) from the Chinese Liverwort Marchantia polymorpha. Chem Biodivers 3:34

    CAS  Google Scholar 

  76. Numata A, Katsuno T, Yamamoto K, Nishda T, Takemura T, Seto K (1984) Plant Constituents Biologically Active to Insects. IV. Antifeedants for the Larvae of the Yellow Butterfly, Eurema hecabe mandarina, in Arachniodes standishii. Chem Pharm Bull 32:325

    CAS  Google Scholar 

  77. Ono K, Sakamoto T, Asakawa Y (1992) Constituents from Cell Suspension Cultures of Selected Liverworts. Phytochemistry 30:567

    Google Scholar 

  78. Ono K, Sakamoto T, Tanaka H, Asakawa Y (1996) Sesquiterpenoids from a Cell Suspension Culture of the Liverwort Porella vernicosa Lindb. Flavour Fragr J 11:53

    CAS  Google Scholar 

  79. Perry NB, Foster LM (1995) Sesquiterpene/Quinol from a New Zealand Liverwort. Riccardia crassa J Nat Prod 58:1131

    CAS  Google Scholar 

  80. Perry NB, Burgess EJ, Tangney RS (1996) Cytotoxic 8,9-Secokaurane Diterpenes from a New Zealand Liverwort. Lepidolaena taylorii Tetrahedron Lett 37:9387

    CAS  Google Scholar 

  81. Perry NB, Foster LM, Lorimer SD, May BCH, Weavers RT, Toyota M, Nakaishi E, Asakawa Y (1996) Isoprenyl Phenyl Ethers from Liverworts of the Genus Trichocolea: Cytotoxic Activity, Structural Corrections, and Synthesis. J Nat Prod 59:729

    CAS  Google Scholar 

  82. Perry NB, Burgess EJ, Baek S-H, Weavers RT, Geis W, Mauger AB (1999) 11-Oxygenated Cytotoxic 8,9-Secokauranes from a New Zealand Liverwort. Lepidolaena taylorii Phytochemistry 50:423

    CAS  Google Scholar 

  83. Perry NB, Burgess EJ, Baek SH, Weavers RT (2001) The First Atisane Diterpenoids from a Liverwort: Polyols from Lepidolaena clavigera. Org Lett 3:4243

    CAS  Google Scholar 

  84. Perry NB, Burgess EJ, Foster LM, Gerard PJ (2003) Insect Antifeedant Sesquiterpene Acetals from the Liverwort Lepidoleana clavigera. Tetrahedron Lett 44:1651

    CAS  Google Scholar 

  85. Perry NB, Burgess EJ, Foster LM, Gerard PJ, Toyota M, Asakawa Y (2008) Insect Antifeedant Sesquiterpene Acetals from the Liverwort Lepidoleana clavigera. 2. Structures, Artifacts and Activity. J Nat Prod 71:258

    CAS  Google Scholar 

  86. Pino JA, Rosado A, Goire I, Roncal E (1995) Evaluation of Flavor Characteristic Compounds in Dill Herb Essential Oil by Sensory Analysis and Gas Chromatography. J Agric Food Chem 43:1307

    CAS  Google Scholar 

  87. Qu J, Xie C, Guo H, Yo W, Lou H (2007) Antifungal Dibenzofuran Bis(bibenzyl)s from the Liverwort Asterella angusta. Phytochemistry 68:1767

    CAS  Google Scholar 

  88. Quang DN, Asakawa Y (2010) Chemical Constituents of the Vietnamese Liverwort Porella densifolia. Fitoterapia 81:659

    CAS  Google Scholar 

  89. Sadamori M (2009) Studies on the New Biologically Active Substances of Tahitian and Tokushima’s Plagiochila Genus. Tokushima Bunri University, Tokushima, Japan, Master’s Thesis

    Google Scholar 

  90. Scher JM, Burgess EJ, Lorimer SD, Perry NB (2002) A Cytotoxic Sesquiterpene and Unprecedented Sesquiterpene-Bisbibenzyl Compounds from the Liverwort Schistochila glaucescens. Tetrahedron 58:7875

    CAS  Google Scholar 

  91. Scher JM, Speakman J-B, Zapp J, Becker H (2004) Bioactivity Guided Isolation of Antifungal Compounds from the Liverwort Bazzania trilobata (L.) S.F. Gray. Phytochemistry 65:2583

    CAS  Google Scholar 

  92. Scher JM, Schinkovitz A, Zapp J, Wang Y, Franzblau SG, Beker H (2010) Structure and Anti-TB Activity of Trachylobanes from the Liverwort Jungermannia exsertifolia ssp. cordifolia. J Nat Prod 73:656

    CAS  Google Scholar 

  93. Schwartner C, Michel C, Stettmaier K, Wagner H, Bors W (1996) Marchantins and Related Polyphenols from Liverwort: Physicochemical Studies of their Radical-Scavenging Properties. Free Radical Biol Med 20:237

    CAS  Google Scholar 

  94. Shi Y-Q, Qu X-J, Liao Y-X, Xie C-F, Cheng Y-N, Li S, Lou HX (2008) Reversal Effect of a Macrocyclic Bisbibenzyl Plagiochin E on Multidrug Resistance in Adriamycin-Resistant K562/A02 Cells. Eur J Pharmacol 584:66

    CAS  Google Scholar 

  95. Shi Y-Q, Liao Y-X, Qu X-J, Yuan H-Q, Li S, Qu J-B, Lou HX (2008) Marchantin C, a Macrocyclic Bisbibenzyl, Induces Apoptosis of Human Glioma A172 Cells. Cancer Lett 262:173

    CAS  Google Scholar 

  96. Shi Y-Q, Zhu C-J, Yuan H-Q, Li B-Q, Gao J, Qu X-J, Sun B, Cheng Y-N, Li S, Li X, Lou H-X (2009) Marchantin C, a Novel Microtubule Inhibitor from Liverwort with Anti-tumor Activity both in vivo and in vitro. Cancer Lett 276:160

    CAS  Google Scholar 

  97. Shu Y-F, Wei H-C, Wu C-L (1994) Sesquiterpenoids from Liverworts Lepidozia vitrea and L. fauriana. Phytochemistry 37:773

    CAS  Google Scholar 

  98. Shy H-S, Wu C-L, Paul C, König WA, Ean U-J (2002) Chemical Constituents of Two Liverworts Metacalypogeia alternifolia and Chandonanthus hirtellus. J Chin Chem Soc 49:593

    CAS  Google Scholar 

  99. Socolsky C, Muruaga N, Bardón A (2005) Drimanes and Other Terpenoids from the Fern Thelypteris hispidata (Decne.) Reed. Chem Biodivers 2:1105

    CAS  Google Scholar 

  100. Suzuki I, Kondoh M, Harada M, Koizumi N, Fujii M, Nagashima F, Asakawa Y, Watanabe Y (2004) An ent-Kaurene Diterpene Enhances Apoptosis Induced by Tumor Necrosis Factor in Human Leukemia Cells. Planta Med 70:723

    CAS  Google Scholar 

  101. Suzuki I, Kondoh M, Nagashima F, Fujii M, Asakawa Y, Watanabe Y (2004) A Comparison of Apoptosis and Necrosis Induced by ent-Kaurene-type Diterpenoids in HL-60 Cells. Planta Med 70:401

    CAS  Google Scholar 

  102. Suzuki T, Tomehiro N, Sato Y, Kobayashi T, Ishii-Watanabe A, Shinozaki Y, Nishimaki-Mogami T, Hashimoto T, Asakawa Y, Inoue K, Ohno Y, Yamaguchi T, Kawanishi T (2008) The Novel Compounds that Activate Farnesoid X Receptor: The Diversity of Their Effects on Gene Expression. J Pharmacol Sci 107:285

    CAS  Google Scholar 

  103. Taira Z, Takei M, Endo K, Hashimoto T, Sakiya Y, Asakawa Y (1994) Marchantin A Trimethyl Ether: Its Molecular Structure and Tubocurarine-like Skeletal Muscle Relaxation Activity. Chem Pharm Bull 42:52

    CAS  Google Scholar 

  104. 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

    CAS  Google Scholar 

  105. 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

    CAS  Google Scholar 

  106. Toyota M, Asakawa Y (1994) Volatile Constituents of the Liverwort Chiloscyphus pallidus (Mitt.) Engel & Schuster. Flavour Fragr J 9:237

    CAS  Google Scholar 

  107. Toyota M, Koyama H, Asakawa Y (1997) Volatile Components of the Liverworts Archilejeunea olivacea. Cheilolejeunea imbricata and Leptolejeunea elliptica Phytochemistry 44:1261

    CAS  Google Scholar 

  108. Toyota M, Tanimura K, Asakawa Y (1998) Cytotoxic 2,3-Secoaromadendrane-type Sesquiterpenoids from the Liverwort Plagiochila ovalifolia. Planta Med 64:462

    CAS  Google Scholar 

  109. Toyota M, Omatsu I, Braggins J, Asakawa Y (2009) Pungent Aromatic Compounds from New Zealand Liverwort Hymenophyton flabellatum. Chem Pharm Bull 57:1015

    CAS  Google Scholar 

  110. Wang X-N, Yu W-T, Lou H-X (2005) Antifungal Constituents from the Chinese Moss Homalia trichomanoides. Chem Biodivers 2:139

    CAS  Google Scholar 

  111. Wei H-C, Ma S-J, Wu C-L (1995) Sesquiterpenoids and Cyclic Bisbibenzyls from the Liverwort Reboulia hemisphaerica. Phytochemistry 39:91

    CAS  Google Scholar 

  112. Wong S-M, Oshima Y, Pezzuto J, Fong H, Farnsworth N (1986) Plant Anticancer Agents XXXIX. Triterpenes from Isis missouriensis (Iridaceae). J Pharm Sci 75:317

    CAS  Google Scholar 

  113. 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

    CAS  Google Scholar 

  114. Wu X-Z, Cheng A-X, Sun L-M, Lou H-X (2008) Effect of Plagiochin E, an Antifungal Macrocyclic Bis(bibenzyl), on Cell Wall Chitin Synthesis in Candida albicans. Acta Pharmacol Sin 29:1478

    CAS  Google Scholar 

  115. Wu X-Z, Cheng A-X, Sun L-M, Sun S-J, Lou H-X (2009) Plagiochin E, an Antifungal Bis(bibenzyl), Exerts its Antifungal Activity Through Mitochondrial Dysfunction-Induced Reactive Oxygen Species Accumulation in Candida albicans. Biochim Biophys Acta 1790:770

    CAS  Google Scholar 

  116. Wu X-Z, Chang W-Q, Cheng A-X, Sun L-M, Lou H-X (2010) Plagiochin E, an Antifungal Active Macrocyclic Bis(bibenzyl), Induced Aapoptosis in Candida albicans through a Metacaspase-dependent Apoptotic Pathway. Biochim Biophys Acta 1800:439

    CAS  Google Scholar 

  117. Xi G-M, Sun B, Jiang H-H, Kong F, Yuean H-Q, Lou H-X (2010) Bisbibenzyl Derivatives Sensitize Vincristine-Resistant KB/VCR Cells to Chemotherapeutic Agents by Retarding P-gp Activity. Bioorg Med Chem 18:6725

    CAS  Google Scholar 

  118. Xie C-F, Qu J-B, Wu X-Z, Liu N, Ji M, Lou H-X (2010) Antifungal Macrocyclic Bis(bibenzyls) from the Chinese Liverwort Plagiochasma intermedium L. Nat Prod Res 24:515

    CAS  Google Scholar 

  119. Yoshida T, Hashimoto T, Takaoka S, Kan Y, Tori M, Asakawa Y (1996) Phenolic Constituents of the Liverwort: Four Novel Cyclic Bisbibenzyl Dimers from Blasia pusilla L. Tetrahedron 52:14487

    CAS  Google Scholar 

  120. Yoshikawa H, Ichiki Y, (Doi) Sakakibara K, Tamura H, Suiko M (2002) The Biological and Structural Similarity Between Lunularic Acid and Abscisic Acid. Biosci Biotechnol Biochem 66:840

    CAS  Google Scholar 

  121. 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

    CAS  Google Scholar 

  122.  

    Google Scholar 

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho 180, 770-8514, Tokushima, Japan

    Prof. Dr. Yoshinori Asakawa, Dr. Agnieszka Ludwiczuk & Dr. Fumihiro Nagashima

  2. Department of Pharmacognosy with Medicinal Plant Unit, Medical University of Lublin, 1 Chodzki Str, 20-093, Lublin, Poland

    Dr. Agnieszka Ludwiczuk

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  1. Prof. Dr. Yoshinori Asakawa
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  2. Dr. Agnieszka Ludwiczuk
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  3. Dr. Fumihiro Nagashima
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Correspondence to Yoshinori Asakawa .

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Asakawa, Y., Ludwiczuk, A., Nagashima, F. (2013). Biologically Active Compounds of the Marchantiophyta and 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_7

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