LEK. SIROV. LEK. SIROV. God. XXI Vol. XXI Broj 21 No. 21 Str. 17 – 29 PP. 17 – 29 Beograd 2001. Belgrade 2001. Pregledni lanak – Review UDC 633.88:615.322 BRYOPHYTES AS A POTENTIAL SOURCE OF MEDICINAL COMPOUNDS* Sabovljevi Marko1, Bijelovi Aneta2, Grubiši Dragoljub3 1 Department of Plant Ecology and 2 Department of Plant Physiology; Institute of Botany and Botancal Garden, Faculty of Biology, University of Belgrade, Belgrade 3 Institute for Biological Research ''Siniša Stankovi '', Belgrade SUMMARY Bryophytes (mosses, liverworts and hornworts) are the second biggest group of plants after flowering plants, with approximately 28.000 species worldwide. However, not even a part as flowering plants, bryophytes are used as medicinal plants. Bryophyte chemistry is poorly known, and the results on this issue are very scattered. The reason for this is hard identification and small amount of the same species available for analyses by usually sophisticated methods. They are extremely rich in terpenoids, phenols (flavonoids and bibenzyl derivatives), glycosides and fatty acids, but also in same rare aromatic compounds. Bryophytes are considered as a “remarkable reservoir” of new, natural products or secondary compounds, many of which have shown interesting biological activity. These activities can be presented as: antimicrobial, antifungal, cytotoxic, antitumor, vasopressin (VP) antagonist, cardiotonic, allergy causing, irritancy and tumor promoting, insect anti-feedant, insecticidal, molluscicidal, piscicidal, plant growth regulatory, superoxide anion radical release inhibition and 5-lipoxygenase, calmodulin, hyaluronidase and cyclooxygenase inhibition features of bryophytes. Some latest results also predict beneficial influence of bryophytes in AIDS therapy (some bibenzyles of liverworts). The subject matter of the present paper is focussed on the medicinal uses and chemical constituents of bryophytes. * Plenarno predavanje sa sedme manifestacije "Dani lekovitog bilja", Beograd 2001., štampano u celini. 17 INTRODUCTION Bryophytes are the second biggest group of land plants after the flowering plants with about 20.000 to 28.000 species. Three main groups characterize bryophytes. These are: hornworts (Anthocerotopsida), liverworts (Marchantiopsida) and mosses (Bryopsida). They live in all zonobioms from the desert to the polar, but not in the seas. However, the small size of these plants as well as usually not huge biomass in the nature, made these plants neglected for wide use. Even though, these plants are very used by northern people where bryophytes have significant biomass and where they are easy available to the people. Bryophytes have been long considered to be insignificant in the economy except for those mosses used in packing, plugging and decoration. The exception is widely used Sphagnum, as peat or as a surgical dressing. Bryophytes are highly used in horticulture in Far East, and Chinese and Indian people use them widely in ethno therapeutics (1, 2). Chemical components of these plants can be used as biologically active agents. Many bryophyte compounds have shown interesting biological activity with particular reference to their application in medicine and agriculture for all round benefit of living beings (3). In Asia, already 500 bryophytes have been studied with respect to their chemistry, pharmacology and application as cosmetics and medicinal drugs (4). BACKGROUND In ancient times medicinal uses of plants were often suggested by the similarity of their shape and structure to some organ in the human or animal body. The surface of some liverworts (e.g. Marchantia polymorpha) presented the patterns similar to those of cross section of animal livers, and hence they were believed to cure ailments (5). Another example is Polytrichum commune, which is commonly called hair cup moss, because it bears hairy calyptra. Expressed oil form this moss was used by the ladies of ancient time on their hair (6). Gasuite Indians of Utah (USA) were used several kinds of mosses in their ethnobryology. These mosses are: Philonotis, Bryum, Mnium species and various hypnaceous form. They were used to alleviate the pain of burns, directly put to the burnt places, or were crashed to a kind of paste and were applied as poultice. These and similar forms were used as a covering for bruises and wounds or as padding under splints in setting broken bones (7). Alaskian indigenes used mosses by mixing them with grease to make salve (5). Polytrichum juniperinum was used in medicinal purposes to relieve burns by northern Cheyenne Indians of Montana (USA) (8). Kumar et al. (1) emphasizes the use of Plagiochasma appendiculatum by Gaddi tribes of Himachal Pradesh State in India for treating skin diseases. The fresh mature thalli with female receptacle is made into paste with water and the paste is applied externally twice a day for a week, for the treatment of burns, boils, blisters on the body and also skin eruptions caused by hot sunlight in the summer. 18 According to Ding (9) nearly 40 bryophyte species have been used as a crude drugs by the Chinese people. Some of these species are hepatics Frullania tamarisci, Reboulia hemisphaerica, Conocephalum conicum, Marchantia polymorha and mosses Sphagnum spp., Weissia controversa, Funaria hygrometrica, Bryum argenteum, Rhodobryum roseum, Climacium dendroides and Polytrichum commune. Among these species Sphagnum teres is very popular to apply for eye diseases. Rhodobryum giganteum and R. roseum are widely used within China for cardiovascular disease and nervous prostrations. Polytrichum commune is used as an antipyretic, diuretic and hemostatic and Haplocaldium microphyllum is applied for tonsillitis, bronchitis, timpanists and cystitis. Conocephalum conicum and Marchantia polymorpha, mixed with vegetable oils, are used as ointments for boils, eczema, cuts, bites and burns (9, 10, 11). Wu (10) reports that Chinese peasants use Rhodobryum giganteum to cure angina, because it contains volatile oils, lactones and amino acids. Indirectly, bryophytes provide special conditions for ethno medicinal production. For example, the aphid Schlechtendalia chinensis over winter in cocoons in bryophytes, and parasitizing on Rhus javanica induce great number of gullnuts that are source of tannic acid used by people. So, people rise Rhus and bryophytes together (10, 11). Sphagnum has absorbent qualities superior to cotton and its antibiotic qualities are an added feature. It has been used as surgical dressing because of better and faster absorption. CHEMICAL CONSTITUENTS ISOLATED FROM BRYOPHYTES Since 1960 interest in analysis of chemicals isolated from bryophytes has been increased. It is confirmed that bryophytes posses great number of different chemical constituents. Carbohydrates are widely presented as mono and polysaccharides (fructose, glucose, sucrose, sorbose, arabinose, mannose, galactose and others), (12). Steroids are various in bryophytes, as well (sitosterol, stigmasterol, brassicasterol, campesterol). Some genera (Chiloscyphus, Plagiochila, Scapania) posses cholesterol. Lipids are often in bryophytes, as simple lipids (triglycerids and waxes) as well as structure complex lipids (glyco- and phospholipids). It is interesting the presence of various fatty acids with many number of unsaturated bands (table 1.). Bryophytes posses proteins as well as amino acids and it is possible to use them as a source of certain enzymes (table 2). Some other substances isolated from bryophytes are organic acids (cis-aconitic acid, citric acid, malic acid, malonic acid, shikimic acid, fumaric acid, succinic acid, cinnamic acid), polyacetilens and mineral compounds (12). Bryophytes posses many different chemical constituents of whom organic compounds that have attract attention are: terpenoids, flavonoids, lignans, growth substances, antibiotics, lipids and sterols. Polyphenols and terpenoids (table 3.) should be mentioned as a potential group of organic compounds with pharmacological activity. Phenolic acids, lignans and lignins are often presented in bryophytes from the group of polyphenols. However, flavonoids are the 19 most interested polyphenols (13) (table 4). All terpenoid classes are isolated from mosses and liverworts (monoterpenoids, diterpenoids, sesquiterpenoids and etheric oils) (table 3). It is interesting that moss and liverwort species are sources of tetraterpenoid carotenoids (table 5). Table 1. Fatty acids and esters from some of the liverworts. Taxon Asterella Conocephalum Diplophyllum Lophocolea Marchantia Mylia Pellia Fatty acid(s) 10,15-dihydroxihexadecanoic acid, hexadecanoic acid, 15hydroxyhexadecanoic acid, cis-9, cis-12, cis-15 octadecatrienoic acid eicosanoic acid, eicosenoic acid, fatty acid ethyl ester (n-C14-C24), hexadecanoic acid, 2-hydroxyhexadecanoic acid, 2hydroxyoctadecanoic acid, 2-hydroxytetra-contanoic acid, 2hydroxytriacontanoic acid, octadecanoic acid, tetracontanoic acid, tetracosanoic acid, triacontanoic acid n-C36-C50 esters diglycerides, eicosanoic acid, 5,8,11,14,17-eicosapentaenoic acid, 5,8,11,14-eicosatetraenoic acid, glycolipods, hexadecanoic acid, 9hexadecenoic acid, monoglycerides, cis-9-, cis-12-, cis-15octadecatrienoic acid, cis-9-octadecenoic acid, phospholipids, tetradecanoic acid, triglycerides docosanoic acid, 5,8,11,14,17-eicosapentaenoic acid, 5,8,11,14eicosatetraenoic acid, hexadecanoic acid, 9-hexadecenoic acid, cis-12octadecadienoic acid, octadecanoic acid, cis-9-octadecenoic acid n-C38-C52 esters fatty acid methyl ester (n-C10-C16-C18) Table 2. Enzymes met within the bryophytes Taxon MOSSES Abietinella Atrichum Aulacomnium Brachythecium Campylium Catoscopium Ceratodon Cratoneuron Dicranum Distichium Ditrichum Eurhynchium Fontinalis 20 Enzyme(s) oxalic acid oxydase allantoicase, allantoinase dehydrogenase, cinnamyl alcohol dehydrogenase -fructosidase, oxalic acid oxydase dehydrogenase dehydrogenase transfer RNAnucleotidyl transferase dehydrogenase acid phosphatase, cytochrome oxidase, -fructosidase, oxalic acid oxidase, peroxidase, succinate dehydrogenase dehydrogenase dehydrogenase dehydrogenases, oxalic acid oxidase carbonic acid anhydrase, oxalic acid oxidase Funaria Homalothecium Hylocomium Hypnum Leucobryum Mnium Philonotis Pleurozium Pogonatum phenylalanin ammonium lyase dehydrogenases dehydrogenases oxalic acid oxidase oxalic acid oxidase catalase, oxalic acid oxidase dehydrogenases dehydrogenases cis-3-hexanal synthetase, n-hexanal synthetase Polytrichum acid phosphatase, allantoicase, allantoinase, amylase, cytochrome oxidase, dehydrogenases, -fructosidase, maltase, oxalic acid oxidase, peroxidase, phosphatase, succinate dehydrogenase dehydrogenases dehydrogenases, oxalic acid oxidase ascorbic acid oxidase, cinnamyl alcohol dehydrogenase, -fructosidase, peroxidase, phenolase dehydrogenases, -fructosidase dehydrogenases dehydrogenases Ptilium Rhytidiadelphus Sphagnum Thudium Tomenthypnum Tortula HEPATICS Asterella Chiloscyphus Conocephalum Frullania Lophocolea amylase, butyrase, catalase, invertase, laccase, lipase, maltase, a proteolytic enzyme, urease urease lunularic acid decarboxylase oxalic acid oxidase urease Table 3. Terpenoids met within some well studied bryophytes Taxon Conocephalum conicum Frullania tamarisci Jungermannia cordifolia Jungermannia obovata Porella platyphylla Radula complanata Terpenoids -pinene, camphen, sabinene, myrcene, - and -terpinene, limonene, p-cymene terpinen-4-ol, lineoyl acetate, bornyl acetate, -terpineol - and -pinene, camphen -pinene, camphen, myrcene, -terpinene, limonene, -terpinene, terpinolene, p-cymene -pinene, camphen, myrcene, -terpinene, limonene, -terpinene, terpinolene, p-cymene -pinene, camphen, sabinene, -terpinene, limonene, p-cymene, phellandrene, terpinolene -and -pinene, camphene 21 (-)-longifolene, (-)-longiborneol Scapania undulata Thamnium alopecurum Thuidium tamarisci 22(29)-hopene 22(29)-hopene, 7-fernene, 9(11)-fernene, 21-hopene Table 4. Flavonoid types sintetized by several moss genera TAXON O-glyc. C-glyc. Flavonols Biflavons Aurons Antitrichia Bartramia Bryum Campylopus Dicranoloma Dicranum Encalypta Funaria Hedwigia Hylocomium Philonotis Plagiomnium Pleurozium Racomitrium Rhizomnium Iso Dihydro Macroyclic 3-deoxy flavons flavons biflavonoids antocyanins + + + + + + + + + + + + + + + + + + + + + + + + + + + + + Table 5. Carotenoids met within some bryophytes Taxa MOSSES Aulacomnium Bryum Ditrichum Entodon Fontinalis Hygrohypnum Mnium Philonotis Pohlia Polytrichum Sphagnum 22 Carotenoids - and - carotene, lutein, neo-, viola- and zeaxanthin - carotene, epoxylutein, lutein, neo-, viola-, zea- and cryptoxanthin - and - carotene, lutein, neo-, viola- and zeaxanthin - and - carotene, lutein, neo-, viola-, crypto- and zeaxanthin auro-, neo- and violaxanthin, - and - carotene, epoxylutein, lutein, neo- -carotene - and - carotene, lutein, neo-, viola- and zeaxanthin - and - carotene, lutein, viola- and zeaxanthin - and - carotene, lutein, neo-, viola- and zeaxanthin - carotene, lutein, neo-, viola- and zeaxanthin anthera-, viola- and zeaxanthin, - and - carotene, lutein, neoxanthine, neo-A - and - carotene, lutein, neo-, viola- and zeaxanthin Thudium LIVERWORTS Aneura Asterella Conocephalum Lophocolea Marchantia Pellia Riccardia Ricciocarpos Sphaerocarpos - and - carotene, lutein, viola- and zeaxanthin - carotene - and - carotene, lutein, neo-, viola- and zeaxanthin - and - carotene, lutein, neo-, viola- and zeaxanthin - carotene, lutein, anthera-, neo-, viola- and zeaxanthin - carotene, lutein, anthera-, neo-, viola- and zeaxanthin, phytochrome neo- and violaxanthin - carotene - carotene - and - carotene, lutein, anthera-, neo-, viola- and zeaxanthin GROWTH REGULATORS ISOLATED FROM BRYOPHYTES Bryophytes posses the same phytohormones as vascular plants: auxines, gibberellins, cytokinins and ethylene. Bryokinin (specific cytokinin) can replace kinetin as a growth factor in tissue culture of vascular plants. In mosses, bryokinin is physiologically active at several stages of development. At the caulonema stage it promotes bud formation. In the phase immediately before sexual maturation it supports apogamous sporogonium formation. In the phase of sexual maturation it promotes archegonium differentiation. Natural dormancy has been correlated with the levels of an internal inhibitor in many plants. From Lunularia cruciata it has been separated chemical compound termed stilbenes commonly known as lunularic acid (Fig. 1). This compound is characteristic for liverworts and algae and it is taken that it fulfils the same growth regulating functions as abscisid acid (ABA) in mosses, hornworts, pteridophytes and vascular plants. Lunularic acid is also present in aquatic vascular plant Hydrangea macrophylla. Acetylcholine, neurohormone from the animals, has been isolated from the moss callus and its concentration is regulated by the phytochrome. Many undermined growth regulated substances are considered to be in bryophytes. Factor F, thermolabile compound, is considered to be responsible for growth of caulonema and inhibition of bud formation, but the chemical structure of this compound is not known. Factor H, thermostable and chemically undermined compound, is primarily responsible for bud formation and secondary for inhibition of caulonemal growth. Thin layer chromatographic studies have indicated that this factor contains two active ingredients: steroids and terpens, and any of known phytohormones. Gemma factor is a morphoregulatory substance that inhibits protonemal growth and induces production of gemmae. This compound has two fractions, one of which is heat labile that inhibits protonemal growth and the other one, heat stabile, induce gemmae formation. Sporogon factor is labile substance that is translocated from the sporophyte into the protonema where it induces apogamus sporophyting. 23 Figure 1: Some compounds isolated from Bryophytes: 1. lunularic acid; 2. pinguisone; 3. myliol; 4. (+) – plagiochiline A; 5. (-) – lepidonzenal; 6. diplophyllin; 7. (-) – frullanoide; 8. (-) – oxyfrullanoide; 9. (-)--cyclocostunolide; 10. (-) – eremofrullanoide; 11. marchantin A; 12. riccardin A; 13. riccardin B; 14. perottetin E. OH HOOC O H HO O HO 1 2 3 AcO O O H O O H AcO CHO 4 5 6 O H O O H O O O 7 8 O 9 OH OH OH O O O OH O 11 12 MeO O OH OH 10 O O OH O 13 HO 14 PHARMACOLOGICAL ACTIVITY OF BRYOPHYTES For a long time it has been known antibiotic influence of liverworts Marchantia, Conocephalum, Jungermannia, Riccia, Anthoceros and mosses Polytrichum, Atrichum, Dicranum, Mnium, Polytrichum and Sphagnum (14). 24 Chopra and Kumra (12) mention that extracts of Marchantia polymorpha, M. stellata, Polytrichum commune and another Polytrichum species posses antitumor elements. Antimicrobial activity has been confirmed for Conocephalum conicum, Dumortiera hirsuta, Astrella sanguinea Marchantia paleacea, Brachytecium procumbens, Sphagnum portoricense and S. strictum. The first two against fungus Candida albicans and Sphagna inhibit growth of the bacteria Staphylococcus aureus, Sarcina lutea and Pseudomonas aeruginosus. It is accepted that active compounds against bacteria are probably polyphenolics that act in a manner similar to that of substances reported in vascular plants. The antibiotic activity of bryophytes, as another plant groups, varies from species to species. It also depends on the age of the plant, season of collection, and the ecological niche (12, 15). Bryophytes also have antifungal property. Pogonatum aloides, Plagiothecium denticulatum and Diplophyllum albicans were particularly remarkable in this respect. From Porella isolated cinnamolid shows antifungal activity against dermatophytes like Trichophyton rubrum, T. mentagrophytes and Microsporum gypseum. Lunularin and lunularic acids showed antifungal activity against spore germination of Alternaria brassicola, Botrytis cinerea, Septoria nodorum and Uromyces fabae. Matsuo et al. (16, 17, 18) found that methanol extract of bryophytes, Herberta adunca and Odontoschisma denudatum inhibits the growth of some pathogenic fungi (Botrytis cinerea, Phizoctonia solani and Pythium debaryanum). The antifungal substances are: (-) herbertenol, (-) herebrtenol, (-) formylherbertenol and (+) acetoxyodontoschismenol. It is supposed that bryophytes contain antifeedant substances (compounds inhibiting feeding), effective in protection against insect and other animal attack. Benešova et al. (19), Benešova and Herout (20) and Benešova et al. (21) highlighted pinguisone and myliol (sesquiterpen alcohol) as a potential antifeedant against insect (Fig. 1). The first one was isolated from Aneura pinguis and the second one from Mylia taylorii. Asakawa (22) found a sesquiterpene hemiacetal - plagiochiline A (Fig. 1) that was commonly distributed in Plagiochila species. This compound inhibits the feeding of an afrincan worm (Spodoptera exempta), and this compound is also reported to be extremely poisonous to mice (2). Asakawa (23) emphasized that crude bitter principles obtained from Gymnocolea inflata and Jamsoniella autumnalis had intense antiphagic activity against Spodoptera spp. Kanaski and Ohta (24) isolated a piscicidal component from Marchantia polymorpha. The active substance was determined as the sesquiterpene lactone: (+) - costunolide. Asakawa at al. (25) also mentioned sesquiterpene lactones: diplophillin and frullanoid isolated from Diplophillum sp. and Frunallia sp. respectively, to have piscicidal activity of some fish (Fig. 1). Besides, mentioned growth regulator substances, a type of allelopathy between bryophytes and other plants is sometimes encountered, which suggest that bryophytes produce some allomones. Aqueous extract of the mosses Polytrichum commune and Sphagnum spp. inhibited the growth of Pinus and Picea seedlings, but stimulated the growth of Larix seedlings (26). Huneck and Schreiber (27) tested the plant growth inhibitory activity of five bryophyte terpenoids: gymnocolin, drimenol, longiborneol, longifolene and scapanin and endogenous hormone lunularic acid. They found these substances to be growth inhibitors on cress root and oat seedlings at 10-3 to 10-4 M and 25 growth promoters at 10-6 to 10-7 M, while lunularic acid showed only a weak effect on the growth of higher plants. Extracts of Polytrichum juniperinum have necrotising capacity against Sarcoma 37 implanted in CAF1 mice (2). Tulipinolide that has inhibitory activity against human carcinoma of the nasopharynx, zaluzalin that has inhibitory activity to p - 388 lymphocytic leukemia and costunolide that has antitumor capacity, all sesquiterpenoids, were isolated from Conocephalum supradecompositum, Frullania tamarisci, F. monocera, Porella japonica and Wiesnerella denudata. Ohta et al. (28) isolated diplophyllin (Fig. 1) from Diplophyllum albicans and D. taxifolium that have - methylene - lactone unit that shows significant activity against human epidermoid carcinoma. Asakawa et al. (22) presented the results of a study on cytotoxicity against the KB cell of the cyclic bibenzyl and acyclic bibenzyl derivatives obtained form liverworts. Marchantin A (Fig. 1) isolated from Marchantia polymorpha, M. paleacea var. diptera and M. tosana, riccardin A and B (Fig. 1) from Riccardia multifida and perrottetin E (Fig. 1) from Radula perrottetii. They also reported that plagiochiline A (Fig. 1) isolated from Plagiochila spp., apinguisane sesquiterpene alcohol and monoterpene ether obtained from Trocholejeunea sandvicensis also showed cytotoxicity against KB cells. Knoche et al. (29) and Mitchell et al. (30) noticed that workers in the forest industries of France and Canada often suffer from allergenic contact dermatitis caused by certain chemical constituents of epiphytic liverworts Frullania and Radula. They isolated a new sesquiterpenoid named (-) – frullanolide (Fig. 1) from Frullania tamarisci that is an allergen causing allergenic contact dermatitis. (+) - frullanolide was obtained from another Frullania species (Frullania dilatata) which also had allergenic potential. Later, many new allergens from Frullania species have been determined: (-) - oxyfrullanolide, (-) - cis - cyclo - costunolide, (+) - epoxyfrullanolide and (-) – eremofrullanolide (Fig. 1). Many bryophyte species have their own particular tastes and posses sometimes very distinctive odors. For example, Schuster (31) reported aromas of some liverworts: Leptolejeunea spp. have an intensive and diagnostic odor of licorice, Conocephalum conicum has a very strong mushroom smell, Moerckia spp. possess an intense unpleasant odor, Riella an anise like odor, Solenostoma obovatum has carrot like odor, Lophozia bicrenata has a pleasant odor similar to cedar oil, Lophocolea heterophylla and Lophocolea minor possess a rather distinctive mossy smell and Geocalyx graveolens has a turpentine like odor. Some chemical components of these taste and smell have recently been detected as new substances to science (32, 33, 34, 23, 35, 36, 37,38). CONCLUSION Bryophytes remain poorly known group of plant, in comparison to vascular plants. Many things still have to be done for better understanding and use of these plants. 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Christal structure analysis.Tetrahedron lettters 24: 115 - 116. 28 BRYOPHYTA, POTENCIJALNE LEKOVITE SIROVINE Sabovljevi Marko1, Bijelovi Aneta2, Grubiši Dragoljub3 1 Odsek za ekologiju bilja, Institut za botaniku i botani ka bašta, Biološki fakultet, Universitet u Beogradu 2 Odsek za fiziologiju bilja, Institut za botaniku i botani ka bašta, Biološki fakultet, Universitet u Beogradu 3 Institut za biološka istraživanja ''Siniša Stankovi '' IZVOD Bryophyta (mahovine, jetrenja e i rožnja e) su druga po veli ini grupa biljaka, odmah posle cvetnica, sa oko 28.000 vrsta širom sveta. Ipak, ak ni delom kao cvetnice, briofite se ne koriste u terapijske svrhe. Hemijski sastav sastojaka briofita je veoma slabo poznat, a podaci o tome su vrlo neobjedinjeni. Razlog tome je teška identifikacija briofita i mala koli ina jedne iste vrste koja je dostupna za obi no vrlo fine analize. Briofite su veoma bogate terpenoidima, fenolima (flavonoidi i derivati bibenzila), glikozidima, masnim kiselinama, proteinima, ali i nekim drugim retkim aromati nim jedinjenjima. Danas se briofite smatraju zna ajnim rezervoarima novih prirodnih produkata i sekundarnih jedinjenja od kojih mnoga imaju interesantnu biološku aktivnost. Biološka aktivnost briofita može se grubo predstaviti slede im dejstvima: antimikrobno, antifungalno, citotoksi no, antitumorsko, kardiotoni no, alergeno, nadražuju e i tumor pospešuju e, insekticidno, moluscicidno i piscicidno. Neka jedinjenja briofita takodje štite biljke od insekata, regulišu rast biljaka, inhibiraju oslobadjanje superoksid anjon radikala ili vrše inaktivaciju radikala, inhibiraju aktivnost 5-lipoksigenaze, kalmodulina, hijaluronidaze i ciklooksigenaze. Poslednji podaci govore i o anti-HIV aktivnosti nekih jedinjenja iz briofita (neki bibenzili jetrenja a). U radu su izložena lekovita svojsta i hemijski sastav briofita. 29