Pungent and bitter, cytotoxic and antiviral terpenoids from some bryophytes and inedible fungi.

Most liverworts elaborate characteristic odiferous, pungent and bitter tasting compounds many of which show antimicrobial, antifungal, antiviral, allergenic contact dermatitis, cytotoxic, insecticidal, anti-HIV, superoxide anion radical release, plant growth regulatory, neurotrophic, NO production inhibitory, muscle relaxant, antiobesity, piscicidal and nematocidal activities. Several inedible mushrooms produce female spider pheromones, strong antioxidant, and cytotoxic compounds. The present paper is concerned with the extraction and isolation of terpenoids from some bryophytes and inedible fungi and their pungent and bitter taste, and cytotoxic and antiviral activity.

Cytotoxic bibenzyls, and germacrane- and pinguisane-type sesquiterpenoids from Indonesian, Tahitian and Japanese liverworts.

Cytotoxic bibenzyls, and germacrane- and pinguisane-type sesquiterpenoids have been isolated from unidentified Indonesian and Tahitian Frullania sp. and Japanese Porella perrottetiana by using a combination of chromatographic methods. The structure activity relationship (SAR) study showed that the presence of a phthalide group in bibenzyls, an alpha-methylene-gamma-lactone in germacrane-type sesquiterpenoids, and beta-hydroxycarbonyl in pinguisane-type sesquiterpenoids play an important role in providing cytotoxic activity against both human promyelocytic leukemia (HL-60) and human pharyngeal squamous carcinoma (KB) cell lines. The structure of each isolated compound was elucidated by using spectroscopic methods and the cytotoxicity was determined by using the WST-8 colorimetric assay.

The quaternary indole alkaloids from two Sumatran Lerchea species.

The Sumatran forest plants Lerchea cf. bracteata and L. parviflora were found to contain alkaloids and their extract showed siginificant activity toward some testing pathogenic microbes. Isolation work on L.cf bracteata yielded known quaternary alkaloid N(b)-methylantirhine (2) while L. parviflora gave 5,6-dihydroflavopereirine (3).

The coloring constituents of Scleroderma sinnamariense (Sclerodermaceae).

Two known coloring constituents, methyl 4,4'-dimethoxyvulpinate (1) and 4,4'-dimethoxyvulpinic acid (2) have been isolated from the fruit body of fungus Scleroderma sinnamariense Mont. The methanolic extract, its fractions and compound (2) showed moderate activity to inhibit the growth of some pathogenic testing microbes used.

Volatile components of selected liverworts, and cytotoxic, radical scavenging and antimicrobial activities of their crude extracts.

Crude extracts of the Tahitian liverworts Mastigophora diclados and Frullania sp., the Indonesian Frullania sp., Dumortiera hirsuta and Marchantia sp., and the Japanese Porella perrottetiana were investigated chemically by using gas chromatography-mass spectrometry (GC-MS). All extracts contained various volatile sesqui- and diterpenoids and a few aromatic compounds. The Tahitian M. diclados and Frullania sp., and the Indonesian Frullania sp. exhibited cytotoxic activity against HL-60 and KB cell lines. The extracts of the Tahitian M. diclados and the Indonesian Marchantia sp. showed radical scavenging activity, whereas the crude extracts of the Tahitian M. diclados and Frullania sp., and the Indonesian Frullania and Marchantia sp. showed antimicrobial activity against Staphylococcus aureus and Bacillus subtilis.

Zierane sesquiterpene lactone, cembrane and fusicoccane diterpenoids, from the Tahitian liverwort Chandonanthus hirtellus.

Cembrane-type diterpenoids, 13,18,20-epi-iso-chandonanthone (1) and (8E)-4alpha-acetoxy-12alpha,13alpha-epoxycembra-1(15),8-diene (2), two fusicoccane-type diterpenoids, fusicoauritone 6alpha-methyl ether (3) and 6beta,10beta-epoxy-5beta-hydroxyfusicocc-2-ene (4) and a zierane sesquiterpene gamma-lactone, chandolide (5) were isolated from the Tahitian liverwort Chandonanthus hirtellus (Web.) Mitt., together with eight known diterpenoids, chandonanthine (6), fusicogigantone A (7), fusicogigantone B (8), fusicogigantepoxide (9), anadensin (10), fusicoauritone (11), ent-verticillol (12) and ent-epi-verticillol (13). Their structures were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analyses. Compounds 1, 5 and 10 showed weak cytotoxic activity against HL-60. Compound 3 also indicated weak cytotoxic activity against KB cell lines.

Cytotoxic, radical scavenging and antimicrobial activities of sesquiterpenoids from the Tahitian liverwort Mastigophora diclados (Brid.) Nees (Mastigophoraceae).

A drimane, (+)-drimenol (1), five known herbertanes, (-)-alpha-herbertenol (2), (-)-herbertenediol (3), mastigophorene A (4), (-)-mastigophorene C (5) and (-)-mastigophorene D (6), a pimarane, (-)-ent-pimara-8(14),15-dien-19-oic acid (7), and two eudesmanolides, (-)-diplophyllolide A (8) and (-)-diplophyllin (9) were isolated from the Tahitian Mastigophora diclados (Brid.) Nees. Herbertane sesquiterpenes (2, 3, 5 and 6) showed cytotoxicity against HL-60 and KB cell lines, radical scavenging activity and antimicrobial activity against Bacillus subtilis. (-)-Diplophyllolide A (8) also exhibited cytotoxicity against HL-60 and KB cell lines.

Volatile components from selected Tahitian liverworts.

Six Tahitian liverworts, Trichocolea pluma, Chandonanthus hirtellus, Mastigophora diclados, Jungermannia sp., Plagiochila sp. and Cyathodium foetidissimum were chemically investigated. All of these liverworts produce their own characteristic compounds. Vanillic acid methyl ester was isolated for the first time from T. pluma. Skatol is responsible for the very intense unpleasant odor of C. foetidissimum. Herbertane-type sesquiterpenoids are peculiar components of M. diclados, and fusicoccane-type diterpenoids were identified in Pagiochila sp. Cembranes and ent-verticillanes were isolated from C. hirtellus and also detected in Jungermannia species. C. hirtellus also biosynthesizes algal components and such results may suggest that some liverworts originate from algae.

Furoquinoline alkaloids from Melicope bonwickii (F.Muell.) T.Hartley.

Investigation on the leaves of Melicope bonwickii (F.Muell.) T.Hartley (Rutaceae) afforded a new 7-(2'-hydroxy-3'-chloroprenyloxy)-4-methoxyfuroquinoline (1) together with the known 7-(2',3'-epoxyprenyloxy)-4-methoxyfuroquinoline (2), evellerine (3) kokusaginine (4) and an amide aurantiamide acetate (5). Compounds 1 and 2 showed significant activity against cervical cell lines (Hela).