Hachimijiogan, a traditional herbal medicine, modulates adipose cell function and ameliorates diet-induced obesity and insulin resistance in mice.

(HJG) has originally been used to ameliorate a variety of symptoms associated with low ambient temperatures. However, its pharmacological action in metabolic organs remains unclear. We hypothesized that HJG may modulate metabolic function and have a potential therapeutic application to metabolic diseases.

Multitasking bamboo leaf-derived compounds in prevention of infectious, inflammatory, atherosclerotic, metabolic, and neuropsychiatric diseases.

Bamboo is a medicinal plant, and has long been used as a traditional/folk medicine and a food preservative in Japan. Bamboo leaf contains many active ingredients with medicinal benefits. In particular, recent studies demonstrated that bamboo leaf extract and its constituents have great potential to prevent infectious, inflammatory, cardiovascular, metabolic, and neurological/neuropsychiatric diseases.

Potential Anti-allergic Effects of Bibenzyl Derivatives from Liverworts, Radula perrottetii.

The liverwort contains various bibenzyl derivatives which are known to possess various biological activities, such as anti-inflammatory effects. Mast cells (MC) play crucial roles in allergic and inflammatory diseases; thus, inhibition of MC activation is pivotal for the treatment of allergic and inflammatory disorders. We investigated the effects of perrottetin D (perD), isolated from , and perD diacetate (Ac-perD) on antigen-induced activation of MCs.

Distribution of Bibenzyls, Prenyl Bibenzyls, Bis-bibenzyls, and Terpenoids in the Liverwort Genus .

Plants of the genus are chemically very distinct from the other liverworts since they mainly elaborate bibenzyls including bibenzyl cannabinoids and prenyl bibenzyl derivatives, as well as bis-bibenzyls. Several of these components show biological activities such as psychoactivity, vasopressin antagonist, antimicrobial, antifungal, and NO production inhibitory activity, and cytotoxic activity against human cancer cell lines. While distribution of terpenoids in species is in general very limited, some Portuguese species are rich sources of sesquiterpenoids.

Terpenoids, Flavonoids and Acetogenins from Some Malagasy Plants.

Humulanes, drimanes, ent-kaurane, lupane, cycloartane, flavanone, flavones and quinol derivatives were isolated from Malagasy Cussonia vantsilana, Helichrysum gymnocephalum, Phyllarthron madagascariense, Gomphocarpus fructicosus, Cinnamosma sp. and C. fragrans, and their structures elucidated by using extensive NMR analysis.

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.

Phytochemical and biological studies of bryophytes.

The bryophytes contain the Marchantiophyta (liverworts), Bryophyta (mosses) and Anthocerotophyta (hornworts). Of these, the Marchantiophyta have a cellular oil body which produce a number of mono-, sesqui- and di-terpenoids, aromatic compounds like bibenzyl, bis-bibenzyls and acetogenins. Most sesqui- and di-terpenoids obtained from liverworts are enantiomers of those found in higher plants.

Terpenoids and bibenzyls from three Argentine liverworts.

A new rosane diterpenoid, 3a-hydroxy-5,15-rosadien-11-one (3), was isolated, together with a known rosane diterpenoid, 5,15-rosadiene-3,11-dione (4), and an aromadendrane sesquiterpenoid, ent-cyclocolorenone (5), from the Et(2)O extract of an unidentified Argentine liverwort Anastrophyllum species. Moreover, four known sesquiterpene lactones 6-9 and two known bibenzyls 10, 11 were isolated from the Et(2)O extracts of Argentine Frullania brasiliensis and Radula voluta, respectively. The structures of compounds 3-11 were determined by the use of NMR techniques.

Chemosystematics of Porella (Marchantiophyta, Porellaceae).

The taxonomy of the liverwort genus Porella based on plant morphology has been regarded as difficult. Recent DNA-based studies have brought new insights into the systematics of these liverworts and have uncovered some novel relationships that allowed the resolution of controversial treatments based on morphology. One of the outstanding features of these plants, in addition to their form, is their chemical composition, which is characterized by great diversity of secondary metabolites.

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.

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.

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).

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.

Sesqui- and diterpenoids from three New Zealand liverworts: Bazzania novae-zelandiae, Gackstroemia sp. and Dendromastigophora sp.

Two new sesquiterpenoids, 1 and 2, were isolated from the unidentified liverwort Gackstroemia species, and three known sesquiterpenoids, 3-5, and a known sesqui- (6) and diterpenoid (7) were isolated from Bazzania novae-zelandiae and the unidentified Dendromastigophora species, respectively. Their structures were determined by spectroscopic analysis.

Rare prenylated flavonoids from Tephrosia purpurea.

Chemical investigations of aerial parts of Tephrosia purpurea yielded the rare prenylated flavonoids, tephropurpulin A (1) and isoglabratephrin (2), in addition to a previously identified flavonoid, glabratephrin (3). Structures were established by 1D and 2D NMR spectroscopy, as well as by HR-MS analysis; for compounds 2 and 3, structures were confirmed by X-ray analysis.

New ent-Verticillane Diterpenoids from the Japanese Liverwort Jackiella javanica.

Three new ent-verticillane diterpenoids have been isolated from the Japanese liverwort Jackiella javanica, together with known sesqui- and diterpenoids. Their absolute configurations were established by X-ray crystallographic analysis and circular dichroism spectroscopy.

Bazzanane sesquiterpenoids from the New Zealand liverwort Frullania falciloba.

Two new bazzanane-type sesquiterpenoids have been isolated from the New Zealand liverwort Frullania falciloba. Their structures were confirmed by NMR and CD spectroscopy and chemical reactivity.

Diterpenoids and aromatic compounds from the three New Zealand liverworts Jamesoniella kirkii, Balantiopsis rosea, and Radula species.

Three new aromatics were isolated from the New Zealand liverwort Balantiopsis rosea. A new bibenzyl was isolated from an unidentified Radula species, together with known bibenzyls. Jamesoniella kirkii yielded three known ent-isopimarane and two ent-kaurane diterpenoids.

Induction of apoptosis by new ent-kaurene-type diterpenoids isolated from the New Zealand liverwort Jungermannia species.

Some diterpenoids show various biological activities, including anti-inflammatory, anti-HIV and anti-tumor activity. Previously, we have focused our research on the apoptosis-inducing properties of diterpenoids and found that some ent-kaurene-type diterpenoids induced apoptosis in human leukemia HL-60 cells. In this study, we have investigated the induction of apoptosis in HL-60 cells by the novel ent-kaurene-type diterpenoids, jungermannenones A (JA), B (JB), C (JC) and D (JD), isolated from the New Zealand liverwort Jungermannia species.

New sesquiterpenoid from the New Zealand liverwort Lepidozia spinosissima.

A new cyclogorgonane-type sesquiterpenoid, 1,5-cyclo-3,6-gorgonadien-15,11-olide was isolated from the New Zealand liverwort Lepidozia spinosissima, together with three known sesquiterpenoids. Their structures were established by the extensive NMR techniques and chemical reaction.

ent-Verticillane-type diterpenoids from the Japanese liverwort Jackiella javanica.

Three ent-verticillane diterpenoids and two ent-sesquiterpenoids were isolated from the Japanese liverwort Jackiella javanica Schiffn. together with five known ent-verticillane and three ent-kaurane diterpenoids, and three sesquiterpenoids. Five ent-verticillane epoxides were synthetically prepared from ent-verticillols action to clarify the absolute configuration of natural ent-9,10-epoxyverticillol.

Activation of p38 mitogen-activated protein kinase during ent-11alpha-hydroxy-16-kauren-15-one-induced apoptosis in human leukemia HL-60 cells.

Kaurene-type diterpenes possess various biological activities including antitumor and anti-inflammatory effects. Indeed, we have found that an ent-kaurene diterpene, ent-11alpha-hydroxy-16-kauren-15-one (KD), induced apoptosis via caspase-8 activation in human promyelocytic leukemia HL-60 cells. However, the mechanism of caspase-8 activation by KD is not clear.

An ent-kaurene diterpene enhances apoptosis induced by tumor necrosis factor in human leukemia cells.

Some antitumor agents, including tumor necrosis factor-alpha (TNF-alpha) and camptothecin (CPT), often cause resistance of tumor cells to antitumor agents through activation of the nuclear factor-kappa B (NF-kappa B) pathway that leads to up-regulation of anti-apoptotic proteins. Therefore, co-treatment of an inhibitor of the NF-kappa B pathway with antitumor agents is a useful strategy for chemotherapy. Here we report that ent-11 alpha-hydroxy-16-kauren-15-one (KD) selectively inhibits NF-kappa B-dependent gene expression due to treatment with TNF-alpha.

New sesquiterpenoids from the New Zealand liverwort Chiloscyphus subporosus.

A new aromadendrane-type sesquiterpenoid, 4(15)-aromadendren-12,5alpha-olide and an aromadendrane-guaianolide dimer have been isolated from the New Zealand liverwort Chiloscyphus subporosus. Their structures were established by extensive NMR techniques and X-ray crystallographic analysis.