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Four novel macrocyclic bis(bibenzyl) dimers, named pusilatins A–D have been isolated from the liverwort, Blasia pusilla, and their structures established by a combination of high resolution NMR spectra, X-ray crystallographic analysis and chemical degradation.

The stereostructure of plagiochiline A (1) isolated from the liverwort Plagiochila fruticosa has been established by X-ray crystallographic analysis. Plagiochiline A was converted into plagiochilal B (2) and furanoplagiochilal (3) by human saliva, and stearoylvelutinal (4) isolated from the fungus Lactarius vellerus was converted into velleral (5), also by human saliva.

Two novel bicyclic sesquiterpenoids, trifarienols A and B with a new carbon skeleton, trifarane, have been isolated from the Malaysian liverwort, Cheilolejeunea trifaria , and their absolute structures established by a combination of NMR, CD, and X-ray crystallographic analysis.

From the slime mould Lycogala epidendrum, four unusual new acylglycerols, lycogarides D-G, were isolated. Their structures were determined by spectroscopic and chemical methods. Also, the known lycogalic acid dimethyl esters A and B were obtained.

Nudenoic acid, a new sesquiterpene possessing a novel tricyclic skeleton, was isolated from a Taiwanese liverwort Mylia nuda. The structure of nudenoic acid was determined by spectroscopic means and X-ray analysis.

(R) and (S)-2-anthrylmethoxyacetic acids (2ATMA) have been prepared to elucidate the absolute configuration of long-chain compounds containing a secondary hydroxy group, methyl 9-hydroxystearate and 10-nonacosanol (ginnol).

From the ether extract of the liverwort Odontoschisma denudatum , two novel diterpenoids, neodenudatenones A and B, having a new carbon skeleton named neodenudatenone-type have been isolated. Their absolute structures were determined by a combination of high resolution 2D-NMR and CD spectra, and chemical degradation.

Three new β-coumaranones, sparanone A, sparanone B and sparanoside B, were isolated from bulbs of Sparaxis tricolor. Their stereostructures were established on the basis of chemical evidence and spectroscopic studies.

Two new pinguisane-type, three new Diels-Alder reaction-type dimeric pinguisane sesquiterpenoids and known sesqui and diterpenoids were isolated from the ether extract of the Japanese liverwort Porella acutifolia subsp. tosano. Their absolute stereostructures were established by a combination of extensive 2D-NMR, CD spectra, X-ray crystallographic analysis, modified Mosher's method and chemical correlation.

Striatenic acid has been isolated from the liverwort Cheilolejeunea serpentina collected in Malaysia and its structure was determined on the basis of extensive 2D NMR techniques. The absolute configuration was established by synthesis of the optically active methyl ester.

Three new cyclic bis(bibenzyls), 2,12-dichloroisoplagiochin D, 12,7′-dichloroisoplagiochin D and 12,10′-dichloroisoplagiochin C have been isolated from the liverwort Herbertus sakuraii belonging to the Herbertaceae, together with isoplagiochin C and isoplagiochin D which have been isolated from the liverwort Plagiochila fruticosa. Their structures have been elucidated by a combination of 2D-NMR, CD spectra, X-ray crystallographic analysis and comparison of the spectral data with those of the known isoplagiochins. 2,12-Dichloroisoplagiochin D and 12-chloroisoplagiochin D have also been isolated from the liverwort Mastigophola diclados, belonging to the Mastigophoroideae. H. sakuraii is chemically closely related to Mastigophora diclados.

The Marchantiophyta (liverworts) produce which show interesting biological activity such as antimicrobial, antifungal, antiobesity and muscle relaxing activity etc. and are of very valuable for the chemosystematic and evolutional study of the Marchantiophyta and pteridophytes. The isolation, identification, structural elucidation and total synthesis of these characteristic natural products and their biological activity are reviewed.

From Cladonia rangiferina were isolated two novel abietane diterpenoids, hanagokenols A (1) and B (2). Also in this investigation, four known abitetane diterpenoids (3-6), four known labdane diterpenoids (7-10), one known isopimarane diterpenoid (11), and six known aromatic compounds were isolated. These structures were elucidated primarily through extensive NMR experiments. Hanagokenol A (1) was a unique abietane diterpene having an ether linkage between C-6 and C-18 of sugiol. Hanagokenol B (2) is also a unique secoabietane diterpene, having gamma-lactone which occurred by cleavage and subsequently oxidation between C-6/C-7 of 12-hydroxydehydroabietinol. Furthermore, all the isolated compounds (1-17) were tested for the antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE).

Four azaphilones named cohaerins C–F, along with 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl were isolated from the methanolic extract of the stromata of Annulohypoxylon cohaerens (Ascomycetes, Xylariaceae). Cohaerins C–E constitute typical azaphilones, bearing a γ-lactone ring, while cohaerin F has an unprecedented carbon skeleton, lacking the lactone ring of the azaphilones and with an aliphatic side chain being attached directly to the azaphilone backbone by a C–C bond. Their structures were determined by 2D NMR, IR, UV, and CD spectroscopy. They showed moderate inhibitory activity of nitric oxide production in RAW cells, and strong and nonselective antimicrobial effects.

Nootkatone (2), the most important and expensive aromatic of grapefruit, decreases the somatic fat ratio, and thus its demand is increasing in the cosmetic and fiber sectors. A sesquiterpene hydrocarbon, (+)-valencene (1), which is cheaply obtained from Valencia orange, was biotransformed by the green algae Chlorella species and fungi such as Mucor species, Botryosphaeria dothidea, and Botryodiplodia theobromae to afford nootkatone (2) in high yield.

Chromatographic fractionation of the methanol extract of fruiting bodies of the inedible Japanese mushroom Thelephora terrestris (Thelephoraceae) has led to the isolation and characterization of two unusual new pregnane-type steroids, 2beta,3alpha-dihydroxypregna-4,7,16-trien-12,20-dione (2) and 1alpha,2beta,3alpha-trihydroxypregna-4,7,16-trien-12,20-dione (3) named terresterones A and B (2, 3), as well as the previously known compound stizophyllin, now assigned as 2beta,3alpha,12beta-trihydroxypregna-4,7,16-trien-20-one (1). Elucidation of their structures and the revision of the stereochemical assignment of stizophyllin were achieved by means of extensive 1D and 2D NMR, UV, CD, IR, MS and molecular modeling experiments. This paper presents the first report on the isolation of true pregnane-type steroids from the Fungi kingdom.

Azaphilones, named cohaerins A and B were isolated from stromata of the xylariaceous ascomycete Hypoxylon cohaerens. Their absolute structures were determined by spectroscopic methods (2D NMR, MS, IR, UV CD), and subsequently confirmed by acetylation. Stromatal metabolite profiles of several taxa of Hypoxylon sect. Annulata were also generated using analytical HPLC with diode array and MS detection. The cohaerins were neither found in other Hypoxylon spp., nor in other Xylariaceae. However, they were present even in holotype material of H. cohaerens, collected over 200 years ago. The binaphthalene BNT was also omnipresent in sect Annulata, and its derivatives, the benzo[j]fluoranthenes daldinone A and truncatone, as well as presumably related compounds. These fungi were found devoid of other types of azaphilone pigments of the Xylariaceae, such as mitorubrins and daldinins, the latter of which are widespread in certain groups of Hypoxylon sect. Hypoxylon. Hence, chemotaxonomic data largely support the current generic concept. The original source of truncatone was identified as Hypoxylon annulatum.

Four new azaphilones named sassafrins A–D ( 1–4 ) were isolated from the methanol extract of the stromata of the fungus Creosphaeria sassafras (Xylariaceae, Ascomycetes). Their structures were elucidated by 2D NMR, HR-MS, IR, UV and CD spectroscopy. Sassafrin D ( 4 ) possesses a novel skeleton and its biosynthetic pathway is also discussed. In addition, all compounds showed broad-spectrum antimicrobial activity. Their apparently unique occurrence in C. sassafras supports the status of this fungus as a member of a distinct genus within the Xylariaceae, coinciding with molecular and morphological traits.

5alpha-substituted swainsonine analogues were synthesized by Mannich reaction of an in situ generated (-)-swainsonine iminium ion intermediate. 5alpha-substituted swainsonine analogues were epimerized to their 5beta-isomers in protic solvent. [reaction: see text]

Five novel p-terphenyl derivatives called curtisians M-Q (1-5) were isolated from the methanolic extract of fruit bodies of the Basidiomycete Paxillus curtisii. Their structures were elucidated by two dimensional (2D) NMR, MS, IR, and UV spectroscopy, and chemical reaction. Their antioxidative activities were also investigated.

Four p -terphenyl derivatives named curtisians E–H ( 1–4 ) were isolated from the methanolic extract of fruit bodies of the Basidiomycete Paxillus curtisii by a combination of Sephadex LH-20, silica gel column chromatography and preparative reversed phase HPLC. The relative stereochemistries of the curtisians were elucidated by 2D NMR, MS, IR and UV spectroscopy with the absolute configurations at C 3a–3d of the side chains being established as S by GC–MS on a chiral column previously used for separation of authentic standards.

Five p-terphenyl derivatives named thelephantins D-H (1-5) together with nine known compounds, thelephantins A-C (6-8), ganbajunin E (9), p-hydroxylbenzoic acid (10), ganbajunin C (11), thelephorin A (12), 2-O-methylatromentin (13) and atromentin (14), were isolated from the methanolic extract of fruit bodies of the Thelephoraceous Basidiomycete Thelephora aurantiotincta. Their structures were elucidated by high-resolution MS, 2D NMR, IR and UV spectroscopic analysis.

Three squalene-type triterpenoids named concentricols B, C and D ( 1 – 3 ) were isolated from the ethyl acetate extract of fruiting bodies of the xylariaceous ascomycete Daldinia concentrica . Their absolute structures were elucidated by analysis of 2D NMR, MS, IR and UV spectra, and the modified Mosher's method.

The reaction of nitro olefins with thiolate anions followed by protonation at −78 o C gives anti-β-nitro sulfides. This procedure can be applied to the anti-selective preparation of β-nitro ethers and β-nitro selenides. The reaction of cyclic nitro olefins with aryl thiol gives cis-β-nitro sulfide in excellent selectivity. The conjugate addition of alkylaluminum reagents to phenylthio β-nitro olefins followed by protonation at −78 o C also results in selective formation of anti-β-nitro sulfides. Theoretical calculations show that the methylthio group on the β-position covers the one side of the nitronate plane effectively to give the anti isomer in a stereoselective way