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Phellibarin D ( 1 ), the first B/C ring-rearranged lanostane triterpenoid possessing a 6/5/7/5 ring framework, was isolated from Phellinus rhabarbarinus . This compound’s structure was determined via comprehensive NMR and MS analyses. In addition, 1 exhibited cytotoxicity against five human cancer cell lines and inhibitory activity against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages.

(+)- and (−)-Ganodilactone (1), a pair of novel meroterpenoid dimers possessing a unique 5′H-spiro[chroman-4,2′-furan]-2,5′-dione ring system, along with their biogeneticly-related compound, ganomycin I (2), were discovered from the fruiting bodies of Ganoderma leucocontextum. The structures and absolute configurations were assigned with the aid of 1D and 2D NMR spectra, HRESIMS analysis and ECD calculations. (±)-, (+)-, and (−)-ganodilactone (1) showed pancreatic lipase inhibitory activities and exhibited the IC50 values as 27.3, 4.0, and 2.5 μM, respectively.

Various diazabicyclic β-lactams are prepared starting from chiral proline or piperidine derivatives using the title method as key step.

Fifteen new triterpenoids, including terreolides A-C (I) possessing a unique trioxaspiroketal system and terreolides D-F (II) having an unprecedented carbon skeleton, are isolated from the title mushroom.

Six new ent-15-oxokauran-19-oic acid derivatives, named pterisolic acids A-F (1-6), were isolated from the ethanol extract of the fern Pteris semipinnata (Pteridaceae), and the structures of these new ent-kauranoids were elucidated on the basis of extensive spectroscopic studies and single crystal X-ray diffraction analysis.

The diterpenoids nigernin A (I) and B (II) and the nitrogenous terphenyl derivative phellodonin (III) are isolated from the title fungus for the first time.

The structure elucidation of the four new neo-clerodane diterpenoids (I) and (II), isolated from a traditional Chinese medicinal plant, is described.

This review surveys the chemical, biological and mycological literature dealing with the isolation, structure elucidation, biological activities, and synthesis of pigments manufactured by those fungi that produce conspicuous fruiting bodies (macromycetes).

A flexible and practical strategy toward the synthesis of rare 2H-furo[3,2-b]benzopyran-2-one skeleton has been developed. With a microwave-assisted cyclization-dehydration as the key transformation, the first total synthesis of pulverolide has been completed in 10 steps with 9% overall yield, leading to the revision of its proposed structure. (C) 2010 Elsevier Ltd. All rights reserved.

using the Pictet—Spengler reaction of tryptophan ester (I) with aldehydes (II) followed by aromatization using cyanuric chloride

The isolation, structure elucidation, and relative stereochemistry assignment of a novel illudane-illudane bis-sesquiterpene, agrocybone (1), from the basidiomycete Agrocybe salicacola, were reported. Agrocybone represents a structure with eight rings (including two Spiro rings) and seven stereogenic carbon atoms. Agrocybone was found to exhibit weak antiviral activity against respiratory syncytial virus (RSV) with IC(50) value of 100 mu M. (C) 2010 Elsevier Ltd. All rights reserved.

Four new vibralactone derivatives, named vibralactones G-J (1-4), together with vibralactone (5) have been isolated from cultures of the basidiomycete Boreostereum vibrans. The new structures were elucidated by means of spectroscopic methods.

A New diterpene with a neodolastane skeleton, named 2,5-epoxy-5,13-dihydroxyneodolast-3-en-14-one (1), was isolated from cultures of the basidiomycete Trametes corrugate together with guanacastepene E. The structure of 1 was elucidated on the basis of extensive spectroscopic analysis including IR, MS, 1D and 2D NMR experiments.

Two new metabolites, named crispacolide (1) and 3-acetyl-4-hydroxymethyl-tetrahydrofuran (2), were isolated from the fruiting bodies of basidiomycete Sparassis crispa (Wulf.) Fr. The structures and stereochemistry were established on the basis of spectroscopic means.

Concentricolide, a novel compound with anti-HIV-1 activity and isolated from ascomycete Daldinia concentrica, has been synthesised for the first time as a racemate from furan-3-carbaldehyde and dihydrofuran-2(3H)-one via a Diels-Alder reaction. The identity of the synthetic sample was verified by comparison of its spectral data with those of an authentic sample.

A new acridone alkaloid, 1,3-dihydroxy-4-methoxy-10-methylacridone (1), was isolated from leaves of the plant Micromelum integerrimum, together with two known carbazole alkaloids, glycozolinol (2) and methyl carbazole-3-carboxylate (3). Their structures were elucidated by extensive spectroscopic analysis.

Two new perulactone-type withanolides, named perulactone C (1) and perulactone D (2), together with four known compounds, perulactone (3), perulactone B (4), blumenol A, and (+)-(S)-dehydrovomifoliol, were isolated from the aerial parts of Physalis peruviana. The structures of the new compounds were elucidated on the basis of 1D- and 2D-NMR experiments, including HMBC, HSQC, 1H,1H-COSY, and ROESY, as well as HR-MS.

Two new furanoid norditerpenes (1, 2) were isolated from the root tubers of Dioscorea bulbifera L. Their structures were established on the basis of extensive spectroscopic analysis.

Two new ent-kaurane diterpene derivatives, sculponeatins N (1) and O (2), and a new A-ring contracted oleanane triterpenoid, sculponeatic acid (5), were isolated from the plant Isodon sculponeata. Their structures were elucidated on the basis of extensive spectroscopic analysis. This is the first report of natural occurrence of an A-ring contracted oleanane triterpenoid.

A new drimane sesquiterpenoid, 3-keto-drimenol (1), were isolated from cultures of the basidiomycete Clitocybe conglobata together with 3 beta-hydroxy-11-acetyldrimene (2), 3 beta-hydroxydrimenol (3), 11,12-dihydroxydrimene (4), 3 beta-hydroxy-11,12-O-isopropyidrimene (5), and 3 beta,11,12-trihydroxydrimene (6). Their structures were established from MS and NMR experiments. Compounds 1, 3, and 6 showed inhibitory activities against two isozymes of 11 beta-hydroxysteroid dehydrogenases with IC50 1.7-8.0 mu g/ml (human 11 beta-HSD1), 10.7-24.1 mu g/ml (mouse 11 beta-HSD1); 177.0-220.0 mu g/ml (human 11 beta-HSD2),250.5-500.2 mu g/ml (mouse 11 beta-HSD2), respectively, which catalyze the interconversion of active cortisol and inactive cortisone.

Five new secondary metabolites derived from pentanol, namely catathelasmols A-E (1-5), were isolated from the fruiting bodies of the basidiomycete Catathelasma imperiale. Their structures were elucidated on the basis of spectroscopic analysis, and the absolute configurations were determined by computational chemistry. Compounds 3, 4 and 5 showed inhibitory activities against two isozymes of 11 beta-hydroxysteroid clehydrogenases (11 beta-HSD1 and 11 beta-HSD2), with IC(50) values of 28.7-62.3 mu g ml(-1) (human 11 beta-HSD1), 30.4-149.2 mu g ml(-1) (mouse 11 beta-HSD1), 5.1-177 mu g ml(-1) (human 11 beta-HSD2) and 32.3-129 mu g ml(-1) (mouse 11 beta-HSD2), which catalyze the interconversion of cortisol and cortisone. The Journal of Antibiotics (2009) 62, 239-242; doi:10.1038/ja.2009.17; published online 27 March 2009

An unusual highly functionalized lactarane sesquiterpene, named velleratretraol (1), was isolated from the ethanol extract of the fruiting body of the mushroom Lactarius vellereus. Its structure was determined through spectroscopic analysis and single-crystal X-ray diffraction studies. The proposed assignment of the absolute configuration is based on computational results. It showed weak activity against HIV-1 cells with an effective concentration of 68.0 mu g ml(-1) and a selectivity index of 2.0.

Six new sesquiterpenes having the botryane carbon skeleton (1 similar to 6), together with known compounds (7 similar to 10) were induced and isolated from the ascomycete Daldinia concentrica (strain S 0318). Structures elucidation was accomplished by NMR spectroscopic and X-ray crystallographic studies.

Four new natural products possessing vibralactone skeleton, 1,5-secovibralactone (1), vibralactone B (2), vibralactone C (3) and acetylated vibralactone (4), together with known compound vibralactone (5), had been isolated from cultures of the basidiomycete Boreostereum vibrans. The structures of 1-4 were elucidated on the basis of spectroscopic methods. The absolute configuration of 1 was suggested to be S by computational methods.

Two new highly oxygenated lanostane triterpenoids, ganoderic acid AP2 (1) and ganoderic acid AP3 (2), were isolated from the fruiting bodies of the fungus Ganoderma applanatum (Ganodermataceae), along with four known analogues, ganoderenic acids A, B, D and G (3-6). The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis.

Two new guaiane-type sesquiterpene lactones with an unusual sulfonic acid group, sulfocostunolide A (1) and sulfocostunolide B (2), were isolated from the roots of Saussurea lappa. Their structures were elucidated on the basis of extensive spectroscopic analysis.

Daldinin A, B, C with a new skeleton, together with four known compounds, were induced and isolated from cultures of the ascomycete Daldinia concentrica. Their structures were elucidated by spectroscopic analysis, and that of daldinin A was confirmed by single-crystal X-ray diffraction.

A new farnesyl phenol named (+)-(R)-grifolinone C (1) has been isolated from the fruiting bodies of the basidiomycete Albatrellus confluens. (+)-(R)-Grifolinone C (1), a dimeric meroterpenoid, is accompanied by albatrellin (2), grifolinone B (3), grifolin (4), and grifolinone A (5). Albatrellin (2) exhibited cytotoxic activity against HepG2 human lung carcinoma cells with IC50 value of 1.55 mu g ml(-1). The structures were established on the basis of spectral evidence (IR, ID- and 2D-NMR, and MS analyses).

Flazin isolated from the fruiting bodies of Suillus granulatus was found to possess weak anti-HIV activity (EC50=2.36 mu m, TI= 12.1). To establish a SAR study, 46 flazin analogues were synthesized, and their anti-HIV activities were evaluated in vitro. Among them, flazinamide (9a) showed the most potent activity with an EC50 value of 0.38 pm and a TI value of 312.0. The results suggested that appropriate substituents at positions 3, 1', and 5' of flazin might play a crucial role in determining their anti-HIV activities, and that flazinamide can be considered as a promising, readily available anti-HIV agent.

Guajadial (1), a novel caryophyllene-based meroterpenoid, was isolated from the Leaves of Psidium guajava (guava). The structure and relative stereochemistry of guajadial (1) were elucidated by extensive spectroscopic analysis. A possible biosynthetic pathway for 1 was proposed.

Anew spiroaxane sesquiterpene (15-hydroxy-6 alpha,12-epoxy-7 beta, 10 alpha H,11 beta H-spiroax-4-ene, 1) was isolated from the culture broth of the basidiomycete Pholiota adiposa. The structure of 1 was established on the basis of MS, IR, ID, and 2D NMR experiments.

A novel sesquiterpene named cyclopinol (1) together with two related known compounds, cyclocalopin A (2) and O-acetylcyclocalopin A (3), has been isolated from the basidiomycete Boletus calopus. The structure of compound 1 was established on the basis of spectral methods (MS, IR, 1D, and 2D NMR experiments).

Two new benzopyran-4-one derivatives, applanatins A (1) and B (2), were isolated from the fruiting bodies of the fungus Ganoderma applanatum (Ganodermataceae), along with one known analogue, ganoderma aldehyde (3), as well as four known ganoderenic acids. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis. The partial assignments of the NMR spectra of 3 were also revised.

Two new highly oxidized humulane sesquiterpenes, mitissimols F (1) and G (2), were isolated from the fruiting bodies of Lactarius mitissimus. Their structures were elucidated by using extensive spectroscopic techniques including 1D- and 2D-NMR experiments. The absolute configuration of mitissimol F (1) was determined by 1H-NMR resolution of its diastereoisomeric α-methoxy-α-(trifluoromethyl)benzeneacetates (MTPA). It was shown to be (1S,3E,6S,8R,9R,10S,11R)-8,9 : 10,11-diepoxy-1,6-dihydroxyhumul-3-en-5-one (=(1S,2R,4R,6S,8E,11S,12R)-6,11-dihydroxy-1,6,10,10-tetramethyl-3,13-dioxatricyclo[10.1.0.02,4]tridec-8-en-7-one).

One lactone marasmane sesquiterpene named 8 alpha,13-dihydroxy-marasm-5-oic acid gamma-Iactone (1) and one unsaturated marasmane sesquiterpene named 13-hydroxy-marasm-7(8)-en-5-methoxy gamma-acetal (2) together with a known compound: 7 alpha,8 alpha,13-trihydroxy-marasm-5-oic acid gamma-lactone (3) were isolated from the fruiting bodies of Russula foetens. Their structures were established on the basis of spectral methods (MS, IR, 1D and 2D NMR experiments).

A new purple azulene pigment (1) was isolated from the fruiting bodies of the basidiomycete Lactarius deliciosus together with one known pigment (2). The structures of the pigments were established on the basis of spectral evidence (MS, IR, 1D- and 2D-NMR experiments).

A fungal pigment, hypocrellin D (1), together with three known perylenequinone derivatives hypocrellin A (2), B (3) and C (4), was isolated from the fruiting bodies of Shiraia bambusicola. Its structure was elucidated on the basis of spectral data including 2D NMR experiments. Hypocrellin D (1) significantly inhibited the growth of tumor cell lines Bel-7721, A-549 and Anip-973 with IC50 values of 1.8, 8.8, 38.4 microg/ml, respectively.