He-Ping Chen

South-Central Minzu University · School of Pharmaceutical Sciences

Secondary metabolites of higher fungi (mushrooms) are an underexplored resource compared to plant-derived secondary metabolites. An increasing interest in mushroom natural products has been noted in recent years. This chapter gives a comprehensive overview of the secondary metabolites from higher fungi, with 765 references highlighting the isolatio...

Matsutakone (1), a novel sterol with an unprecedented polycyclic ring system, together with a new norsteroid matsutoic acid (2), were isolated from the fruiting bodies of Tricholoma matsutake. Their structures and absolute configurations were assigned by extensive spectroscopic analyses and computational methods. Bioassay results showed that compou...

Five new triterpenoids, irpeksins A–E (1–5), were isolated from fruiting bodies of the medicinal fungus Irpex lacteus. The structures as well as absolute configurations of the new compounds were established via extensive spectroscopic analysis, computational methods, and Cotton effects. Compounds 1–4 are featured by a scaffold of 1,10-seco- and rin...

Irpexolidal (1), a triterpenoid with an unprecedented carbon skeleton, along with its biogenetic-related compound irpexolide A (2), were isolated from the fruiting bodies of the medicinal fungus Irpex lacteus. Irpexolidal features a 6/5/6/5/6/5-fused polycyclic skeletal system which arises from the eburicane-type triterpene by a 6,7-seco-6,8-cyclo...

A variety of novel natural products with significant bioactivities are produced by the basidiomycete Boreostereum vibrans. In the present study, we describe 16 novel natural oximes and oxime esters with a vibralactone backbone, vibralactoximes, which were isolated from the scale-up fermentation broth of B. vibrans. Their structures were determined...

The ethnobotanical plant Marsdenia tenacissima has been used for hundreds of years for Dai people in Yunnan Province, China. Previously, chemical investigations on this plant have revealed that pregnane glycosides were the main biological constituents. Nine new pregnane glycosides, marsdeosides A–I (1–9), were isolated from cultivated dried stems o...

Two triterpenes, ganoaustralins A (1) and B (2), featuring unprecedented 6/6/6/5/6 scaffolds were isolated from the fruiting bodies of the mushroom Ganoderma australe. The structures were determined by extensive NMR and HRESIMS spectroscopic analysis. The absolute configuration of the C-25 in ganoaustralin A was assigned by the phenylglycine methyl...

Chemical investigation on the medicinal fungus Ganoderma australe led to the identification of ten new nor-lanostane triterpenes, namely two hexa-nor ones, ganoaustratetraenones A ( 1 ) and B ( 2 ), five penta-nor ones, ganoaustraldehydes A–E ( 3 – 7 ), and three tetra-nor ones ganoaustrenoic acids A–C ( 8 – 10 ). The chemical structures along with...

One new prenylated benzenoid, (±)-chevalieric acid ( 1 ), and four new anthraquinone derivatives, (10 S ,12 S )-, (10 S ,12 R )-, (10 R ,12 S )-, and (10 R ,12 R )-chevalierone ( 2 – 5 ), together with ten previously described compounds ( 6 – 15 ), were isolated from the fungus Aspergillus chevalieri (L. Mangin) Thom and Church. The structures of n...

Cordycicadins A-D (1-4) are four novel polyketides that were isolated from the liquid fermentation of the insect-pathogenic fungus Cordyceps cicadae JXCH1. The structures were determined by a combination of spectroscopic analysis, single-crystal X-ray diffraction, and computational methods. Compounds 1, 3, and 4 harbor an unusual exocyclic enol eth...

Eight undescribed lanostane triterpenoids (1–8) were isolated from cultures of the basidiomycete Ganoderma weberianum TBRC-BCC 60642. The structural types of lanostane constituents were different between mycelial cultures and fruiting bodies. Lanostanes 2, 3 and 6 showed moderate antimalarial activity against Plasmodium falciparum K1 (IC50 10–15 μM...

Eight undescribed phenylpropanoid-dihydrochalcone hybrids, namely (+)- and (−)-malahupin A, (+)- and (−)-malahupin B, (±)-malahupin C, malahupinosides A and B, 7‴-epi-malahupinoside B, together with two known compounds, phloretin and phlorizin, were isolated from the leaves of the folk medicinal plant Malus hupehensis. Their structures were elucida...

Twelve new lanostane triterpenoids (1–5, 7–13) were isolated from the fruiting bodies of the fungus Ganoderma australe. The structures of the new compounds were elucidated by extensive 1D and 2D NMR, and HRESIMS spectroscopic analysis. All the triterpenes are featured by 20(22)E configurations which are uncommon in the Ganoderma triterpene family....

Eighteen linear triquinane sesquiterpenoids (LTSs), including seventeen previously undescribed ones (hirsutuminoids A-Q), were isolated from the fermentation of the fungus Stereum hirsutum (Willd.) Pers. The structures and absolute configurations of the isolates were characterized by extensive spectroscopic analysis (1D, 2D NMR, and HRMS data), tog...

Structure- and mechanism-based redesign of the Fe(II)/2-oxoglutarate-dependent oxygenase AndA was performed. The function of AndA was expanded to catalyze a spiro-ring formation reaction from an isomerization reaction. The redesigned AndA...

Epigenetic modifiers are proved to be effective specialized products-mining tools by rationally regulating the gene expression of fungal biosynthetic pathways. Chemical investigation on the histone deacetylase inhibitor (HDI) vorinostat (also known as SAHA)-modified cultures of the basidiomycete Cyathus stercoreus (Schwein.) De Toni (Nidulariaceae)...

Non-heme iron and α-ketoglutarate-dependent (Fe/αKG) oxygenases catalyze various oxidative biotransformations. Due to their catalytic flexibility and high efficiency, Fe/αKG oxygenases have attracted keen attention for their application as biocatalysts. Here, we report the biochemical and structural characterizations of the unusually promiscuous an...

A photoinduced intramolecular cyclization of allyl acrylates to synthesize fully substituted spiro-γ-butyrolactone compounds is described. The reaction is believed to undergo activation of the carbonyl group upon ultraviolet irradiation, 1,4-hydrogen...

Xylongoic acids A–C, three isopimarane diterpene derivatives were isolated from the rice cultures of Xylaria longipes HFG1018, a fungicolous fungus isolated from the fruiting bodies of the wood-decay and medicinal fungus Fomitopsis betulina. The structures of the isolated compounds were determined by extensive analysis of NMR and HRESIMS data.

Prenyltransferase (PTase) enzymes play crucial roles in natural product biosynthesis by transferring isoprene unit(s) to target substrates, thereby generating prenylated compounds. The prenylation step leads to a diverse group of natural products with improved membrane affinity and enhanced bioactivity, as compared to the non-prenylated forms. The...

Ochracines F-L (1-7), seven previously undescribed chamigrane and cadinane sesquiterpenoids, together with four known chamigranes were isolated from cultures of the wood-decaying fungus Steccherinum ochraceum HFG119. Ochracines F-L were structurally characterized by extensive analysis of HRMS and NMR spectroscopic data. The relative configurations...

A new irlactane-type, namely irlactin K ( 1 ), and 22 tremulane-type sesquiterpenes including fourteen previously undescribed ones, namely irpexolactins A–N ( 2 – 15 ), and a known irlactane-type sesquiterpenoid, were isolated from the fermentation broth of the medicinal fungus Irpex lacteus HFG1102. The structures of all the isolates were characte...

Matsudipeptides A (1) and B (2), two previously undescribed diketopiperazines with peroxy-groups, were isolated from the fruiting bodies of the basidiomycete Tricholoma matsutake. These two compounds were featured by unusual scaffolds biogenetically related with cyclic dipeptide. Their structures were elucidated by analysis of spectroscopic data an...

Xylarilongipins A (1) and B (2), two diterpenes each with an unusual cage-like bicyclo[2.2.2]octane moiety, along with their biosynthetic precursor hymatoxin L (3), were isolated from the culture broth of the fungicolous fungus Xylaria longipes HFG1018 inhabiting in the medicinal fungus Fomitopsis betulinus. The structures as well as the absolute c...

Eighteen new nor-isopimarane diterpenes, xylarinorditerpenes A-R (1-18), along with two previously reported compounds, 14α,16-epoxy-18-norisopimar-7-en-4α-ol (19) and the labdane-type diterpene agatadiol (20), were isolated from cultures of the fungicolous fungus Xylaria longipes HFG1018 isolated from the wood-rotting basidiomycete Fomitopsis betul...

Extensive studies have revealed that triterpenoids, meroterpenoids, and polysaccharides are the main constituents of the well-known traditional Chinese medicinal mushroom Ganoderma. In this study, we report seven previously undescribed sesquiterpenoids, including six gymnomitranes (1–6) and a novel type of sesquiterpenoid (8), together with a polyk...

Ochracines A-E, five previously undescribed norsesquiterpenes featured by unusual scaffolds biogenetically related to chamigrane, were isolated from the cultures of Steccherinum ochraceum. Ochracines A (1) and B (2) represent the first examples of norsesquiterpenes with an unprecedented 1,2-6,7-diseco-1,8-cyclochamigrane scaffold. Ochracines C-D (3...

Aurantiadioic acids A (1) and B (2), two new furan-containing polyketides, and aurantoic acid A (3), a new natural product, were isolated from the liquid fermentation of the sika deer dung-derived actinomycete Actinocorallia aurantiaca. The structures of the new compounds were established by extensive spectroscopic methods, including 1D & 2D NMR, H...

Two new C13‐polyketides, aureonitols A‐B (1‐2), along with five known compounds (3‐7), were isolated from the solid fermentation culture of the plant endophytic fungus Chaetomium globosum from the aerial parts of Salvia miltiorrhiza. The structures and absolute configurations of 1‐2 were determined by comprehensive spectroscopic data analysis, and...

Two previously undescribed cadinane-type sesquiterpenoids, rigidoporones A and B (1 and 2), along with an undescribed racemic indolizine alkaloid, (±)-rigidoporine A (3), were isolated from the rice fermentation of the wood-decay fungus Rigidoporus microporus. The structures of the compounds were established by extensive spectroscopic methods, incl...

Ten previously undescribed triterpenoid congeners, namely irpeksolactins A–J, together with eighteen known ones, were isolated from the fruiting bodies of the rainforest-dwelling medicinal fungus Irpex lacteus. The structures of all the isolates were characterized by extensive spectroscopic approaches, including 1D & 2D NMR and MS spectroscopic met...

A new cadinane-type sesquiterpenoid, microporotriol (1), together with four known compound, 5-methylresorcinol (2), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (3), (22E,24R)-ergosta-5,7,22-trien-3β-ol (4), (22E,24R)-5α,8α-epidioxy-ergosta-6,22-dien-3β-ol (5), were isolated from the fermentation broth of the wood decaying fungus Microporus affinis...

Phytochemical investigation on the fermentation broth of the fungus Stereum hirsutum led to the isolation of ten steroids, including two previously unreported ones, namely steresterones A (1) and B (2). The semi-synthesis products 3a and 3b were prepared by reduction of the known compound 3 with NaBH4. Their structures and absolute configurations w...

Two highly conjugated alkaloids xylaridines A (1) and B (2) were obtained as racemates from the fungus Xylaria longipes. They were resoluted into optically pure enantiomers, respectively. Their structures were determined by extensive spectroscopic analyses, X-ray diffraction, and equivalent circulating density (ECD) calculations. Compound 1 possess...

Two new Tricholoma terpenoids, tricholopardins A and B, were isolated from the fruiting bodies of the basidiomycetes Tricholoma pardinum. Their structures were elucidated by spectroscopic methods, as well as electronic circular dichroism and optical rotatory dispersion calculations. Tricholopardin A potently inhibited nitric oxide production in lip...

Three previously undescribed cyathane-type diterpenoids, hericinoids A-C (1‒3) and three known analogues (4‒6) have been isolated from fermentation broth of Hericium erinaceus. Their structures of hericinoids A-C were determined by in-depth analyses of NMR spectra and HRESIMS. The absolute configurations of compounds 1 and 2 were determined by the...

The phytochemical study of the fruiting bodies of Albatrellus confluens afforded three pairs of new N-Oxidized L-Isoleucine derivatives epimers, confluenines A–F (1–6). The structures of these compounds were deduced using spectroscopic techniques, and the absolute configurations of the compounds were assigned by comparison between experimental and...

Eight undescribed lanostane triterpenoids, pardinols A‒H, along with one previously reported lanostane triterpenoid, namely saponaceol B, were isolated from the fruiting bodies of Tricholoma pardinum. Their structures and stereoconfigurations were established via combination of extensive spectroscopic analyses, alkaline methanolysis method and TDDF...

Three new vibralactone derivatives, namely vibralactones U–W (1–3), together with vibralactone (4), have been isolated from cultures of the basidiomycete Boreostereum vibrans. Their structures were determined on the basis of spectroscopic methods and literature data. All compounds showed no activities to five human cancer cell lines.

Five vibralactone derivatives containing γ, δ, ε-lactone cores, namely vibralactones X (1), Y (2), and Z1-Z3 (3-5), together with the known vibralactone, have been isolated from cultures of the basidiomycete Boreostereum vibrans. Compounds 3-5 possessed a novel bis-γ-lactone group which was found in vibralactone derivatives for the first time. Comp...

Four eburicane-type triterpenoids with malonyl modifications, namely irpexoates A–D (1–4), were isolated from the fruiting bodies of the medicinal fungus Irpex lacteus. The structures of the new compounds were established by extensive spectroscopic methods, including 1D and 2D NMR, HRESIMS spectroscopic analysis. Irpexoate B (2) displayed weak cyto...

Six previously undescribed 5,6-seco-tremulane analogues, together with two known ones, were isolated from the culture broth of the medicinal fungus Irpex lacteus HFG1102. The structures of the new compounds were elucidated via extensive spectroscopic methods, including NMR and HRMS spectroscopic analyses. Graphical Abstract Electronic supplementa...

This study features the isolation and identification of twelve lanostane-type triterpenoids, namely lepiotaprocerins A–L (1–12), from the fruiting bodies of Poland-collected edible mushroom Macrolepiota procera. Their structures as well as absolute configurations were ambiguously established by extensive spectroscopic analyses, ECD calculation, and...

Three new lactones, xylanilyticolides A–C (1–3), were isolated from cultures of the actinomycete Promicromonospora xylanilytica YIM 61515. Their structures were elucidated by 1D and 2D NMR spectroscopic data in conjunction with HRESIMS analysis. Compound 1 exhibited potent cytotoxicities against five human cancer cell lines HL-60, A-549, SMMC-7721,...

Two new sesquiterpenes, daedaleanols A (1) and B (2), together with three known sesquiterpenes (3–5), were isolated from cultures of the basidiomycete Daedalea incana. Their structures were elucidated on the basis of extensive spectroscopic means. All compounds were tested for their cytotoxicities against three human cancer cell lines.

Three new podocarpane diterpenoids, namely anemhupehins A–C (1–3), together with four known analogues (4–7), have been isolated from aerial parts of Anemone hupehensis. Their structures were characterized based on extensive spectroscopic data. Compounds 1 and 4 showed certain cytotoxicities against human cancer cell lines. Graphical Abstract Elec...

A scale-up fermentation of the fungus Boreostereum vibrans facilitated the isolation of six new vibralactone biogenesis-associated analogues, namely vibralactamide A (1), vibralactone T (2), 13-O-lactyl vibralactone (3), 10-O-acetyl vibralactone G (4), (11R,12R)- and (11S,12R)-vibradiol (5, 6). Their structures were established via extensive spectr...

Ten new highly oxygenated lanostane triterpenoids, stereinones A-J (1-10), were isolated from the fruiting bodies of the basidiomycete Stereum sp. Compounds 3 and 4 are structurally characterized as intact lanostane-type triterpenoids containing unusual 1,2-diketone functionality at C-11 and C-12, while compound 10 is a 24-methylene-lanostane. The...

Twelve new lanostane triterpenoids, sterenoids A–L (1–12) have been isolated from fruiting bodies of the basidiomycete Stereum sp. Compounds 1–12 are rare 14(13→12)abeo-lanostane triterpenoids featuring remarkable 13R configurations that discriminate from the previously covered counterparts. Their structures and absolute configurations are assigned...

Seven previously undescribed polyketides, namely childinins A-G, and one previously undescribed 8,14-seco-ergosterol, namely childinasterone A, were obtained from the fruiting bodies of Daldinia childiae. Their structures and absolute configurations were established via extensive spectroscopic analyses, single-crystal X-ray diffraction, and TDDFT/E...

Nicotabin A (1), a sesquiterpenoid derivative possessing a fused 5/6/5/5/5 ring system, was isolated from leaves of Nicotiana tabacum. The structure was elucidated by extensive spectroscopic methods and confirmed by single crystal X-ray diffraction. The plausible biosynthetic pathway for 1 was proposed. Compound 1 inhibited nitric oxide production...

Betulactones A (1) and B (2) were isolated from the cultures of basidiomycete Lenzites betulinus. Betulactone A (1) was a novel highly oxygenated rigid spiro-γ-lactone with the 5/5/6 ring system rarely found in fungal sources while betulactone B (2) was a highly degraded sterol. These structures were elucidated by extensive spectroscopic methods an...

Thirteen new acetylenic acids and their derivatives, craterellynes G-Q (1, 2, 4-10, 12, 13), 9-epi-craterellyne H (3), 14-O-ethyl-craterellyne O (11), were isolated from the fruiting bodies of edible mushrooms Craterellus lutescens. The structures of these compounds were identified by various spectroscopic and chemical means. The stereoconfiguratio...

Two new alkaloids (1–2), together with six known compounds (3–8), were isolated from cultures of the endophytic fungus Stagonosporopsis oculihominis. Their structures were elucidated through extensive spectroscopic methods including 2D NMR and HRMS analyses. The absolute configurations of 1 was determined by the comparison of experimental and theor...

Five new acetylenic acid analogues, craterellynes A–E (1–5), together with three known compounds (6–8), were isolated from the fruiting bodies of Craterellus lutescens. Their structures were elucidated on the basis of spectroscopic and chemical means. The absolute configurations of 1–6 were determined by the modified Mosher method.

Six new lanostane-type triterpenoids, namely leucocontextins S–X (1–6), together with twelve known compounds, were isolated from the fruiting bodies of Ganoderma leucocontextum. Their structures were established by MS and NMR data. Graphical Abstract

(+)- 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...

Four new polycylic alkaloids, lucidimine A-D, were isolated from the fruiting bodies of Ganoderma lucidum. Their chemical structures were established based on 1D and 2D NMR data as well as HREIMS/HRESIMS analyses.

Studies of the fermentation broth of fungus Antrodiella gypsea led to the isolation of a new bisabolane-type sesquiterpenoid that was named gypseatriol (1), together with the known compound 2,10-dodecadiene-1,6,7-triol (2). The structure of this new metabolite was assigned by analysis of 2D NMR and HR-EI-MS. Absolute configuration was assigned by s...

Four new spiroaxane sesquiterpenes, tramspiroins A-D (1-4), one new rosenonolactone 15,16-acetonide (5), and the known drimane sesquiterpenes isodrimenediol (6) and funatrol D (7) have been isolated from the cultures of Basidiomycete Trametes versicolor. The structures of new compounds were elucidated by means of spectroscopic methods. Compounds 1-...

The unusual fused β-lactone vibralactone was isolated from cultures of the basidiomycete Boreostereum vibrans and has been shown to significantly inhibit pancreatic lipase. In this study, a structure-based lead optimization of vibralactone resulted in three series of 104 analogs, among which compound C1 exhibited the most potent inhibition of pancr...

A novel C25 sterol peroxide, phomasterol A (1), together with two known compounds (2-3), was isolated from the endophytic fungus Phoma sp. EA-122. The structure of phomasterol A (1) was elucidated by MS, 1D, and 2D NMR data analyses. Phomasterol A (1) was evaluated for its inhibitory activities against protein-tyrosine phosphatases MEG2 and PTP1Bc,...

Five new triquinane-type sesquiterpenes, antrodins A-E (1-5) and a new gymnomitrane sesquiterpene, antrodin F (6), together with three known compounds 7-9 were isolated from fermentation of Antrodiella albocinnamomea. Their structures were elucidated through extensive spectroscopic methods including 2D NMR and HRMS analyses. The absolute configurat...

Two new compounds, maniesculentins A (1) and B (6), together with four known ones were isolated from the stems of Manihot esculenta Crantz. The structures of the new compounds were elucidated by extensive spectroscopic methods including NMR spectroscopy and mass spectrometry. The two new compounds (1, 6) were assayed for antibacterial activity agai...

Two new triterpenoids, (24E)-9α,11α-epoxy-3β-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 → 12)abeo-lanosta-8,22,24-trien-26,23-olide (2) were isolated from dried fruiting bodies of fungus Ganoderma lucidum. The structures of these two new compounds were elucidated on the basis of extensive spectroscopic analyses. Compoun...

Four new sesquiterpenoids, namely 12-hydroxy-3-oxodrimenol (1), 11-hydroxyacetoxydrim-7-en-3β-ol (2), 2,6-dimethyl-7,10-epoxy-10-hydroxymethyldodeca-2,11-dien-6-ol (3), and 7,10-epoxy-2,6,10-trimethyldodeca-2,11-diene-4,6-diol (4), along with fourteen known compounds, were isolated from the cultures of Phellinidium sulphurascens. The structures of...

Five new tremulane sesquiterpenes (1-5), together with seven known ones (6-12), were isolated from cultures of the fungus Phellinus igniarius. The new compounds were established as 6β,11,12-trihydroxy-tremul-1(10)-ene (1), 11,12-dihydroxyl-7β-peroxy-hydroxyl-tremul-1(10)-ene (2), 6β,12-dihydroxy-tremulene (3), 10β,12-dihydroxy-tremulene (4), and 12...

Phytochemical reinvestigation on the cultural broth of Boreostereum vibrans led to the isolation of six new vibralactone derivatives, vibralactone N (1), vibralactone O (2), vibralactone P (3), 10-lactyl vibralactone G (4), (3S*, 4R*)-6-acetoxymethyl-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol (5), vibralactone Q (6). Their structures were elucid...

Three new bisabolane sesquiterpenoids, inonotic acid A (1), 3-O-formyl inonotic acid A (2), inonotic acid B (3), and one new drimane sesquiterpenoid 3α,6β-dihydroxycinnamolide (4), were isolated from the fruiting bodies of mushroom Inonotus rickii. Their structures were elucidated by means of extensive spectroscopic methods. Compound 4 had moderate...

Two new cytochalsians, multirostratin A (1) and 20-oxo-deoxaphomin (2), together with five known analogues (3-7), were obtained from the endophytic fungus Phoma multirostrata EA-12. The structures of 1 and 2 were elucidated by MS and 1D- and 2D-NMR spectroscopic data analyses, as well as by comparison of data with those of analogues reported in the...

Three novel degraded steroids, named albocisterols A-C (1-3), have been isolated from cultures of Antrodiella albocinnamomea. Their structures were defined by comprehensive spectroscopic analysis and single crystal X-ray crystallography. The mixture of compounds 2 and 3 exhibited significant inhibitory activities against protein tyrosine phosphatas...