Yung-Shun Su

Secondary Metabolites from the Endophytic Fungus Annulohypoxylon stygium BCRC 34024

A new γ-butyrolactone, annulostygilactone (1), along with nine known compounds consisting of seven benzenoids [p-hydroxybenzaldehyde (2), methylparaben (3), p-hydroxybenzoic acid (4), syringaldehyde (5), eugenol (6), vanillic acid (7), and ferulic acid (8)], and two triterpenoids [ursolic acid (9) and _-daucosterol (10)] were isolated from the endophytic fungus Annulohypoxylon stygium BCRC 34024. Their structures were determined based on their 1D and 2D NMR and HR-ESI-MS spectral data as well as comparison with previous literature data. All compounds were found for the first time in this species. It is worthy of note that this is the first report of secondary metabolites isolated from this fungus. The inhibitory effects of some isolates (compounds 1, 9, and 10) on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages were evaluated. Compound 1 showed stronger inhibition of NO production than the positive control quercetin.

Phytochemical Investigation of Annulohypoxylon ilanense, an Endophytic Fungus Derived from Cinnamomum Species

Cultivation of the fungal strain Annulohypoxylon ilanense, an endophytic fungus isolated from the wood of medicinal plant Cinnamomum species, resulted in the isolation of one new furanoid derivative, ilanefuranone (1), one new pyrrole alkaloid, ilanepyrrolal (2), and one new biarylpropanoid derivative, ilanenoid (3), together with 22 known compounds, of which one α‐tetralone analog, (−)‐(4R)‐3,4‐dihydro‐4,6‐dihydroxynaphthalen‐1(2H)‐one (4) was isolated for the first time from a natural source. The structures were elucidated on the basis of physicochemical evidence, in‐depth NMR spectroscopic analysis, and high‐resolution mass spectrometry, and the antimycobacterial activities were also evaluated.

Chemical constituents of red yeast rice fermented with the fungus Monascus pilosus

A chemical study on the n-BuOH-soluble fraction of the 95% EtOH extract of red yeast rice fermented with the fungus Monascus pilosus (Eurotiaceae) has resulted in the isolation of one new azaphilone derivative, designated as monapilosusazaphilone (1), together with nine known compounds, (+)-5,5′-dimethoxylariciresinol (2), (+)-lariciresinol (3), (+)-5-methoxylariciresinol (4), a mixture of 3β-hydroxylstigmast-5-en-7-one (5) and 3β-hydroxystigmasta-5,22-dien-7-one (6), 6β-hydroxystigmast-4-en-3-one (7), 6β-hydroxystigmasta-4,22-dien-3-one (8), N-cis-feruloylmethoxytyramine (9), and scopoletin (10). Their structures were elucidated by 1D and 2D-NMR spectroscopy together with HR-ESI-MS analysis, and comparison of the spectroscopic data with those reported for structurally related compounds.

Secondary metabolites from the endophytic fungus Annulohypoxylon boveri var. microspora BCRC 34012

A chemical study on the n-BuOH-soluble fraction of the 95% EtOH extract of long-grain rice (Oryza sativa) fermented with the endophytic fungus Annulohypoxylon boveri var. microspora (BCRC 34012) has resulted in the isolation of one new natural azaphilone derivative, designated as annulohypoxyboverin (1) together with 12 known compounds, (3R,6R,7E)-3-hydroxy-4,7-megstigma-dien-9-one (2), α-tocopheryl quinone (3), isofraxidin (4), coumarin (5), cinnamic acid (6), a mixture of palmitic acid (7) and stearic acid (8), N-cis-feruloyltyramine (9), luteolin (10), kaempferol (11), kaempferitrin (12), and 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl (13). Annulohypoxyboverin (1) contains a dihydrobenzofuran-2,4-dione backbone, 1-hydroxyhexyl side chain, and one γ-lactone ring. Their structures were elucidated by spectroscopic analyses including 1D and 2D NMR experiments, and by HR-ESI-MS. The relative configuration of 1 was confirmed by NOESY experiment. Other known compounds were identified by comparing their spectral data with those of literature data.

A New Pyrrole Metabolite from the Endophytic Fungus of Xylaria papulis

One new pyrrole derivative, papupyrrolal (1), together with seven known metabolites consisting of three flavonoids [myricitrin (2), quercitrin (3), and myricetin (4)], and four triterpenoids [3β-trans-p-coumaroyloxy-2α,23-dihydroxyolean-12-en-28-oic acid (5), chebuloside I (6), arjunolic acid (7), and taraxerol (8)] were isolated from the endophytic fungus Xylaria papulis BCRC 09F0222. Structures were established on the basis of their spectroscopic data, including 1H NMR, 13C NMR, HSQC, HMBC, as well as by HR-ESI-MS experiments and comparison with literature data. It is worthy to mention that this is the first report on secondary metabolites from this fungus.

Chemical Constituents from a Soil‐Derived Actinomycete, Actinomadura miaoliensis BCRC 16873, and Their Inhibitory Activities on Lipopolysaccharide‐Induced Tumor Necrosis Factor Production

An investigation on the secondary metabolites from the BuOH extract of the fermentation broth of the thermotolerant polyester‐degrading actinomycete Actinomadura miaoliensis BCRC 16873 was carried out. One previously undescribed α‐pyrone (=pyran‐2‐one) derivative, designated as miaolienone (1), and a new butanolide, miaolinolide (2), together with 13 known compounds, 3–15, were obtained. Their structures were established on the basis of extensive 1D‐ and 2D‐NMR analyses in combination with HR‐MS experiments. In addition, the isolated compounds 1–15 were evaluated for the inhibitory effects of the isolates on the production of tumor necrosis factor (TNF‐α) induced by lipopolysaccharide (LPS). Among the isolates, 1 and 2 significantly inhibited TNF‐α production in U937 cells in vitro, and the IC50 values were 0.59 and 0.76 μM, respectively. Compounds 3–5 displayed moderate inhibitory activities on LPS‐induced TNF‐α production.

New Metabolite Isolated from the Fungus Monascus pilosus

A new isochroman analogue, named monascuspilorin (1), was obtained from the n-BuOH-soluble fraction of the 95% EtOH extract of red mold rice fermented with the fungus Monascus pilosus BCRC 38072 (Eurotiaceae). The structure of the new compound was elucidated by comprehensive spectroscopic analysis, especially HR-ESI-MS and NMR experiments.

Metabolites Isolated from an Endophytic Fungus of Annulohypoxylon elevatidiscus

One new furanoid, elevafuranone (1), along with six known compounds constisting of three flavonoids [7-O-methylnaringenin (2), pinocembrin (3), and (–)-epicatechin (4)] and three alphatics [β-sitosterol (5), methyl linoleate (6), and 2,3-dihydroxypropyl palmitate (7)], were isolated from an endophytic fungus Annulohypoxylon elevatidiscus BCRC 34014. Their structures were determined based on their 1D and 2D NMR and HR-ESI-MS spectral data, as well as comparison with previous literature data. All compounds were found for the first time in this species. It is worth mentioning that this is the first study of secondary metabolites isolated from this fungus.