Jin-Chuan Zhou

Naphtho‐γ‐pyrones from Endophyte Aspergillus niger Occurring in the Liverwort Heteroscyphus tener (Steph.) Schiffn.

Bioactivity‐guided fractionation of the cytotoxic extract of Aspergillus niger, an endophytic fungus from the Chinese liverwort Heteroscyphus tener (Steph.) Schiffn., afforded five new naphtho‐γ‐pyrones, rubrofusarin‐6‐O‐α‐D‐ribofuranoside (1), (R)‐10‐(3‐succinimidyl)‐TMC‐256A1 (2), asperpyrone E (3), isoaurasperone A (4), and isoaurasperone F (5), as well as four known ones, dianhydroaurasperone C (6), aurasperone D (7), asperpyrone D (8), and asperpyrone A (9), together with a cytotoxic cyclic pentapeptide, malformin A1 (10). Their structures were determined by extensive spectroscopic analysis. The absolute configurations of dimeric naphtho‐γ‐pyrones 3–9 were also determined by analysis of their respective CD spectra.

Marsupellins A-F, ent-longipinane-type sesquiterpenoids from the Chinese liverwort Marsupella alpine with acetylcholinesterase inhibitory activity.

Acetylcholinesterase (AChE) inhibitory activity-guided fractionation of the Chinese liverwort Marsupella alpine afforded six new [marsupellins A-F (1-6)] and three known (7-9) ent-longipinane-type sesquiterpenoids. The structures were determined from MS and NMR spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Compounds 1-9 exhibited moderate to weak AChE inhibitory activity.

A new diketopiperazine heterodimer from an endophytic fungus Aspergillus niger.

One new diketopiperazine heterodimer, asperazine A (1), and eight known compounds, asperazine (2), cyclo(d-Phe-l-Trp) (3), cyclo(l-Trp-l-Trp) (4), 4-(hydroxymethyl)-5,6-dihydro-pyran-2-one (5), walterolactone A (6), and campyrones A–C (7–9), were isolated from an endophytic fungus Aspergillus niger. Their structures were determined unequivocally on the basis of extensive spectroscopic data analysis. This is the first report of the presence of compound 3 as a natural product. Cytotoxicity test against human cancer cell lines PC3, A2780, K562, MBA-MD-231, and NCI-H1688 revealed that compounds 1 and 2 had weak activities.

Secondary Metabolites from Aspergillus fumigatus, an Endophytic Fungus from the Liverwort Heteroscyphus tener (Steph.) Schiffn.

Three new metabolites, asperfumigatin (1), isochaetominine (10), and 8′‐O‐methylasterric acid (21), together with nineteen known compounds, were obtained from the culture of Aspergillus fumigatus, an endophytic fungus from the Chinese liverwort Heteroscyphus tener (Steph.) Schiffn. Their structures were established by extensive analysis of the spectroscopic data. The absolute configurations of 1 and 10 were determined by analysis of their respective CD spectra. Cytotoxicity of these isolates against four human cancer cell lines was also determined.

Diterpenoids from the Chinese Liverwort Heteroscyphus tener and Their Antiproliferative Effects

Four new ent-labdane diterpenoids, heteroscyphins A-D (1-4), and four known diterpenoids (5-8) were isolated from the Chinese liverwort Heteroscyphus tener (Steph.) Schiffn. The absolute configuration of compound 1 was defined by single-crystal X-ray diffraction using Cu Kα radiation. Cytotoxicity tests revealed that compounds 3 and 5 exhibited modest activity against seven cancer cell lines. Compound 5 showed inhibitory effects on prostate cancer (PCa) cell proliferation but with less inhibition on non-neoplastic prostate epithelial cells. Compound 5 markedly caused cell growth arrest at the G0/G1 phase and induced cellular apoptosis through ROS-mediated DNA damage in PCa cells.

Scapairrins A–Q, Labdane-Type Diterpenoids from the Chinese Liverwort Scapania irrigua and Their Cytotoxic Activity

Seventeen new labdane-type diterpenoids, scapairrins A-Q (1-17), including six pairs of diastereoisomers, and three known analogues (18-20) were isolated from the Chinese liverwort Scapania irrigua. The structures of 1-17 were determined based on a combination of the analysis of their MS and NMR spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Cytotoxicity testing showed that compounds 7-10 exhibited inhibitory activities against a small panel of human cancer cell lines.

Cembrane-type diterpenoids from the Chinese liverworts Chandonanthus hirtellus and C. birmensis.

Six new cembrane-type diterpenoids (1-6) were isolated from two species of Chandonanthus: Chandonanones A, B, and D-F (1, 2, and 4-6) were isolated from C. hirtellus, and chandonanones B, C, E, and F (2, 3, 5, and 6) from C. birmensis. Five known diterpenoids, (8E)-4α-acetoxy-12α,13α-epoxycembra-1(15),8-diene (7), isochandonanthone (8), chandonanthone (9), anadensin (10), and 2,10,14-triacetoxy-7,8,18,19-diepoxydolabell-3(E)-ene (11), were also obtained. The structures of the new metabolites were established by analyses of their spectroscopic data (1D NMR, 2D NMR, HRESIMS, and IR). The absolute configurations of compounds 1 and 2 were unequivocally confirmed using single-crystal X-ray diffraction analysis with Cu Kα radiation. Cytotoxicity tests of the isolated diterpenoids against seven cancer cell lines (DU145, PC3, A549, PC12, NCI-H292, NCI-H1299, and A172) revealed that some of the diterpenoids had weak activity.

Terpenoids from the Chinese liverwort Plagiochila pulcherrima and their cytotoxic effects

Three new pimarane-type diterpenoids, 7β,11α-dihydroxypimara-8(14),15-diene (1), 1β,11α-dihydroxypimara-8(14),15-diene (2), and 11α-hydroxypimara-8(14),15-diene (3), five 2,3-secoaromadendrane-type sesquiterpenoids, including a new one, ethyoxyplagiochiline A2 (4), and three known fusicoccane-type diterpenoids were isolated from the Chinese liverwort Plagiochila pulcherrima. Their structures were established on the basis of extensive spectroscopic analysis. Compounds 6 and 7 exhibited moderate inhibitory activity on the proliferation of human cancer cell lines Hela, A172, and H460. Moreover, the cytotoxicity of compound 6 to Hela cells was related to apoptotis as confirmed by DAPI nuclear staining and flow cytometry.

Terpenoids from Diplophyllum taxifolium with quinone reductase-inducing activity

Two new ent-prenylaromadendrane-type diterpenoids, diplotaxifols A (1) and B (2), a new ent-eudesmol, ent-eudesma-4(15),11(13)-dien-6α,12-diol (3), eight new eudesmanolides enantiomers (4-11) of the corresponding compounds from higher plants along with four known ent-eudesmanolides (12-15) were isolated from the 95% EtOH extract of Chinese liverwort Diplophyllum taxifolium. Their structures were elucidated on the basis of MS, NMR and IR spectral data, and confirmed by single-crystal X-ray diffraction analysis. The quinone reductase-inducing activity of the compounds was evaluated.

Polyacetylated labdane-type diterpenoids, ptychantins P–R from Chinese liverwort Ptychanthus striatus

Three new polyacetylated labdane diterpenoids ptychantins P–R (1–3) and four known compounds (4–7) were isolated from an EtOH extract of the Chinese liverwort Ptychanthus striatus (Lehm. & Lindenb.) Nees. Their structures were established by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D NMR, and 2D NMR).