Lithocarpinols A(1) and B(2), a pair of tenellone diastereoisomers with novel fused skeleton were isolated from the deep-sea derived fungus Phomopsis lithocarpus FS508. Their structures were elucidated by comprehensiv...Lithocarpinols A(1) and B(2), a pair of tenellone diastereoisomers with novel fused skeleton were isolated from the deep-sea derived fungus Phomopsis lithocarpus FS508. Their structures were elucidated by comprehensive spectroscopic analyses, X-ray diffraction and quantum molecular calculation. Their plausible biogenetic pathway featured an intriguing carbonyl-ene cyclization. Lithocarpinol A exhibited moderate inhibitory effect against HepG-2 and A549 tumor cell lines with IC_(50) values of 9.4 μmol/L and10.9 μmol/L,respectively.展开更多
Lithocarpins E-G,featuring a rare naturally-occurring highly oxygenated tenellone-macrolide skeleton,were isolated from the culture extract of a marine-derived fungus Phomopsis lithocarpus FS508.Their structures were ...Lithocarpins E-G,featuring a rare naturally-occurring highly oxygenated tenellone-macrolide skeleton,were isolated from the culture extract of a marine-derived fungus Phomopsis lithocarpus FS508.Their structures were fully elucidated by NMR and MS spectroscopic analyses and electronic circular dichroism calculations.Compounds 1-3 were evaluated for their in vitro cytotoxicities against HepG2,MCF-7,SF-268,as well as A549 cell lines,among which,compound 1 exhibited inhibitory activity against HepG2 cells with an IC_(50) value of 6.3 μmol/L.The further mechanistic investigation demonstrated that lithocarpin E could cause the apoptosis of HepG2 cells through activation of p-ERK,Bax,and caspase-3 gene expressions.展开更多
Hawanoids A–E(1–5), five highly cyclized diterpenoids were isolated from the deep-sea-derived fungus Paraconiothyrium hawaiiense FS482. Compounds 1 and 2 possessed an unprecedented tetracyclo[6.6.2.0^(2,7).0^(11,15)...Hawanoids A–E(1–5), five highly cyclized diterpenoids were isolated from the deep-sea-derived fungus Paraconiothyrium hawaiiense FS482. Compounds 1 and 2 possessed an unprecedented tetracyclo[6.6.2.0^(2,7).0^(11,15)]cetane carbon skeleton while 3 and 4 possessed an unusual 11,14-macrocyclic ether moiety in phomactin family. Their structures including the stereo-chemistry were determined through spectroscopic analysis, X-ray diffractions and computational calculations. The plausible biosynthetic pathway was proposed based on the predicted biosynthetic gene cluster. All of the isolated compounds exhibited inhibitory activities against PAF-induced platelet aggregation. The molecular docking study was carried out understand the interaction between the PAF receptor and hawanoids with different skeletons.展开更多
基金financially supported by the Science and Technology Program of Guangzhou, China(No. 201607020018)the Team Project of the Natural Science Foundation of Guangdong Province (No. 2016A030312014)+2 种基金the National Natural Science Foundation of China (No. 31272087)the Guangdong Provincial Project for Science and Technology (Nos. 2015A030302061, 2016A020222022)the Guangdong Provincial Innovative Development of Marine Economy Regional Demonstration Projects (No. GD2012-D01-002)
文摘Lithocarpinols A(1) and B(2), a pair of tenellone diastereoisomers with novel fused skeleton were isolated from the deep-sea derived fungus Phomopsis lithocarpus FS508. Their structures were elucidated by comprehensive spectroscopic analyses, X-ray diffraction and quantum molecular calculation. Their plausible biogenetic pathway featured an intriguing carbonyl-ene cyclization. Lithocarpinol A exhibited moderate inhibitory effect against HepG-2 and A549 tumor cell lines with IC_(50) values of 9.4 μmol/L and10.9 μmol/L,respectively.
基金Guangdong Provincial Special Fund for Marine Economic Development Project([2020]042)the National Natural Science Foundation of China(41906106)+3 种基金the Guangdong Special Support Program(2019TQ05Y375)Team Project of the Natural Science Foundation of Guangdong Province(2016A030312014)the GDAS_Project of Science and Technology Development(2019GDASYL-0103007)We sincerely thank Mr.Can Li of central laboratory of Southern Medical University for NMR measurements.
文摘Lithocarpins E-G,featuring a rare naturally-occurring highly oxygenated tenellone-macrolide skeleton,were isolated from the culture extract of a marine-derived fungus Phomopsis lithocarpus FS508.Their structures were fully elucidated by NMR and MS spectroscopic analyses and electronic circular dichroism calculations.Compounds 1-3 were evaluated for their in vitro cytotoxicities against HepG2,MCF-7,SF-268,as well as A549 cell lines,among which,compound 1 exhibited inhibitory activity against HepG2 cells with an IC_(50) value of 6.3 μmol/L.The further mechanistic investigation demonstrated that lithocarpin E could cause the apoptosis of HepG2 cells through activation of p-ERK,Bax,and caspase-3 gene expressions.
基金funded by National Natural Science Foundation of China (Nos. 41906106, 31272087)the Natural Science Foundation of Guangdong Province, China (No. 2021A1515011416)+1 种基金Guangdong Special Support Program (No. 2019TQ05Y375)Guangdong Provincial Special Fund for Marine Economic Development Project (No. GDNRC [2021]054)。
文摘Hawanoids A–E(1–5), five highly cyclized diterpenoids were isolated from the deep-sea-derived fungus Paraconiothyrium hawaiiense FS482. Compounds 1 and 2 possessed an unprecedented tetracyclo[6.6.2.0^(2,7).0^(11,15)]cetane carbon skeleton while 3 and 4 possessed an unusual 11,14-macrocyclic ether moiety in phomactin family. Their structures including the stereo-chemistry were determined through spectroscopic analysis, X-ray diffractions and computational calculations. The plausible biosynthetic pathway was proposed based on the predicted biosynthetic gene cluster. All of the isolated compounds exhibited inhibitory activities against PAF-induced platelet aggregation. The molecular docking study was carried out understand the interaction between the PAF receptor and hawanoids with different skeletons.
