Protoilludane, Illudalane, and Botryane Sesquiterpenoids from the Endophytic Fungus Phomopsis sp. TJ507A

Journal of Natural Products
Shuangshuang XieYonghui Zhang

Abstract

To explore the chemical diversity of metabolites from endophytic fungi, the strain Phomopsis sp. TJ507A, isolated from the medicinal plant Phyllanthus glaucus, was investigated. A 2,3- seco-protoilludane-type sesquiterpenoid (1), eight protoilludane-type sesquiterpenoids (2-9), four illudalane-type sesquiterpenoids (10a/10b, 11, and 12), and a botryane-type sesquiterpenoid (13) in addition to seven known sesquiterpenoids (14-20) were identified from the liquid culture of the fungus. Structures of the isolated compounds, including their absolute configurations, were elucidated based on extensive spectroscopic analyses, a modified Mosher analysis, electronic circular dichroism (ECD) calculations, and [Rh2(OCOCF3)4]-induced ECD spectra as well as X-ray crystallographic analyses. Compound 1 represents the first example of a naturally occurring sesquiterpenoid containing the unusual 2,3- seco-protoilludane scaffold. Compounds 1 ( p < 0.001); 2-6, 15, and 18 ( p < 0.01); and 7, 9, and 20 ( p < 0.05) displayed β-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitory activities ranging from 19.4% to 43.8% at the concentration of 40 μM. LY2811376 was used as the positive control with an inhibitory activity of 38.6% ( p < 0....Continue Reading

References

Feb 26, 2000·Journal of Natural Products·R Durán-PatrónI G Collado
Aug 6, 2000·Acta Crystallographica. Section A, Foundations of Crystallography·H D Flack, G Bernardinelli
Apr 17, 2001·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·K FabianO Sterner
Sep 8, 2001·Natural Product Reports·R X Tan, W X Zou
Sep 27, 2002·Chembiochem : a European Journal of Chemical Biology·Helge Björn BodeAxel Zeeck
Feb 28, 2004·Journal of Natural Products·Gary StrobelJames Harper
Mar 25, 2005·Journal of Natural Products·Karsten KrohnBarbara Schulz
Dec 3, 2005·Bioorganic & Medicinal Chemistry·Liliana M FinkielszteinGraciela Y Moltrasio Iglesias
Sep 26, 2007·Journal of Chemical Information and Modeling·Mikko J Vainio, Mark S Johnson
Nov 19, 2009·Journal of Natural Products·George R PettitLinda Richert
Dec 19, 2009·Journal of Computational Chemistry·J Santeri PuranenMark S Johnson
Feb 24, 2011·Journal of Natural Products·Chulida HemtasinPalangpon Kongsaeree
Apr 8, 2011·Journal of Natural Products·Liang XiongJiangong Shi
Apr 5, 2013·Organic Letters·Brett D SchwartzAnthony C Willis
Jul 13, 2013·Chemistry & Biodiversity·Shao-Hua WuYou-Wei Chen
Aug 22, 2013·Organic Letters·Anthony PitavalAntonio M Echavarren
Aug 24, 2013·ACS Synthetic Biology·Zengyi ShaoHuimin Zhao
Feb 18, 2014·Alzheimer's & Dementia : the Journal of the Alzheimer's Association·Debomoy K LahiriNigel H Greig
Jul 30, 2014·Journal of Agricultural and Food Chemistry·Mary-Lorène GoddardEliane Abou-Mansour
Dec 3, 2014·Organic Letters·Hucheng ZhuYonghui Zhang
Mar 27, 2015·Natural Product Research·A M D A SiriwardaneYoshinori Fujimoto
Jul 18, 2015·Journal of the American Chemical Society·Christopher R Ellis, Jana Shen
Aug 26, 2015·Journal of Natural Products·Yuanyuan LuYonghui Zhang
Feb 4, 2016·The Journal of Organic Chemistry·Ee Ling ChangMartin G Banwell
Apr 27, 2017·Journal of Natural Products·Yi GuoYonghui Zhang

❮ Previous
Next ❯

Citations

Oct 9, 2018·Chemistry & Biodiversity·Yuben QiaoYonghui Zhang
Mar 23, 2019·Chemical Communications : Chem Comm·Zhixiong ZengYandong Zhang
Dec 8, 2019·The Journal of Antibiotics·E-Eum WooBong-Sik Yun
Sep 18, 2020·Organic & Biomolecular Chemistry·Huibo LiuWeimin Zhang
Dec 17, 2019·Natural Product Research·Xin-Ming SongChang-Ri Han
Feb 4, 2021·Fitoterapia·Peng ZhouYonghui Zhang
Jul 7, 2020·Journal of Microbiology and Biotechnology·Kashvintha NagarajanWen-Nee Tan
Aug 7, 2021·Journal of Fungi·Humberto E OrtegaLuis Cubilla-Rios
Aug 25, 2020·The Journal of Organic Chemistry·Robert GastonGregory B Dudley
Aug 14, 2019·The Journal of Organic Chemistry·Kazuma ShimodaKiyosei Takasu

❮ Previous
Next ❯

Related Concepts

Related Feeds

Alzheimer's Disease: APP

Amyloid precursor protein (APP) proteolysis is critical for the development of Alzheimer's disease, a neurodegenerative disease associated with accumulation of amyloid plaques in the brain. Here is the latest research on APP and Alzheimer's disease.