Two new polyketides, penifellutins A (1) and B (2), possessing a 22 carbon linear skeleton, were isolated from a co-culture of the deep-sea-derived fungi Penicillium crustosum PRB-2 and Penicillium fellutanum HDN14-32...Two new polyketides, penifellutins A (1) and B (2), possessing a 22 carbon linear skeleton, were isolated from a co-culture of the deep-sea-derived fungi Penicillium crustosum PRB-2 and Penicillium fellutanum HDN14-323. Meanwhile, two esterification products of 1, penifellutins C (3) and D (4), were obtained because compound 1 could be esterified spontaneously when stored in methanol. Their configurations were difficult to determine because of chiral central crowdedness, structural flexibility and instability. As such, we solved this issue by comprehensively using Mo2(OAc)4-based CD experiments, density functional theory calculation of 13C NMR, DP4 + probability analysis and many chemical reactions, including making acetonide derivative, Mosher’s method, PGME method, etc. Compounds 1 and 2 show obvious inhibitory activity on the liver hyperplasia of zebrafish larvae at a concentration of 10 μmol/L, while 3 and 4 show no activity, indicating that two carboxyls in the structure are important active sites.展开更多
Two new phenylpropanoid glycosides named cuneataside E (1) and cuneataside F (2), were isolated from the aerial parts of Lespedeza cuneata (Dum. Cours.) G. Don, whose structures were E and Z isomer, respectively. Thei...Two new phenylpropanoid glycosides named cuneataside E (1) and cuneataside F (2), were isolated from the aerial parts of Lespedeza cuneata (Dum. Cours.) G. Don, whose structures were E and Z isomer, respectively. Their structures were elucidated on the basis of comprehensive spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR). In in vitro bioassays at 10 mu mol/L, compound 1 showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HeG2 cells. (C) 2016 Chinese Pharmaceutical Association and Institute of Materia Medica, Chinese Academy of Medical Sciences. Production and hosting by Elsevier B.V. This is an open access article under the CC BY-NC-ND展开更多
Main observation and conclusion Two new pairs of monoterpenoid indole alkaloids(MIAs)enantiomers as well as their new congeners were isolated from stems of Tabernaemontana bovina Lour.(Apocynaceae).Their structures we...Main observation and conclusion Two new pairs of monoterpenoid indole alkaloids(MIAs)enantiomers as well as their new congeners were isolated from stems of Tabernaemontana bovina Lour.(Apocynaceae).Their structures were elucidated by spectroscopic analyses and confirmed by X-ray diffractions and computational calculations.Tabovine A,tabovine B and tabovines C-D possessed unprecedented 6/5/5/6/6,6/5/5/6/5 and 6/5/6/6/6 ring systems,respectively.It is the first time to report co-occurring enantiomers of MIAs.Additionally,the explanation concerning biogenesis of MIAs was provided.The findings would open a new window where we could disclose more diverse MIAs.展开更多
Phytochemical investigations on Tabernaemontana divaricata led to the isolation of seven undescribed monoterpenoid indole alkaloids,taberdicatines A-G(1-7).Taberdicatines A-C might be derived from Aspidosperma-type al...Phytochemical investigations on Tabernaemontana divaricata led to the isolation of seven undescribed monoterpenoid indole alkaloids,taberdicatines A-G(1-7).Taberdicatines A-C might be derived from Aspidosperma-type alkaloid,less skeletal carbons in 1-2 and an additional carbon in 3.Taberdicatines D-E(4-5)were attributed to Iboga alkaloids with enantiomeric skeleton,respectively.Alkaloid 3 could promote the neurite growth of mouse primary cortical neurons at the concentration of 5 pimol/L.展开更多
基金supported by the National Natural Science Foundation of China(41806167,81670709)Project funded by China Postdoctoral Science Foundation(2017M622286)+2 种基金Qingdao Postdoctoral Applied Research Project Financially Supported by Qingdao Municipal Bureau of Human Resource and Social Security,Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology(LMDBKF201805)High-level Talents Research Fund of Qingdao Agricultural University(Grants 665/1120034)We thank Dr.Zhiyuan Gong(National Univeristy of Singapore)for the gift of Tg(Fabp10-rtTA:TRE-eGFPKRASV12)transgenic line.
文摘Two new polyketides, penifellutins A (1) and B (2), possessing a 22 carbon linear skeleton, were isolated from a co-culture of the deep-sea-derived fungi Penicillium crustosum PRB-2 and Penicillium fellutanum HDN14-323. Meanwhile, two esterification products of 1, penifellutins C (3) and D (4), were obtained because compound 1 could be esterified spontaneously when stored in methanol. Their configurations were difficult to determine because of chiral central crowdedness, structural flexibility and instability. As such, we solved this issue by comprehensively using Mo2(OAc)4-based CD experiments, density functional theory calculation of 13C NMR, DP4 + probability analysis and many chemical reactions, including making acetonide derivative, Mosher’s method, PGME method, etc. Compounds 1 and 2 show obvious inhibitory activity on the liver hyperplasia of zebrafish larvae at a concentration of 10 μmol/L, while 3 and 4 show no activity, indicating that two carboxyls in the structure are important active sites.
基金financially supported by the National Mega-project for Innovative Drugs(No.2012ZX09301002-002)National Natural Science Foundation of China(Nos.81560632 and 81202546)
文摘Two new phenylpropanoid glycosides named cuneataside E (1) and cuneataside F (2), were isolated from the aerial parts of Lespedeza cuneata (Dum. Cours.) G. Don, whose structures were E and Z isomer, respectively. Their structures were elucidated on the basis of comprehensive spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR). In in vitro bioassays at 10 mu mol/L, compound 1 showed moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HeG2 cells. (C) 2016 Chinese Pharmaceutical Association and Institute of Materia Medica, Chinese Academy of Medical Sciences. Production and hosting by Elsevier B.V. This is an open access article under the CC BY-NC-ND
基金This work was supported by the National Natural Science Foundation of China(Nos.31872677,31370377)Computational resources used in this work were supported in part by SciGrid,Chinese Academy of Sciences.
文摘Main observation and conclusion Two new pairs of monoterpenoid indole alkaloids(MIAs)enantiomers as well as their new congeners were isolated from stems of Tabernaemontana bovina Lour.(Apocynaceae).Their structures were elucidated by spectroscopic analyses and confirmed by X-ray diffractions and computational calculations.Tabovine A,tabovine B and tabovines C-D possessed unprecedented 6/5/5/6/6,6/5/5/6/5 and 6/5/6/6/6 ring systems,respectively.It is the first time to report co-occurring enantiomers of MIAs.Additionally,the explanation concerning biogenesis of MIAs was provided.The findings would open a new window where we could disclose more diverse MIAs.
基金the National Natural Science Foundation of China(Nos.31872677,31370377).Computational resources used in this work were supported in part by SciGrid,Chinese Academy of Sciences.
文摘Phytochemical investigations on Tabernaemontana divaricata led to the isolation of seven undescribed monoterpenoid indole alkaloids,taberdicatines A-G(1-7).Taberdicatines A-C might be derived from Aspidosperma-type alkaloid,less skeletal carbons in 1-2 and an additional carbon in 3.Taberdicatines D-E(4-5)were attributed to Iboga alkaloids with enantiomeric skeleton,respectively.Alkaloid 3 could promote the neurite growth of mouse primary cortical neurons at the concentration of 5 pimol/L.
