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Weiming Zhu - One of the best experts on this subject based on the ideXlab platform.
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ophiobolins from the mangrove fungus Aspergillus ustus
2018Co-Authors: Tonghan Zhu, Jie Fan, Liping Wang, Guoliang Zhu, Yi Wang, Kui Hong, Pawinee Piyachaturawat, Arthit Chairoungdua, Weiming ZhuAbstract:Seven new ophiobolins (1–5, 12, and 14) along with the 11 known analogues (6–11, 13, 15–18) were isolated from the ethyl acetate extracts of the liquid and solid cultures of the mangrove fungus Aspergillus ustus 094102. The structures including the absolute configurations of the seven new compounds were elucidated by spectroscopic analysis, chemical methods, and quantum ECD calculations. Compounds 4–8 and 11–15 showed cytotoxicities against the G3K, MCF-7, MD-MBA-231, MCF/Adr, A549, and HL-60 human cancer cell lines with the IC50 values ranging from 0.6 to 9.5 μM.
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Sesterterpene ophiobolin biosynthesis involving multiple gene clusters in Aspergillus ustus
2016Co-Authors: Chai Hangzhen, Tonghan Zhu, Yongfeng Liu, Huiying Meng, Xianqiang Zhou, Guolin Zhou, Xue Yang, Weiming ZhuAbstract:Terpenoids are the most diverse and abundant natural products among which sesterterpenes account for less than 2%, with very few reports on their biosynthesis. Ophiobolins are tricyclic 5–8–5 ring sesterterpenes with potential pharmaceutical application. Aspergillus ustus 094102 from mangrove rizhosphere produces ophiobolin and other terpenes. We obtained five gene cluster knockout mutants, with altered ophiobolin yield using genome sequencing and in silico analysis, combined with in vivo genetic manipulation. Involvement of the five gene clusters in ophiobolin synthesis was confirmed by investigation of the five key terpene synthesis relevant enzymes in each gene cluster, either by gene deletion and complementation or in vitro verification of protein function. The results demonstrate that ophiobolin skeleton biosynthesis involves five gene clusters, which are responsible for C15, C20, C25, and C30 terpenoid biosynthesis.
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new isochromane derivatives from the mangrove fungus Aspergillus ustus 094102
2015Co-Authors: Peipei Liu, Tonghan Zhu, Kui Hong, Cong Wang, Weiming ZhuAbstract:Four new isochromane derivatives (1-4) along with the known peniciphenol (5) and (R)-2-(hydroxymethyl)-3-(2-hydroxypropyl)pheno (6) were isolated from the EtOAc extract of the fermentation broth of the mangrove fungus, Aspergillus ustus 094102. The structures of the new compounds including the absolute configuration were elucidated on the basis of spectroscopic analysis, CD and ECD calculation. Compounds 1 and 2 exhibited α-glucosidase inhibition and anti-oxidation against DPPH radical with IC50 values of 1.4 mM and 25.7 μM, respectively.
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sesquiterpenoids and benzofuranoids from the marine derived fungus Aspergillus ustus 094102
2009Co-Authors: Yi Wang, Kui Hong, Peipei Liu, Chengdu Miao, Weiming ZhuAbstract:Eight drimane sesquiterpenes (1-8), six isochromane derivatives (9-14), and three known compounds, daldinin B (15), 9alpha-hydroxy-6beta-[(2E,4E,6E)-octa-2,4,6-trienoyloxy]-5alpha-drim-7-en-11,12-olide (16), and pergillin (17), were isolated from the EtOAc extract of the marine-derived fungus Aspergillus ustus 094102. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The cytotoxic effects on A549 and HL-60 cell lines were evaluated by SRB and MTT methods. ustusorane E (13) showed significant cytotoxicity against HL-60 cells with an IC50 value of 0.13 microM. ustusolates C (6) and E (8) exhibited moderate cytotoxicity against A549 and HL-60 cells with IC50 values of 10.5 and 9.0 microM, respectively, and ustusolate A (4) showed weak cytotoxicity against HL-60 and A549 cells with IC50 values of 20.6 and 30.0 microM, respectively.
Olesya I Zhuravleva - One of the best experts on this subject based on the ideXlab platform.
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new dihydrobenzofuranoid from the marine derived fungus Aspergillus ustus kmm 4664
2019Co-Authors: G K Oleinikova, V A Denisenko, Dmitrii V Berdyshev, N I Menzorova, Olesya I Zhuravleva, N N Kirichuk, Roman S Popov, Shamil Sh AfiyatullovAbstract:One new dihydrobenzofuran derivative (1), known depsipeptide emericellamide A (2), three known drimanes (3–5) and two artifact drimane derivatives (6, 7) were isolated from the marine-derived fungu...
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two new sesterterpenoids terretonins h and i from the marine derived fungus Aspergillus ustus
2016Co-Authors: G K Oleinikova, V A Denisenko, Dmitrii V Berdyshev, M A Pushilin, Natalia N Kirichuk, N I Menzorova, Alexandra S Kuzmich, Ekaterina A Yurchenko, Olesya I ZhuravlevaAbstract:Abstract Two new sesterterpenoids, terretonins H ( 1 ) and I ( 2 ), together with two known compounds, strobilactone A ( 3 ) and cerebroside D ( 4 ), were isolated from the lipophilic extract of the marine-derived fungus Aspergillus ustus KMM 4664. The structures of compounds 1 and 2 were determined based on spectroscopic methods and confirmed by X-ray crystallographic analysis of terretonin H. All compounds were tested for cytotoxic and embryotoxic effects using sperm and developing embryos of the sea urchin Strongylocentrotus intermedius and human cancer cells.
Kui Hong - One of the best experts on this subject based on the ideXlab platform.
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genome mining reveals a multiproduct sesterterpenoid biosynthetic gene cluster in Aspergillus ustus
2021Co-Authors: Jingjing Guo, Yousheng Cai, Fangcai Cheng, Chenjie Yang, Wenqi Zhang, Jingjing Yan, Zixin Deng, Kui HongAbstract:Genome mining of Aspergillus ustus 094102 enabled the discovery of a multiproduct bifunctional terpene synthase (BTS), AuAS. Heterologous expression of AuAS led to the discovery of five new sesterterpenes, and coexpression of the upstream CYP450 monooxygenase (AuAP450) generated four new sesterterpene alcohols. Additionally, aspergilol A showed cytotoxic activities against MCF-7, MDA-MB231, and HepG2 cancer cells (IC50 21.20-48.76 μM), and aspergilol B exhibited a cytotoxic effect on MCF-7 cells (IC50 27.41 μM).
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ophiobolins from the mangrove fungus Aspergillus ustus
2018Co-Authors: Tonghan Zhu, Jie Fan, Liping Wang, Guoliang Zhu, Yi Wang, Kui Hong, Pawinee Piyachaturawat, Arthit Chairoungdua, Weiming ZhuAbstract:Seven new ophiobolins (1–5, 12, and 14) along with the 11 known analogues (6–11, 13, 15–18) were isolated from the ethyl acetate extracts of the liquid and solid cultures of the mangrove fungus Aspergillus ustus 094102. The structures including the absolute configurations of the seven new compounds were elucidated by spectroscopic analysis, chemical methods, and quantum ECD calculations. Compounds 4–8 and 11–15 showed cytotoxicities against the G3K, MCF-7, MD-MBA-231, MCF/Adr, A549, and HL-60 human cancer cell lines with the IC50 values ranging from 0.6 to 9.5 μM.
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Ophiobolins from the Mangrove Fungus Aspergillus ustus
2017Co-Authors: Tonghan Zhu, Jie Fan, Liping Wang, Guoliang Zhu, Yi Wang, Kui Hong, Pawinee Piyachaturawat, Arthit ChairoungduaAbstract:Seven new ophiobolins (1–5, 12, and 14) along with the 11 known analogues (6–11, 13, 15–18) were isolated from the ethyl acetate extracts of the liquid and solid cultures of the mangrove fungus Aspergillus ustus 094102. The structures including the absolute configurations of the seven new compounds were elucidated by spectroscopic analysis, chemical methods, and quantum ECD calculations. Compounds 4–8 and 11–15 showed cytotoxicities against the G3K, MCF-7, MD-MBA-231, MCF/Adr, A549, and HL-60 human cancer cell lines with the IC50 values ranging from 0.6 to 9.5 μM
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new isochromane derivatives from the mangrove fungus Aspergillus ustus 094102
2015Co-Authors: Peipei Liu, Tonghan Zhu, Kui Hong, Cong Wang, Weiming ZhuAbstract:Four new isochromane derivatives (1-4) along with the known peniciphenol (5) and (R)-2-(hydroxymethyl)-3-(2-hydroxypropyl)pheno (6) were isolated from the EtOAc extract of the fermentation broth of the mangrove fungus, Aspergillus ustus 094102. The structures of the new compounds including the absolute configuration were elucidated on the basis of spectroscopic analysis, CD and ECD calculation. Compounds 1 and 2 exhibited α-glucosidase inhibition and anti-oxidation against DPPH radical with IC50 values of 1.4 mM and 25.7 μM, respectively.
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sesquiterpenoids and benzofuranoids from the marine derived fungus Aspergillus ustus 094102
2009Co-Authors: Yi Wang, Kui Hong, Peipei Liu, Chengdu Miao, Weiming ZhuAbstract:Eight drimane sesquiterpenes (1-8), six isochromane derivatives (9-14), and three known compounds, daldinin B (15), 9alpha-hydroxy-6beta-[(2E,4E,6E)-octa-2,4,6-trienoyloxy]-5alpha-drim-7-en-11,12-olide (16), and pergillin (17), were isolated from the EtOAc extract of the marine-derived fungus Aspergillus ustus 094102. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The cytotoxic effects on A549 and HL-60 cell lines were evaluated by SRB and MTT methods. ustusorane E (13) showed significant cytotoxicity against HL-60 cells with an IC50 value of 0.13 microM. ustusolates C (6) and E (8) exhibited moderate cytotoxicity against A549 and HL-60 cells with IC50 values of 10.5 and 9.0 microM, respectively, and ustusolate A (4) showed weak cytotoxicity against HL-60 and A549 cells with IC50 values of 20.6 and 30.0 microM, respectively.
G K Oleinikova - One of the best experts on this subject based on the ideXlab platform.
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new dihydrobenzofuranoid from the marine derived fungus Aspergillus ustus kmm 4664
2019Co-Authors: G K Oleinikova, V A Denisenko, Dmitrii V Berdyshev, N I Menzorova, Olesya I Zhuravleva, N N Kirichuk, Roman S Popov, Shamil Sh AfiyatullovAbstract:One new dihydrobenzofuran derivative (1), known depsipeptide emericellamide A (2), three known drimanes (3–5) and two artifact drimane derivatives (6, 7) were isolated from the marine-derived fungu...
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two new sesterterpenoids terretonins h and i from the marine derived fungus Aspergillus ustus
2016Co-Authors: G K Oleinikova, V A Denisenko, Dmitrii V Berdyshev, M A Pushilin, Natalia N Kirichuk, N I Menzorova, Alexandra S Kuzmich, Ekaterina A Yurchenko, Olesya I ZhuravlevaAbstract:Abstract Two new sesterterpenoids, terretonins H ( 1 ) and I ( 2 ), together with two known compounds, strobilactone A ( 3 ) and cerebroside D ( 4 ), were isolated from the lipophilic extract of the marine-derived fungus Aspergillus ustus KMM 4664. The structures of compounds 1 and 2 were determined based on spectroscopic methods and confirmed by X-ray crystallographic analysis of terretonin H. All compounds were tested for cytotoxic and embryotoxic effects using sperm and developing embryos of the sea urchin Strongylocentrotus intermedius and human cancer cells.
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nonpolar compounds and free fatty acids from several marine isolates of fungus Aspergillus ustus and actinobacterium nocardiopsis umidischolae
2014Co-Authors: G K Oleinikova, N N Kirichuk, L S Shevchenko, Sh Sh AfiyatullovAbstract:In continuation of research on secondary metabolites of marine fungi and actinobacteria [1, 2], hexane fractions and fractions of free fatty acids and the sterol fraction of actinobacterium were obtained and analyzed from cultures of marine isolates of the fungus Aspergillus ustus KMM 4642 and KMM 4664 isolated from sediment (Okhotsk Shelf, Sakhalin Island, 26.5 m depth) and the actinobacterium Nocardiopsis umidischolae KMM 7036 isolated from Mycale sp. of sponge (Deryugin Basin, Okhotsk Sea). Strain KMM 4642 was cultivated in malt-agar medium prepared with sea water for 14 d [3] and on rice medium prepared with seawater for 21 d [4]. Strain KMM 4664 was cultivated only on rice medium prepared with seawater. Actinobacterium was cultivated in a special medium containing peptone (5.0 g/L), meat extract (3.0), starch (20.0), agar (16.0) and seawater at pH 7.5 and 23°C for 23 d. Cultures were extracted with EtOAc. The extracts were evaporated to dryness. The resulting residues were dissolved in EtOH (10%) and extracted successively with hexane, EtOAc, and BuOH. The hexane fractions were evaporated at reduced pressure and analyzed by GC-MS. The data were compared with the mass spectrometric fragmentation of standards using the NIST98 database. The hexane fraction of A. ustus KMM 4642 consisted of 96.88% diethylhexylphthalate. The remainder consisted of fatty acid ethyl esters and pentadecane. The hexane fraction of A. ustus KMM 4664 contained fatty acid ethyl esters, squalene, octadecane, and sterols such as 24-cholest-4-en-3-one, 24-ethylcholest-7-en-3 -ol, 24-ethylcholesta-3,5-diene, and 24-ethylcholest-5-en-3 -ol at concentrations of 1–2% of the studied mixture. These results differed from those obtained earlier for marine isolates of A. ustus [1]. The hexane fraction of actinobacterium N. umidischolae contained hydrocarbons at concentrations of 1.5–3% that included linear C15, C16, C17, C18, C20, and C22; C18, C19, C20, C22, and C24 with an iso-carbon chain; C18, C19, and C22 with a terminal double bond; and dibutylphthalate (5%) and diethylhexylphthalate (45%). The EtOAc fraction of each culture was chromatographed over a column of silica gel using a hexane–EtOAc gradient (100:0 90:10) to afford fractions of free fatty acids. The obtained total acids were analyzed as the methyl esters (methylated by diazomethane in Et2O) and pyrrolides [5] using GC-MS. Derivatives were identified by comparing their mass spectra with those of standards using the NIST98 database. The composition and content of A. ustus acid esters are given below (mass%):
Lee C Sadkowski - One of the best experts on this subject based on the ideXlab platform.
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primary cutaneous Aspergillus ustus infection second reported case
1998Co-Authors: Rita M Ricci, James S Evans, Jeffrey J Meffert, Leo Kaufman, Lee C SadkowskiAbstract:Abstract We describe the second case of primary cutaneous Aspergillus ustus infection in an immunocompromised patient. Cutaneous aspergillosis was confirmed both by culture and positive fluorescent antibody staining. Few species of Aspergillus are pathogenic in human beings, and fewer still cause primary cutaneous disease. The only other reported case of aspergillosis from Aspergillus ustus occurred in an immunosuppressed patient who was temporally and geographically separated from ours. (J Am Acad Dermatol 1998;38:797-8.)
