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New eudesmane sesquiterpenes from the marine-derived fungus Penicillium thomii

Published on Dec 1, 2015in Phytochemistry Letters1.34
· DOI :10.1016/j.phytol.2015.10.011
Shamil Sh. Afiyatullov15
Estimated H-index: 15
(RAS: Russian Academy of Sciences),
Elena V. Leshchenko4
Estimated H-index: 4
(Far Eastern Federal University)
+ 8 AuthorsDmitrii V. Berdyshev5
Estimated H-index: 5
(RAS: Russian Academy of Sciences)
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Abstract
Abstract Four new eudesmane-type sesquiterpenes thomimarines A–D ( 1 – 4 ) were isolated from the marine-derived fungus Penicillium thomii. Their structures were established based on spectroscopic methods. The absolute configurations of 1 – 4 were determined by time-dependent density functional theory (TD-DFT) calculations of ECD spectra. Inhibitory effects of compounds 1 , 2 and 4 on NO production in LPS-induced RAW 264.7 murine macrophages were evaluated.
  • References (17)
  • Citations (9)
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References17
Newest
Published on Jan 1, 2015in Fitoterapia2.43
Wei Li8
Estimated H-index: 8
(Chinese Academy of Tropical Agricultural Sciences),
Cai-Hong Cai5
Estimated H-index: 5
(Chinese Academy of Tropical Agricultural Sciences)
+ 5 AuthorsHao-Fu Dai19
Estimated H-index: 19
(Chinese Academy of Tropical Agricultural Sciences)
Abstract Five new eudesmane-type sesquiterpenoids ( 1 – 5 ), along with six known ones ( 6 – 11 ), were isolated from Chinese agarwood induced by artificial holing originating from Aquilaria sinensis (Lour.) Gilg (Thymelaeaceae). The structures of the new sesquiterpenoids were established by spectroscopic methods including UV, IR, MS, 1D, and 2D NMR. Compounds 1 , 3 , 6 and 7 exhibited antibacterial activities against both Staphylococcus aureus and Ralstonia solanacearum , and compound 5 only sh...
Published on Oct 18, 2014in Natural Product Research2.00
Jie Zhao1
Estimated H-index: 1
(Xinxiang Medical University),
Jiao Wu1
Estimated H-index: 1
(Xinxiang Medical University),
Fu-lin Yan1
Estimated H-index: 1
(Xinxiang Medical University)
Chemical constituents of EtOAc extract from the rhizomes of traditional Chinese medicine Qian-nian-jian (Homalomena occulta) have been studied, a new sesquiterpenoid, named euadesma-4-ene-1β,15-diol (1), and four related known compounds, polydactin B (2), oplodiol (3), 1β,4β,7α-trihydroxyeudesmane (4), and (–)1β,4β,6α-trihydroxy-eudesmane (5), were isolated. Their structures were elucidated using spectroscopic methods including 1D and 2D NMR techniques and mass spectrometry. All the isolates wer...
Published on Sep 1, 2014in European Journal of Organic Chemistry3.03
Yue Liu8
Estimated H-index: 8
(SPU: Shenyang Pharmaceutical University),
Jiang-Hao Ma2
Estimated H-index: 2
(SPU: Shenyang Pharmaceutical University)
+ 11 AuthorsLiqin Ding9
Estimated H-index: 9
(Tianjin University of Traditional Chinese Medicine)
Eight eudesmane-type sesquiterpenes – phaeusmanes A–H (1–8) – isolated for the first time in this work, and four others (9–12) isolated for the first time from plants in this work, together with fourteen known eudesmane derivatives, were isolated from the rhizomes of Curcuma phaeocaulis. Their structures were elucidated by 1D and 2D NMR and CD spectroscopy and HRMS. Compound 8 is the first example of a nitrogen-containing eudesmane-type sesquiterpene isolated from the genus Curcuma. Furthermore,...
Published on Jan 1, 2014in Journal of the Brazilian Chemical Society1.33
Ning-Ning Yang2
Estimated H-index: 2
(Chinese Academy of Tropical Agricultural Sciences),
Qing-Yun Ma10
Estimated H-index: 10
(Chinese Academy of Tropical Agricultural Sciences)
+ 6 AuthorsYou-Xing Zhao10
Estimated H-index: 10
(Chinese Academy of Tropical Agricultural Sciences)
A investigacao quimica das culturas do fungo Marasmiellus ramealis resultou na primeira isolacao de onze compostos incluindo dois novos sesquiterpenoides do tipo eudesmano 14(10→1)abeo-eudesmano-13-hidroxil-11-eno, 14(10→1)abeo-eudesmano-11,13-diol, e o novo derivado de meleina (R)-(-)-5-etoxicarbonil meleina. A atividade inibitoria da aceticolinesterase (AChE) dos dois primeiros compostos foi avaliada, que mostraram ser ativos com uma porcentagem de inibicao de 29 e 41%, respectivamente, em uma...
Published on Jul 1, 2013in Basic & Clinical Pharmacology & Toxicology2.45
Diogo S. Bomfim4
Estimated H-index: 4
(UFS: Universidade Federal de Sergipe),
Rosana P. C. Ferraz5
Estimated H-index: 5
(UFS: Universidade Federal de Sergipe)
+ 4 AuthorsDaniel P. Bezerra24
Estimated H-index: 24
(FIOCRUZ: Oswaldo Cruz Foundation)
Eudesmols are naturally occurring sesquiterpenoid alcohols that present cytotoxic effect to cancer cells. Herein, all eudesmol isomers displayed cytotoxicity to different tumour cell lines. a-Eudesmol showed IC50 values ranging from 5.38 1.10 to 10.60 1.33 lg/mL for B16-F10 and K562 cell lines, b-eudesmol showed IC50 values ranging from 16.51 1.21 to 24.57 2.75 lg/mL for B16-F10 and HepG2 cell lines, and c-eudesmol showed IC50 values ranging from 8.86 1.27 to 15.15 1.06 lg/mL for B16-F10 and K56...
Published on Jul 1, 2013in Bioorganic & Medicinal Chemistry Letters2.45
Bei Jiang1
Estimated H-index: 1
(JNU: Jinan University),
Wen-Jing Wang7
Estimated H-index: 7
(JNU: Jinan University)
+ 8 AuthorsXiao-Qi Zhang18
Estimated H-index: 18
(JNU: Jinan University)
Abstract The fruits of Alpinia oxyphylla are used as healthcare products for the protection on neurons and prevention of dementia. Two new noreudesmane sesquiterpenoids, (5 R ,7 S ,10 S )-5-hydroxy-13-noreudesma-3-en-2,11-dione ( 1 ) and (10 R )-13-noreudesma-4,6-dien-3,11-dione ( 2 ), and a new eudesmane sesquiterpenoid, (5 S ,8 R ,10 R )-2-oxoeudesma-3,7(11)-dien-12,8-olide ( 3 ), as well as 12 known sesquiterpenoids, were isolated from the fruits of A. oxyphylla . The structures of the new co...
Published on May 7, 2012in Inorganic Chemistry4.85
Tsun-Wei Shiue2
Estimated H-index: 2
,
Yen-Hao Chen4
Estimated H-index: 4
+ 5 AuthorsYun-Ming Wang18
Estimated H-index: 18
The stable, water-soluble, and nonfluorescent FA-OMe can sense nitric oxide (NO) and form the intensely fluorescent product dA-FA-OMe via reductive deamination of the aromatic primary amine. The reaction is accompanied by a notable increase of the fluorescent quantum yield from 1.5 to 88.8%. The deamination mechanism of FA-OMe with NO was proposed in this study. The turn-on fluorescence signals were performed by suppression of photoinduced electron transfer (PeT), which was demonstrated by densi...
Published on Sep 20, 2009in Natural Product Research2.00
Y.M. Hu2
Estimated H-index: 2
(CPU: China Pharmaceutical University),
Z.L. Yang1
Estimated H-index: 1
(CPU: China Pharmaceutical University)
+ 1 AuthorsWen-Cai Ye31
Estimated H-index: 31
(CPU: China Pharmaceutical University)
A new sesquiterpeniod, 6α, 7α, 10α-trihydroxyisoducane (1), together with two known sesquiterpenoids, oplodiol (2) and oplopanone (3), were isolated from the chloroform extract of the rhizomes of Homalomena occulta. Their structures were elucidated by 1D and 2D NMR spectral interpretation.
Published on May 1, 2008in Phytochemistry2.90
Nancy Vera7
Estimated H-index: 7
,
Rosana I. Misico6
Estimated H-index: 6
(Facultad de Ciencias Exactas y Naturales)
+ 2 AuthorsAlicia Bardón18
Estimated H-index: 18
Abstract Eudesmane-type sesquiterpenoids 3α-(2,3-epoxy-2-methylbutyryloxy)-4α-formoxy-11-hydroxy-6,7-dehydroeudesman-8-one ( 1 ) and 3α-(2,3-epoxy-2-methylbutyryloxy)-4α,7α,11-trihydroxyeudesman-8-one ( 2 ), together with 10 known structurally related eudesmanes were isolated from the CHCl 3 extract of aerial parts of Pluchea sagittalis (Lamarck) Cabrera. Their structures were deduced by extensive application of 1 and 2D NMR spectroscopic techniques and high and low resolution CIMS. X-ray crysta...
Published on Dec 1, 2003in Journal of Natural Products4.26
Margherita Gavagnin26
Estimated H-index: 26
,
Ernesto Mollo26
Estimated H-index: 26
+ 2 AuthorsGuido Cimino40
Estimated H-index: 40
The ethereal extract of the Antarctic gorgonian Dasystenella acanthina was found to contain three main nonpolar and relatively transient sesquiterpene metabolites (1−3), which were isolated and submitted to spectral analysis. Two of them were identified as the previously reported compounds trans-β-farnesene (1) and isofuranodiene (3), whereas the third metabolite, the furanoeudesmane 2, was unknown. The structure elucidation of this new sesquiterpene was solved mainly on the basis of its spectra...
Cited By9
Newest
Published on Sep 1, 2018in Chemistry of Natural Compounds0.57
Sh. Sh. Afiyatullov8
Estimated H-index: 8
(RAS: Russian Academy of Sciences),
E. V. Leshchenko3
Estimated H-index: 3
(RAS: Russian Academy of Sciences)
+ 1 AuthorsOlesya I. Zhuravleva5
Estimated H-index: 5
(RAS: Russian Academy of Sciences)
Published on Jan 5, 2018in Marine Drugs3.77
Hee Jae Shin17
Estimated H-index: 17
,
Byeoung-Kyu Choi1
Estimated H-index: 1
+ 7 AuthorsJihoon Lee22
Estimated H-index: 22
A new α-pyrone merosesquiterpenoid possessing an angular tetracyclic carbon skeleton, ochraceopone F (1), and four known secondary metabolites, aspertetranone D (2), cycloechinulin (3), wasabidienone E (4), and mactanamide (5), were isolated from the marine fungus Aspergillus flocculosus derived from a sponge Stylissa sp. collected in Vietnam. The structures of Compounds 1–5 were elucidated by analysis of 1D and 2D NMR spectra and MS data. All the isolated compounds were evaluated for anti-proli...
Published on Jan 1, 2018in Chemistry of Natural Compounds0.57
M. P. Sobolevskaya6
Estimated H-index: 6
(RAS: Russian Academy of Sciences),
S. A. Dyshlovoy1
Estimated H-index: 1
(UHH: University of Hamburg)
+ 3 AuthorsSh. Sh. Afiyatullov8
Estimated H-index: 8
(RAS: Russian Academy of Sciences)
Published on Sep 1, 2017in Chemistry of Natural Compounds0.57
G. K. Oleinikova1
Estimated H-index: 1
(Pacific Institute),
Elena V. Leshchenko4
Estimated H-index: 4
(Far Eastern Federal University)
+ 5 AuthorsSh. Sh. Afiyatullov3
Estimated H-index: 3
(Pacific Institute)
Published on Mar 1, 2017in Chemistry of Natural Compounds0.57
Sh. Sh. Afiyatullov8
Estimated H-index: 8
(RAS: Russian Academy of Sciences),
E. V. Leshchenko3
Estimated H-index: 3
(Far Eastern Federal University)
+ 9 AuthorsEvgeny A. Pislyagin7
Estimated H-index: 7
(RAS: Russian Academy of Sciences)
Published on Feb 17, 2017in Marine Drugs3.77
Shamil Sh. Afiyatullov15
Estimated H-index: 15
,
Elena V. Leshchenko4
Estimated H-index: 4
(Far Eastern Federal University)
+ 9 AuthorsSergey A. Dyshlovoy15
Estimated H-index: 15
Twelve new polyketides, zosteropenillines A–L (1–12), together with known polyketide pallidopenilline A (13), were isolated from the ethylacetate extract of the fungus Penicillium thomii associated with the seagrass Zostera marina. Their structures were established based on spectroscopic methods. The absolute configuration of zosteropenilline A (1) as 4R, 5S, 8S, 9R, 10R, and 13S was determined by a combination of the modified Mosher’s method, X‐ray analysis, and NOESY data. Absolute configurati...
Published on Dec 23, 2016in Journal of Natural Products4.26
M. P. Sobolevskaya6
Estimated H-index: 6
,
Elena V. Leshchenko4
Estimated H-index: 4
+ 13 AuthorsEvgeny A. Pislyagin7
Estimated H-index: 7
Eleven new polyketides, pallidopenillines 1–11, were isolated from the alga-derived fungus Penicillium thomii. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (1) as 4R, 5S, 8S, 9R, 10R, 13R was established using a combination of the modified Mosher’s method, X-ray analysis, and NOESY data. The absolute configurations of 2–5 were determined by time-dependent density functional theory calculations of the ECD spect...
Published on Nov 1, 2016in Chemistry of Natural Compounds0.57
G. K. Oleinikova1
Estimated H-index: 1
(Pacific Institute),
E. V. Leshchenko3
Estimated H-index: 3
+ 6 AuthorsSh. Sh. Afiyatullov3
Estimated H-index: 3
(Pacific Institute)
View next paperZosteropenillines: Polyketides from the MarineDerived Fungus Penicillium thomii