scholarly journals Restricticin B from the Marine Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

2020 ◽  
Author(s):  
Byeonung-Kyu Choi ◽  
Shin-Young Park ◽  
Song-Hee Jo ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Optical Rotation ◽  
2D Nmr ◽  
Marine Fungus ◽  
No Production ◽  
Spectroscopy Data ◽  
Penicillium Janthinellum ◽  
Etoac Extract ◽  
Data Comparison ◽  
Nmr Data

A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2-5) were obtained from the EtOAc extract of the marine fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via analyses of NOESY spectroscopy data, comparison of optical rotation values with those of restricticin derivatives reported and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

scholarly journals Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

Marine Drugs ◽  
2020 ◽  
Vol 18 (9) ◽  
pp. 465
Author(s):  
Byeoung-Kyu Choi ◽  
Song-Hee Jo ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
Hwa-Sun Lee ◽  
...  
Keyword(s):  
Inflammatory Mediators ◽  
Inhibitory Activity ◽  
Optical Rotation ◽  
2D Nmr ◽  
Planar Structure ◽  
No Production ◽  
Spectroscopy Data ◽  
Penicillium Janthinellum ◽  
Etoac Extract ◽  
Nmr Data

A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2–5) were obtained from the EtOAc extract of the marine-derived fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via the analyses of NOESY spectroscopy data, the comparison of optical rotation values with those of reported restricticin derivatives and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

scholarly journals Two New Phomaligols from the Marine-Derived Fungus Aspergillus flocculosus and Their Anti-Neuroinflammatory Activity in BV-2 Microglial Cells

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 65
Author(s):  
Byeoung-Kyu Choi ◽  
Duk-Yeon Cho ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
Hee Jae Shin
Keyword(s):  
Nitric Oxide ◽  
Mass Spectrometry ◽  
Optical Rotation ◽  
Chemical Oxidation ◽  
Culture Broth ◽  
Membered Ring ◽  
Microglial Cells ◽  
No Production ◽  
Nmr Data ◽  
Ic50 Value

Two new phomaligols, deketo-phomaligol A (1) and phomaligol E (2), together with six known compounds (3–8) were isolated from the culture broth of the marine-derived fungus Aspergillus flocculosus. Compound 1 was first isolated as a phomaligol derivative possessing a five-membered ring. The structures and absolute configurations of the new phomaligols were determined by detailed analyses of mass spectrometry (MS), nuclear magnetic resonance (NMR) data, optical rotation values and electronic circular dichroism (ECD). In addition, the absolute configurations of the known compounds 3 and 4 were confirmed by chemical oxidation and comparison of optical rotation values. Isolated compounds at a concentration of 100 μM were screened for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. Among the compounds, 4 showed moderate anti-neuroinflammatory effects with an IC50 value of 56.6 μM by suppressing the production of pro-inflammatory mediators in activated microglial cells without cytotoxicity.

scholarly journals Chemical Constituents from Scindapsus officinalis (Roxb.) Schott. and Their Anti–Inflammatory Activities

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2577 ◽  
Author(s):  
Hongjing Dong ◽  
Yanling Geng ◽  
Xueyong Wang ◽  
Xiangyun Song ◽  
Xiao Wang ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
No Production ◽  
Inhibitory Effects ◽  
Nmr Data ◽  
Extensive Analysis ◽  
Ic50 Values ◽  
Monoterpene Glycoside ◽  
Anti Inflammatory

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

scholarly journals New Ophiobolin Derivatives from the Marine Fungus Aspergillus flocculosus and Their Cytotoxicities against Cancer Cells

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 346 ◽  
Author(s):  
Byeoung-Kyu Choi ◽  
Phan Thi Hoai Trinh ◽  
Hwa-Sun Lee ◽  
Byeong-Woo Choi ◽  
Jong Soon Kang ◽  
...  
Keyword(s):  
Cancer Cells ◽  
Cell Lines ◽  
Cancer Cell ◽  
Chemical Shifts ◽  
Optical Rotation ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Marine Fungus ◽  
Side Chain ◽  
Spectroscopic Methods

Five new sesterterpenes, 14,15-dehydro-6-epi-ophiobolin K (1), 14,15-dehydro- ophiobolin K (2), 14,15-dehydro-6-epi-ophiobolin G (3), 14,15-dehydro-ophiobolin G (4) and 14,15-dehydro-(Z)-14-ophiobolin G (5), together with four known ophiobolins (6–9) were isolated from the marine fungus Aspergillus flocculosus derived from the seaweed Padina sp. collected in Vietnam. The five new ophiobolins were first isolated as ophiobolin derivatives consisting of a fully unsaturated side chain. Their structures were elucidated via spectroscopic methods including 1D, 2D NMR and HR-ESIMS. The absolute configurations were determined by the comparison of chemical shifts and optical rotation values with those of known ophiobolins. All compounds (1–9) were then evaluated for their cytotoxicity against six cancer cell lines, HCT-15, NUGC-3, NCI-H23, ACHN, PC-3 and MDA-MB-231. All the compounds showed potent cytotoxicity with GI50 values ranging from 0.14 to 2.01 μM.

scholarly journals Structure Revision and Protein Tyrosine Phosphatase Inhibitory Activity of Drazepinone

Marine Drugs ◽  
2021 ◽  
Vol 19 (12) ◽  
pp. 714
Author(s):  
Fei Cao ◽  
Li Pan ◽  
Wen-Bin Gao ◽  
Yun-Feng Liu ◽  
Cai-Juan Zheng ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Chemical Shifts ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Nmr Data ◽  
Structure Revision ◽  
Ic50 Values

From the marine-derived fungus Penicillium sumatrense (Trichocomaceae), a pair of enantiomers [(+)-1 and (−)-1] were isolated with identical 1D NMR data to drazepinone, which was originally reported to have a trisubstituted naphthofuroazepinone skeleton. In this study, we confirmed the structures of the two enantiomers as drazepinone and revised their structures by detailed analysis of extensive 2D NMR data and a comparison of the calculated 13C chemical shifts, ECD, VCD, and ORD spectra with those of the experiment ones. (+)-1 and (−)-1 were evaluated for their PTP inhibitory activity in vitro. (−)-1 showed selective PTP inhibitory activity against PTP1B and TCPTP with IC50 values of 1.56 and 12.5 μg/mL, respectively.

scholarly journals Corylucinine, a new Alkaloid from Corydalis cava (Fumariaceae), and its Cholinesterase Activity

2012 ◽  
Vol 7 (7) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Zdeněk Novák ◽  
Jakub Chlebek ◽  
Lubomír Opletal ◽  
Pavel Jiroš ◽  
Kateřina Macáková ◽  
...  
Keyword(s):  
Human Plasma ◽  
Human Blood ◽  
Inhibitory Activity ◽  
Cholinesterase Activity ◽  
Optical Rotation ◽  
2D Nmr ◽  
Esi Ms

A new benzyldihydroisoquinoline alkaloid (1) was isolated from the tubers of Corydalis cava and named corylucinine. Additionally, 8-trichloromethyl-7,8-dihydropalmatine (2), an isolation artifact of tetrahydropalmatine, was obtained. The structures were established by spectroscopic (including 2D NMR and optical rotation) and HR-ESI-MS methods. Both compounds were tested for human blood acetylcholinesterase (HuAChE) and human plasma butyrylcholinesterase (HuBuChE) inhibitory activity. In comparison with the used standards, both compounds showed only moderate inhibitory activity against HuAChE (IC50, HuAChE = 127.6 ± 5.2 μM for 1, and IC50, HuAChE = 82.9 ± 3.9 μM for 2) and none against HuBuChE.

scholarly journals A New Trinor-guaiane Sesquiterpene from an Indonesian Soft Coral Anthelia sp

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Novriyandi Hanif ◽  
Anggia Murni ◽  
Marie Yamauchi ◽  
Masahiro Higashi ◽  
Junichi Tanaka
Keyword(s):  
Soft Coral ◽  
Optical Rotation ◽  
2D Nmr ◽  
Planar Structure ◽  
Nmr Data ◽  
Relative Stereochemistry ◽  
Absolute Stereochemistry

A new trinor-guaiane sesquiterpene has been isolated from an Indonesian soft coral Anthelia sp. The planar structure, possessing an octahydroazulene skeleton, and relative stereochemistry were established by analyzing 1D and 2D NMR data, including NOE experiments. Its absolute stereochemistry was elucidated to be 1 S, 4 S, 7 R, and 10 R by comparing observed and calculated optical rotation values. The new compound showed weak cytotoxicity against NBT-T2 cells.

scholarly journals Antimicrobial activity of natural compounds from sponge – derived fungus Aspergillus flocculosus 01NT.1.1.5

2020 ◽  
Vol 16 (4) ◽  
pp. 729-735
Author(s):  
Phan Thi Hoai Trinh ◽  
Tran Thi Thanh Van ◽  
Bui Minh Ly ◽  
Byeoung Kyu Choi ◽  
Hee Jae Shin ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Culture Medium ◽  
Antimicrobial Agents ◽  
2D Nmr ◽  
Marine Fungus ◽  
Antimicrobial Drugs ◽  
Etoac Extract ◽  
E Coli ◽  
Chemical Structures ◽  
Pathogenic Microbes

The Aspergillus fungi have been an important source of natural products that are useful for exploration in medicine, agriculture and industry. In our continuous investigation to search for new antimicrobial agents from marine-derived fungi, one new phomaligol A2 (1), together with three known compounds, wasabidienone E (2), aspertetranone D (3) and mactanamide (4), were obtained from the EtOAc extract of the culture medium of the marine-derived fungus Aspergillus flocculosus (A. flocculosus) 01NT.1.1.5 isolated from the sponge Stylissa sp. at Nhatrang Bay, Vietnam. Their chemical structures were elucidated by analysis of 1D and 2D NMR and mass spectroscopic data, as well as by comparison of the corresponding data to those previously reported in the literature. Furthermore, the aim of this study was also to evaluate the antimicrobial activity of these compounds against pathogenic microbes including Escherichia coli (E. coli) ATCC 25922, Pseudomonas aeruginosa (P. aeruginosa) ATCC 27853, Staphylococcus aureus (S. aureus) ATCC 25923, Bacillus cereus (B. cereus) ATCC 11778, Streptococcus faecalis (S. faecalis) ATCC 19433, Listeria monocytogenes (L. monocytogenes) ATCC 19111, and Candida albicans (C. albicans) ATCC 10231. Among the compounds, 1-3 were inhibitory on the growth of the yeast C. albicans with minimum inhibitory concentration (MIC) value of 16 μg/mL, which was more potent than amoxicillin and cefotaxime (MIC > 256 μg/mL), antimicrobial drugs as positive references. Moreover, compounds 1-4 were also found to be active against other pathogens including P. aeruginosa and S. faecalis with MIC values of 16 μg/mL and 32 μg/mL, respectively. Compound 4 had no inhibitory activity against L. monocytogenes, whereas compounds 1-3 had ability to against this strain with MICs of 32 to 64 μg/mL. Four of tested compounds exhibited antibacterial activity against B. cereus and E. coli with MIC values of 64-128 μg/mL. This is the first report about these compounds with antimicrobial activity obtained from marine fungus A. flocculosus isolated in Vietnam.

scholarly journals Streptoglycerides E–H, Unsaturated Polyketides from the Marine-Derived Bacterium Streptomyces specialis and Their Anti-Inflammatory Activity

Marine Drugs ◽  
2022 ◽  
Vol 20 (1) ◽  
pp. 44
Author(s):  
Hee Jae Shin ◽  
Chang-Su Heo ◽  
Cao Van Anh ◽  
Yeo Dae Yoon ◽  
Jong Soon Kang
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Ring System ◽  
Membered Ring ◽  
Inflammatory Activity ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Nmr Data ◽  
Ic50 Values ◽  
Anti Inflammatory

Four new streptoglycerides E–H (1–4), with a rare 6/5/5/-membered ring system, were isolated from a marine-derived actinomycete Streptomyces specialis. The structures of 1–4 were elucidated by detailed analysis of HRESIMS, 1D and 2D NMR data and ECD spectra as well as comparison of their spectroscopic data with those reported in literature. Compounds 1–4 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production in Raw 264.7 cells with IC50 values ranging from 3.5 to 10.9 µM. Especially, 2 suppressed mRNA expression levels of iNOS and IL-6 without cytotoxicity.

scholarly journals New Purinyl-Steroid and Other Constituents from the Marine Fungus Penicillium brefeldianum ABC190807: Larvicidal Activities against Aedes aegypti

2021 ◽  
Vol 2021 ◽  
pp. 1-6
Author(s):  
Zong-Min Hou ◽  
Sen-Quan Yu ◽  
Min Tao ◽  
Cai-Bei Xia ◽  
Yu-Lian Xia ◽  
...  
Keyword(s):  
Aedes Aegypti ◽  
Larvicidal Activity ◽  
2D Nmr ◽  
Marine Fungus ◽  
Mangrove Sediment ◽  
Health Issues ◽  
Etoac Extract ◽  
The Third ◽  
Larvicidal Activities ◽  
Third Instar Larvae

Mosquitoes historically threatened human health; the major mosquito-related global health issues include malaria, dengue fever, yellow fever, and Zika, as well as several other vector-borne outbreaks. Here, the EtOAc extract of the mangrove sediment fungus Penicillium brefeldianum ABC190807 exerted larvicidal activities against the third instar larvae of Aedes aegypti with an LC50 of 0.089 mg/mL. One new purinyl-steroid (ergosta-4,6,8(14),22-tetraen-3-(6-amino-9H-purin-9-yl) (1)), along with six (2–7) known compounds, were isolated from the EtOAc extract of Penicillium brefeldianum ABC190807. Structures of the compounds were elucidated via 1D/2D NMR and HR-ESI-MS data. Respective spectral data were compared with those of known compounds. Among all compounds whose larvicidal activity against the third instar larvae of Aedes aegypti was evaluated, compounds 2 and 7 showed larvicidal activity with respective LC50 values of 0.452 and 0.337 mg/mL.

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