scholarly journals Alkaloids From the Marine Fungus Lecanicillium fusisporum Using an Amino Acid-Directed Strategy

2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110460
Author(s):  
Qin Huang ◽  
Hou-Jin Li ◽  
Chang-Bai Huang ◽  
Zi-Han Wang ◽  
Wen-Jian Lan ◽  
...  
Keyword(s):  
Amino Acid ◽  
Spectroscopic Data ◽  
Marine Fungi ◽  
Optical Rotation ◽  
Indole Alkaloid ◽  
2D Nmr ◽  
Marine Fungus ◽  
Culture Broth ◽  
Synthetic Approach ◽  
C Nmr

An amino acid-directed strategy has been developed to explore the potential of marine fungi to produce alkaloids. The marine fungus Lecanicillium fusisporum was cultured in glucose-peptone-yeast (GPY) medium to which were added L-tryptophan, L-phenylalanine, L-threonine, D, L-methionine, L-serine, L-lysine and L-valine. A new indole alkaloid, lecasporinoid (1), along with five known alkaloids (2−6) were discovered from the culture broth. The planar structure of lecasporinoid (1) was determined by HR-ESIMS, and 1D and 2D NMR spectroscopic data. The absolute configuration was established by optical rotation and 13C NMR calculations combining with a chemical synthetic approach.

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.

Cytotoxic constituents of Alocasia macrorrhiza

2017 ◽  
Vol 72 (1-2) ◽  
pp. 21-25 ◽  
Author(s):  
Marwa Elsbaey ◽  
Kadria F.M. Ahmed ◽  
Mahmoud F. Elsebai ◽  
Ahmed Zaghloul ◽  
Mohamed M.A. Amer ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Spectroscopic Data ◽  
Human Cancer ◽  
Indole Alkaloid ◽  
Acid Methyl Ester ◽  
2D Nmr ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Acid Methyl ◽  
First Time

AbstractAn indole alkaloid, 2-(5-hydroxy-1H-indol-3-yl)-2-oxo-acetic acid (1) isolated for the first time from nature, in addition to the nine known compounds 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (2), alocasin B (3), hyrtiosin B (4), α-monopalmitin (5), 1-O-β-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (6), 3-epi-betulinic acid (7), 3-epi-ursolic acid (8),β-sitosterol (9) andβ-sitosterol 3-O-β-D-glucoside (10) were isolated from the rhizomes ofAlocasia macrorrhiza(Araceae). Their structures were elucidated by 1D and 2D NMR spectroscopic data. Of these compounds,6exhibited the strongest cytotoxicity against the four tested human cancer cell lines (IC50of about 10 µM against Hep-2 larynx cancer cells).

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.

Peptaibol metabolites of Tolypocladium geodes

1996 ◽  
Vol 74 (2) ◽  
pp. 165-172 ◽  
Author(s):  
Youla S. Tsantrizos ◽  
Sotiria Pischos ◽  
Françoise Sauriol ◽  
Paul Widden
Keyword(s):  
Amino Acid ◽  
2D Nmr ◽  
Chemical Shift Assignments ◽  
Pentanoic Acid ◽  
2D Nmr Spectroscopy ◽  
New Members ◽  
The Common ◽  
Unusual Amino Acid ◽  
Acid Unit ◽  
C Nmr

Three antibiotic peptides, LP237-F8 (1), F5 (2), and F7 (3), were isolated from the liquid culture of the fungus Tolypocladium geodes. Chemical shift assignments of the 1H and 13C NMR resonances and sequencing of these metabolites were achieved by extensive high-field 2D NMR spectroscopy. The N-terminal of peptides 1 and 2 is protected with an octanoyl (Oc) fatty acid unit, whereas that of peptide 3 is protected with a decanoyl (Dec) unit. The C-terminal of all three peptides is protected with the amino alcohol leucinol (Lol). All three metabolites contain the common amino acids Ala, Phe or Tyr, Pro, and Gln, as well as the unusual amino acid α-aminoisobutyric acid (Aib). In addition, peptides 1 and 2 contain the amino acid α-amino-α-ethyl-n-pentanoic acid (α-ethylnorvaline, EtNor), which has not been previously reported as a constituent of a natural product. Metabolites 1, 2, and 3 are new members of the class of natural products known as peptaibols. Key words: Tolypocladium geodes, peptaibols, leucinol, α-amino-α-ethyl-n-pentanoic acid.

scholarly journals Fusariumins B-D, Three New Alkylamine Octanoylated Derivatives from Fusarium sp

2018 ◽  
Vol 13 (1) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Liang-Yan Liu ◽  
Tao Feng ◽  
Zheng-Hui Li ◽  
Ji-Kai Liu
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Culture Broth ◽  
Fusarium Sp ◽  
Octanoyl Group

Three new alkylamine octanoylated derivatives, fusariumins B-D (1-3), and four known compounds 4-7 were isolated from the culture broth of the fungus Fusarium sp. Compounds 1-3 maintaining an unusual tetradecan-2-amine or tetradecan-3-amine moiety with an octanoyl group were characterized based on HRMS, 1D and 2D NMR spectroscopic data.

scholarly journals Oleanane-type Triterpene Glycosides from Glycyrrhiza Uralensis

2007 ◽  
Vol 2 (3) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Jinwei Li-Yang ◽  
Jun-ichiro Nakajima ◽  
Nobuhito Kimura ◽  
Kazuki Saito ◽  
Shujiro Seo
Keyword(s):  
Natural Products ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Mass Spectrometric ◽  
Triterpene Glycosides ◽  
Glycyrrhiza Uralensis ◽  
Nmr Data ◽  
Nmr Methods ◽  
First Time ◽  
C Nmr

Chemical investigation of the roots of Glycyrrhiza uralensis resulted in the isolation of six oleanane-type triterpene glycosides (1 – 6), including one new saponin (1) and two (2 and 3) obtained as natural products for the first time. The new licorice saponin (1) was identified as 22β–acetoxylglycyrrhizin from [α]D, mass spectrometric, and UV, IR, and NMR spectroscopic data.. Full assignments of 1H and 13C-NMR data for compounds 2, 3, 4, 5 and 6 were made for the first time according to 2D NMR methods.

Two New Limonoids With A 3-O-β-Tigloyl Group From The Seeds Of The Chinese Mangrove Xylocarpus Granatum

2007 ◽  
Vol 62 (6) ◽  
pp. 859-862 ◽  
Author(s):  
Jun Wu ◽  
Minyi Li ◽  
Si Zhang ◽  
Qiang Xiao ◽  
Qingxin Li
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Nmr Data ◽  
Xylocarpus Granatum ◽  
Nmr Techniques ◽  
Noesy Spectra ◽  
C Nmr

A new mexicanolide and a new phragmalin, named 30α-hydroxyl xylogranatin A and xylogranatin E2, respectively, have been isolated from the seeds of a Chinese mangrove Xylocarpus granatum. Their structures were identified on the basis of spectroscopic data. Each of them has a 3-O-β -tigloyl group. The first complete assignments of 1H and 13C NMR data for these limonoids were achieved by means of 2D NMR techniques, including 1H-1H COSY, HSQC, HMBC and NOESY spectra

scholarly journals Novel 1,3-Benzodioxole From Marine-Derived Actinomycete in East Vietnam Sea

2020 ◽  
Vol 15 (5) ◽  
pp. 1934578X2092004
Author(s):  
Dao Phi Thi ◽  
Huong Doan Thi Mai ◽  
Duc Danh Cao ◽  
Quyen Vu Thi ◽  
Mai Anh Nguyen ◽  
...  
Keyword(s):  
2D Nmr ◽  
Culture Broth ◽  
Genus Streptomyces ◽  
Nmr Data ◽  
Actinomycete Strain ◽  
Spectral Data Analysis ◽  
And Staphylococcus Aureus ◽  
16Srrna Gene ◽  
Mcf 7 ◽  
C Nmr

Analysis of an antimicrobial extract from the culture broth of the marine-derived actinomycete Streptomyces sp. G261 led to the isolation of a new 1,3-benzodioxole derivative (1), together with 10 known compounds 2-11. The actinomycete strain G261 was isolated from sediment, collected at Cu Lao Cham, Quang Nam in Vietnam. The taxonomic identification of the strain G261 was achieved by analysis of 16SrRNA gene sequences. On the basis of morphological and phylogenetic evidence, the actinomycete strain G261 was assigned to the genus Streptomyces. The structures of the isolated compounds were established by their spectral data analysis, including mass spectrometry, 1-dimensional nuclear magnetic resonance (1D-NMR), and 2D-NMR. The structure of 1 was confirmed by comparison of the calculated with experimental 13C NMR data. Compound 1 exhibited antimicrobial activity against Enterococcus faecalis and Staphylococcus aureus with minimum inhibitory concentration values of 128 and 256 µg/mL, respectively. Whereas, compound 1 had a weak inhibition when tested against 4 cancer cell lines, KB, LU-1, HepG-2, and MCF-7.

scholarly journals Exploration of Indole Alkaloids from Marine Fungus Pseudallescheria boydii F44-1 Using an Amino Acid-Directed Strategy

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 77 ◽  
Author(s):  
Mei-Xiang Yuan ◽  
Yi Qiu ◽  
Yan-Qin Ran ◽  
Gong-Kan Feng ◽  
Rong Deng ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Culture Medium ◽  
Indole Alkaloids ◽  
Great Influence ◽  
Uv Spectra ◽  
Marine Fungus ◽  
Culture Broth ◽  
Comprehensive Analysis ◽  
Pseudallescheria Boydii

The composition of the culture medium has great influence on the metabolite production of the marine fungus Pseudallescheria boydii F44-1. By adding amino acids to GPY culture medium, two new bisindole alkaloids, pseudboindoles A and B (1 and 2), together with 11 known indole alkaloids were isolated from the culture broth. Their structures were elucidated by comprehensive analysis of the NMR, MS, IR, and UV spectra. The 3,3′-cyclohexylidenebis(1H-indole) (3) showed cytotoxic activity against various cancer cell lines.

Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species

2016 ◽  
Vol 71 (11-12) ◽  
pp. 387-392 ◽  
Author(s):  
Samar S.A. Mourshid ◽  
Jihan M. Badr ◽  
April L. Risinger ◽  
Susan L. Mooberry ◽  
Diaa T.A. Youssef
Keyword(s):  
Fatty Acid ◽  
Cyclopiazonic Acid ◽  
2D Nmr ◽  
Culture Broth ◽  
Fatty Acid Esters ◽  
Spectroscopic Techniques ◽  
Penicillium Species ◽  
H Nmr ◽  
Acid Esters ◽  
C Nmr

Abstract Two new antimicrobial fatty acid esters, penicilloitins A and B (1 and 2), along with α-cyclopiazonic acid (3), tryptamine (4) and indole-3-carbaldehyde (5), were isolated from mycelial extracts and the culture broth of a marine endophytic Penicillium species and their structures established by spectroscopic techniques including 1D (1H NMR and 13C NMR) and 2D NMR (COSY, multiplicity-edited HSQC, and HMBC) as well as HRESIMS. Of these compounds, 1, 3 and 4 displayed modest antimicrobial activity.

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