scholarly journals Cytotoxic Secondary Metabolites Isolated from the Marine Alga-Associated Fungus Penicillium chrysogenum LD-201810

Marine Drugs ◽  
2020 ◽  
Vol 18 (5) ◽  
pp. 276
Author(s):  
Lin-Lin Jiang ◽  
Jin-Xiu Tang ◽  
Yong-Heng Bo ◽  
You-Zhi Li ◽  
Tao Feng ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Cell Lines ◽  
Penicillium Chrysogenum ◽  
Marine Alga ◽  
2D Nmr ◽  
Ionization Mass ◽  
Human Carcinoma ◽  
Hydroxyphenylacetic Acid ◽  
The Absolute ◽  
Circular Dichroïsm

A new pentaketide derivative, penilactonol A (1), and two new hydroxyphenylacetic acid derivatives, (2’R)-stachyline B (2) and (2’R)-westerdijkin A (3), together with five known metabolites, bisabolane-type sesquiterpenoids 4–6 and meroterpenoids 7 and 8, were isolated from the solid culture of a marine alga-associated fungus Penicillium chrysogenum LD-201810. Their structures were elucidated based on extensive spectroscopic analyses, including 1D/2D NMR and high resolution electrospray ionization mass spectra (HRESIMS). The absolute configurations of the stereogenic carbons in 1 were determined by the (Mo2(OAc)4)-induced circular dichroism (CD) and comparison of the calculated and experimental electronic circular dichroism (ECD) spectra, while the absolute configuration of the stereogenic carbon in 2 was established using single-crystal X-ray diffraction analysis. Compounds 2 and 3 adapt the 2’R-configuration as compared to known hydroxyphenylacetic acid-derived and O-prenylated natural products. The cytotoxicity of 1–8 against human carcinoma cell lines (A549, BT-549, HeLa, HepG2, MCF-7, and THP-1) was evaluated. Compound 3 exhibited cytotoxicity to the HepG2 cell line with an IC50 value of 22.0 μM. Furthermore, 5 showed considerable activities against A549 and THP-1 cell lines with IC50 values of 21.2 and 18.2 μM, respectively.

scholarly journals LAMA-1: A Cerebroside Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum

Metabolites ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 75
Author(s):  
Samah O. Alshehri ◽  
Rania T. Malatani ◽  
Hanin A. Bogari ◽  
Ahmad O. Noor ◽  
Amany K. Ibrahim ◽  
...  
Keyword(s):  
Cell Lines ◽  
Penicillium Chrysogenum ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Human Carcinoma ◽  
Sulforhodamine B ◽  
Ic50 Values ◽  
Hepg2 Cell Lines

Chemical investigation of the ethyl acetate extract of Penicillium chrysogenum strain S003, a fungus isolated from Red Sea deep sediment, led to the isolation of a cerebroside molecular species LAMA (1) along with three other known compounds, ergosterol (2), epidioxyergosterol (3), and kojic acid (4). The structures of the isolated compounds were elucidated by interpretation of spectral data, including detailed 1D and 2D NMR (One and two dimensional Nuclear Magnetic Resonance) and mass spectrometry. The cytotoxic activities of isolated compounds 1–4 against five human carcinoma cells were evaluated using sulforhodamine B (SRB) assay. Compounds 2 and 3 displayed promising cytotoxic profiles against lung cancer (A-549), prostate (DU-145), breast adenocarcinoma (MCF-7), and hepatocellular (HepG2) cell lines, with IC50 values of 21.26, 19.3; 1.50, 6.10; 16.95, 13.6; and 2.89, 3.07 µM, respectively, while they were inactive against HeLa cells. Compounds 1 and 4 showed weak cytotoxic profiles against all cell lines under investigation.

Two Rare Hydroazulene-type Sesquiterpenes from the Roots of Aristolochia yunnanensis

2014 ◽  
Vol 69 (6) ◽  
pp. 742-746 ◽  
Author(s):  
Zhuo Du ◽  
Feng-Ni Wen ◽  
Ji-Ping Zhang ◽  
Jian-Feng Wua ◽  
Fang Liu ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Cell Lines ◽  
Spectroscopic Data ◽  
Cytotoxic Activities ◽  
Moderate Activity ◽  
Electronic Circular Dichroism ◽  
The Third ◽  
The Absolute ◽  
First Time ◽  
Circular Dichroïsm

Two new sesquiterpenes, named aristoyunnolin I (1) and J (2), together with eight known compounds (3 - 10) were isolated from the roots of Aristolochia yunnanensis. Compounds 1 and 2 feature a rare hydroazulene-type sesquiterpene skeleton and represent the third and fourth examples of this kind found in nature. The structures were determined from spectroscopic data, and the absolute configurations of 1 - 3 were assigned by comparing experimental with simulated electronic circular dichroism (ECD) spectra. Compounds 1, 2, 6 - 10 were isolated from this plant for the first time. The cytotoxic activities of 1 - 10 were evaluated against P-388 and A-549 cell lines. Only compounds 4 and 5 showed moderate activity with IC50 values ranging from 12.0 to 18.2 μM.

scholarly journals A New Diterpenoid with a Rearranged Skeleton from Salvia prattii

2017 ◽  
Vol 12 (8) ◽  
pp. 1934578X1701200
Author(s):  
Hiroshi Kawabe ◽  
Riyo Suzuki ◽  
Hiroshi Hirota ◽  
Keiichi Matsuzaki ◽  
Xun Gong ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Hela Cell ◽  
Cell Lines ◽  
Absolute Configuration ◽  
Electronic Circular Dichroism ◽  
Methyl Group ◽  
Spectroscopic Analyses ◽  
Hela Cell Lines ◽  
The Absolute ◽  
Circular Dichroïsm

A new diterpenoid with a rearranged skeleton, prattinin A (1), was isolated along with five known compounds (2–6) from the roots of Salvia prattii. The structure of 1 bearing a methyl group at the C-5 position was established by extensive spectroscopic analyses and the absolute configuration of 1 was elucidated by comparing the calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1, 3, 4, and 5 exhibited moderate or weak cytotoxicity against HL-60 and HeLa cell lines.

scholarly journals Structures and Absolute Configurations of Diketopiperazine Alkaloids Chrysopiperazines A–C from the Gorgonian-Derived Penicillium chrysogenum Fungus

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 250 ◽  
Author(s):  
Xu ◽  
Mao ◽  
Xue ◽  
Qi ◽  
Wei ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Penicillium Chrysogenum ◽  
Vibrational Circular Dichroism ◽  
Aliphatic Chain ◽  
Electronic Circular Dichroism ◽  
First Report ◽  
The Absolute ◽  
Circular Dichroïsm

Three new diketopiperazine alkaloids, including two oxepine‐containing diketopiperazines, chrysopiperazines A and B (1 and 2), and one quinazoline‐containing diketopiperazine, chrysopiperazine C (5), together with three known analogues (3, 4, and 6), were isolated from the gorgonian-derived Penicillium chrysogenum fungus. The relative and absolute configurations of C-3 and C-15 in 1 and 2, C-3 and C-14 in 5 were established by NOE modified Marfey’s analysis and electronic circular dichroism (ECD) calculations. Particularly, the absolute configurations of C-19 in 1 and 3, which was very challenging to be identified due to the flexible conformation in a short aliphatic chain, were successfully determined by the vibrational circular dichroism (VCD) method, supplying with a reliable and optional method to define the absolute configurations. Additionally, this is the first report on oxepine-containing diketopiperazines from the genus Penicillium.

(-)-Strempeliopine, stereoselective total synthesis and the determination of absolute configuration

1986 ◽  
Vol 51 (8) ◽  
pp. 1731-1742 ◽  
Author(s):  
Josef Hájíček ◽  
Jan Trojánek
Keyword(s):  
Circular Dichroism ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Determination Of Absolute Configuration ◽  
Natural Base ◽  
The Absolute ◽  
Circular Dichroïsm

A synthesis of (±)-strempeliopine (II) is described, the key step of which is the stereoselective reductive rearrangement of 18-methylene-1,2-dehydroaspidospermidine (XI). The absolute configuration of the natural (-)-base II was determined as (2S, 7R, 20R, 21R) on the basis of its synthesis from (+)-18-methylenevincadifformine (XVII) the configuration of which was derived from a comparison of circular dichroism properties of bases with a β-anilinoacrylate chromophore. The biogenesis of the alkaloids of the schizozygane type is discussed.

scholarly journals Absolute Configuration Sensing of Chiral Aryl- and Aryloxy-Propionic Acids by Biphenyl Chiroptical Probes

Chemosensors ◽  
2021 ◽  
Vol 9 (7) ◽  
pp. 154
Author(s):  
Stefania Vergura ◽  
Stefano Orlando ◽  
Patrizia Scafato ◽  
Sandra Belviso ◽  
Stefano Superchi
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Environmental Pollutants ◽  
Red Shift ◽  
Electronic Circular Dichroism ◽  
Configuration Assignment ◽  
Clear Sign ◽  
The Absolute ◽  
Circular Dichroïsm

The absolute configuration of chiral 2-aryl and 2-aryloxy propionic acids, which are among the most common chiral environmental pollutants, has been readily and reliably established by either electronic circular dichroism spectroscopy or optical rotation measurements employing suitably designed 4,4′-disubstituted biphenyl probes. In fact, the 4,4′-biphenyl substitution gives rise to a red shift of the diagnostic electronic circular dichroism signal of the biphenyl A band employed for the configuration assignment, removing its overlap with other interfering dichroic bands and allowing its clear sign identification. The largest A band red shift, and thus the most reliable results, are obtained by employing as a probe the 4,4′-dinitro substituted biphenylazepine 3c. The method was applied to the absolute configuration assignment of 2-arylpropionic acids ibuprofen (1a), naproxen (1b), ketoprofen (1c) and flurbiprofen (1d), as well as to the 2-aryloxypropionic acids 2-phenoxypropionic acid (2a) and 2-naphthoxypropionic acid (2b). This approach, allowing us to reveal the sample’s absolute configuration by simple optical rotation measurements, is potentially applicable to online analyses of both the enantiomeric composition and absolute configuration of these chiral pollutants.

Absolute configuration determination of theanti-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization withL-prolinol

2013 ◽  
Vol 69 (11) ◽  
pp. 1411-1413 ◽  
Author(s):  
Yuko Kawanami ◽  
Hidekazu Tanaka ◽  
Jun-ichi Mizoguchi ◽  
Nobuko Kanehisa ◽  
Gaku Fukuhara ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Circular Dichroism ◽  
Carboxylic Acid ◽  
Absolute Configuration ◽  
Void Space ◽  
Circular Dichroism Spectra ◽  
The Absolute ◽  
Circular Dichroïsm ◽  
Hydrogen Bonded

The absolute configuration has been established of the enantiopureanti-head-to-head cyclodimer of anthracene-2-carboxylic acid (AC) cocrystallized with L-propinol and dichloromethane [systematic name: (S)-2-(hydroxymethyl)pyrrolidin-1-ium (5R,6S,11R,12S)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11-bis([1,2]benzeno)dibenzo[a,e][8]annulene-2-carboxylate dichloromethane monosolvate], C5H12NO+·C30H19O4−·CH2Cl2. In the crystal structure, the AC dimer interacts with L-prolinol through a nine-membered hydrogen-bonded ring [R22(9)], while the dichloromethane molecule is incorporated to fill the void space. The absolute configuration determined in this study verifies a recent assignment made by comparing theoreticalversusexperimental circular dichroism spectra.

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