scholarly journals Penigrisacids A–D, Four New Sesquiterpenes from the Deep-Sea-Derived Penicillium griseofulvum

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 507 ◽  
Author(s):  
Cui-Ping Xing ◽  
Chun-Lan Xie ◽  
Jin-Mei Xia ◽  
Qing-Mei Liu ◽  
Wei-Xiang Lin ◽  
...  
Keyword(s):  
Tumor Cells ◽  
Deep Sea ◽  
Optical Rotation ◽  
Electronic Circular Dichroism ◽  
Planar Structures ◽  
Extensive Analysis ◽  
Ic50 Value ◽  
Penicillium Griseofulvum ◽  
The Absolute ◽  
New Compounds

Four new (penigrisacids A–D, 1–4) and one known (5) carotane sesquiterpenoids were isolated from the deep-sea-derived fungus Penicillium griseofulvum, along with four known compounds (6–9). The planar structures and relative configurations of the new compounds were determined by extensive analysis of the NMR and HRESIMS data. The absolute configurations were established by comparison of the experimental and calculated ECD (electronic circular dichroism) spectra or OR (optical rotation) value. Compound 9 exhibited potent anti-food allergic activity with IC50 value of 28.7 μM, while 4 showed weak cytotoxicity against ECA-109 tumor cells (IC50 = 28.7 μM).

scholarly journals Anti-Food Allergic Compounds from Penicillium griseofulvum MCCC 3A00225, a Deep-Sea-Derived Fungus

Marine Drugs ◽  
2021 ◽  
Vol 19 (4) ◽  
pp. 224
Author(s):  
Cui-Ping Xing ◽  
Dan Chen ◽  
Chun-Lan Xie ◽  
Qingmei Liu ◽  
Tian-Hua Zhong ◽  
...  
Keyword(s):  
Deep Sea ◽  
Spectroscopic Data ◽  
Positive Control ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ic50 Value ◽  
Penicillium Griseofulvum ◽  
New Compounds ◽  
Basophilic Leukemia

Ten new (1–10) and 26 known (11–36) compounds were isolated from Penicillium griseofulvum MCCC 3A00225, a deep sea-derived fungus. The structures of the new compounds were determined by detailed analysis of the NMR and HRESIMS spectroscopic data. The absolute configurations were established by X-ray crystallography, Marfey’s method, and the ICD method. All isolates were tested for in vitro anti-food allergic bioactivities in immunoglobulin (Ig) E-mediated rat basophilic leukemia (RBL)-2H3 cells. Compound 13 significantly decreased the degranulation release with an IC50 value of 60.3 μM, compared to that of 91.6 μM of the positive control, loratadine.

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.

scholarly journals New Chromones from a Marine-Derived Fungus, Arthrinium sp., and Their Biological Activity

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1982 ◽  
Author(s):  
Jie Bao ◽  
Fei He ◽  
Jin-Hai Yu ◽  
Huijuan Zhai ◽  
Zhi-Qiang Cheng ◽  
...  
Keyword(s):  
Biological Activity ◽  
Deep Sea ◽  
Spectroscopic Data ◽  
Radical Scavenging ◽  
Antioxidant Property ◽  
Electronic Circular Dichroism ◽  
Chromone Derivatives ◽  
Ic50 Values ◽  
Ester Method ◽  
The Absolute

Five new chromone derivatives, arthones A–E (1–5), together with eight known biogenetically related cometabolites (6–13), were isolated from a deep-sea-derived fungus Arthrinium sp. UJNMF0008. Their structures were assigned by detailed analyses of spectroscopic data, while the absolute configurations of 1 and 5 were established by electronic circular dichroism (ECD) calculations and that of 2 was determined by modified Mosher ester method. Compounds 3 and 8 exhibited potent antioxidant property with DPPH and ABTS radical scavenging activities, with IC50 values ranging from 16.9 to 18.7 μM. Meanwhile, no compounds indicated obvious bioactivity in our antimicrobial and anti-inflammatory assays at 50.0 μM.

scholarly journals Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 164 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wan Liu ◽  
Runzhu Fan ◽  
Shouye Han ◽  
Yuanli Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Chemical Study ◽  
Positive Control ◽  
Hydroxyl Group ◽  
Etoac Extract ◽  
The Third ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time

A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

Isoprenylated Phenolic Compounds from Morus macroura as Potent Tyrosinase Inhibitors

Planta Medica ◽  
2017 ◽  
Vol 84 (05) ◽  
pp. 336-343 ◽  
Author(s):  
Yifan Wang ◽  
Liangjin Xu ◽  
Wen Gao ◽  
Lixin Niu ◽  
Chunyue Huang ◽  
...  
Keyword(s):  
Kojic Acid ◽  
Positive Control ◽  
Diels Alder ◽  
Extensive Analysis ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Tyrosinase Inhibitors ◽  
Inhibitory Activities ◽  
New Compounds

AbstractThree new Diels-Alder adducts, macrourins E – G (1–3), one new 2-arylbenzofuran, macrourin H (4), and eight known Diels-Alder adducts (5–12) were isolated from Morus macroura. Their structures were elucidated through extensive analysis of spectroscopic data. The 1H NMR and ECD trends in the determination of the configurations of these Diels-Alder adducts were summarized. The tyrosinase inhibitory activities of all compounds isolated were evaluated, and the new compounds (1–4) as well as the eight known compounds (5–12) were found to be potent with IC50 values ranging from 0.39 to 4.54 µM. Among them, 1 showed the best tyrosinase inhibitory activity with an IC50 value of 0.39 µM, approximately 50 times stronger than the positive control, kojic acid.

scholarly journals Novel Bisabolane Sesquiterpenes from the Marine-derived Fungus Verticillium tenerum

2010 ◽  
Vol 5 (4) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Celso Almeida ◽  
Somaia Elsaedi ◽  
Stefan Kehraus ◽  
Gabriele M. König
Keyword(s):  
Absolute Configuration ◽  
Cd Spectroscopy ◽  
Mass Spectrometric ◽  
Planar Structures ◽  
The Absolute ◽  
New Compounds ◽  
Mass Spectrometric Techniques

Chemical investigations of the marine-derived fungus Verticillium tenerum yielded two new hydroxylated bisabolane-type sesquiterpenes verticinol A (1) and B (2). The planar structures of the new compounds were elucidated by employing spectroscopic (NMR, UV, and IR) and mass spectrometric techniques. The absolute configuration of the cyclohexenyl moiety was deduced by a combination of CD spectroscopy and NOESY measurements.

New Phenolic Glycosides and Lignans from the Roots of Lilium dauricum

Planta Medica ◽  
2021 ◽  
Author(s):  
Xiao Xia ◽  
Jiao Zhang ◽  
Xiao-Jiang Wang ◽  
Yan Lu ◽  
Dao-Feng Chen
Keyword(s):  
Inhibitory Activity ◽  
Phenolic Glycosides ◽  
Anticomplementary Activity ◽  
Chemical Methods ◽  
Electronic Circular Dichroism ◽  
Circular Dichroism Analysis ◽  
Ic50 Values ◽  
The Absolute ◽  
New Compounds ◽  
Circular Dichroïsm

AbstractThree new phenolic glycosides, carvacrol-2-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (1), 1-methyl-3-isopropylphenol-4-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (2), p-methoxythymol-5-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (3), and a pair of new 8-O-4′ neolignan enantiomers (5a/5b), together with 26 known compounds (4, 6 – 30) were isolated from the roots of Lilium dauricum. The structures of the new compounds were elucidated based on extensive spectroscopic and chemical methods, and the absolute configurations of 5a and 5b were established by electronic circular dichroism analysis. Nine compounds (1, 3, 4, 8, 9, 17, 25, 29, and 30) exhibited potent α-glucosidase inhibitory activity with IC50 values ranging from 73.4 µM to 988.2 µM. Besides, compound 19 displayed strong anticomplementary activity (CH50: 71.6 µM).

scholarly journals Sesquiterpenoids from Artemisia vestita and Their Antifeedant and Antifungal Activities

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3671
Author(s):  
Ying-Hui Ding ◽  
Hui-Ting Wang ◽  
Sha Shi ◽  
Yao Meng ◽  
Jin-Chao Feng ◽  
...  
Keyword(s):  
Plutella Xylostella ◽  
Spectroscopic Data ◽  
Pathogenic Fungi ◽  
Plant Pathogenic Fungi ◽  
Electronic Circular Dichroism ◽  
Antifungal Activities ◽  
Data Analyses ◽  
The Absolute ◽  
New Compounds ◽  
Third Instar Larvae

Four new sesquiterpenoids, named artemivestinolide D–G (1–4) and three known sesquiterpenoids (5–7), were isolated from Artemisia vestita. The structures of these new compounds were determined based on extensive spectroscopic data analyses. Furthermore, the electronic circular dichroism data determined the absolute configurations of the new compounds. The antifeedant and antifungal activities of the isolates were evaluated against third-instar larvae of Plutella xylostella and three plant pathogenic fungi. Compounds 1–7 showed moderate antifeedant activities and compounds 1–4 and 6–7 exhibited antifungal activities.

scholarly journals Natural Products Analysis  of South Pacific Marine  Sponges

2021 ◽  
Author(s):  
◽  
Taitusi Taufa
Keyword(s):  
Natural Products ◽  
New Zealand ◽  
Secondary Metabolites ◽  
Optical Rotation ◽  
Screening Method ◽  
Marine Sponges ◽  
Ic50 Value ◽  
Products Analysis ◽  
New Compounds ◽  
Cacospongia Mycofijiensis

<p>This thesis describes the isolation and structure elucidation of 15 new secondary metabolites from Tongan and New Zealand marine sponges. A total of 18 sponge specimens were subjected to an NMR-based screening method, of which four were analysed in detail. Examination of a two-sponge association, Stelletta crater and Desmacella dendyi from New Zealand, resulted in the isolation of two new 4-methylenesterols, craterols A (94) and B (95). To the best of the author’s knowledge, compounds 94 and 95 represent the first secondary metabolites to be reported from either species. Both 94 and 95 possess a double bond between C-5 and C-6, a feature that is unprecedented in this subgroup of marine natural products. An investigation of a Tongan sponge Zyzzya fuliginosa afforded two new pyrroloquinoline alkaloids, 6-bromodamirone B (182) and makaluvamine W (183). Makaluvamine W (183) contains an oxazole moiety, which is uncommon in this group of natural products. Both 182 and 183 lacked activity against the human promyelocytic leukemia cells (HL-60). Five new compounds were isolated from a Tongan sponge of the genus Leucetta, including two glycerol lipids (238 and 239), three glycerol ethers (244–246) and an imidazole alkaloid (243). Naamidine K (243) is a new addition to the naamidine family, while the glycerol metabolites are non-imidazole alkaloid additions to the group of compounds reported from this genus. A spectroscopic investigation into the Tongan sponge Cacospongia mycofijiensis yielded four new zampanolide analogues (282–285) and a new oxygenated sesquiterpene, isodictyodendrillin A (280). The isolation of the zampanolide analogues gives insight into the structure-activity relationship (SAR) in this family of compounds. Zampanolides B–D (282–284) displayed potent antiproliferative activity towards HL-60 cell lines in the low nanomolar range (3–5 nM), while zampanolide E (285) was significantly less potent with an IC50 value of 306 nM. In addition, the re-isolation of dactylolide (281) and zampanolide A (278) from this sponge, established a firm conclusion regarding the controversial configuration of dactylolide (281), which possesses the same absolute configuration as (–)-zampanolide A (278) and has a levorotatory optical rotation.</p>

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