scholarly journals New Hydroxydecanoic Acid Derivatives Produced by an Dndophytic Yeast Aureobasidium pullulans AJF1 from Flowers of Aconitum carmichaeli

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4051
Author(s):  
Choi ◽  
Kim ◽  
Choi ◽  
Kang ◽  
Shim
Keyword(s):  
Secondary Metabolites ◽  
Aureobasidium Pullulans ◽  
Large Scale ◽  
Biologically Active ◽  
Cytotoxic Activities ◽  
Chemical Methods ◽  
Nmr Data ◽  
Aconitum Carmichaeli ◽  
Modified Mosher’S Method ◽  
Mcf 7

Endophytes have been recognized as a source for structurally novel and biologically active secondary metabolites. Among the host plants for endophytes, some medicinal plants that produce pharmaceuticals have been reported to carry endophytes, which could also produce bioactive secondary metabolites. In this study, the medicinal plant Aconitum carmichaeli was selected as a potential source for endophytes. An endophytic microorganism, Aureobasidium pullulans AJF1, harbored in the flower of Aconitum carmichaeli, was cultured on a large scale and extracted with an organic solvent. Extensive chemical investigation of the extracts resulted in isolation of three lipid type compounds (1–3), which were identified to be (3R,5R)-3,5-dihydroxydecanoic acid (1), (3R,5R)-3-(((3R,5R)-3,5-dihydroxydecanoyl)oxy)-5-hydroxydecanoic acid (2), and (3R,5R)-3-(((3R,5R)-5-(((3R,5R)-3,5-dihydroxydecanoyl)oxy)-3-hydroxydecanoyl)oxy)-5-hydroxydecanoic acid (3) by chemical methods in combination with spectral analysis. Compounds 2 and 3 had new structures. Absolute configurations of the isolated compounds (1–3) were established using modified Mosher’s method together with analysis of NMR data for their acetonide derivatives. All the isolates (1–3) were evaluated for antibiotic activities against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and their cytotoxicities against MCF-7 cancer cells. Unfortunately, they showed low antibiotic activities and cytotoxic activities.

scholarly journals Chemical constituents of the lichen Roccella sinensis growing in Binh Thuan province

2019 ◽  
Vol 2 (5) ◽  
pp. 63-67
Author(s):  
Huy Thuc Duong ◽  
Hao Xuan Bui
Keyword(s):  
Spectroscopic Analysis ◽  
Chemical Constituents ◽  
Human Lung Cancer ◽  
Cytotoxic Activities ◽  
Human Breast ◽  
Nmr Data ◽  
Liver Hepatocellular Carcinoma ◽  
First Time ◽  
Layer Chromatography ◽  
Mcf 7

The lichen Roccella sinensis has not been studied chemically. This research described the isolation and elucidation of compounds isolated from the lichen Roccella sinensis collected in Binh Thuan. Phytochemistry investigation of this lichen was carried out by using normal phase silica gel column chromatography and thin-layer chromatography. Six compounds was isolated. Their structures were established by extensively spectroscopic analysis as well as comparison with NMR data in the literatures. They are (+)-D-montagnetol (1), (+)-D-erythrin (2), lecanorin (3), 1-acetylerythritol (4), (E)-nostodione A (5), and 2,4-dihydroxyphthalide (6). This is the first time compounds 3 6 were found in the Roccella genus. Compounds 1, 2, and 6 were evaluated for their cytotoxic activities against HepG2 (liver hepatocellular carcinoma), NCI-H460 (human lung cancer), MCF-7 (human breast cancer), and HeLa (human epithelial cancer) and all of them showed no activity.

scholarly journals Biologically Active Metabolites from the Marine Sediment-Derived Fungus Aspergillus flocculosus

Marine Drugs ◽  
2019 ◽  
Vol 17 (10) ◽  
pp. 579 ◽  
Author(s):  
Anton Yurchenko ◽  
Phan Trinh ◽  
Elena Girich (Ivanets) ◽  
Olga Smetanina ◽  
Anton Rasin ◽  
...  
Keyword(s):  
Marine Sediment ◽  
Coupling Constants ◽  
Biologically Active ◽  
Human Breast ◽  
Active Metabolites ◽  
The Absolute ◽  
New Compounds ◽  
Biologically Active Metabolites ◽  
Modified Mosher’S Method ◽  
Mcf 7

Four new compounds were isolated from the Vietnamese marine sediment-derived fungus Aspergillus flocculosus, one aspyrone-related polyketide aspilactonol G (2), one meroterpenoid 12-epi-aspertetranone D (4), two drimane derivatives (7,9), together with five known metabolites (1,3,5,6,8,10). The structures of compounds 1–10 were established by NMR and MS techniques. The absolute stereoconfigurations of compounds 1 and 2 were determined by a modified Mosher’s method. The absolute configurations of compounds 4 and 7 were established by a combination of analysis of ROESY data and coupling constants as well as biogenetic considerations. Compounds 7 and 8 exhibited cytotoxic activity toward human prostate cancer 22Rv1, human breast cancer MCF-7, and murine neuroblastoma Neuro-2a cells.

scholarly journals Secondary Metabolites from the Liverwort Ptilidium pulcherrimum

2009 ◽  
Vol 4 (10) ◽  
pp. 1934578X0900401 ◽  
Author(s):  
Dong-Xiao Guo ◽  
Yu Du ◽  
Yan-Yan Wang ◽  
Ling-Mei Sun ◽  
Jian-Bo Qu ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Hela Cells ◽  
Aromatic Compounds ◽  
Chemical Methods ◽  
Pentacyclic Triterpenoids ◽  
Nmr Data ◽  
Extensive Analysis ◽  
Pc3 Cells

A new trinortriterpenoid, diospyrolide acetate (1) and a new diphenylmethane derivative, pulcherrimumin (12), together with ten known pentacyclic triterpenoids (2–11) and four aromatic compounds (13–16), were isolated from the liverwort Ptilidium pulcherrimum. Their structures were established on the basis of extensive analysis of NMR data and by chemical methods. The cytotoxicity of compounds 1–16 was evaluated against the PC3, MDA-MB-231, and Hela cells lines. Ursane triterpenoids 8–10 exhibited moderate cytotoxicity against PC3 cells with IC50 values ranging from 10.1 to 39.7 μM.

scholarly journals Serratia marcescens Quinoprotein Glucose Dehydrogenase Activity Mediates Medium Acidification and Inhibition of Prodigiosin Production by Glucose

2012 ◽  
Vol 78 (17) ◽  
pp. 6225-6235 ◽  
Author(s):  
James E. Fender ◽  
Cody M. Bender ◽  
Nicholas A. Stella ◽  
Roni M. Lahr ◽  
Eric J. Kalivoda ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Serratia Marcescens ◽  
Large Scale ◽  
Transcriptional Control ◽  
Glucose Dehydrogenase ◽  
Model Organism ◽  
Inhibitory Effect ◽  
Biologically Active ◽  
Scale Production ◽  
Content Type

ABSTRACTSerratia marcescensis a model organism for the study of secondary metabolites. The biologically active pigment prodigiosin (2-methyl-3-pentyl-6-methoxyprodiginine), like many other secondary metabolites, is inhibited by growth in glucose-rich medium. Whereas previous studies indicated that this inhibitory effect was pH dependent and did not require cyclic AMP (cAMP), there is no information on the genes involved in mediating this phenomenon. Here we used transposon mutagenesis to identify genes involved in the inhibition of prodigiosin by glucose. Multiple genetic loci involved in quinoprotein glucose dehydrogenase (GDH) activity were found to be required for glucose inhibition of prodigiosin production, including pyrroloquinoline quinone and ubiquinone biosynthetic genes. Upon assessing whether the enzymatic products of GDH activity were involved in the inhibitory effect, we observed thatd-glucono-1,5-lactone andd-gluconic acid, but notd-gluconate, were able to inhibit prodigiosin production. These data support a model in which the oxidation ofd-glucose by quinoprotein GDH initiates a reduction in pH that inhibits prodigiosin production through transcriptional control of the prodigiosin biosynthetic operon, providing new insight into the genetic pathways that control prodigiosin production. Strains generated in this report may be useful in large-scale production of secondary metabolites.

scholarly journals Structurally Diverse Polycyclic Salicylaldehyde Derivative Enantiomers from a Marine-Derived Fungus Eurotium sp. SCSIO F452

Marine Drugs ◽  
2021 ◽  
Vol 19 (10) ◽  
pp. 543
Author(s):  
Wei-Mao Zhong ◽  
Xiao-Yi Wei ◽  
Yu-Chan Chen ◽  
Qi Zeng ◽  
Jun-Feng Wang ◽  
...  
Keyword(s):  
A549 Cell ◽  
13C Nmr ◽  
Large Scale ◽  
Chemical Constituents ◽  
Chemical Diversity ◽  
Cytotoxic Activities ◽  
X Ray Diffraction ◽  
X Ray ◽  
Spectroscopic Analyses ◽  
Mcf 7

To enlarge the chemical diversity of Eurotium sp. SCSIO F452, a talented marine-derived fungus, we further investigated its chemical constituents from a large-scale fermentation with modified culture. Four pairs of new salicylaldehyde derivative enantiomers, euroticins F-I (1–4), as well as a known one eurotirumin (5) were isolated and characterized. Compound 1 features an unprecedented constructed 6/6/6/5 tetracyclic structures, while 2 and 3 represent two new types of 6/6/5 scaffolds. Their structures were established by comprehensive spectroscopic analyses, X-ray diffraction, 13C NMR, and electronic circular dichroism calculations. Selected compounds showed significant inhibitory activity against α-glucosidase and moderate cytotoxic activities against SF-268, MCF-7, HepG2, and A549 cell lines.

scholarly journals Sesquiterpene Quinones and Diterpenes from Smenospongia cerebriformis and Their Cytotoxic Activity

2017 ◽  
Vol 12 (4) ◽  
pp. 1934578X1701200
Author(s):  
Le Thi Huyen ◽  
Dan Thuy Hang ◽  
Nguyen Xuan Nhiem ◽  
Bui Huu Tai ◽  
Hoang Le Tuan Anh ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Nmr Data ◽  
Mcf 7

Using various chromatographic methods, one new sesquiterpene quinone named smenohaimien F (1) and five known, neodactyloquinone (2), dactyloquinone C (3), dactyloquinone D (4), isoamijiol (5), and amijiol (6), were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis, HR-ESI-MS, and by comparing with the NMR data reported in the literature. The cytotoxic activities of the all compounds were evaluated on five human cancer cell lines, LU-1, HL-60, SK-Mel-2, HepG-2, and MCF-7. Compound 4 was found to exhibit significant cytotoxic activities on all tested human cancer cell lines with IC50 values ranging from 0.7 to 1.6 μg/mL.

scholarly journals Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

2015 ◽  
Vol 11 ◽  
pp. 2334-2342 ◽  
Author(s):  
Qun Göthel ◽  
Thanchanok Sirirak ◽  
Matthias Köck
Keyword(s):  
Data Analysis ◽  
Cell Lines ◽  
Nmr Assignment ◽  
Cytotoxic Activities ◽  
Nmr Data ◽  
The Caribbean ◽  
Mcf 7 ◽  
C Nmr

Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1), aplysinin A (2), and aplysinin B (3), together with 15 known compounds (4–18) were isolated from the sponge Aplysina lacunosa collected from Stirrup Cay, Bahamas. The structures of the isolated compounds were identified on the basis of MS and NMR data analysis. The 13C NMR assignment of spirocyclohexadienylisoxazoline moieties of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild to moderate cytotoxic activities against KB-31 and FS4-LTM cell lines. Only aplysinin A (2) exhibited cytotoxicity against MCF-7 cells.

scholarly journals Bioactivity Screening and Identification of Secondary Metabolites from Fungal Endophytes of Carica papaya L. Leaves

2021 ◽  
Vol 20 (4) ◽  
pp. 217
Author(s):  
Israt Farha Lini ◽  
Rabita Zinnurine ◽  
Md. Habibur Rahman ◽  
Mst. Nadira Begum ◽  
Farhana Afroz ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Endophytic Fungi ◽  
Large Scale ◽  
Carica Papaya ◽  
Fungal Endophytes ◽  
Diffusion Method ◽  
Cytotoxic Activities ◽  
Alternariol Monomethyl Ether ◽  
Chemical Screening

<strong>Objectives:</strong> This work describes the chemical and <em>in-vitro</em> bioactivity studies on endophytic fungi derived from the leaves of <em>Carica papaya</em> L. <strong>Methods:</strong> Column Chromatography was employed for isolation of fungal metabolites. Nuclear Magnetic Resonance (NMR) spectral data was utilized to elucidate the structure of the isolated compounds and physicochemical properties of them were also examined. As a part of<em> in-vitro</em> bioactivity screening disc diffusion method, 1, 1-diphenyl-2- picryl-hydrazyl (DPPH) scavenging assay and brine shrimp lethality bioassay were conducted to evaluate antimicrobial, antioxidant and cytotoxic activities, respectively.<strong> Results:</strong> A total of four fungal isolates were identified as endophytic fungi and purified from the young leaves of <em>Carica papaya</em>. These fungi, encoded as CPLE-1, CPLE-2, CPLE-3 and CPLE-4, were identified up to the genus level on the basis of their macroscopic and microscopic characteristics as <em>Colletotrichum</em> sp., <em>Carvularia</em> sp., and next two as <em>Alternaria</em> sp., respectively. Chemical profiling and preliminary bioactivity screening of the fungal endophytes signified strain CPLE-3 with highest potentiality to produce bioactive compounds which directs its large scale cultivation. Ergosterol and Alternariol monomethyl ether were isolated from the ethyl acetate extract of the fungus, CPLE-3. <strong>Conclusion:</strong> Bioactivity and chemical screening of the endophytic fungal extracts of <em>Carica papaya</em> leaf along with the isolation of fungal secondary metabolites suggested these endophytic fungi to be possible source of bioactive leads for developing new and improved medicines.

scholarly journals Rhinoclactones A-E, Resorcylic Acid Analogs from Desert Plant Endophytic Fungus Rhinocladiella similis

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1405 ◽  
Author(s):  
Luying Li ◽  
Xiaoyan Zhang ◽  
Xiangmei Tan ◽  
Bingda Sun ◽  
Bin Wu ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Cytotoxic Activities ◽  
Desert Plant ◽  
Ionization Mass ◽  
X Ray Diffraction ◽  
Nmr Data ◽  
The Common ◽  
Resorcylic Acid Lactones ◽  
New Compounds ◽  
Modified Mosher’S Method

Seven resorcylic acid lactones (RALs) including five new analog rhinoclactones, A–E (1, 2, 4–6), were isolated from an endophytic fungus Rhinocladiella similis in the plant Agriophyllum squarrosum collected from the Tengger Desert of the Ningxia Province, China. The structures of these new compounds were determined by HR-ESI-MS (High Resolution Electrospray Ionization Mass Spectrometry), NMR data, modified Mosher’s method, and X-ray diffraction experiments. All compounds isolated from this fungus possessed the 16-OMe/14-OH, not the common 16-OH/14-OH or 16-OH/14-OMe groups on the aromatic ring, which are rarely found in nature. Compound 7 displayed cytotoxic activities against HCT116 and HeLa cancer cell lines. The possible biosynthesis of 1–7 is suggested, and the potential ecological roles of these fungal secondary metabolites is discussed.

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