scholarly journals Asperienes A–D, Bioactive Sesquiterpenes from the Marine-Derived Fungus Aspergillus flavus

Marine Drugs ◽  
2019 ◽  
Vol 17 (10) ◽  
pp. 550 ◽  
Author(s):  
Yun-Feng Liu ◽  
Yu-Fei Yue ◽  
Li-Xi Feng ◽  
Hua-Jie Zhu ◽  
Fei Cao
Keyword(s):  
Cell Lines ◽  
Aspergillus Flavus ◽  
Solid Medium ◽  
Biological Activities ◽  
Antitumor Agent ◽  
Minor Components ◽  
Electronic Circular Dichroism ◽  
The Future ◽  
Ic50 Values ◽  
First Time

Marine-derived fungi of the genera Aspergillus could produce novel compounds with significant bioactivities. Among these fungi, the strain Aspergillus flavus is notorious for its mutagenic mycotoxins production. However, some minor components with certain toxicities from A. flavus have not been specifically surveyed and might have potent biological activities. Our investigation of the marine-derived fungus Aspergillus flavus CF13-11 cultured in solid medium led to the isolation of four C-6′/C-7′ epimeric drimane sesquiterpene esters, asperienes A–D (1–4). Their absolute configurations were assigned by electronic circular dichroism (ECD) and Snatzke’s methods. This is the first time that two pairs of C-6′/C-7′ epimeric drimane sesquiterpene esters have successfully been separated. Aperienes A–D (1–4) displayed potent bioactivities towards four cell lines with the IC50 values ranging from 1.4 to 8.3 μM. Interestingly, compounds 1 and 4 exhibited lower toxicities than 2 and 3 toward normal GES-1 cells, indicating more potential for development as an antitumor agent in the future.

Phytochemical Constituents of Annona reticulata and their Cytotoxic Activity

2020 ◽  
Vol 17 (3) ◽  
pp. 206-210
Author(s):  
Ty Viet Pham ◽  
Thang Quoc Le ◽  
Anh Tuan Le ◽  
Hung Quoc Vo ◽  
Duc Viet Ho
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Structural Determination ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
Phytochemical Constituents ◽  
First Time ◽  
Annona Reticulata

A phytochemical investigation of the leaves of Annona reticulata led to the isolation and structural determination of β-sitosterol (1), ent-pimara-8(14),15-dien-19-oic acid (2), ent-pimara- 8(14),15-dien-19-ol (3), quercetin (4), quercetin 3-O-α-L-arabinopyranoside (5), and a mixture of quercetin 3-O-β-D-galactopyranoside (6a) and quercetin 3-O-β-D-glucopyranoside (6b). Of these, compounds 2 and 3 were isolated from the genus Annona for the first time. Compound 3 showed strong cytotoxicity against SK-LU-1 and SW626 cell lines with IC50 values of 17.64 ± 1.07 and 19.79 ± 1.41 μg mL-1, respectively.

Naphthoquinone-based hydrazone hybrids: synthesis and potent activity against cancer cell lines

2020 ◽  
Vol 16 ◽  
Author(s):  
Délis Galvão Guimarães ◽  
Arlan de Assis Gonsalves ◽  
Larissa Araújo Rolim ◽  
Edigênia Cavalcante Araújo ◽  
Victória Laysna dos Anjos Santos ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Biological Activities ◽  
Supporting Electrolyte ◽  
Cancer Cell Lines ◽  
Molecular Structures ◽  
Cytotoxic Activities ◽  
Electrochemical Studies ◽  
Ic50 Values

Background: Natural naphthoquinones have shown diversified biological activities including antibacterial, antifungal, antimalarial, and cytotoxic activities. However, they are also compounds with acute cytotoxicity, immunotoxicity, carcinogenesis, and cardio- and hepatotoxicity, then the modification at their redox center is an interesting strategy to overcome such harmful activity. Objective: In this study, four novel semisynthetic hydrazones, derived from the isomers α- and β-lapachones (α and β, respectively) and coupled with the drugs hydralazine (HDZ) and isoniazid (ACIL), were prepared, evaluated by electrochemical methods and assayed for anticancer activity. Method: The semisynthetic hydrazones were obtained and had their molecular structures established by NMR, IR, and MS. Anticancer activity was evaluated by cell viability determined by reduction of 3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide (MTT). The electrochemical studies, mainly cyclic voltammetry, were performed, in aprotic and protic media. Result: The study showed that the compounds 2, 3, and 4 were active against at least one of the cancer cell lines evaluated, being compounds 3 and 4 the most cytotoxic. Toward HL-60 cells, compound 3 was 20x more active than β-lapachone, and 3x more cytotoxic than doxorubicin. Furthermore, 3 showed an SI value of 39.62 for HL-60 cells. Compound 4 was active against all cancer cells tested, with IC50 values in the range 2.90–12.40 μM. Electrochemical studies revealed a profile typical of self-protonation and reductive cleavage, dependent on the supporting electrolyte. Conclusion: These results therefore indicate that compounds 3 and 4 are strong candidates as prototypes of new antineoplastic drugs.

scholarly journals Biogenic Iodine and Iodine-Containing Metabolites

2006 ◽  
Vol 1 (2) ◽  
pp. 1934578X0600100 ◽  
Author(s):  
Valery M Dembitsky
Keyword(s):  
Marine Invertebrates ◽  
Biological Activities ◽  
Biological Significance ◽  
Covalent Bond ◽  
Minor Components ◽  
Marine Area ◽  
The Future ◽  
Comprehensive Survey ◽  
Living Organisms

This review is intended as a comprehensive survey of iodinated metabolites possessing carbon–iodine covalent bond, which have been obtained from living organisms. Generally thought to be minor components produced by many different organisms these interesting compounds now number more than 110. Many from isolated and identified iodine-containing metabolites showed high biological activities. Recent research, especially in the marine area, indicates this number will increase in the future. Sources of iodinated metabolites include microorganisms, algae, marine invertebrates, and some animals. Their origin and possible biological significance have also been discussed.

scholarly journals Labdane and Abietane Diterpenoids from Juniperus oblonga and Their Cytotoxic Activity

Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1561 ◽  
Author(s):  
Qiao ◽  
Khutsishvili ◽  
Alizade ◽  
Atha ◽  
Borris
Keyword(s):  
Cell Lines ◽  
Human Tumor ◽  
2D Nmr ◽  
Human Tumor Cell Lines ◽  
Abietane Diterpenoids ◽  
Whole Plant ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
First Time ◽  
Mcf 7

A phytochemical investigation of the whole plant of Juniperus oblonga led to the isolationof one previously undescribed labdane diterpenoid, (4R,5S,9S,10R)‐13‐des‐ethyl‐13‐oxolabda‐8(17),11E‐dien‐19‐oic acid (1), together with nine known diterpenoids (2–3, 6–12), two lignans (4, 5),and a coumarin (13). The structures of all the compounds were elucidated on the basis ofspectrometric data, primarily one‐dimensional (1D)‐ and two‐dimensional (2D)‐NMR and massspectrometry. Electronic circular dichroism (ECD) calculations determined the absoluteconfiguration of 1. In addition, the isolated compounds were evaluated for their cytotoxic activityagainst three human tumor cell lines (HepG2, MCF‐7, and HeLa). 6,12‐Dihydroxyabieta‐5,8,11,13‐tetraen‐7‐one (6) showed moderate cytotoxicity against all three cell lines with IC50 values rangingfrom 24.41 μM to 58.39 μM and trilobinone (10) showed weaker activity with IC50 values rangingfrom 56.93 μM to 79.98 μM. None of the isolated diterpenoids have been previously reported fromJuniperus oblonga, and five compounds are here reported from the genus Juniperus for the first time.

scholarly journals Bioactivity-Guided Purification of Novel Herbal Antioxidant and Anti-NO Compounds from Euonymus laxiflorus Champ.

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 120 ◽  
Author(s):  
Van Nguyen ◽  
San-Lang Wang ◽  
Anh Nguyen ◽  
Zhi-Hu Lin ◽  
Chien Doan ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Natural Products ◽  
Biological Activities ◽  
The Novel ◽  
Health Food ◽  
Ic50 Values ◽  
Comparable Activity ◽  
New Compounds ◽  
First Time ◽  
Antidiabetic Effects

Euonymus laxiflorus Champ., a medicinal herb collected in Vietnam, has been reported to show several potent bioactivities, including anti-NO, enzyme inhibition, hypoglycemic and antidiabetic effects. Recently, the antioxidant activity of Euonymus laxiflorus Champ. trunk bark (ELCTB) has also been reported. However, the active antioxidant and anti-NO constituents existing in ELCTB have not been reported in the literature. The objective of this study was to purify the active antioxidants from ELCTB and investigate the anti-NO effect of the major constituents. Twenty-two phenolics isolated from ELCTB, including 12 compounds newly isolated in this study (1–12) and 10 constituents obtained from our previous work, were evaluated for their antioxidant activity. Of these, 12 compounds (4–6, 9, 13–15, 18–22) showed a potent antioxidant capacity (FRS50 = 7.8–58.11 µg/mL), in comparison to α-tocopherol (FRS50 = 23 µg/mL). In the anti-NO activity tests, Walterolactone A (1a) and B (1b) β-d-glucopyranoside (13) demonstrated the most effective and comparable activity to that of quercetin with max inhibition and IC50 values of 100%, 1.3 µg/mL, and 100%, 1.21 µg/mL, respectively. The crude extract and its major compounds showed no cytotoxicity on normal cells. Notably, three constituents (9, 11, and 12) were identified as new compounds, another three constituents, including 1, 7, and 8, were found to be new natural products, constituents 9 and 13 were determined to be new antioxidants, and compound 13 was reported to have novel potent anti-NO activity for the first time. The results of this study contribute to the enrichment of new natural products and compounds, as well as the novel biological activity of constituents isolated from Euonymus laxiflorus Champ. The current study also indicates ELCTB as a rich natural source of active phenolics. It is suggested that ELCTB could be developed as a health food with promising antioxidant and anti-NO effects, as well as other beneficial biological activities.

scholarly journals Four New ent-Kaurane Diterpene Glycosides from Isodon henryi

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2736 ◽  
Author(s):  
Liu ◽  
Zhang ◽  
Wu ◽  
Chen ◽  
Li ◽  
...  
Keyword(s):  
Cell Lines ◽  
Human Cancer ◽  
Spectroscopic Methods ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Aerial Parts ◽  
Ic50 Values ◽  
Hct 116 ◽  
Relationship Of ◽  
First Time

To obtain diterpene glycosides from an aqueous extract of the aerial parts of Isodon henryi and further investigate their cytotoxicities, in this study, a total of seven compounds were isolated, including six ent-kaurane diterpene glycosides (1–6) and one diterpene aglycon (7). Among the seven ent-kaurane diterpenes obtained, four were novel compounds, including ent-7,20-epoxy- kaur-16-en-1α,6β,7β,15β-tetrahydroxyl-11-O-β-d-glucopyranoside (1), ent-7,20-epoxy-kaur-16-en- 6β,7β,14β,15β-tetrahydroxyl-1-O-β-d-glucopyranoside (2), ent-7,20-epoxy-kaur-16-en-6β,7β,15β- trihydroxyl-1-O-β-d-glucopyranoside (3), and ent-7,20-epoxy-kaur-16-en-7β,11β,14α,15β-tetrahydr- oxyl-6-O-β-d-glucopyranoside (4), and three were isolated from this plant for the first time (5–7). Their structures were elucidated by utilizing spectroscopic methods and electronic circular dichroism analyses. Furthermore, the cytotoxicities of all seven compounds were investigated in four human cancer cell lines, including A2780, BGC-823, HCT-116, and HepG2. The IC50 values of these diterpenes ranged from 0.18 to 2.44 mM in the tested cell lines. In addition, the structure–cytotoxicity relationship of diterpene glycosides was also evaluated to study the effect of glycosylation on the cytotoxicity of diterpene compounds.

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 Development of Nimesulide Analogues as Dual Tubulin and HSP27 Inhibitor for Treating Female Cancers

2020 ◽  
Author(s):  
Laila Jarragh Alhadad ◽  
Fars Alanazi ◽  
Gamaleldin Harisa
Keyword(s):  
Breast Cancer ◽  
Ovarian Cancer ◽  
Cell Lines ◽  
Biological Activities ◽  
Critical Role ◽  
Biological Evaluation ◽  
Crystallographic Analysis ◽  
Skbr3 Cell ◽  
Chemical Structures ◽  
Ic50 Values

Tubulin and heat shock protein 27 (HSP27) are up-regulated in cancer cells, and play a critical role in cell division, and proliferation. Therefore, they are targets for discovery of anticancer therapy. The objective of this study is to design, characterize, and biologically evaluate the nimesulide analogues to combat female cancer such as ovarian cancer, and breast cancer. Herein, the nimesulide analogues are designed to target both tubulin and HSP27 functions. Ovarian cancer (SKOV3) and breast cancer (SKBR3) cell lines were used as surrogate models to test the nimesulide analogs biological activities using MTT assay. In the present study, four nimesulide analogues were designed, synthesized and the chemical structures were with the biological evaluation were studied. The synthesized agents were characterized by 1H-NMR, 13C-NMR, the molecular weight was confirmed using GC-MS technique, and melting point. Besides, the agent L4 structure was confirmed using X-ray crystallographic analysis. The present data revealed that nimesulide analogs have potent anticancer activity against SKOV3and SKBR3 cell lines. The IC50 values for both SKOV3 and SKBR3 cell lines treated with the agents showed a potent cell growth inhibition range of 0.23-2.02 µM and 0.50-3.73 µM respectively. In conclusion, the designed nimesulide analogues can target both tubulins, and HSP27 concurrently, and they are promising agents as future chemotherapy female cancers.

Antioxidant, cytotoxic activity and pharmacokinetic studies by SwissAdme, Molinspiration, Osiris and DFT of PhTAD-substituted dihydropyrrole derivatives

2021 ◽  
Vol 17 ◽  
Author(s):  
Arif Ayar ◽  
Masuk Aksahin ◽  
Seda Mesci ◽  
Burak Yazgan ◽  
Melek Gül ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Heterocyclic Compounds ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Molecular Structures ◽  
Biologically Active ◽  
Pharmacokinetic Studies ◽  
Ic50 Values ◽  
Mcf 7

Background: Pyrrole compounds having a heterocyclic structure are the most researched and biological activities such as antioxidant and anticancer. Objective: Herein is a first effort to study the significance of heterocyclic compounds to include pyrrole and triazolidine-3,5-dion moiety, on the pharmacokinetic, antioxidant activity and cytotoxic activity on MCF-7 and MCF-12A cell lines. Method: The molecular structures of compounds I-XIV were simulated by the theoretical B3LYP/DFT method. Pharmacokinetic studies of PhTAD-substituted heterocyclic compounds (I-XIV) were analyzed to show Lipinski's rules via in-silico methods of Swiss-ADME. The drug likeness calculations were carried out Molinspiration analyses. The some toxicity risk parameter can be quantified using Osiris. Antioxidant activities determined by DPPH, Fe+2 ions chelating and reducing. Cytotoxic activity measured by MTT and RTCA. Results: Compared with the DPPH activity, the metal chelating activity exhibited serious similar antioxidant effects by PhTAD substituted pyrrole compounds. The same compounds showed the highest activity among the two antioxidant activities. The IC50 values of the compounds are in the range of 12 and 290 µM in MCF-7 cell line. In the MTT and RTCA assays, All compounds showed cytotoxic activity, but about half of the fourteen compounds showed high cytotoxicity. IC50 values of the compounds are in the range of 5 and 54 µM for MTT and range of 1.5 and 44 µM for RTCA. Conclusion: Data of the antioxidant and cytotoxic activity of PhTAD-substituted dihydropyrrole-derived compounds in MCF-7 and MCF-12A cell lines confirmed that the compounds are a biologically active compound and is notable for anti-cancer researches.

scholarly journals New Hybrid Compounds Combining Fragments of Usnic Acid and Monoterpenoids for Effective Tyrosyl-DNA Phosphodiesterase 1 Inhibition

Biomolecules ◽  
2021 ◽  
Vol 11 (7) ◽  
pp. 973
Author(s):  
Nadezhda S. Dyrkheeva ◽  
Aleksandr S. Filimonov ◽  
Olga A. Luzina ◽  
Alexandra L. Zakharenko ◽  
Ekaterina S. Ilina ◽  
...  
Keyword(s):  
Cell Lines ◽  
Anticancer Agents ◽  
Biological Activities ◽  
Usnic Acid ◽  
Topoisomerase 1 ◽  
Binding Domains ◽  
Promising Therapeutic Target ◽  
Wide Range ◽  
Ic50 Values ◽  
Low Cytotoxicity

Usnic acid (UA) is a secondary metabolite of lichens that exhibits a wide range of biological activities. Previously, we found that UA derivatives are effective inhibitors of tyrosyl-DNA phosphodiesterase 1 (TDP1). It can remove covalent complex DNA-topoisomerase 1 (TOP1) stabilized by the TOP1 inhibitor topotecan, neutralizing the effect of the drugs. TDP1 removes damage at the 3′ end of DNA caused by other anticancer agents. Thus, TDP1 is a promising therapeutic target for the development of drug combinations with topotecan, as well as other drugs for cancer treatment. Ten new UA enamino derivatives with variation in the terpene fragment and substituent of the UA backbone were synthesized and tested as TDP1 inhibitors. Four compounds, 11a-d, had IC50 values in the 0.23–0.40 μM range. Molecular modelling showed that 11a-d, with relatively short aliphatic chains, fit to the important binding domains. The intrinsic cytotoxicity of 11a-d was tested on two human cell lines. The compounds had low cytotoxicity with CC50 ≥ 60 μM for both cell lines. 11a and 11c had high inhibition efficacy and low cytotoxicity, and they enhanced topotecan’s cytotoxicity in cancerous HeLa cells but reduced it in the non-cancerous HEK293A cells. This “protective” effect from topotecan on non-cancerous cells requires further investigation.

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