Rubesanolides F and G: Two Novel Lactone-Type Norditerpenoids from Isodon rubescens

A phytochemical investigation of the leaves of the medicinal plant Isodon rubescens led to the isolation of the two new degraded abietane lactone diterpenoids rubesanolides F (1) and G (2). Their structures were elucidated based on the analyses of the HRESIMS and 1D/2D NMR spectral data, and their absolute configurations were determined by ECD spectrum calculations and X-ray single crystal diffraction methods. Compounds 1 and 2, with a unique γ-lactone subgroup between C-8 and C-20, were found to form a carbonyl carbon at C-13 by removal of the isopropyl group in an abietane diterpene skeleton. Rubesanolide G (2) is a rare case of abietane that possesses a cis-fused configuration between rings B and C. The two isolates were evaluated for their biological activities against two cancer cell lines (A549 and HL60), three fungal strains (Candida alba, Aspergillus niger and Rhizopus nigricans) and three bacterial strains (Escherichia coli, Staphylococcus aureus and Bacillus subtilis).

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Cyclopeptide Derivatives from the Sponge-Derived Fungus Acremonium persicinum F10

Marine Drugs ◽

10.3390/md19100537 ◽

2021 ◽

Vol 19 (10) ◽

pp. 537

Author(s):

Yingxin Li ◽

Zhiyong Li

Keyword(s):

Amino Acids ◽

Aspergillus Niger ◽

Diffraction Analysis ◽

2D Nmr ◽

Ferric Ions ◽

Single Crystal Diffraction ◽

X Ray ◽

Planar Structures ◽

Anti Fungal

Cyclopeptides usually play a pivotal role, either in the viability or virulence of fungi. Two types of cyclopeptides, six new hydroxamate siderophore cyclohexapeptides (1–6), including acremonpeptides E and F, and their complexes with aluminum and ferric ions; one new cyclic pentapeptolide, aselacin D (9); together with a known compound, aselacin C (10), were isolated and characterized from the sponge-derived fungus Acremonium persicinum F10. In addition, two new siderophore analogues chelating gallium ions (Ga3+), Ga (Ⅲ)-acremonpeptide E (7) and Ga (Ⅲ)-acremonpeptide F (8), using isolated acremonpeptides E and F, were prepared. The planar structures of 1–10 were elucidated by HRESIMS and (1D and 2D) NMR. The absolute configurations of amino acids were determined by means of the advanced Marfey’s method and X-ray single-crystal diffraction analysis. X-ray fluorescence (XRF) spectrometer was performed to disclose the elements of compound 1, indicating the existence of aluminum (Al). Al (Ⅲ)-acremonpeptides E (1), Ga (Ⅲ)-acremonpeptides E (5), Al (Ⅲ)-acremonpeptide F (7), and Ga (Ⅲ)-acremonpeptide F (8) displayed high in vitro anti-fungal activities, which are comparable to amphotericin B, against Aspergillus fumigatus and Aspergillus niger.

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Phytochemical investigation of the antisalmonellal effect of Cyperus sphacelatus Rottb. (Cyperaceae)

Current Chinese Science ◽

10.2174/2210298101666210302105522 ◽

2021 ◽

Vol 01 ◽

Author(s):

Napoleon A. Mfonku ◽

Gabriel T. Kamsu ◽

Norbert Kodjio ◽

Jie Ren ◽

James A. Mbah ◽

...

Keyword(s):

Typhoid Fever ◽

Antimicrobial Agents ◽

Methylene Chloride ◽

2D Nmr ◽

Sub Saharan Africa ◽

Resistant Isolate ◽

Bacterial Strains ◽

Phytochemical Investigation ◽

Methylene Chloride Extract ◽

Sub Saharan

Background: Typhoid fever is a major health burden in Sub-Saharan Africa. Conventional anti-typhoid drugs are becoming more and more unavailable to most patients in Africa due to the increased costs and emerging drug resistance. Therefore, there is a need for discovery of new antimicrobial agents to combat typhoid fever. Objective: This work aimed to investigate the bioactive components in Cyperus sphacelatus Rottb. (Cyperaceae) and test the antisalmonellal activity of the isolated compounds. Methods: Compound purification was done through column chromatography. Structure elucidation was accomplished based on the 1D and 2D NMR, IR and mass spectra. The biological assay was done using five bacterial strains, including Salmonella enterica subsp. enterica sérovars Typhi ATCC 6539 (STS), S. enterica subsp. enterica sérovars Typhi (ST), S. enteritidis (STE), S. enterica subsp. enterica sérovars Typhimurim (STM), and a resistant isolate of S. enterica subsp. enterica sérovars Typhi (ST566). Results: Three natural products were isolated from the methylene chloride extract of the rhizomes of C. sphacelatus, including a new furanoquinone, scabequinon-6(14)-ene (1) and two known compounds, cyperotundone (2) and vanillin (3). Compound 1 showed moderate antisalmonellal activity, with a minimal inhibitory concentration (MIC) of 32 µg/mL against STM and STS. The best inhibitory result was obtained with compound 2 on STM with a MIC of 8 µg/mL. Compound 2 also gave the best minimum bactericidal concentration (MBC) of 32 µg/mL on the STM strain. Conclusion: Discovery of the three antisalmonellal compounds from C. sphacelatus supports the addition of this plant to typhoid fever preparations.

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Evaluation of Biological Activities of Chemically Synthesized Silver Nanoparticles

Journal of Nanomaterials ◽

10.1155/2015/789178 ◽

2015 ◽

Vol 2015 ◽

pp. 1-7 ◽

Cited By ~ 6

Author(s):

Ashraf A. Mostafa ◽

Shaban R. M. Sayed ◽

Essam N. Solkamy ◽

Mujeeb Khan ◽

Mohammed Rafi Shaik ◽

...

Keyword(s):

Silver Nanoparticles ◽

Biological Activities ◽

Inhibition Zone ◽

Salmonella Typhi ◽

Bacterial Strains ◽

X Ray ◽

Transmission Electron ◽

Antiseptic Agent ◽

Synthesized Materials ◽

Strong Antimicrobial Activity

Silver nanoparticles were synthesized by the earlier reported methods. The synthesized nanoparticles were characterized using ultraviolet-visible spectrophotometry (UV/Vis), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDX), and X-ray powder diffraction (XRD). The synthesized materials were also evaluated for their antibacterial activity against Gram positive and Gram negative bacterial strains. TEM micrograph showed the spherical morphology of AgNPs with size range of 40–60 nm.The synthesized nanoparticles showed a strong antimicrobial activity and their effect depends upon bacterial strain as AgNPs exhibited greater inhibition zone forPseudomonas aeruginosa(19.1 mm) followed byStaphylococcus aureus(14.8 mm) andS. pyogenes(13.6 mm) while the least activity was observed forSalmonella typhi(12.5 mm) at concentration of 5 µg/disc. The minimum inhibitory concentration (MIC) of AgNPs againstS. aureuswas 2.5 µg/disc and less than 2.5 µg/disc forP. aeruginosa. These results suggested that AgNPs can be used as an effective antiseptic agent for infectious control in medical field.

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Tryptanthrin Sulfonate: Crystal Structure, Cytotoxicity and DNA Binding Studies

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.554-556.1694 ◽

2012 ◽

Vol 554-556 ◽

pp. 1694-1699

Author(s):

Li Fang Zhao ◽

Yan Cheng Liu ◽

Qi Pin Qin ◽

Wen Zu Ya ◽

Hai Chun Duan

Keyword(s):

Water Solubility ◽

Biological Activities ◽

Uv Spectroscopy ◽

Binding Mode ◽

Intrinsic Binding Constant ◽

Binding Studies ◽

Single Crystal Diffraction ◽

X Ray ◽

Calf Thymus ◽

Dna Binding Studies

Tryptanthrin (TPT), which is an indoloquinazoline alkaloid with multiple biological activities, was studied on its sulfonation in order to increase its water solubility. An 8-substituted tryptanthrin sulfonate (TPTS) was synthesized and structurally characterized by IR, 1H-NMR, ESI-MS, as well as X-ray single crystal diffraction analysis. The interactional mechanism of TPTS with calf thymus DNA (ctDNA) was further studied by UV spectroscopy and DNA viscosity experiment. The addition of ctDNA into the TPTS solution induced moderate hypochromicity on its electronic absorption spectrum, by which an intrinsic binding constant of 1.10×104 M-1 was achieved. While addition of TPTS caused significant increasement on the viscosity of ctDNA solution. The results suggest that TPTS interacts with ctDNA mainly by intercalative binding mode.

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Isolation of phytoconstituents and evaluation of biological potentials of Berberis hispanica from Algeria

Bangladesh Journal of Pharmacology ◽

10.3329/bjp.v13i2.36133 ◽

2018 ◽

Vol 13 (2) ◽

pp. 179 ◽

Cited By ~ 2

Author(s):

Redouane Lemoui ◽

Samira Benyahia ◽

Labib Noman ◽

Ilham Bencherchar ◽

Feyza Oke-Altuntas ◽

...

Keyword(s):

Biological Activities ◽

Radical Scavenging Activity ◽

Video Clip ◽

Radical Scavenging ◽

2D Nmr ◽

Butylated Hydroxytoluene ◽

Klebsiella Pneumonia ◽

Bacterial Strains ◽

Remarkable Effect ◽

Berberis Hispanica

The aim of this study was to isolate the phytoconstituents and evaluate the biological activities of Berberis hispanica. Three phenolic compounds (tamarixetin, caffeic acid and rutin) were isolated from B. hispanica. The structures of the pure compounds were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR, and HPLC-TOF/MS. In addition, antimicrobial, anti-oxidant and anti-proliferative effects of the extracts, some fractions and isolated compounds were evaluated. The extracts of B. hispanica were evaluated against six bacterial strains and exhibited the highest activity against Klebsiella pneumonia (15 mm at 100 mg/mL). Fraction T36 (IC50<5 μg/mL) from the n-butanol extract displayed higher radical scavenging activity than butylated hydroxytoluene. The isolated compounds were evaluated for their antiproliferative effects against human cervical adenocarcinoma (HeLa) cell line by real time cell analyzer assay and tamarixetin exhibited the remarkable effect (IC50<50 μg/mL) on HeLa cells. This study supports the documented medicinal effects of B. hispanica.Video Clip of Methodology:Antiproliferative Assay: 4 min 31 sec <a href="https://www.youtube.com/v/vi_fS47fpY0&t=3s">Full Screen</a> <a href="https://www.youtube.com/watch?v=vi_fS47fpY0&t=3s">Alternate</a>

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Sugar Containing Compounds and Biological Activities of Lagochilus setulosus

Molecules ◽

10.3390/molecules26061755 ◽

2021 ◽

Vol 26 (6) ◽

pp. 1755

Author(s):

Davlat Kh. Akramov ◽

Nilufar Z. Mamadalieva ◽

Andrea Porzel ◽

Hidayat Hussain ◽

Mthandazo Dube ◽

...

Keyword(s):

Methanolic Extract ◽

Biological Activities ◽

2D Nmr ◽

Septoria Tritici ◽

2D Nmr Spectroscopy ◽

Aerial Parts ◽

Spectroscopic Analyses ◽

Phytochemical Investigation ◽

Diphenyl Tetrazolium Bromide

Phytochemical investigation of the methanolic extract obtained from the aerial parts of Lagochilus setulosus (Lamiaceae) afforded the new compound 1-methoxy-3-O-β-glucopyranosyl-α-l-oliose (1) together with five known glycosides, namely sitosterol-3-O-β-glucoside (2), stigmasterol-3-O-β-glucoside (3), pinitol (4), 6β-hydroxyl-7-epi-loganin (5), and chlorotuberoside (6). The structures of these compounds were elucidated by extensive spectroscopic analyses, especially HR-MS, 1D and 2D NMR spectroscopy. The in vitro cytotoxic activity of the methanolic extract and the isolated compounds was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and crystal violet (CV) staining assays. In addition, the antifungal activities of the components were evaluated against Botrytis cinerea, Septoria tritici, and Phytophthora infestans. The anthelmintic potential was determined against Caenorhabditis elegans nematodes. Neither the extract nor the isolated compounds showed promising activity in all the bioassays.

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Dianthiamides A–E, Proline-Containing Orbitides from Dianthus chinensis

Molecules ◽

10.3390/molecules26237275 ◽

2021 ◽

Vol 26 (23) ◽

pp. 7275

Author(s):

Jin Woo Lee ◽

Jun Gu Kim ◽

Jae Sang Han ◽

Yong Beom Cho ◽

Yu Jin Lee ◽

...

Keyword(s):

Cyclic Peptides ◽

Biological Activities ◽

2D Nmr ◽

Amino Acid Residues ◽

A549 Cell Line ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Wide Range ◽

Weak Activity ◽

Whole Plants

Orbitides are plant-derived small cyclic peptides with a wide range of biological activities. Phytochemical investigation of the whole plants of Dianthus chinensis was performed with the aim to discover new bioactive orbitides. Five undescribed proline-containing orbitides, dianthiamides A–E (1–5), were isolated from a methanolic extract of Dianthus chinensis. Their structures were elucidated by extensive analysis of 1D and 2D NMR and HRESI–TOF–MS as well as ESI–MS/MS fragmentation data. The absolute configuration of the amino acid residues of compounds 1–5 was determined by Marfey’s method. All compounds were tested for their cytotoxic activity, and dianthiamide A (1) exhibited weak activity against A549 cell line with IC50 value of 47.9 μM.

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The Phytochemical Investigation and Biological Activities of Berberis Orthobotrys

International Journal of Phytomedicine ◽

10.5138/09750185.1899 ◽

2017 ◽

Vol 9 (2) ◽

Cited By ~ 2

Author(s):

Akber Dad ◽

Iftikhar Ali ◽

Nadja Engel ◽

Muhammad Atif ◽

Hidayat Hussain ◽

...

Keyword(s):

Antifungal Activity ◽

Fusarium Solani ◽

Leaf Extract ◽

Biological Activities ◽

2D Nmr ◽

Published Data ◽

Root Extract ◽

Spectroscopic Methods ◽

Phytochemical Investigation ◽

First Time

The leaf extract of Berberis orthobotrys Bien. ex Aitch. (B.o.) afforded three compounds viz., β-sitosterol (1), sesamin (2) and 10-eicosanol (3) which were identified by spectroscopic methods including 1D and 2D NMR, GC-MS, IR and comparison of their spectral data with the published data. To the best of our knowledge these three compounds are reported here for the first time to be isolated from Berberis orthobotrys Bien. ex Aitch. (B.o.). Moreover the root extract exhibited good antilieshmanial activity and root and fruit extracts demonstrated minor antifungal activity against Fusarium solani.

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A Novel Anticancer Diterpenoid from Jatropha Gossypifolia

Natural Product Communications ◽

10.1177/1934578x1200700204 ◽

2012 ◽

Vol 7 (2) ◽

pp. 1934578X1200700

Author(s):

Abiodun Falodun ◽

Udo Kragl ◽

Serge-Mitherand Tengho Touem ◽

Alexander Villinger ◽

Thomas Fahrenwaldt ◽

...

Keyword(s):

Bacterial Infections ◽

2D Nmr ◽

Root Bark ◽

X Ray ◽

Isolation And Characterization ◽

Phytochemical Investigation ◽

Jatropha Gossypifolia ◽

Methylene Group

Jatropha gossypifolia root bark is used in ethnomedicine for bacterial infections and cancer of the lungs. Phytochemical investigation resulted in the isolation and characterization of a potent anticancer and novel lathyrane diterpenoid compound, abiodone, with an unusual methylene group. The structure of this novel compound was established by 1D, and 2D NMR spectroscopic experiments and confirmed by X-ray analysis.

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Phytochemical Analysis and Antioxidant Capacity of BM-21, a Bioactive Extract Rich in Polyphenolic Metabolites from the Sea Grass Thalassia testudinum

Natural Product Communications ◽

10.1177/1934578x1200700117 ◽

2012 ◽

Vol 7 (1) ◽

pp. 1934578X1200700 ◽

Cited By ~ 3

Author(s):

Erik L. Regalado ◽

Roberto Menendez ◽

Olga Valdés ◽

Ruth A. Morales ◽

Abilio Laguna ◽

...

Keyword(s):

Biological Activities ◽

Radical Scavenging ◽

Ethanol Extract ◽

Natural Antioxidants ◽

2D Nmr ◽

Thalassia Testudinum ◽

Phytochemical Analysis ◽

Isolation And Identification ◽

Phytochemical Investigation ◽

Potential Applications

The aqueous ethanol extract of Thalassia testudinum leaves (BM-21) is now being developed in Cuba as an herbal medicine due to its promising pharmacological properties. Although some interesting biological activities of BM-21 have already been reported, its chemical composition remains mostly unknown. Thus, we now describe the qualitative and quantitative analyzes of BM-21 using standard phytochemical screening techniques, including colorimetric quantification, TLC and HPLC analyses. Phytochemical investigation of BM-21 resulted in the isolation and identification of a new phenolic sulfate ester (1), along with ten previously described phenolic derivatives (2-11), seven of which have never been previously reported from the genus Thalassia. The structures of these compounds were established by analysis of their spectroscopic (1D and 2D NMR) and spectrometric (HRMS) data, as well as by comparison of these with those reported in the literature. Furthermore, BM-21 was found to exhibit strong antioxidant activity in four different free radical scavenging assays (HO•, RO2•, O2-• and DPPH•). Consequently, this is the first study which highlights the phytochemical composition of BM-21 and demonstrates that this product is a rich source of natural antioxidants with potential applications in pharmaceutical, cosmetic and food industries.

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