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

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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Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽

10.3390/molecules24183336 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3336 ◽

Cited By ~ 2

Author(s):

Ping-Chen Tu ◽

Han-Chun Tseng ◽

Yu-Chia Liang ◽

Guan-Jhong Huang ◽

Te-Ling Lu ◽

...

Keyword(s):

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Isolation And Characterization ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Anti Inflammatory ◽

New Compounds ◽

First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

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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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Secondary Metabolites with Anti-Inflammatory Activities from One Actinobacteria Amycolatopsis taiwanensis

Molecules ◽

10.3390/molecules26195765 ◽

2021 ◽

Vol 26 (19) ◽

pp. 5765

Author(s):

Yung-Shun Su ◽

Ming-Der Wu ◽

Jih-Jung Chen ◽

Ming-Jen Cheng ◽

Yueh-Hsiung Kuo ◽

...

Keyword(s):

Spectroscopic Data ◽

2D Nmr ◽

No Production ◽

The North ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Production Activity ◽

Inos Inhibitor ◽

Ic50 Values ◽

New Compounds

Phytochemical investigation and chromatographic separation of extracts from one new actinobacteria strain Amycolatopsis taiwanensis that was isolated from soil of Yilan township, in the north of Taiwan, led to the isolation of nine new compounds, amycolataiwanensins A–I (1–9, resp.), and one new natural product, namely amycolataiwanensin J (10). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic-data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Of the isolates, 3, 5, 7 and 8 exhibited potent anti-NO production activity, with IC50 values of 17.52, 12.31, 17.81 and 13.32 μM, respectively, compared to that of quercetin, an iNOS inhibitor with an IC50 value of 35.94 μM. This is the first report on indole metabolite from the genus Amycolatopsis.

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

Molecules ◽

10.3390/molecules26133865 ◽

2021 ◽

Vol 26 (13) ◽

pp. 3865

Author(s):

Kang He ◽

Juan Zou ◽

Yu-Xue Wang ◽

Chen-Liang Zhao ◽

Jiang-Hai Ye ◽

...

Keyword(s):

Rare Case ◽

Biological Activities ◽

2D Nmr ◽

Bacterial Strains ◽

Isopropyl Group ◽

Carbonyl Carbon ◽

Single Crystal Diffraction ◽

Rhizopus Nigricans ◽

X Ray ◽

Phytochemical Investigation

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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Cyclic Polyketides with α-Glucosidase Inhibitory Activity from Endiandra kingiana Gamble and Molecular Docking Study

Records of Natural Products ◽

10.25135/rnp.227.20.11.1889 ◽

2021 ◽

Vol 15 (5) ◽

pp. 414-419

Author(s):

Mohamad Nurul Azmi Mohamad Taib ◽

Nur Amirah Saad ◽

Mohamad Hafizi Abu Bakar ◽

Mohammad Tasyriq Che Omar ◽

Ahmad Nazif Aziz ◽

...

Keyword(s):

Molecular Docking ◽

Active Site ◽

Methanolic Extract ◽

Docking Study ◽

2D Nmr ◽

Inhibition Activity ◽

Molecular Docking Study ◽

Phytochemical Investigation ◽

Ic50 Value

A phytochemical investigation of the methanolic extract of Endiandra kingiana (bark) led to the isolation of four major compounds which are kingianic acid A (1), tsangibeilin B (2), kingianin A (3) and kingianin F (4). The structures were determined by 1D- and 2D-NMR analysis in combination with HRMS experiments. The compounds were screened for their in vitro α-glucosidase inhibition activity. Among them, compounds 3-4 showed potent α-glucosidase inhibition activity with IC50 value at 11.9 ± 2.0 µM and 19.7 ± 1.5 µM, respectively. The molecular docking study found that both compounds were bound into the active site of the N-terminal of MGAM, and thus agreed with the in vitro α-glucosidase enzyme inhibition activity results.

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Two New Iridoid Glucosides from the Whole Plant of Patrinia scabiosifolia Link

Molecules ◽

10.3390/molecules26144201 ◽

2021 ◽

Vol 26 (14) ◽

pp. 4201

Author(s):

Shikai Sun ◽

Jiang Fu ◽

Kaidong Liu ◽

Mingzhu Dai ◽

Yong Li ◽

...

Keyword(s):

Gene Expression ◽

Chinese Medicine ◽

2D Nmr ◽

Inflammatory Activity ◽

Spectroscopic Analyses ◽

Whole Plant ◽

Phytochemical Investigation ◽

Iridoid Glucosides ◽

Anti Inflammatory ◽

Whole Plants

As a traditional Chinese medicine, Patrinia scabiosifolia Link has been used to treat various inflammatory-related diseases, and recent studies have shown that it possesses potent anti-inflammatory activity. Therefore, phytochemical investigation on whole plants of P. scabiosifolia were carried out, which led to the isolation of two new iridoid glucosides, patriniscabiosides A (1) and B (2), together with six known compounds (3–8). The structural elucidation of all compounds was performed by HRESIMS and extensive spectroscopic analyses including IR, 1D, 2D NMR, and electronic circular dichroism (ECD). All the isolated compounds were tested for their anti-inflammatory activity using the NF-κB-Dependent Reporter Gene Expression Assay, and compound 3 displayed anti-inflammatory activity through the inhibition of the NF-κB pathway, with an inhibitory rate of 73.44% at a concentration of 10 μM.

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New chalcone derivatives having pyrazole and sulfonamide pharmacophores as carbonic anhydrase inhibitors

Letters in Drug Design & Discovery ◽

10.2174/1570180817999201001160414 ◽

2020 ◽

Vol 17 ◽

Author(s):

Mehtap Tugrak ◽

Halise Inci Gul ◽

Hulya Akincioglu ◽

Ilhami Gulcin

Keyword(s):

Carbonic Anhydrase ◽

Biological Activities ◽

Drug Candidate ◽

Carbonic Anhydrase Inhibitors ◽

Reference Drug ◽

Lead Compounds ◽

Chemical Structures ◽

Ic50 Value ◽

Wide Range ◽

Ic50 Values

Background: Sulfonamide, pyrazole and chalcone pharmacophores are an important compounds in medicinal chemistry. They have wide range of biological activities including carbonic anhydrase (CA) inhibitory activities. Introduction: Carbonic anhydrase I and II inhibitors are used for the treatment of some disease such as retinal and cerebral edema (CAI), edema, epilepsy, and glaucoma (CA II). The available drugs in market have some limitations or side effect problems. So, there is a need to develop new drug candidate compound/s to overcome the problems at issue. In this study, a series of compounds MS4-MS10, (E)-4-(4-(3-aryl)-3-oxoprop-1-en-1-yl)-3-phenyl-1H-pyrazol-1-yl) benzenesulfonamides, were designed to discover new carbonic anhydrase inhibitors using hibryd approach. Methods: The compounds MS4-MS10 were synthesized as shown in Scheme 1 and their chemical structures were confirmed by 1H NMR, 13C NMR and HRMS spectra. Carbonic anhydrase (CAs, E.C.4.2.1.1) inhibitory effects of MS4-MS10 were tested on the hCA I and II isoenzymes by previously reported procedures. Results and Discussons: Carbonic anhydrase inhibitors results of the MS4-MS10 were presented in Table 1 as IC50 values (nM). They were inhibition range of 27.8-87.3 towards hCA I and 24.4-54.8 towards hCA II while reference drug AAZ IC50 values were 384.2 (hCA I) and 36.9 (hCA II). MS7 and MS9 had 13.8 (hCA I) and 1.5 (hCA II) times more potent CA inhibition than reference compound AAZ, respectively. Conclusion: MS7 (Ar: 2,4,5-trimethoxy phenyl) towards hCA I and MS9 (Ar: 3,4-dimethoxy phenyl) towards hCA II were the lead compounds of our series with the lowest IC50 value and can be considered for further studies.

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4-Hydroxy-trans-cinnamate Derivatives and Triterpene from Barleria cristata

Dhaka University Journal of Pharmaceutical Sciences ◽

10.3329/dujps.v12i2.17623 ◽

2014 ◽

Vol 12 (2) ◽

pp. 143-145 ◽

Cited By ~ 4

Author(s):

Nipa Chowdhury ◽

Abdullah Al Hasan ◽

Fakir Shahidullah Tareq ◽

Monira Ahsan ◽

ATM Zafrul Azam

Keyword(s):

Medicinal Plant ◽

Biological Activities ◽

Chemical Constituents ◽

Spectroscopic Methods ◽

Isolation And Characterization ◽

Phytochemical Investigation ◽

Organic Extracts ◽

Whole Plants ◽

Important Medicinal Plant

Barleria cristata is an important medicinal plant of Bangladesh. Many compounds of diverse biological activities were isolated from different Barleria species, including irridoids, flavonoids and phenylethanoid derivatives in addition to other groups of chemical constituents. This paper presents the chemical investigation of the whole plants of B.cristata. Classic phytochemical investigation of organic extracts of the whole plants of B. cristata together with spectroscopic methods led to the isolation and characterization of 4-hydroxy-trans-cinnamate derivatives (1-3) and a triterpene, namely oleanolic acid (4). Dhaka Univ. J. Pharm. Sci. 12(2): 143-145, 2013 (December) DOI: http://dx.doi.org/10.3329/dujps.v12i2.17623

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Cyclic Peptides from the Soft Coral-Derived Fungus Aspergillus sclerotiorum SCSIO 41031

Marine Drugs ◽

10.3390/md19120701 ◽

2021 ◽

Vol 19 (12) ◽

pp. 701

Author(s):

Jieyi Long ◽

Yaqi Chen ◽

Weihao Chen ◽

Junfeng Wang ◽

Xuefeng Zhou ◽

...

Keyword(s):

Cyclic Peptides ◽

Soft Coral ◽

2D Nmr ◽

X Ray Diffraction ◽

X Ray ◽

Cyclic Hexapeptide ◽

Ic50 Value ◽

Ic50 Values ◽

Cyclic Hexapeptides ◽

Aspergillus Sclerotiorum

Three novel cyclic hexapeptides, sclerotides C–E (1–3), and a new lipodepsipeptide, scopularide I (4), together with a known cyclic hexapeptide sclerotide A (5), were isolated from fermented rice cultures of a soft coral-derived fungus: Aspergillus sclerotiorum SCSIO 41031. The structures of the new peptides were determined by 1D and 2D NMR spectroscopic analysis, Marfey’s method, ESIMS/MS analysis, and single crystal X-ray diffraction analysis. Scopularide I (4) exhibited acetylcholinesterase inhibitory activity with an IC50 value of 15.6 μM, and weak cytotoxicity against the human nasopharyngeal carcinoma cell line HONE-EBV with IC50 values of 10.1 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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