scholarly journals Microbial Transformation of neo-Clerodane Diterpenoid, Scutebarbatine F, by Streptomyces sp. CPCC 205437

2021 ◽  
Vol 12 ◽  
Author(s):  
Dewu Zhang ◽  
Xiaoyu Tao ◽  
Guowei Gu ◽  
Yujia Wang ◽  
Wenxia Zhao ◽  
...  
Keyword(s):  
Influenza A ◽  
Microbial Transformation ◽  
Cancer Cell Line ◽  
Antibacterial Activities ◽  
Positive Control ◽  
Cytotoxic Activities ◽  
Ionization Mass ◽  
Nmr Data ◽  
First Time ◽  
New Metabolites

Biotransformation of the neo-clerodane diterpene, scutebarbatine F (1), by Streptomyces sp. CPCC 205437 was investigated for the first time, which led to the isolation of nine new metabolites, scutebarbatine F1–F9 (2–10). Their structures were determined by extensive high-resolution electrospray ionization mass spectrometry (HRESIMS) and NMR data analyses. The reactions that occurred included hydroxylation, acetylation, and deacetylation. Compounds 2–4 and 8–10 possess 18-OAc fragment, which were the first examples of 13-spiro neo-clerodanes with 18-OAc group. Compounds 7–10 were the first report of 13-spiro neo-clerodanes with 2-OH. Compounds 1–10 were biologically evaluated for the cytotoxic, antiviral, and antibacterial activities. Compounds 5, 7, and 9 exhibited cytotoxic activities against H460 cancer cell line with inhibitory ratios of 46.0, 42.2, and 51.1%, respectively, at 0.3 μM. Compound 5 displayed a significant anti-influenza A virus activity with inhibitory ratio of 54.8% at 20 μM, close to the positive control, ribavirin.

scholarly journals Sesquiterpenoids From the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11

2021 ◽  
Vol 12 ◽  
Author(s):  
Ting Shi ◽  
Xiang-Qian Li ◽  
Li Zheng ◽  
Ya-Hui Zhang ◽  
Jia-Jia Dai ◽  
...  
Keyword(s):  
Pathogenic Fungi ◽  
Antibacterial Activities ◽  
Aeromonas Salmonicida ◽  
Systematic Research ◽  
Cytotoxic Activities ◽  
Hepg2 Cell Lines ◽  
New Compounds ◽  
The Antarctic ◽  
First Time ◽  
Hepatoma Hepg2

The fungal strains Pseudogymnoascus are a kind of psychrophilic pathogenic fungi that are ubiquitously distributed in Antarctica, while the studies of their secondary metabolites are infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11 led to the isolation of six new tremulane sesquiterpenoids pseudotremulanes A–F (1–6), combined with one known analog 11,12-epoxy-12β-hydroxy-1-tremulen-5-one (7), and five known steroids (8–12). The absolute configurations of the new compounds (1–6) were elucidated by their ECD spectra and ECD calculations. Compounds 1–7 were proved to be isomeride structures with the same chemical formula. Compounds 1/2, 3/4, 1/4, and 2/3 were identified as four pairs of epimerides at the locations of C-3, C-3, C-9, and C-9, respectively. Compounds 8 and 9 exhibited cytotoxic activities against human breast cancer (MDA-MB-231), colorectal cancer (HCT116), and hepatoma (HepG2) cell lines. Compounds 9 and 10 also showed antibacterial activities against marine fouling bacteria Aeromonas salmonicida. This is the first time to find terpenoids and steroids in the fungal genus Pseudogymnoascus.

scholarly journals Cytotoxic Pentacyclic Triterpenoids from Combretum oliviforme

2010 ◽  
Vol 5 (7) ◽  
pp. 1934578X1000500
Author(s):  
Xiao-Peng Wu ◽  
Chang-Ri Han ◽  
Guang-Ying Chen ◽  
Yuan Yuan ◽  
Jian-Ying Xie
Keyword(s):  
Cytotoxic Activity ◽  
Cancer Cell Line ◽  
Lung Cancer Cell Line ◽  
Human Lung Cancer ◽  
Ionization Mass ◽  
Human Gastric Cancer ◽  
Pentacyclic Triterpenoids ◽  
Acetyl Group ◽  
First Time

Four pentacyclic triterpenoids were obtained from the leaves of Combretum oliviforme Chao, 3β–hydroxyolean–12–en–28–oic acid (1), 23– O–[α-L-(4′-acetylrhamnopyranosyl)]–imberbic acid (2), 23–acetoxy–3β–acetylimberbic acid–29–methyl ester (3), and 23– O–[α-L-rhamnopyranosyl]-1,3β-diacetylimberbic acid (4). Hydrolysis of 2 and 4 gave 23–hydroxyimberbic acid (5). The structures were elucidated by NMR, electrospray ionization mass spectrometry (ESIMS) and comparison with literature data. Compounds 1, 2, 3 and 4 were isolated from C. oliviforme Chao leaves for the first time and 3 for the first time from any natural source. All compounds were tested in vitro for their activity against human lung cancer cell line SPC-A-1, human erythroleukaemic line K562 and human gastric cancer SGC-7901 cells. Compounds 1, 3, 4 and 5 had cytotoxic activity for the three cell lines with IC50 0.69-69.68 μM. These results suggest that the presence of acetyl group in the triterpene aglycone structure plays an essential role for cytotoxic activity.

In Vitro Human Dihydroorotate Dehydrogenase Inhibitory, Anti-inflammatory and Cytotoxic Activities of Alkaloids from the Seeds of Nigella glandulifera

Planta Medica ◽  
2018 ◽  
Vol 84 (14) ◽  
pp. 1013-1021 ◽  
Author(s):  
Jun-Bo Gao ◽  
Xing-Jie Zhang ◽  
Rui-Han Zhang ◽  
Li-Li Zhu ◽  
De-Bing Pu ◽  
...  
Keyword(s):  
Folk Medicine ◽  
Positive Control ◽  
Cytotoxic Activities ◽  
Dihydroorotate Dehydrogenase ◽  
X Ray Diffraction ◽  
Ic50 Values ◽  
Pharmacologically Active ◽  
Pharmacologically Active Compounds ◽  
First Time

AbstractFour new dolabellane-type diterpene alkaloids, glandulamines A – D (1 – 4), together with twelve known compounds (5 – 16), were isolated from the seeds of Nigella glandulifera using repeated column chromatography and semipreparative HPLC. The structures of 1 – 16 were elucidated based on NMR data analysis, HRMS experiments and other spectroscopic interpretations. The absolute configuration of 5 was determined by single-crystal X-ray diffraction data for the first time. Compounds 10 and 12 showed human dihydroorotate dehydrogenase inhibitory activity with IC50 values of 61.1 ± 5.3 and 45.9 ± 3.0 µM, respectively. Molecular docking of the active compound 12 and positive control teriflunomide on the inhibitor-binding site of human dihydroorotate dehydrogenase was subsequently performed to visualize the interaction pattern. In addition, compounds 8 and 10 exhibited inhibitory effects against lipopolysaccharide-induced nitric oxide production with inhibition rates of 61 and 41%, respectively, at the concentration of 10 µM. Compounds 9 and 12 showed cytotoxic activities with cell viability varying from 29 ~ 57% at 100 µM against T98G, U87, U251, and GL261 glioma cancer cell lines. These data provide new insights on the pharmacologically active compounds of this plant widely used in folk medicine.

scholarly journals Nimesulide Based Novel Glycolamide Esters: Their Design, Synthesis, and Pharmacological Evaluation

2013 ◽  
Vol 2013 ◽  
pp. 1-8 ◽  
Author(s):  
Kavitha Kankanala ◽  
Vangala Ranga Reddy ◽  
Yumnam Priyadarshini Devi ◽  
Lakshmi Narasu Mangamoori ◽  
Khagga Mukkanti ◽  
...  
Keyword(s):  
Cancer Cell Line ◽  
Human Colon ◽  
Colon Cancer Cell Line ◽  
Cytotoxic Activities ◽  
Step Method ◽  
Human Colon Cancer ◽  
Cytotoxic Effects ◽  
Design Synthesis ◽  
First Time

The nimesulide based novel glycolamide esters were designed and synthesized for the first timeviaa three-step method starting from nimesulide. Structures of the synthesized compounds were confirmed by spectroscopic analysis. All the synthesized compounds were examined for their cytotoxic effectsin vitro,some of which showed significant cytotoxic activities against HCT-15 human colon cancer cell line.

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 Anthraquinone Derivatives from a Marine-Derived Fungus Sporendonema casei HDN16-802

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 334 ◽  
Author(s):  
Xueping Ge ◽  
Chunxiao Sun ◽  
Yanyan Feng ◽  
Lingzhi Wang ◽  
Jixing Peng ◽  
...  
Keyword(s):  
Chlorine Atom ◽  
Anticoagulant Activity ◽  
Antitubercular Activity ◽  
Antibacterial Activities ◽  
Cytotoxic Activities ◽  
Spectroscopic Techniques ◽  
Addition Compound ◽  
Anthraquinone Derivatives ◽  
Ic50 Values ◽  
First Time

Five new anthraquinone derivatives, auxarthrols D–H (1–5), along with two known analogues (6–7), were obtained from the culture of the marine-derived fungus Sporendonema casei. Their structures, including absolute configurations, were established on the basis of NMR, HRESIMS, and circular dichroism (CD) spectroscopic techniques. Among them, compound 4 represents the second isolated anthraquinone derivative with a chlorine atom, which, with compound 6, are the first reported anthraquinone derivatives with anticoagulant activity. Compounds 1 and 3 showed cytotoxic activities with IC50 values from 4.5 μM to 22.9 μM, while compounds 1, 3–4, and 6–7 showed promising antibacterial activities with MIC values from 12.5 μM to 200 μM. In addition, compound 7 was discovered to display potential antitubercular activity for the first time.

scholarly journals Dihydroisocoumarins and Dihydroisoflavones from the Rhizomes of Dioscorea collettii with Cytotoxic Activity and Structural Revision of 2,2′-Oxybis(1,4-di-tert-butylbenzene)

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5381
Author(s):  
Songsong Jing ◽  
Zhuo Qu ◽  
Chengcheng Zhao ◽  
Xia Li ◽  
Long Guo ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
13C Nmr ◽  
The Other ◽  
Cytotoxic Activities ◽  
Spectroscopic Methods ◽  
1H And 13C Nmr ◽  
Structural Revision ◽  
Nmr Data ◽  
H460 Cell ◽  
First Time

The investigation of the constituents of the rhizomes of Dioscorea collettii afforded one new dihydroisocoumarin, named (−)-montroumarin (1a), along with five known compounds—montroumarin (1b), 1,1′-oxybis(2,4-di-tert-butylbenzene) (2), (3R)-3′-O-methylviolanone (3a), (3S)-3′-O-methylviolanone (3b), and (RS)-sativanone (4). Their structures were elucidated using extensive spectroscopic methods. To the best of our knowledge, compound 1a is a new enantiomer of compound 1b. The NMR data of compound 2 had been reported but its structure was erroneous. The structure of compound 2 was revised on the basis of a reinterpretation of its NMR data (1D and 2D) and the assignment of the 1H and 13C NMR data was given rightly for the first time. Compounds 3a–4, three dihydroisoflavones, were reported from the Dioscoreaceae family for the first time. The cytotoxic activities of all the compounds were tested against the NCI-H460 cell line. Two dihydroisocoumarins, compounds 1a and 1b, displayed moderate cytotoxic activities, while the other compounds showed no cytotoxicity.

α-Glucosidase Inhibitory Compounds in Malus Halliana Koehne Tea

2017 ◽  
Vol 17 (3) ◽  
pp. 236-241 ◽  
Author(s):  
Feng Fajin ◽  
Yin Zhenhua ◽  
Wang Pengyu ◽  
Zhang Qianjun ◽  
Kang Wenyi
Keyword(s):  
Mass Spectrum ◽  
Inhibitory Activity ◽  
Positive Control ◽  
Inhibitory Effects ◽  
Butanol Extract ◽  
Nmr Data ◽  
Inhibitory Compounds ◽  
First Time ◽  
Better Than ◽  
C Nmr

The aim of this study was to isolate α-glucosidase inhibitory constituents from Malus halliana Koehne tea. The ethyl acetate and n-butanol extract of M. halliana tea showed α-glycosidase inhibitory activity (IC50 332.24 and 168.92 μg/mL, respectively) and eleven compounds (1–11) were isolated and identified by extensive NMR data (1H and 13C NMR) and mass spectrum. Eleven compounds were isolated from this plant for the first time, and compounds 2, 4, 5, 7 and 8 were isolated from the genus for the first time. The α-glucosidase inhibitory activity of compounds 6, 8, 9 and 10 (IC50 6.32, 15.53, 37.68 and 7.87 μM) were better than that of other compounds (IC50 > 200 μM). Compounds 1~5 and 11 displayed moderate inhibitory effects on α-glucosidase, with IC50 values of 226.76~435.56 μM, whereas compound 7 (IC50 3246.17 μM) was inactive, and lower than that of acarbose as positive control (IC50 1819.72 μM).

scholarly journals Bufadienolides from the Venom of Bufo Bufo gargarizans and Their Enzyme Inhibition Activities and Brine Shrimp Lethality

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Jian Xiao ◽  
Xiang Zhao ◽  
Wan-Tong Zhong ◽  
Fu-Rong Jiao ◽  
Xiao-Ling Wang ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Brine Shrimp ◽  
Bufo Bufo ◽  
Positive Control ◽  
Single Crystal Diffraction ◽  
X Ray ◽  
Nmr Data ◽  
Bufo Gargarizans ◽  
First Time ◽  
Potent Inhibitory Activity

A new bufadienolide named dyscinobufotalin (1), along with twenty known bufadienolides (2–21) were isolated from the venom of Bufo bufo gargarizans. Their structures were elucidated by spectroscopic analysis. The absolute configuration of the new natural product 2 was determined by X-ray single crystal diffraction and the complete NMR data for 3 was delivered for the first time. Both compounds 4 and 8 showed comparable α-glucosidase inhibitory activity (IC50 values of 0.25 and 0.26 μM, respectively) to the positive control acarbose (IC50 value of 0.42 μM), and 5 displayed potent inhibitory activity on acetylcholinesterase with an IC50 value of 0.12 μM. Moreover, 5, 8 and 13 presented moderate toxicity against brine shrimp.

scholarly journals Tangutidines A–C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum

2021 ◽  
Author(s):  
Hao-Yi Li ◽  
Bing-Chao Yan ◽  
Li-Xin Wei ◽  
Han-Dong Sun ◽  
Pema-Tenzin Puno
Keyword(s):  
Spectroscopic Data ◽  
Cytotoxic Activities ◽  
Diterpene Alkaloids ◽  
Nmr Data ◽  
Whole Plant ◽  
Detailed Interpretation ◽  
First Time

AbstractThree new diterpene alkaloids, tangutidines A–C (1–3), and four known alkaloids (4–7) were isolated from the whole plant of Aconitum tanguticum, from which amphoteric diterpene alkaloids (1–3) were obtained for the first time. The structures of 1–3 were elucidated by detailed interpretation of spectroscopic data, including MS and NMR data. All of them were evaluated for their cytotoxic activities. Graphic Abstract

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