scholarly journals Acylated Aminooligosaccharides with Inhibitory Effects against α-Amylase from Streptomyces sp. HO1518

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 403 ◽  
Author(s):  
Hai-Li Liu ◽  
Heng-Chao E ◽  
Ding-An Xie ◽  
Wen-Bo Cheng ◽  
Wan-Qi Tao ◽  
...  
Keyword(s):  
Type Ii Diabetes ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Ionization Mass ◽  
Inhibitory Effects ◽  
Streptomyces Sp ◽  
Nmr Data ◽  
New Compounds ◽  
Drug Leads ◽  
Clinical Drug

Five new acylated aminooligosaccharides (1–5), together with one known related analogue (6), were isolated from Streptomyces sp. HO1518. Their structure was identified by extensive spectroscopic analysis, including 1D and 2D NMR data and high resolution electrospray ionization mass spectrometry (HRESIMS), and by comparison with those reported in the literature. All of the new compounds showed more promising porcine pancreatic α-amylase (PPA) inhibitory activities than the clinical drug acarbose, indicating them as potential pharmaceutical drug leads toward type II diabetes.

scholarly journals Triterpene Bisdesmosides from the Stems of Akebia Quinata

2008 ◽  
Vol 3 (6) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Yoshihiro Mimaki ◽  
Saya Doi
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Triterpene Saponins ◽  
Nmr Data ◽  
New Compounds ◽  
Chemical Evidence

Five new triterpene saponins (1–5) were isolated from the stems of Akebia quinata. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were determined to be 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1), 3β-[( O-β-D-glucopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (2), 3β-[( O-β-D-glucuronopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (3), 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (4), and 3β-[( O-β-D-glucopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-23,29-dihydroxy-olean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (5), respectively.

scholarly journals Steroidal Saponins from the Rhizomes of Ruscus Hypophyllum

2008 ◽  
Vol 3 (10) ◽  
pp. 1934578X0800301 ◽  
Author(s):  
Yoshihiro Mimaki ◽  
Tsukasa Aoki ◽  
Maki Jitsuno ◽  
Akihito Yokosuka ◽  
Ceyda Sibel Kiliç ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Promyelocytic Leukemia ◽  
Leukemia Cells ◽  
Steroidal Saponins ◽  
Furostanol Saponins ◽  
Nmr Data ◽  
Spirostanol Saponins ◽  
New Compounds ◽  
Chemical Evidence

Phytochemical screening of the rhizomes of Ruscus hypophyllum (Liliaceae) has resulted in the isolation of five spirostanol saponins (1-5) including a new saponin (4) and nine furostanol saponins (6–14) including three new saponins (9–11), together with a known cholestane glycoside (15) and a new cholestane glycoside (16). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence. The spirostanol saponins 1, 2, and 5 showed moderate cytotoxic activity against HL-60 human promyelocytic leukemia cells.

scholarly journals Natalenamides A–C, Cyclic Tripeptides from the Termite-Associated Actinomadura sp. RB99

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3003 ◽  
Author(s):  
Seoung Rak Lee ◽  
Dahae Lee ◽  
Jae Sik Yu ◽  
René Benndorf ◽  
Sullim Lee ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cyclic Peptides ◽  
Culture Broth ◽  
Resonance Spectroscopy ◽  
Ionization Mass ◽  
Inhibitory Effects ◽  
Associated Bacteria ◽  
Chemical Structures ◽  
New Compounds ◽  
Powerful Strategy

In recent years, investigations into the biochemistry of insect-associated bacteria have increased. When combined with analytical dereplication processes, these studies provide a powerful strategy to identify structurally and/or biologically novel compounds. Non-ribosomally synthesized cyclic peptides have a broad bioactivity spectrum with high medicinal potential. Here, we report the discovery of three new cyclic tripeptides: natalenamides A–C (compounds 1–3). These compounds were identified from the culture broth of the fungus-growing termite-associated Actinomadura sp. RB99 using a liquid chromatography (LC)/ultraviolet (UV)/mass spectrometry (MS)-based dereplication method. Chemical structures of the new compounds (1–3) were established by analysis of comprehensive spectroscopic methods, including one-dimensional (1H and 13C) and two-dimensional (1H-1H-COSY, HSQC, HMBC) nuclear magnetic resonance spectroscopy (NMR), together with high-resolution electrospray ionization mass spectrometry (HR-ESIMS) data. The absolute configurations of the new compounds were elucidated using Marfey’s analysis. Through several bioactivity tests for the tripeptides, we found that compound 3 exhibited significant inhibitory effects on 3-isobutyl-1-methylxanthine (IBMX)-induced melanin production. The effect of compound 3 was similar to that of kojic acid, a compound extensively used as a cosmetic material with a skin-whitening effect.

scholarly journals Quantum Mechanics-Based Structure Analysis of Cyclic Monoterpene Glycosides from Rhodiola Rosea

2020 ◽  
Author(s):  
Yu Tang ◽  
J. Brent Friesen ◽  
David C. Lankin ◽  
James McAlpine ◽  
Dejan Nikolić ◽  
...  
Keyword(s):  
Quantum Mechanics ◽  
Spectroscopic Analysis ◽  
Spatial Arrangement ◽  
Spin Coupling ◽  
Rhodiola Rosea ◽  
Analysis Software ◽  
Nmr Data ◽  
Biological Studies ◽  
Spin Analysis ◽  
New Compounds

NMR- and MS-guided metabolomic mining for new phytoconstituents from a widely used dietary supplement, <i>Rhodiola rosea</i>, yielded two new (+)-myrtenol glycosides, <b>1</b> and <b>2</b>, and two new cuminol glycosides (<b>3</b> and <b>4</b>), along with three known analogues (<b>5</b>–<b>7</b>). The structures of the new compounds were determined by extensive spectroscopic analysis. Quantum Mechanics-driven <sup>1</sup>H iterative Full Spin Analysis (QM-HiFSA) decoded the spatial arrangement of the methyl groups in <b>1</b> and <b>2</b>, as well as other features not recognizable by conventional methods, including higher order spin-coupling effects. The application of QM-HiFSA will provide a definitive reference point for future phytochemical and biological studies of <i>R. rosea</i> as a resilience botanical. Application of a new NMR data analysis software package, CT, for QM-based iteration of NMR spectra is also discussed.

scholarly journals Conjugated Polyene Ketones From the Marine Sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110437
Author(s):  
Bui H. Tai ◽  
Dan T. Hang ◽  
Do T. Trang ◽  
Pham H. Yen ◽  
Phan T. T. Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Marine Sponge ◽  
Human Cancer ◽  
2D Nmr ◽  
Ionization Mass ◽  
Hep G2 ◽  
Human Cancer Cells ◽  
Resolution Electron ◽  
New Compounds ◽  
First Time

Five conjugated polyene ketones (1-5) were isolated from the methanol extract of the marine sponge Clathria ( Thalysias) reinwardti (Vosmaer, 1880) living in the coastal waters of Vietnam. Their structures were determined to be 8-(2′,3′,4′-trimethylphenyl)-6-methyl-oct-3( E),5( E),7( E)-trien-2-one (1), 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo- β-ionone (4), and 4-(2′,3′,4′-trimethylphenyl)-but-3( E)-en-2-one (5), by extensive analysis of high-resolution electron spray ionization mass spectrum (HR-ESI-MS), one-dimensional, and two-dimensional (2D) nuclear magnetic resonance (NMR) spectra, as well as by comparison of the spectral data with those reported in the literature. Compound 1 was new, compounds 2 to 4 were isolated from nature for the first time, and the chemical structure as well as the NMR assignments, of 5 were indicated by 2D NMR for the first time. Additionally, compound 5 exhibited cytotoxic activity against the human cancer cells SK-LU-1, SK-Mel-2, MCF-7, and Hep-G2 with half-minimal inhibitory concentration (IC50) values of 15.12 ± 3.43, 17.41 ± 2.83, 33.12 ± 3.39, and 34.38 ± 3.52 µM, respectively, but displayed only a weak cytotoxic effect on the normal HEK-239A cells (IC50 64.67 ± 3.67 µM). Compound 5 also significantly increased Caspase-3 activity in SK-LU-1 cells at concentrations of 10, 15, and 20 µM.

scholarly journals α-Amylase and α-Glucosidase Inhibitory Activities of Chemical Constituents from Wedelia chinensis (Osbeck.) Merr. Leaves

2018 ◽  
Vol 2018 ◽  
pp. 1-8 ◽  
Author(s):  
Nguyen Phuong Thao ◽  
Pham Thanh Binh ◽  
Nguyen Thi Luyen ◽  
Ta Manh Hung ◽  
Nguyen Hai Dang ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Inhibitory Effects ◽  
Meoh Extract ◽  
Inhibitory Activities ◽  
Isolated Compound ◽  
New Compounds ◽  
Modified Mosher’S Method

As part of an ongoing search for new natural products from medicinal plants to treat type 2 diabetes, two new compounds, a megastigmane sesquiterpenoid sulfonic acid (1) and a new cyclohexylethanoid derivative (2), and seven related known compounds (3–9) were isolated from the leaves of Wedelia chinensis (Osbeck.) Merr. The structures of the compounds were conducted via interpretation of their spectroscopic data (1D and 2D NMR, IR, and MS), and the absolute configurations of compound 1 were determined by the modified Mosher’s method. The MeOH extract of W. chinensis was found to inhibit α-amylase and α-glucosidase inhibitory activities as well as by the compounds isolated from this extract. Furthermore, compound 7 showed the strongest effect with IC50 values of 112.8 ± 15.1 μg/mL (against α-amylase) and 785.9 ± 12.7 μg/mL (against α-glucosidase). Compounds 1, 8, and 9 showed moderate α-amylase and α-glucosidase inhibitory effects. Other compounds showed weak or did not show any effect on both enzymes. The results suggested that the antidiabetic properties from the leaves of W. chinensis are not simply a result of each isolated compound but are due to other components such as the accessibility of polyphenolic groups to α-amylase and α-glucosidase activities.

scholarly journals New Cyclopentyl Fatty Acid and Cyanohydrin Glycosides from Fruits of Hydnocarpus hainanensis

2017 ◽  
Vol 12 (2) ◽  
pp. 1934578X1701200
Author(s):  
Thanh Tra Nguyen ◽  
Bich Ngan Truong ◽  
Huong Doan Thi Mai ◽  
Marc Litaudon ◽  
Van Hung Nguyen ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Cytotoxic Activity ◽  
Cell Line ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
New Compounds ◽  
Line Compound

Three new compounds, hydnohainanic acid (1), and hydnohainanin A (2) and B (3) were isolated from the fruits of Hydnocarpus hainanensis (Achariaceae). Their structures were determined by spectroscopic analysis, including 2D NMR, and MS. Compounds 1-3 were evaluated for their cytotoxic activity against the KB cell line. Compound 1 had a moderate cytotoxicity with an IC50 value of 32.5 μg/mL, while the two remaining compounds did not exhibit inhibition, even at a concentration of 128 μg/mL.

scholarly journals Chemical Constituents from Scindapsus officinalis (Roxb.) Schott. and Their Anti–Inflammatory Activities

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2577 ◽  
Author(s):  
Hongjing Dong ◽  
Yanling Geng ◽  
Xueyong Wang ◽  
Xiangyun Song ◽  
Xiao Wang ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
No Production ◽  
Inhibitory Effects ◽  
Nmr Data ◽  
Extensive Analysis ◽  
Ic50 Values ◽  
Monoterpene Glycoside ◽  
Anti Inflammatory

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

scholarly journals UPLC-PDA-QTOFMS-guided isolation of prenylated xanthones and benzoylphloroglucinols from the leaves of Garcinia oblongifolia and their migration-inhibitory activity

2016 ◽  
Vol 6 (1) ◽  
Author(s):  
Hong Zhang ◽  
Dan Zheng ◽  
Zhi-Jie Ding ◽  
Yuan-Zhi Lao ◽  
Hong-Sheng Tan ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Soluble Fraction ◽  
2D Nmr ◽  
Acetone Extract ◽  
Cancer Cell Migration ◽  
Transwell Migration Assay ◽  
Migration Assay ◽  
Protein Levels ◽  
Snail Protein ◽  
New Compounds

Abstract A UPLC-PDA-QTOFMS-guided isolation strategy was employed to screen and track potentially new compounds from Garcinia oblongifolia. As a result, two new prenylated xanthones, oblongixanthones D and E (1–2), six new prenylated benzoylphloroglucinol derivatives, oblongifolins V–Z (3–7) and oblongifolin AA (8), as well as a known compound oblongifolin L (9), were isolated from the EtOAc-soluble fraction of an acetone extract of the leaves of Garcinia oblongifolia guided by UPLC-PDA-QTOFMS analysis. The structures of the new compounds were elucidated by 1D- and 2D-NMR spectroscopic analysis and mass spectrometry. Experimental and calculated ECD spectra were used to determine the absolute configurations. The results of wound healing and transwell migration assay showed that oblongixanthones D (1), E (2), and oblongifolin L (9) have the ability to inhibit cancer cell migration in lower cytotoxic concentrations. Western blotting results showed that these compounds exhibited an anti-metastasis effect mainly through downregulating RAF protein levels. In addition, 2 and 9 could inhibit phospho-MEK and phospho-ERK at downstream. Moreover, 1, 2, and 9 could inhibit snail protein level, suggesting that they could regulate the EMT pathway.

scholarly journals Polyhydroxylated Steroidal Saponins from the Rhizomes of Convallaria majalis

2007 ◽  
Vol 2 (5) ◽  
pp. 1934578X0700200
Author(s):  
Taro Higano ◽  
Minpei Kuroda ◽  
Maki Jitsuno ◽  
Yoshihiro Mimaki
Keyword(s):  
Spectroscopic Analysis ◽  
Methanolic Extract ◽  
2D Nmr ◽  
Chemical Transformations ◽  
Steroidal Saponins ◽  
Nmr Data ◽  
Spirostanol Saponins ◽  
Convallaria Majalis

Six new polyhydroxylated spirostanol saponins (1–6) were isolated from the methanolic extract of the rhizomes of Convallaria majalis. On the basis of extensive spectroscopic analysis, including 2D NMR data, and a few chemical transformations, the structures of 1–6 were determined to be 1β,2β,3β-trihydroxy-5β-spirost-25(27)-en-5-yl β-D-galactopyranoside (1), (25 S)-1β,2β,3β-trihydroxy-5β-spirostan-5-yl β-D-galactopyranoside (2), 1β,2β,3β,4β-tetrahydroxy-5β-spirost-25(27)-en-5-yl β-D-galactopyranoside (3), (25 S)-1β,2β,3β,4β-tetrahydroxy-5β-spirostan-5-yl β-D-galactopyranoside (4), 1β,2β,3β,4β-tetrahydroxyspirost-25(27)-en-5-yl α-L-arabinopyranoside (5), and (25 S)-1β,2β,3β,4β-tetrahydroxy-5β-spirostan-5-yl α-L-arabinopyranoside (6), respectively.

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