New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

Four new eudesmane-type sesquiterpenoids, (1R,5S,6R,7S,9S,10S)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (1), (1R,5S,6S,7R,9S,10S)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (3), (1R,5S,6R,7S,9S,10R)-9-O-(Z-p-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (6), and (1R,5S,6R,7S,9S,10R)-9-O-(E-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (7), were isolated from a 95% EtOH extract of the leaves of Aster koraiensis by repeated chromatography. Moreover, three sesquiterpenoids (2, 4, and 5) and two caffeoylquinic acids (8 and 9) having previously known chemical structures were isolated during the isolation procedure. The four new compounds (1, 3, 6, and 7) were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) interpretation and hydrolysis. Moreover, the absolute configurations of 2, 4, and 5 were determined for the first time in this study. The compounds isolated were tested for their viability on nitric oxide (NO) and prostaglandin E2 (PGE2) production on LPS-stimulated RAW 264.7 cells. Among them, only 7 presented weak inhibitory effects on both NO and PGE2 production.

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

Journal of Analytical Methods in Chemistry ◽

10.1155/2018/2794904 ◽

2018 ◽

Vol 2018 ◽

pp. 1-8 ◽

Cited By ~ 1

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.

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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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Saccharpiscinols A–C: Flavans with Potential Inflammatory Activities from One Actinobacteria Saccharomonospora piscinae

Molecules ◽

10.3390/molecules26164909 ◽

2021 ◽

Vol 26 (16) ◽

pp. 4909

Author(s):

Yung-Shun Su ◽

Jih-Jung Chen ◽

Ming-Jen Cheng ◽

Chee-Yin Chai ◽

Aij-Lie Kwan ◽

...

Keyword(s):

Data Analysis ◽

Chromatographic Separation ◽

Spectroscopic Data ◽

2D Nmr ◽

No Production ◽

Raw 264.7 ◽

Phytochemical Investigation ◽

Inhibitory Activities ◽

New Compounds ◽

First Time

Phytochemical investigation and chromatographic separation of extracts from the actinobacteria strain Saccharomonospora piscinae that was isolated from dried fishpond sediment of Kouhu township, in the south of Taiwan, led to the isolation of three new compounds, saccharpiscinols A–C (1–3, respectively), and three new natural products, namely (2S)-5,7,3′,4′-tetrahydroxy-6,8-dimethylflavanone (4), methyl-4-hydroxy-2-methoxy-6-methylbenzoate (5), and (±)-7-acetyl-4,8-dihydroxy-6-methyl-1-tetralone (6). Compounds 4–6 were reported before as synthesized products, herein, they are reported from nature for the first time. 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. Saccharpiscinol A showed inhibitory activities against LPS-induced NO production.

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One new compound from Borreria alata (Aubl.) DC (Rubiaceae) in Vietnam

Science and Technology Development Journal ◽

10.32508/stdj.v19i1.537 ◽

2016 ◽

Vol 19 (1) ◽

pp. 19-25

Author(s):

Loan Cam To ◽

Tuyen Nguyen Kim Pham ◽

Phung Kim Phi Nguyen

Keyword(s):

Spectroscopic Data ◽

Biological Activities ◽

2D Nmr ◽

Chemical Structures ◽

Anti Inflammatory ◽

First Time

Borreria is a genus of Rubiaceae widespread in tropical and subtropical America, Africa, Asia, and Europe. Studies have confirmed that extracts as well as some isolated compounds of species of Borreria genus possess diverse biological activities, including anti-inflammatory, antitumor, antimicrobial, antioxidant, anti-ulcer… In this paper, we present the chemical structures of four compounds isolated from Borreria alata, collected at Di Linh district, Lam Dong province, Vietnam. 3β, 6β, 23-trihydroxyurs- 12-en-28-oic acid (1), sodium deacetylasperulosidate (2), 7β-hydroxy-11-methylforsythide (3) and sodium loganate (4). Among them, three compounds (1), (2), (3) were known for the first time in Borreria genus to our best knowledge and (4) is a new compound. The chemical structures of these compounds wereelucidated by analysis of 1D and 2D NMR and HR-MS spectroscopic data, as well as by comparison with those reported in the literature.

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Six New Methyl Apiofuranosides from the Bark of Phellodendron chinense Schneid and Their Inhibitory Effects on Nitric Oxide Production

Molecules ◽

10.3390/molecules24101851 ◽

2019 ◽

Vol 24 (10) ◽

pp. 1851 ◽

Cited By ~ 1

Author(s):

Peng-Fei Wang ◽

Yan-Ping Li ◽

Li-Qin Ding ◽

Shi-Jie Cao ◽

Li-Ning Wang ◽

...

Keyword(s):

Nitric Oxide ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Raw 264.7 Cells ◽

Nitric Oxide Production ◽

Inhibitory Effects ◽

Etoh Extract ◽

Oxide Production ◽

No Release ◽

Empirical Approaches

A chemical investigation on 70% EtOH extract from the bark of Phellodendron chinense Schneid (Rutaceae) led to six new methyl apiofuranosides (1–6), and ten known compounds (7–16). All these compounds were characterized by the basic analysis of the spectroscopic data including extensive 1D-, 2D-NMR (HSQC, HMBC), and high-resolution mass spectrometry, and the absolute configurations were determined by both empirical approaches and NOESY. Inhibitory effects of compounds 1–9 and 11–16 on nitric oxide production were investigated in lipopolysaccharide (LPS)-mediated RAW 264.7 cells, as a result, most of these isolates inhibited nitric oxide (NO) release, and among them 9, 11, and 12 displayed the strongest inhibition on NO release at the concentration of 12.5 μM.

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Two New Carboxyethylflavanones from the Heartwood of Dalbergia tonkinensis and Their Antimicrobial Activities

Natural Product Communications ◽

10.1177/1934578x1701201115 ◽

2017 ◽

Vol 12 (11) ◽

pp. 1934578X1701201 ◽

Cited By ~ 2

Author(s):

Ninh The Son ◽

Kenichi Harada ◽

Nguyen Manh Cuong ◽

Yoshiyasu Fukuyama

Keyword(s):

Filamentous Fungus ◽

Spectroscopic Data ◽

2D Nmr ◽

Antimicrobial Activities ◽

Esi Ms ◽

Chemical Structures ◽

Dalbergia Tonkinensis ◽

New Compounds ◽

Antimicrobial Assay ◽

Mic Value

Two new carboxyethylflavanone derivatives, (2 S)-8-carboxyethylnarigenin (2) and (2 S)-6,8-dicarboxyethylpinocembrin (3) were isolated from the heartwood of Dalbergia tonkinensis Prain, along with four known compounds 1, and 4-6. The chemical structures of two new compounds 2 and 3 were elucidated based on analyses of the spectroscopic data, including 1D and 2D NMR, HR-ESI-MS, IR, UV, and CD spectroscopies. By carrying out antimicrobial assay, CH3OH and CHCl3 fractions exhibited weak MIC value at 200 μg/mL against filamentous fungus A. niger (439), whereas the known flavanone 1 and the new carboxyethylflavanone 2 had MIC at 100 μg/mL.

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Azukisapogenol Triterpene Glycosides from Oxytropis chiliophylla Royle

Molecules ◽

10.3390/molecules23102448 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2448

Author(s):

Jun Wang ◽

Hongshuai Yang ◽

Yang Liu ◽

Kelsang Norbo ◽

Kewu Zeng ◽

...

Keyword(s):

Methyl Ester ◽

Glucuronic Acid ◽

Acid Methyl Ester ◽

Triterpene Glycosides ◽

Raw 264.7 Cells ◽

No Production ◽

Acid Methyl ◽

Potent Inhibition ◽

New Compounds ◽

First Time

Eight azukisapogenol triterpene glycosides, including five new compounds, oxychiliotriterpenosides A–E (1–5), two new methyl glucuronide derivatives that proved to be artifacts, oxychiliotriterpenoside E-glucuronic acid methyl ester (6) and myrioside B-glucuronic acid methyl ester (7), and a known one, myrioside B (8), was isolated from the aerial part of Oxytropis chiliophylla Royle. Their structures were elucidated based on extensive spectroscopic analyses and chemical methods. Triterpene glycosides were first obtained from O. chiliophylla, and those containing a galactose unit (1, 2, 5 and 6) and diglucosidic or triglucosidic linkage at C-29 (1–4), were reported from Oxytropis species for the first time, which might be recognized as a chemotaxonomic feature of O. chiliophylla. All isolated compounds were evaluated for their anti-inflammatory activities against NO production using lipopolysaccharide (LPS)-induced RAW 264.7 cells, but no compounds showed potent inhibition on NO production.

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

Molecules ◽

10.3390/molecules23113003 ◽

2018 ◽

Vol 23 (11) ◽

pp. 3003 ◽

Cited By ~ 4

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.

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CONTRIBUTE TO STUDY ON CHEMICAL CONSTITUENTS OF URENA LOBATA (L.) OF VIETNAM

Vietnam Journal of Science and Technology ◽

10.15625/2525-2518/57/2/13019 ◽

2019 ◽

Vol 57 (2) ◽

pp. 162

Author(s):

Quan Minh Pham ◽

Hoai Van Thi Tran ◽

Lam Tien Do ◽

Phuong Lan Doan ◽

Inh Thi Cam ◽

...

Keyword(s):

Mental Disorders ◽

Ethyl Acetate ◽

Ethyl Acetate Extract ◽

Chemical Constituents ◽

2D Nmr ◽

Spectroscopic Methods ◽

Tree Roots ◽

Chemical Structures ◽

Phytochemical Investigation ◽

First Time

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.

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

Natural Product Communications ◽

10.1177/1934578x211043732 ◽

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.

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