scholarly journals Prenylated Flavonoid Glycosides with PCSK9 mRNA Expression Inhibitory Activity from the Aerial Parts of Epimedium koreanum

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3590
Author(s):  
Eeray Kim ◽  
Young-Mi Kim ◽  
Jongmin Ahn ◽  
Hee-Sung Chae ◽  
Young-Won Chin ◽  
...  
Keyword(s):  
Mrna Expression ◽  
Inhibitory Activity ◽  
Soluble Fraction ◽  
Flavonoid Glycosides ◽  
Chemical Methods ◽  
Aerial Parts ◽  
Cholesterol Levels ◽  
Phytochemical Investigation ◽  
Ldl Uptake ◽  
New Compounds

Phytochemical investigation on the n-BuOH-soluble fraction of the aerial parts of Epimedium koreanum using the PCSK9 mRNA monitoring assay led to the identification of four previously undescribed acylated flavonoid glycosides and 18 known compounds. The structures of new compounds were elucidated by NMR, MS, and other chemical methods. All isolated compounds were tested for their inhibitory activity against PCSK9 mRNA expression in HepG2 cells. Of the isolates, compounds 6, 7, 10, 15, and 17–22 were found to significantly inhibit PCSK9 mRNA expression. In particular, compound 7 was shown to increase LDLR mRNA expression. Thus, compound 7 may potentially increase LDL uptake and lower cholesterol levels in the blood.

scholarly journals Four New Pterosins from Pteris cretica and Their Cytotoxic Activities

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2767
Author(s):  
Jian Lu ◽  
Caiying Peng ◽  
Shuang Cheng ◽  
Jianqun Liu ◽  
Qinge Ma ◽  
...  
Keyword(s):  
Human Tumor ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Aerial Parts ◽  
Pteris Cretica ◽  
Phytochemical Investigation ◽  
Hct 116 ◽  
Hct 116 Cells ◽  
New Compounds

Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin 3-O-β-d-glucopyranoside (4), together with five known pterosins 5–9. Their structures were identified mainly on the basis of 1D and 2D NMR spectral data, ESI-MS and literature comparisons. Compounds 1 and 3 were new type of petrosins with a six membered ring between C-14 and C-15. The new compounds were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Results showed that compounds 1 and 2 exhibited cytotoxic activity against HCT-116 cells with IC50 value of 22.4 μM and 15.8 μM, respectively.

scholarly journals Chemical and Biological Investigation of Some Secondary Metabolites in Atriplex Halimus Growing in Egypt

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701 ◽  
Author(s):  
Amal Kabbash ◽  
Nagwa Shoeib
Keyword(s):  
Multidrug Resistance ◽  
Soluble Fraction ◽  
Radical Scavenging ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Dpph Radical ◽  
Biological Investigation ◽  
Atriplex Halimus ◽  
Aerial Parts ◽  
Dpph Radical Scavenging

The n-BuOH-soluble fraction of the MeOH-CH2Cl2 (1:1) extract of the aerial parts of Egyptian Atriplex halimus L. yielded two new flavonol glycosides, designated as atriplexoside A (1) [3′- O-methylquercetin-4′- O-β-apiofuranoside-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside)] and atriplexoside B (2) [3′- O-methylquercetin-4′- O-(5″″- O-β-xylopyranosyl-β-apiofuranoside)-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside)], together with six known compounds: two phenolic glucosides (3, 4), one ecdysteroid (5), one megastigmane (6) and two methoxylated flavonoid glycosides (7, 8). The structures of the compounds were elucidated by detailed spectroscopic analysis, including HR-ESI-MS and 2D-NMR spectroscopic data. DPPH radical scavenging, antileishmanial and anti-multidrug resistance activities were investigated using the n-BuOH-soluble fraction as well as the isolated compounds. Compound 8 (5- O-methylquercetin-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside) presented marked DPPH radical scavenging, weak antileishmanial and anti-multidrug resistance activity while the other tested compounds showed weaker activities.

New Phenolic Glycosides and Lignans from the Roots of Lilium dauricum

Planta Medica ◽  
2021 ◽  
Author(s):  
Xiao Xia ◽  
Jiao Zhang ◽  
Xiao-Jiang Wang ◽  
Yan Lu ◽  
Dao-Feng Chen
Keyword(s):  
Inhibitory Activity ◽  
Phenolic Glycosides ◽  
Anticomplementary Activity ◽  
Chemical Methods ◽  
Electronic Circular Dichroism ◽  
Circular Dichroism Analysis ◽  
Ic50 Values ◽  
The Absolute ◽  
New Compounds ◽  
Circular Dichroïsm

AbstractThree new phenolic glycosides, carvacrol-2-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (1), 1-methyl-3-isopropylphenol-4-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (2), p-methoxythymol-5-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (3), and a pair of new 8-O-4′ neolignan enantiomers (5a/5b), together with 26 known compounds (4, 6 – 30) were isolated from the roots of Lilium dauricum. The structures of the new compounds were elucidated based on extensive spectroscopic and chemical methods, and the absolute configurations of 5a and 5b were established by electronic circular dichroism analysis. Nine compounds (1, 3, 4, 8, 9, 17, 25, 29, and 30) exhibited potent α-glucosidase inhibitory activity with IC50 values ranging from 73.4 µM to 988.2 µM. Besides, compound 19 displayed strong anticomplementary activity (CH50: 71.6 µM).

A dihydrochalcone derivative and further steroidal saponins from Sansevieria trifasciata Prain

2017 ◽  
Vol 72 (11-12) ◽  
pp. 477-482 ◽  
Author(s):  
Billy T. Tchegnitegni ◽  
Rémy B. Teponno ◽  
Kristina Jenett-Siems ◽  
Matthias F. Melzig ◽  
Tomofumi Miyamoto ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Spectroscopic Analysis ◽  
Ionization Mass ◽  
Steroidal Saponins ◽  
Chemical Methods ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Aconitic Acid ◽  
Related Compounds

AbstractPhytochemical investigation of the aerial parts ofSansevieria trifasciata, one of the most common Dracaenaceae plants, has resulted in the isolation of a new dihydrochalcone derivative named trifasciatine C (1), four previously unreported steroidal saponins as two pairs of inseparable regioisomers: trifasciatosides K/L (2/3), M/N (4/5), together with the known 1,2-(dipalmitoyl)-3-O-β-D-galactopyranosylglycerol (6), aconitic acid (7), and 1-methyl aconitic acid (8). Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D nuclear magnetic resonance) and high-resolution electronspray ionization-mass spectrometry, as well as chemical methods and comparison of their spectral data with those of related compounds. Compounds2/3and4/5were evaluated for their antiproliferative activity on Hela cells, and no significant effect was observed.

scholarly journals New Flavonoids from Baeckea Frutescens and their Antioxidant Activity

2008 ◽  
Vol 3 (5) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Tran Hong Quang ◽  
Nguyen Xuan Cuong ◽  
Chau Van Minh ◽  
Phan Van Kiem
Keyword(s):  
Antioxidant Activity ◽  
Ethyl Acetate Extract ◽  
Radical Scavenging ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Dpph Radical ◽  
Aerial Parts ◽  
Baeckea Frutescens ◽  
New Compounds ◽  
Dpph Radical Scavenging

From the ethyl acetate extract of the aerial parts of Baeckea frutescens, a new flavonoid, 6,8-di- C-methylkaempferol (1), and three new flavonoid glycosides, 6,8-di- C-methylkaempferol 3- O-α-L-rhamnopyranoside (2), 6- C-methylquercetin 3- O-α-L-rhamnopyranoside (3), and 6- C-methylquercetin 4′- O-β-D-glucopyranoside (4), along with four known flavonoids were isolated. Their structures were elucidated by extensive spectroscopic methods including 1D and 2D NMR experiments, as well as ESI-MS analysis. All the new compounds were tested for their antioxidant activity in the 1,1-diphenyl-2-pecrylhydrazyl (DPPH) radical scavenging assay system. Compounds 3 and 4 showed potent activity with IC50 values of 12.1 ± 0.5 and 13.5 ± 0.9 (μM), respectively.

Feruloyl sucrose derivatives from Bistorta manshuriensis

2010 ◽  
Vol 88 (6) ◽  
pp. 519-523 ◽  
Author(s):  
Ki Hyun Kim ◽  
Sang Wook Chang ◽  
Kang Ro Lee
Keyword(s):  
Medicinal Plant ◽  
2D Nmr ◽  
Aerial Parts ◽  
Extensive Analysis ◽  
Phytochemical Investigation ◽  
New Compounds ◽  
Chemical Evidence

Bistorta manshuriensis is a well-known Korean medicinal plant traditionally used to treat diarrhea. Phytochemical investigation of the aerial parts of B. manshuriensis led to the isolation of two new feruloyl sucrose derivatives, bistoroside A (1) and bistoroside B (2), together with three known compounds, helonioside A (3), helonioside B (4), and smilaside L (5). The structures of the new compounds were elucidated as (3,6-di-O-Z-feruloyl)-β-D-fructofuranosyl-(1→2)-α-D-glucopyranoside (1) and (3,6-di-O-Z-feruloyl)-β-D-fructofuranosyl-(1→2)-(6′-O-acetyl)-α-D-glucopyranoside (2) on the basis of extensive analysis of 1D and 2D NMR (HMQC and HMBC), HR-FAB-MS, and chemical evidence.

scholarly journals Three Novel Biphenanthrene Derivatives and a New Phenylpropanoid Ester from Aerides multiflora and Their α-Glucosidase Inhibitory Activity

Plants ◽  
2021 ◽  
Vol 10 (2) ◽  
pp. 385
Author(s):  
May Thazin Thant ◽  
Boonchoo Sritularak ◽  
Nutputsorn Chatsumpun ◽  
Wanwimon Mekboonsonglarp ◽  
Yanyong Punpreuk ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Competitive Inhibition ◽  
Positive Control ◽  
The Other ◽  
Biological Investigation ◽  
Phytochemical Investigation ◽  
Whole Plants ◽  
New Compounds ◽  
Burk Plot

A phytochemical investigation on the whole plants of Aerides multiflora revealed the presence of three new biphenanthrene derivatives named aerimultins A–C (1–3) and a new natural phenylpropanoid ester dihydrosinapyl dihydroferulate (4), together with six known compounds (5–10). The structures of the new compounds were elucidated by analysis of their spectroscopic data. All of the isolates were evaluated for their α-glucosidase inhibitory activity. Aerimultin C (3) showed the most potent activity. The other compounds, except for compound 4, also exhibited stronger activity than the positive control acarbose. Compound 3 showed non-competitive inhibition of the enzyme as determined from a Lineweaver–Burk plot. This study is the first phytochemical and biological investigation of A. multiflora.

Anti-Cancer and Immunostimulatory Activity of Chromones and Other Constituents from Cassia petersiana

2007 ◽  
Vol 62 (5-6) ◽  
pp. 331-338 ◽  
Author(s):  
Amira M. Gamal-Eldeen ◽  
Pierre C. Djemgou ◽  
Marguérite Tchuendem ◽  
Bonaventure T. Ngadjui ◽  
Pierre Tane ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Inhibitory Activity ◽  
Immunostimulatory Activity ◽  
Nmr Studies ◽  
Benzoic Acid Derivatives ◽  
Cytotoxic Compound ◽  
Phytochemical Investigation ◽  
Anti Cancer ◽  
Anti Inflammatory ◽  
New Compounds

Phytochemical investigation of Cassia petersiana Bolle leaves afforded four new compounds, including two chromone derivatives, 7-acetonyl-5-hydroxy-2-methylchromone (petersinone 1, 1) and 7-(propan-2ʹ-ol-1ʹ-yl)-5-hydroxy-2-methylchromone (petersinone 2, 2), two benzoic acid derivatives, 5-methyl-3-(propan-2ʹ-on-1ʹ-yl) benzoic acid (petersinone 3, 3) and 5-(methoxymethyl)-3-(propan-2ʹ-ol-1ʹ-yl) benzoic acid (petersinone 4, 4), and glyceryl- 1-tetracosanoate (6), in addition to the known compound sistosterol-3-β-ᴅ-glycoside (5). The structures of these compounds were determined by comprehensive NMR studies, including DEPT, COSY, HMQC, HMBC, MS and IR.Compounds 1, 2, 5 and 6 were tested for antioxidant, anti-cancer and immunostimulatory properties. The biological investigations indicated that compound 6, among others, possessed the highest anti-cancer activity against hepatocellular carcinoma, immunoproliferative activity via induction of T-lymphocytes and macrophage proliferation, anti-inflammatory activity as indicated by NO inhibition, and antioxidant activity against DPPH radicals. Moreover, compound 5 was the most effective cytotoxic compound against breast carcinoma and stimulated a consistent immunoproliferative effect on lymphocytes and macrophages combined with strong NO inhibitory activity, while compound 1 was promising as immunoproliferative agent and may act as anti-inflammatory agent as a consequence of its NO inhibitory activity.

Cotonoates A and B, New Aromatic Esters from Cotoneaster racemiflora

2008 ◽  
Vol 63 (10) ◽  
pp. 1219-1222 ◽  
Author(s):  
Shafiullah Khan ◽  
Shazia Yasmeen ◽  
Nighat Afza ◽  
Abdul Malik ◽  
Lubna Iqbal ◽  
...  
Keyword(s):  
Spectral Analysis ◽  
Methanolic Extract ◽  
Soluble Fraction ◽  
2D Nmr ◽  
Aromatic Esters ◽  
Phytochemical Investigation ◽  
Nmr Techniques ◽  
Inhibitory Activities ◽  
New Compounds

AbstractPhytochemical investigation of the chloroform soluble fraction of the methanolic extract of Cotoneaster racemiflora resulted in the isolation of two new aromatic esters named cotonoates A (1) and B (2) along with the known compound methyl 3,4-dihydroxy-5-methoxybenzoate (3). The structures of the new compounds have been assigned on the basis of spectral analysis including 1D and 2D NMR techniques. Compound 3 shows significant antioxidant and lipoxygenase inhibitory activities.

Polyprenylated Phloroglucinols from Hypericum maculatum

2015 ◽  
Vol 10 (7) ◽  
pp. 1934578X1501000
Author(s):  
Paraskev T. Nedialkov ◽  
Georgi Momekov ◽  
Zlatina K. Kokanova-Nedialkova ◽  
Jörg Heilmann
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Spectral Methods ◽  
Tumor Cell Lines ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Phloroglucinol Derivatives ◽  
New Compounds ◽  
First Time

A detailed phytochemical investigation of the dichloromethane extract of the aerial parts of Hypericum maculatum Crantz. led to the isolation of four new (2-5) and six known (1a/b, 6-10) polyprenylated phloroglucinol derivatives. The new compounds were identified by means of spectral methods (MS, NMR, IR, UV) as ( E)-4-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-2-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl isobutyrate (2), ( E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-4-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl isobutyrate (3), ( E)-4-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-2-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylbutanoate (4) and ( E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-4-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylbutanoate (5). The known compounds have been identified as hyperpolyphyllirin/hyperibine J (1a/b), erectquione A (6), ( E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one (7), ( E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one (8), 1-(5,7-dihydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)chroman-8-yl)-2-methylpropan-1-one (9) and 1-(6,8-dihydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-5-yl)-2-methylpropan-1-one (10). The stereochemistry of 1a is described for the first time. The cytotoxicity of 1-6 on SKW-3, BV-173 and K-562 tumor cell lines was determined using MTT based assays.

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