scholarly journals Nine Unique Iridoids and Iridoid Glycosides From Patrinia scabiosaefolia

2021 ◽  
Vol 9 ◽  
Author(s):  
Zhenhua Liu ◽  
Yun Niu ◽  
Li Zhou ◽  
Lijun Meng ◽  
Sitan Chen ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Chemical Constituents ◽  
Iridoid Glycosides ◽  
Chinese Herb ◽  
2D Nmr ◽  
Iridoid Glycoside ◽  
Cytotoxic Activities ◽  
Medicinal Value ◽  
Patrinia Scabiosaefolia ◽  
Mcf 7

Patrinia scabiosaefolia is a medical and edible Chinese herb with high nutritional and medicinal value. The continuing study of its chemical constituents led to the discovery of nine unique iridoids and iridoid glycosides, including three new iridoids (1-3) and six previously unknown irioid glycosides (5-10), and one known compound (4). Among them, compound 1 was a deformed iridoid, while compounds 3, 5-7, and 10 formed a new ring in their skeletons which was uncommon in this genus. For compound 3, the new ring existed between C-3 and C-10, while a 1,3-dioxane appeared between C-7 and C-10 in compounds 5-7 and 10. Moreover, compound 10 was a bis-iridoid glycoside, which was the first reported in P. scabiosaefolia. And the sugar of irioid glycosides (5-10) was glucose at C-11, except in 9 which had a 5-deoxyglucose moiety. All their structures were confirmed based on the extensive spectroscopic analysis, including IR, UV, HR-ESI-MS, ECD, and 1D- and 2D-NMR experiments. Their cytotoxic activities against HL-60, A-549, SMMC-7721, MCF-7, SW480 were also tested.

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.

Iridoid Glycosides from Lagotis alutacea

2014 ◽  
Vol 69 (7) ◽  
pp. 835-838 ◽  
Author(s):  
Li-Juan Yang ◽  
Na Zhang ◽  
Na Liu ◽  
Xiao-Dong Yang
Keyword(s):  
Cytotoxic Activity ◽  
Spectroscopic Analysis ◽  
Iridoid Glycosides ◽  
Iridoid Glycoside ◽  
Mcf 7

One new iridoid glycoside, lagotisoside F (1), was isolated from Lagotis alutacea, along with three known analogs, lagotisoside D (2), 6-O-α-L-(4″-O-(E)-cinnamoyl) rhamnopyranosyl-catapol (3) and globularin (4). Their structures were elucidated by extensive spectroscopic analysis and by comparison with data reported in the literature. Compounds 1-4were evaluated for cytotoxic activity against HL-60, MCF-7, A549, SW480, and SMMC-7721 cells and exhibited no appreciable activity with IC50 values above 40 μM.

scholarly journals Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (2) ◽  
pp. 1934578X2199334
Author(s):  
Do Thi Trang ◽  
Bui Huu Tai ◽  
Dan Thuy Hang ◽  
Pham Hai Yen ◽  
Phan Thi Thanh Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Spectral Data ◽  
Absolute Configuration ◽  
Marine Sponge ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Extensive Analysis ◽  
First Time ◽  
Tddft Method ◽  
Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha

2021 ◽  
Vol 76 (5-6) ◽  
pp. 213-218
Author(s):  
Usama W. Hawas ◽  
Lamia T. Abou El-Kassem ◽  
Radwan Al-farawati ◽  
Fekri M. Shaher
Keyword(s):  
2D Nmr ◽  
Cytotoxic Activities ◽  
Dpph Radical ◽  
Srb Assay ◽  
Phenolic Metabolites ◽  
2D Nmr Spectra ◽  
New Compounds ◽  
Benzaldehyde Derivatives ◽  
Mcf 7

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.

scholarly journals Chemical Constituents of Cordyceps cicadae

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Zhi-Bo Chu ◽  
Jun Chang ◽  
Ying Zhu ◽  
Xun Sun
Keyword(s):  
Amino Acids ◽  
Spectroscopic Analysis ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Cordyceps Cicadae ◽  
Nmr Techniques ◽  
Dopamine Analogues

One new bifuran derivative (1), together with fourteen known compounds, were isolated from Cordyceps cicadae X. Q. Shing. The known compounds included nine nucleosides, uracil (2), uridine (3), 2′-deoxyuridine (4), 2′-deoxyinosine (5), guanosine (6), 2′-deoxyguanosine (7), thymidine (8), adenosine (9), and 2′-deoxyadenosine (10); three amino acids tryptophan (11), phenylalanine (12), and tyrosine (13); and two dopamine analogues N-acetylnoradrenaline (14) and its dimer, trans–2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-( N-acetyl-2″-amino-ethylene)-1,4-benzodioxane (15). Their structures were decisively elucidated by spectroscopic analysis, including 1D and 2D NMR techniques.

scholarly journals Chemical Constituents of the Aerial Parts of Euphorbia Nematocypha

2016 ◽  
Vol 11 (2) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Chen Xu ◽  
Hai-Yang Jia ◽  
Bo Zuo ◽  
Zhi-Xin Liao ◽  
Lan-Ju Ji ◽  
...  
Keyword(s):  
Oleanolic Acid ◽  
Ellagic Acid ◽  
Betulinic Acid ◽  
Methylene Chloride ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Aerial Parts ◽  
Methylene Chloride Extract ◽  
Oleanane Triterpenoid

Chemical constituents of the dried aerial parts of Euphorbia nematocypha were investigated. A new oleanane triterpenoid, trans, trans-2′,4′-hexadienedioicacid-1′-β-amyrin ester (1), together with, β-amyrin (2), β-amyrin acetate (3), betulinic acid (4), ellagic acid (5), oleanolic acid (6), β-sitosterol (7), kaempferol (8), quercetin (9), lupeol (10) and pseudo-taraxasterol (11) were isolated from the methylene chloride extract. Their structures were elucidated on the basis of extensive spectroscopic (1D- & 2D-NMR) and ESI-MS analysis and comparison with data reported in the literature. The new isolated triterpenoid showed moderate cytotoxic activities against HeLa and MCF-7cell lines.

Characterization, crystal structure and cytotoxic activity of a rare iridoid glycoside from Lonicera saccata

2020 ◽  
Vol 76 (3) ◽  
pp. 269-275
Author(s):  
Zhaoxia Qu ◽  
Li Ma ◽  
Qi Zhang ◽  
Renyong Yang ◽  
Guige Hou ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Iridoid Glycosides ◽  
Three Dimensional ◽  
2D Nmr ◽  
Crystallographic Analysis ◽  
Iridoid Glycoside ◽  
Membered Ring ◽  
Mtt Method ◽  
Liver Hepatocellular Carcinoma

A new iridoid glycoside, methyl (3R,4R,4aS,7S,7aR)-3-hydroxy-7-methyl-5-oxooctahydrocyclopenta[c]pyran-4-carboxylate-3-O-β-D-(1′S,2′R,3′S,4′S,5′R)-glucopyranoside, named loniceroside A, C17H26O10, (1), was obtained from the aerial parts of Lonicera saccata. Its structure was established based on an analysis of spectroscopic data, including 1D NMR, 2D NMR and HRESIMS, and the configurations of the chiral C atoms were determined by X-ray crystallographic analysis. The single-crystal structure reveals that the cyclopenta[c]pyran scaffold is formed from a five-membered ring and a chair-like six-membered ring connected through two bridgehead chiral C atoms. In the solid state, the glucose group of (1) plays an important role in constructing an unusual supramolecular motif. The structure analysis revealed adjacent molecules linked together through intermolecular O—H...O hydrogen bonds to generate a banded structure. Furthermore, the banded structures are linked into a three-dimensional network by interesting hydrogen bonds. Biogenetically, compound (1) carries a glucopyranosyloxy moiety at the C-3 position, representing a rare structural feature for naturally occurring iridoid glycosides. The growth inhibitory effects against human cervical carcinoma cells (Hela), human lung adenocarcinoma cells (A549), human acute mononuclear granulocyte leukaemia (THP-1) and the human liver hepatocellular carcinoma cell line (HepG2) were evaluated by the MTT method.

scholarly journals Flavonoid, Phenylethanoid and Iridoid Glycosides from Globularia aphyllanthes

2009 ◽  
Vol 64 (2) ◽  
pp. 252-256 ◽  
Author(s):  
Hasan Kırmızıbekmez ◽  
Carla Bassarello ◽  
Sonia Piacente ◽  
Galip Akaydın ◽  
İhsan Çalış
Keyword(s):  
Spectroscopic Analysis ◽  
Iridoid Glycosides ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Phenylethanoid Glycosides ◽  
Meoh Extract ◽  
Flavone Glycoside ◽  
Aerial Parts

A new flavone glycoside, 6-hydroxyluteolin 7-O-[6m-benzoyl-β -D-glucopyranosyl-(1 → 2)]-β - D-glucopyranoside (aphyllanthoside, 1) was isolated from the MeOH extract of the aerial parts of Globularia aphyllanthes. Besides this new compound, two flavonoid glycosides (6-hydroxyluteolin 7-O-[6m-(E)-caffeoyl-β -D-glucopyranosyl-(1 → 2)]-β -D-glucopyranoside and isoquercitrin), three phenylethanoid glycosides (verbascoside, rossicaside A, and trichosanthoside A), and 11 iridoid glycosides (aucubin, catalpol, 10-O-benzoylcatalpol, globularin, asperuloside, besperuloside, asperulosidic acid, daphylloside, scandoside, alpinoside and baldaccioside) were also obtained and characterized. Identification of the isolated compounds was carried out by spectroscopic analysis including 1D and 2D NMR experiments as well as HRMS

scholarly journals Anticancer Activities of Chemical Constituents from Leaves and Twigs of Mitrephora winitii

2021 ◽  
Vol 21 (3) ◽  
pp. 699
Author(s):  
Sukee Sukdee ◽  
Puttinan Meepowpan ◽  
Narong Nantasaen ◽  
Siriporn Jungsuttiwong ◽  
Sarinya Hadsadee ◽  
...  
Keyword(s):  
Cancer Cell ◽  
Chemical Constituents ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Anticancer Activities ◽  
Chromatographic Separations ◽  
Chemical Structures ◽  
Anti Cancer ◽  
First Time ◽  
Mcf 7

The genus Mitrephora has been investigated and its anti-inflammatory, anti-bacterial and anti-parasitical activities were examined along with its potential as an anti-cancer cell line and inhibitor for platelet aggregation. In this work, air-dried leaves and twigs of M. winitii were grounded and extracted with n-hexane, ethyl acetate and methanol, respectively. Chromatographic separations of these extracts led to the isolation of three known compounds and one new compound (compound 2). The chemical structures of these were identified using spectroscopic investigation of 1D- and 2D-NMR and the resulting data confirmed these as stigmasterol (1), (3,4-dimethoxyphenyl)(5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)methanol (2), diayangambin (3), and methyl-L-inositol (4). The chemical constituents were reported the first time in M. winitii. Compound 2 showed anti-cancer cell lines with ED50 13.07 µg/mL against KB cells and then was tested for cytotoxicity against MCF-7 cells with ED50 11.77 µg/mL.

scholarly journals Chemical Constituents of the Terrestrial Stems of Ephedra sinica and their PPAR-γ Ligand-Binding Activity

2020 ◽  
Vol 7 (01) ◽  
pp. e12-e16
Author(s):  
Yukiko Matsuo ◽  
Mayu Sasaki ◽  
Haruhiko Fukaya ◽  
Katsunori Miyake ◽  
Riko Takeuchi ◽  
...  
Keyword(s):  
Ligand Binding ◽  
Spectroscopic Analysis ◽  
Binding Assay ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Binding Activity ◽  
Ephedra Sinica ◽  
Ppar Γ ◽  
Bioassay Guided Fractionation ◽  
Ligand Binding Activity

AbstractBioassay-guided fractionation of the MeOH extract of Ephedra sinica terrestrial stems, using a PPAR-γ ligand binding assay, resulted in the isolation of 10 compounds, including one new bisabolane-type sesquiterpenoid (10). The structure of the new compound was determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR. Among the isolated compounds, the sitosterol derivatives (1 and 2), flavonoid glucoside (7), and the new sesquiterpenoid (10), showed significant PPAR-γ ligand-binding activity.

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