scholarly journals 177 Saponins, Including 11 New Compounds in Wild Ginseng Tentatively Identified via HPLC-IT-TOF-MSn, and Differences among Wild Ginseng, Ginseng under Forest, and Cultivated Ginseng

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3371
Author(s):  
Chao-Qun Wang ◽  
Li-Wei Yi ◽  
Lin Zhao ◽  
Yu-Zhen Zhou ◽  
Fang Guo ◽  
...  
Keyword(s):  
Natural Environment ◽  
Mountain Forest ◽  
Characteristic Peak ◽  
Chromatographic Fingerprints ◽  
New Compounds ◽  
First Time ◽  
Peak Pattern ◽  
Wild Ginseng

Wild ginseng (W-GS), ginseng under forest (F-GS, planted in mountain forest and growing in natural environment), and cultivated ginseng (C-GS) were compared via HPLC-DAD and HPLC-IT-TOF-MSn. A total of 199 saponins, including 16 potential new compounds, were tentatively identified from 100 mg W-GS (177 saponins in W-GS with 11 new compounds), F-GS (56 saponins with 1 new compound), and C-GS (60 saponins with 6 new compounds). There were 21 saponins detected from all the W-GS, F-GS, and C-GS. Fifty saponins were only detected from W-GS, including 23 saponins found in ginseng for the first time. Contents of ginsenosides Re (12.36–13.91 mg/g), Rh1 (7.46–7.65 mg/g), Rd (12.94–12.98 mg/g), and the total contents (50.52–55.51 mg/g) of Rg1, Re, Rf, Rb1, Rg2, Rh1, and Rd in W-GS were remarkably higher than those in F-GS (Re 1.22–3.50 mg/g, Rh1 0.15–1.49 mg/g, Rd 0.19–1.49 mg/g, total 5.69–18.74 mg/g), and C-GS (Re 0.30–3.45 mg/g, Rh1 0.05–3.42 mg/g, Rd 0.17–1.68 mg/g, total 2.99–19.55 mg/g). Contents of Re and Rf were significantly higher in F-GS than those in C-GS (p < 0.05). Using the contents of Re, Rf, or Rb1, approximately a half number of cultivated ginseng samples could be identified from ginseng under forest. Contents of Rg1, Re, Rg2, Rh1, as well as the total contents of the seven ginsenosides were highest in ginseng older than 15 years, middle–high in ginseng between 10 to 15 years old, and lowest in ginseng younger than 10 years. Contents of Rg1, Re, Rf, Rb1, Rg2, and the total of seven ginsenosides were significantly related to the growing ages of ginseng (p < 0.10). Similarities of chromatographic fingerprints to W-GS were significantly higher (p < 0.05) for F-GS (median: 0.824) than C-GS (median: 0.745). A characteristic peak pattern in fingerprint was also discovered for distinguishing three types of ginseng. Conclusively, wild ginseng was remarkably superior to ginseng under forest and cultivated ginseng, with ginseng under forest slightly closer to wild ginseng than cultivated ginseng. The differences among wild ginseng, ginseng under forest, and cultivated ginseng in saponin compositions and contents of ginsenosides were mainly attributed to their growing ages.

scholarly journals Azukisapogenol Triterpene Glycosides from Oxytropis chiliophylla Royle

Molecules ◽  
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.

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 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 New Poly(Propylene Imine) Dendrimer Modified with Acridine and Its Cu(II) Complex: Synthesis, Characterization and Antimicrobial Activity

Materials ◽  
2019 ◽  
Vol 12 (18) ◽  
pp. 3020 ◽  
Author(s):  
Paula Bosch ◽  
Desislava Staneva ◽  
Evgenia Vasileva-Tonkova ◽  
Petar Grozdanov ◽  
Ivanka Nikolova ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Copper Ions ◽  
Spectral Characteristics ◽  
Dilution Method ◽  
Pathogenic Microorganisms ◽  
Paramagnetic Resonance ◽  
Poly Propylene ◽  
New Compounds ◽  
First Time

A second-generation poly(propylene imine) dendrimer modified with acridine and its Cu(II) complex have been synthesized for the first time. It has been found that two copper ions form complexes with the nitrogen atoms of the dendrimeric core by coordinate bonds. The new compounds have been characterized by nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), fourier-transform infrared spectroscopy (FTIR) and fluorescence spectroscopy. The spectral characteristics of the modified dendrimer have been measured in different organic solvents, and a negative fluorescence solvatochromism has been observed. The antimicrobial activity of the dendrimers has been tested against model pathogenic microorganisms in agar and by broth dilution method. The cotton fabric treated with both dendrimers has been evaluated towards pathogenic microorganisms. The obtained modified cotton fabrics have been shown to hamper bacterial growth and to prevent biofilm formation. Dendrimer cytotoxicity has been investigated in vitro in the model HEp-2 cell line.

scholarly journals neo-Clerodane Diterpenoids from Scutellaria galericulata

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Petko I. Bozov ◽  
Plamen N. Penchev ◽  
Josep Coll
Keyword(s):  
Acetone Extract ◽  
Aerial Parts ◽  
Nmr Data ◽  
Clerodane Diterpenoids ◽  
New Compounds ◽  
First Time

Four neo-clerodane diterpenoids, neoajugapyrin A, scutegalerins A and B and scutecolumnin C have been isolated from the acetone extract of the aerial parts of Scutellaria galericulata. Neoajugapyrin A and scutecolumnin C are reported in this species for the first time, whereas scutegalerins A and B are new compounds. NMR data of neoajugapyrin A are discussed in detail to support the proposed revised structure of ajugapyrin A.

scholarly journals Synthesis of Substituted 1,3-Diesters of Glycerol Using Wittig Chemistry

2014 ◽  
Vol 9 (5) ◽  
pp. 1934578X1400900
Author(s):  
Henry IC Lowe ◽  
Ngeh J. Toyang ◽  
Charah T. Watson ◽  
Joseph Bryant
Keyword(s):  
Benzoic Acid ◽  
Natural Compound ◽  
Primary Alcohol ◽  
Synthetic Approach ◽  
Triphenyl Phosphine ◽  
Phosphonium Bromide ◽  
New Compounds ◽  
First Time ◽  
Wittig Reagent

1,3-di-O-Cinnamoyl-glycerol is a natural compound isolated from a Jamaican medicinal plant commonly referred to as Ball moss (Tillandsia recurvata). The synthesis of this compound was achieved via a Wittig chemistry process. The synthetic approach started with acylation of a di-protected glycerol with cinnamoyl chloride, deprotection of the glycerol moiety, reaction of the primary alcohol with bromo acetylbromide followed by treatment with triphenyl phosphine to give the corresponding phosphonium bromide. The phosphonium bromide was then converted in situ to the Wittig reagent which is the basis for a novel route to 1,3-di-O-cinnamoyl glycerol. Four analogs were also synthesized, three of which are new and are being reported in this article for the first time. The new compounds include 3-(3,4-diemthoxy-phenyl)-acrylic acid 2-hydroxy-3-(3-ptolyl-acryloyloxy)-propyl ester (3), 2-acetoxy-5-((E)-3-(3-((E’)-3-(3,4-dimethoxyphenyl)acryloyloxy)-2-hydropropoxy)-3-oxoprop-1-enyl)benzoic acid (4) and 4-((E)-3-(3-((E)-3-(3,4-dimethoxyphenyl)acryloyloxy)-2-hydropropoxy)-3-oxoprop-1-enyl)benzoic acid (5). The compounds showed no activity in our anticancer assay.

scholarly journals Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 164 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wan Liu ◽  
Runzhu Fan ◽  
Shouye Han ◽  
Yuanli Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Chemical Study ◽  
Positive Control ◽  
Hydroxyl Group ◽  
Etoac Extract ◽  
The Third ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time

A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

scholarly journals New Compounds RE(Zn,Al)8 and Yb4Zn20.3Al12.7 and their Crystal Structures

2006 ◽  
Vol 61 (7) ◽  
pp. 779-784 ◽  
Author(s):  
Ol’ga Stel’makhovych ◽  
Yurij Kuz’ma
Keyword(s):  
Intermetallic Compound ◽  
Crystal Structures ◽  
Structure Type ◽  
Type Structure ◽  
Space Group ◽  
X Ray ◽  
Structure Space ◽  
New Compounds ◽  
First Time ◽  
The Relationship

The crystal structures of several new compounds have been determined using X-ray analysis. The intermetallic compound HoZn5Al3 (a = 8.586(3), c = 16.538(5) Å , RF = 0.0413, RW = 0.0521) has its own structure type (space group I4/mmm), which has been found for the first time. The following compounds are isostructural with the previous one: YZn5.52Al2.48 (a = 8.6183(1), c = 16.5048(3) Å , RI = 0.078, RP = 0.116), DyZn4.96Al3.04 (a = 8.5887(1), c = 16.5002(3) Å , RI = 0.077, RP = 0.114), ErZn5.37Al2.63 (a = 8.5525(2), c =16.3997(5) Å , RI = 0.081, RP = 0.111), TmZn5.64Al2.36 (a = 8.70429(8), c = 16.3943(4) Å , RI = 0.088, RP = 0.095), LuZn5.58Al2.42 (a = 8.5616(1), c= 16.3052(3) Å , RI =0.081, RP =0.101). The intermetallic compound Yb4Zn20.3Al12.7 (a = 8.6183(1), c = 16.5048(3) Å , RI = 0.085, RP = 0.112) adopts the Yb8Cu17Al49 - type structure (space group I4/mmm). The relationship between the HoZn5Al3-type and the Yb8Cu17Al49-type structures is discussed.

Limonoids from Aphanamixis polystachya Leaves and Their Interaction with Hsp90

Planta Medica ◽  
2018 ◽  
Vol 84 (12/13) ◽  
pp. 964-970 ◽  
Author(s):  
César Muñoz Camero ◽  
Antonio Vassallo ◽  
Marinella De Leo ◽  
Abeer Temraz ◽  
Nunziatina De Tommasi ◽  
...  
Keyword(s):  
Molecular Chaperone ◽  
Natural Compounds ◽  
Spectroscopic Methods ◽  
Phytochemical Study ◽  
Phenolic Derivatives ◽  
New Compounds ◽  
Type 3 ◽  
First Time

AbstractA phytochemical study of n-hexane, CHCl3, and CHCl3-MeOH extracts of Aphanamixis polystachya leaves led to the isolation of 10 compounds. Five of them turned out to be new natural compounds, including two mexicanolide-type (1, 2) and three polyoxyphragmalin-type (3–5) limonoids, together with two known andirobin-type limonoids (6, 7) and three phenolic derivatives. The structures of the new compounds were established on the basis of spectroscopic methods to be 8-hydro-14,15-en-cabralin (1), 3-deacetyl-8-hydro-cabralin-14,15-en-3-one (2), 20,22-dihydroxy-21,23-dimethoxytetrahydrofuran khayanolide A (3), 1-deacetyl-3-dehydroxy-3-oxokhaysenelide E (4), and meliaphanamixin A (5). All compounds were isolated for the first time from this species. The ability of the isolated limonoids to interact with the molecular chaperone Hsp90 was tested. Compounds 6 and 7 were the most active.

scholarly journals New Compounds from Leaves of Smallanthus sonchifolius

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400
Author(s):  
Xiang Zheng ◽  
Gai Kuo ◽  
Dou De-Qiang ◽  
Kang Ting-Guo ◽  
Shi Yu-Yuan ◽  
...  
Keyword(s):  
Benzyl Alcohol ◽  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Trienoic Acid ◽  
Octadecatrienoic Acid ◽  
Smallanthus Sonchifolius ◽  
New Compounds ◽  
First Time ◽  
Chemical Evidence

A new octadecatrienoic acid and a new benzyl glycoside, along with a known compound, were isolated from the leaves of Smallanthus sonchifolius. The structures of the two new compounds were elucidated as 13(R)-hydroxy-octadeca-(9E,11E,15Z)-trienoic acid (1) and benzyl alcohol 7-O-α-L-arabinopyranosyl(1″→2′)-β-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence. The known compound was identified as 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trienoic acid (3) by comparison of its spectral data with that reported. Compound 3 was isolated for the first time from the title plant.

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