Goniothalamin-Related Styryl Lactones: Isolation, Synthesis, Biological Activity and Mode of Action

2020 ◽  
Vol 26 (41) ◽  
pp. 7372-7451 ◽  
Author(s):  
Ronaldo Aloise Pilli ◽  
Ian de Toledo ◽  
Matheus Andrade Meirelles ◽  
Thiago Augusto Grigolo
Keyword(s):  
Biological Activity ◽  
Secondary Metabolites ◽  
Mechanism Of Action ◽  
Mode Of Action ◽  
Folk Medicine ◽  
Biological Profile ◽  
Natural Sources ◽  
Biological Aspects ◽  
First Time ◽  
Styryl Lactones

: This review covers the chemistry and biological aspects of goniothalamin-related styryl lactones isolated from natural sources. This family of secondary metabolites has been reported to display diverse uses in folk medicine, but only a limited number of these compounds have been throughly investigated regarding their biological profile. Herein, we cover the goniothalamin-related styryl lactones having a C6-C3-C4 framework which appeared in the literature for the first time in the period 2000-2017, and the reports on the synthesis, biological activity and mechanism of action which were published from 2007-2017.

scholarly journals Isolation and Identification of the Five Novel Flavonoids from Genipa americana Leaves

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2521 ◽  
Author(s):  
Larissa Silva ◽  
Jovelina Alves ◽  
Emerson da Silva Siqueira ◽  
Manoel de Souza Neto ◽  
Lucas Abreu ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Medicinal Plant ◽  
Ethyl Acetate ◽  
Folk Medicine ◽  
Ethyl Acetate Fraction ◽  
Spectroscopic Methods ◽  
Isolation And Identification ◽  
1H And 13C Nmr ◽  
Chemical Structures ◽  
First Time

Genipa americana is a medicinal plant popularly known as “jenipapo”, which occurs in Brazil and belongs to the Rubiaceae family. It is a species widely distributed in the tropical Central and South America, especially in the Cerrado biome. Their leaves and fruits are used as food and popularly in folk medicine to treat anemias, as an antidiarrheal, and anti-syphilitic. Iridoids are the main secondary metabolites described from G. americana, but few studies have been conducted with their leaves. In this study, the aim was to chemical approach for identify the main compounds present at the extract of G. americana leaves. The powdered leaves were extracted by maceration with EtOH: water (70:30, v/v), following liquid-liquid partition with petroleum ether, chloroform, ethyl acetate and n-butanol. A total of 13 compounds were identified. In addition three flavonoids were isolated from the ethyl acetate fraction: quercetin-3-O-robinoside (GAF 1), kaempferol-3-O-robinoside (GAF 2) and isorhamnetin-3-O-robinoside (GAF 3) and, from n-butanol fraction more two flavonoids were isolated, kaempferol-3-O-robinoside-7-O-rhamnoside (robinin) (GAF 4) and isorhamnetin-3-O-robinoside-7-rhamnoside (GAF 5). Chemical structures of these five flavonoids were elucidated using spectroscopic methods (MS, 1H and 13C-NMR 1D and 2D). These flavonoids glycosides were described for the first time in G. americana.

Secondary metabolites of Helichrysum plicatum DC. subsp. plicatum flowers as strong carbonic anhydrase, cholinesterase and α-glycosidase inhibitors

2020 ◽  
Vol 75 (5-6) ◽  
pp. 153-159
Author(s):  
Tuba Aydin
Keyword(s):  
Secondary Metabolites ◽  
Carbonic Anhydrase ◽  
Folk Medicine ◽  
Inhibitory Effect ◽  
Glycosidase Inhibitors ◽  
Meoh Extract ◽  
Chemical Structures ◽  
Liquid Chromatography Tandem Mass ◽  
First Time

AbstractHelichrysum plicatum species are used in Turkish folk medicine as lithagogue, diuretic, and nephritic. Research on the methanol (MeOH) extract of flowers of H. plicatum DC. subsp. plicatum resulted in the isolation of eight known compounds (1–8). The chemical structures of the compounds were determined as β-sitosterol (1), apigenin (2), nonacosanoic acid (3), astragalin (4), β-sitosterol-3-O-β-D-glucopyranoside (5), helichrysin A (6), helichrysin B (7), and isosalipurposide (8) by spectroscopic and chromatographic/spectrometric methods, including 1D and 2D nuclear magnetic resonance and liquid chromatography-tandem mass spectrometry. Nonacosanoic acid (3) was isolated for the first time from H. plicatum DC. subsp. plicatum. The MeOH extract and isolated compounds were evaluated for their in vitro human carbonic anhydrase I (hCAI) and II (hCAII), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase inhibitory activities. The IC50 values of H. plicatum DC. subsp. plicatum MeOH extract for hCAI, hCAII, AChE, BChE, and α-glycosidase were found to be 77.87, 52.90, 115.50, 117.46, and 81.53 mg/mL, respectively. The compounds showed IC50 values of 1.43–4.47, 1.40–4.32, 1.69–2.90, 1.09–3.89, and 1.61–3.80 μM against hCAI, hCAII, AChE, BChE, and α-glycosidase, respectively. In summary, H. plicatum DC. subsp. plicatum secondary metabolites demonstrated strong inhibitory effects especially against hCAI and hCAII, whereas the MeOH extract showed a weak inhibitory effect on all enzymes.

Isolation of secondary metabolites from the Iranian medicinal plant Eremurus persicus

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Javad Mottaghipisheh ◽  
Norbert Kúsz ◽  
Judit Hohmann ◽  
Yu-Chi Tsai ◽  
Dezső Csupor
Keyword(s):  
Secondary Metabolites ◽  
Medicinal Plant ◽  
Methyl Ether ◽  
Crude Extract ◽  
Folk Medicine ◽  
Isolation And Identification ◽  
Widespread Application ◽  
Chromatographic Techniques ◽  
Endemic Medicinal Plant ◽  
First Time

AbstractEremurus persicus (Jaub. & Spach) Boiss. belonging to Xanthorrhoeaceae family is an endemic medicinal plant widely distributed in Iran. Its leaves have been traditionally used as a food and also as medicinal plant. Regarding the widespread application of E. persicus in Iranian folk medicine, and the insignificant investigation of its components, this study aimed at the isolation and identification of major secondary metabolites of this plant. By applying various chromatographic techniques, corchoionoside A (1), 4-amino-4-carboxychroman-2-one (2), isoorientin (3), ziganein 5-methyl ether (4), auraptene (5), and imperatorin (6) were isolated from the EtOAc and CHCl3 fractions of the crude extract. Except isoorientin (3), all the identified phytoconstituents were reported for the first time from Eremurus genus.

scholarly journals Secondary metabolites of Hypericum monogynum from Pakistan

2009 ◽  
Vol 74 (2) ◽  
pp. 129-132 ◽  
Author(s):  
Mohammad Arfan ◽  
Naila Raziq ◽  
Ivana Aljancic ◽  
Slobodan Milosavljevic
Keyword(s):  
Secondary Metabolites ◽  
Chlorobenzoic Acid ◽  
Natural Sources ◽  
Aerial Parts ◽  
First Time

4-Chlorobenzoic acid (1), quercitrin (2), astilbin (3), along with ?-sitosterol, ?-sitosterol, friedelin and ?-amyrin were isolated from the aerial parts of Hypericum monogynum. Whereas compound 1 was isolated for the first time from natural sources, flavanonol 3 was not found before in these species.

The Pattern of Acetylation Defines the Priming Activity of Chitosan Tetramers

2019 ◽  
Author(s):  
Sven Basa ◽  
Malathi Nampally ◽  
Talita Honorato ◽  
Subha Narayan Das ◽  
Appa Rao Podile ◽  
...  
Keyword(s):  
Biological Activity ◽  
Degree Of Polymerization ◽  
Chitosan Oligosaccharides ◽  
Degree Of Acetylation ◽  
Bona Fide ◽  
First Time ◽  
Priming Activity

The biological activity of chitosans depends on their degree of polymerization (DP) and degree of acetylation (DA). However, information could also be carried by the pattern of acetylation (PA): the sequence of <i>β</i>-1,4-linked glucosamine (deacetylated/D) and <i>N</i>-acetylglucosamine (acetylated/A) units. To address this hypothesis, we prepared partially-acetylated chitosan oligosaccharides from a chitosan polymer (DA=35%, DP<sub>w</sub>=905) using recombinant chitosan hydrolases with distinct substrate and cleavage specificities. The mixtures were separated into fractions DP4–DP12, which were tested for elicitor and priming activities in rice cells. We confirmed that both activities were influenced by DP, <a>but also observed apparent DA-dependent priming activity, with the ADDD+DADD fraction proving remarkably effective</a>. We then compared all four mono-acetylated tetramers prepared using different chitin deacetylases and observed significant differences in priming activity. This demonstrates for the first time that PA influences the biological activity of chitosans, which can now be recognized as <i>bona fide</i> information-carrying molecules

The Pattern of Acetylation Defines the Priming Activity of Chitosan Tetramers

2019 ◽  
Author(s):  
Sven Basa ◽  
Malathi Nampally ◽  
Talita Honorato ◽  
Subha Narayan Das ◽  
Appa Rao Podile ◽  
...  
Keyword(s):  
Biological Activity ◽  
Degree Of Polymerization ◽  
Chitosan Oligosaccharides ◽  
Degree Of Acetylation ◽  
Bona Fide ◽  
First Time ◽  
Priming Activity

The biological activity of chitosans depends on their degree of polymerization (DP) and degree of acetylation (DA). However, information could also be carried by the pattern of acetylation (PA): the sequence of <i>β</i>-1,4-linked glucosamine (deacetylated/D) and <i>N</i>-acetylglucosamine (acetylated/A) units. To address this hypothesis, we prepared partially-acetylated chitosan oligosaccharides from a chitosan polymer (DA=35%, DP<sub>w</sub>=905) using recombinant chitosan hydrolases with distinct substrate and cleavage specificities. The mixtures were separated into fractions DP4–DP12, which were tested for elicitor and priming activities in rice cells. We confirmed that both activities were influenced by DP, <a>but also observed apparent DA-dependent priming activity, with the ADDD+DADD fraction proving remarkably effective</a>. We then compared all four mono-acetylated tetramers prepared using different chitin deacetylases and observed significant differences in priming activity. This demonstrates for the first time that PA influences the biological activity of chitosans, which can now be recognized as <i>bona fide</i> information-carrying molecules

The impact of traditional plants and their secondary metabolites in the discovery of COVID-19 treatment

2020 ◽  
Vol 26 ◽  
Author(s):  
Shabana Bibi ◽  
Ayesha Sarfraz ◽  
Ghazala Mustafa ◽  
Zeeshan Ahmed ◽  
Muhammad Aurang Zeb ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Test System ◽  
Chemical Information ◽  
System Type ◽  
The Family ◽  
Comprehensive Search ◽  
Coronavirus Infection ◽  
The Impact ◽  
First Time ◽  
Plant Sources

Background: Coronavirus Disease-2019 belongs to the family of viruses which cause a serious pneumonia along with fever, breathing issues and infection of lungs for the first time in China and later spread worldwide. Objective: Several studies and clinical trials have been conducted to identify potential drugs and vaccines for Coronavirus Disease-2019. The present study listed natural secondary metabolites identified from plant sources with antiviral properties and could be safer and tolerable treatment for Coronavirus Disease-2019. Methods: A comprehensive search on the reported studies was conducted using different search engine such as Google scholar, SciFinder, Sciencedirect, Medline PubMed, and Scopus for the collection of research articles based on plantderived secondary metabolites, herbal extracts, and traditional medicine for coronavirus infections. Results: Status of COVID-19 worldwide and information of important molecular targets involved in COVID-19 is described and through literature search, is highlighted that numerous plant species and their extracts possess antiviral properties and studied with respect to Coronavirus treatments. Chemical information, plant source, test system type with mechanism of action for each secondary metabolite is also mentioned in this review paper. Conclusion: The present review has listed plants that have presented antiviral potential in the previous coronavirus pandemics and their secondary metabolites which could be significant for the development of novel and a safer drug which could prevent and cure coronavirus infection worldwide.

Strategies for Oral Delivery of Metal-Saturated Lactoferrin

2019 ◽  
Vol 20 (11) ◽  
pp. 1046-1051 ◽  
Author(s):  
Przemysław Gajda-Morszewski ◽  
Klaudyna Śpiewak-Wojtyła ◽  
Maria Oszajca ◽  
Małgorzata Brindell
Keyword(s):  
Biological Activity ◽  
Oral Delivery ◽  
Therapeutic Potential ◽  
Structure And Function ◽  
The Difference ◽  
And Function ◽  
First Time

Lactoferrin was isolated and purified for the first time over 50-years ago. Since then, extensive studies on the structure and function of this protein have been performed and the research is still being continued. In this mini-review we focus on presenting recent scientific efforts towards the elucidation of the role and therapeutic potential of lactoferrin saturated with iron(III) or manganese(III) ions. The difference in biological activity of metal-saturated lactoferrin vs. the unmetalated one is emphasized. The strategies for oral delivery of lactoferrin, are also reviewed, with particular attention to the metalated protein.

Isolation and HPLC Determination of the Chemical Components of Gentianella acuta (Michx.) Hulten

2018 ◽  
Vol 15 (1) ◽  
pp. 21-33
Author(s):  
Ying Wei ◽  
Yongqiao Liu ◽  
Yifan Hele ◽  
Weiwei Sun ◽  
Yang Wang ◽  
...  
Keyword(s):  
Medicinal Plant ◽  
High Speed ◽  
Chemical Constituents ◽  
Folk Medicine ◽  
Gradient Elution ◽  
Chemical Components ◽  
Isolation And Characterization ◽  
Major Chemical ◽  
Main Components ◽  
First Time

Background: Gentianella acuta (Michx.) Hulten is an important type of medicinal plant found in several Chinese provinces. It has been widely used in folk medicine to treat various illnesses. However, there is not enough detailed information about the chemical constituents of this plant or methods for their content determination. Objective: The focus of this work is the isolation and characterization of the major chemical constituents of Gentianella acuta, and developing an analytical method for their determination. Methods: The components of Gentianella acuta were isolated using (1) ethanol extraction and adsorption on macroporous resin. (2) and ethyl acetate extraction and high speed countercurrent chromatography. A HPLC-DAD method was developed using a C18 column and water-acetonitrile as the mobile phase. Based on compound polarities, both isocratic and gradient elution methods were developed. Results: A total of 29 compounds were isolated from this plant, of which 17 compounds were isolated from this genus for the first time. The main components in this plant were found to be xanthones. The HPLC-DAD method was developed and validated for their determination, and found to show good sensitivity and reliability. Conclusion: The results of this work add to the limited body of work available on this important medicinal plant. The findings will be useful for further investigation and development of Gentianella acuta for its valuable medicinal properties.

Apoptosis Caused by Triterpenes and Phytosterols and Antioxidant Activity of an Enriched Flavonoid Extract from Passiflora mucronata

2019 ◽  
Vol 18 (10) ◽  
pp. 1405-1416 ◽  
Author(s):  
Isabel C.V. da Silva ◽  
Goran N. Kaluđerović ◽  
Pollyana F. de Oliveira ◽  
Denise O. Guimarães ◽  
Carla H. Quaresma ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Cell Lines ◽  
Oleanolic Acid ◽  
Folk Medicine ◽  
Hexane Fraction ◽  
Cytotoxicity Test ◽  
B16f10 Cell ◽  
Dpph Method ◽  
Melanoma B16f10 ◽  
First Time

Background: P. mucronata (Pm) comes from South America, Brazil and is characterized as “Maracujá de Restinga”. It is used in folk medicine for its soothing properties and in treating insomnia. Objective: The present study for the first time analyzed the antioxidant and cytotoxicity of the hydroalcoholic leaves extract and fractions from Pm. Method: The cytotoxicity test will be evaluated by different assays (MTT and CV) against human prostate cancer (PC3) and mouse malignant melanoma (B16F10) cell lines, and the antioxidant test by DPPH method. Results: β-Amyrin, oleanolic acid, β-sitosterol and stigmasterol were isolated of the most active, hexane fraction. These substances were tested against the tumor cell lines: β-sitosterol and stigmasterol showed the most relevant activity to PC3 in CV assay and, oleanolic acid to B16F10 by the MTT assay. In addition, it was possible to indicate that the mode of cell death for stigmasterol, presumably is apoptosis. In terms of antioxidant activity, the hydroalcoholic leaves extract presented higher activity (EC50 133.3 µg/mL) compared to the flower (EC50 152.3 µg/mL) and fruit (EC50 207.9 µg/mL) extracts. By the HPLC-MS, it was possible to identify the presence of flavones in the leaf extract (isoschaftoside, schaftoside, isovitexin, vitexin, isoorientin, orientin). Conclusions: P. mucronata hexane fraction showed promising cytotoxic effect against cancer cell lines, and stigmasterol contributes to this activity, inducing apoptosis of these cells. Furthermore, as other Passiflora species, Pm extract showed antioxidant activity and flavones are its major phenolic compounds.

Sign in / Sign up

Export Citation Format

Share Document