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Molecules (Basel, Switzerland) Jun 2024L. (Apiaceae) is a medicinal plant with a well-documented history in phytotherapy. The aim of the present work was to isolate isopimpinellin (5,8-methoxypsoralen; IsoP)...
L. (Apiaceae) is a medicinal plant with a well-documented history in phytotherapy. The aim of the present work was to isolate isopimpinellin (5,8-methoxypsoralen; IsoP) from the fruit of this plant and evaluate its biological activity against selected tumor cell lines. The methanol extract obtained with the use of an accelerated solvent extraction (ASE) method was the most suitable for the quantitative analysis of coumarins in the fruit matrix. The coumarin content was estimated by RP-HPLC/DAD, and the amount of IsoP was found to be 404.14 mg/100 g dry wt., constituting 24.56% of the total coumarin fraction (1.65 g/100 g). This, along with the presence of xanthotoxin (368.04 mg/100 g, 22.36%) and bergapten (253.05 mg/100 g, 15.38%), confirmed fruits as an excellent source of these compounds. IsoP was isolated (99.8% purity) by combined liquid chromatography/centrifugal partition chromatography (LC/CPC) and tested for the first time on its antiproliferative activity against human colorectal adenocarcinoma (HT29, SW620), osteosarcoma (Saos-2, HOS), and multiple myeloma (RPMI8226, U266) cell lines. MTT assay results (96 h incubation) demonstrated a dose- and cell line-dependent decrease in cell proliferation/viability, with the strongest effect of IsoP against the Saos-2 cell line (IC50; 42.59 µM), medium effect against U266, HT-29, and RPMI8226 (IC50 = 84.14, 95.53, and 105.0 µM, respectively), and very weak activity against invasive HOS (IC50; 321.6 µM) and SW620 (IC50; 711.30 µM) cells, as well as normal human skin fibroblasts (HSFs), with IC50; 410.7 µM. The mechanistic study on the Saos-2 cell line showed that IsoP was able to reduce DNA synthesis and trigger apoptosis via caspase-3 activation. In general, IsoP was found to have more potency towards cancerous cells (except for HOS and SW620) than against healthy cells. The Selective Index (SI) was determined, underlining the higher selectivity of IsoP towards cancer cells compared to healthy cells (SI = 9.62 against Saos-2). All these results suggest that IsoP might be a promising molecule in the chemo-prevention and treatment of primary osteosarcoma.
Topics: Humans; Fruit; Cell Line, Tumor; Furocoumarins; Plant Extracts; Ammi; Cell Proliferation; Antineoplastic Agents, Phytogenic; Apoptosis; Chromatography, High Pressure Liquid; Cell Survival
PubMed: 38930940
DOI: 10.3390/molecules29122874 -
Molecules (Basel, Switzerland) Jun 2024Polyphenols from agro-food waste represent a valuable source of bioactive molecules that can be recovered to be used for their functional properties. Another option is...
Synthesis and Isolation of Phenol- and Thiol-Derived Epicatechin Adducts Prepared from Avocado Peel Procyanidins Using Centrifugal Partition Chromatography and the Evaluation of Their Antimicrobial and Antioxidant Activity.
Polyphenols from agro-food waste represent a valuable source of bioactive molecules that can be recovered to be used for their functional properties. Another option is to use them as starting material to generate molecules with new and better properties through semi-synthesis. A proanthocyanidin-rich (PACs) extract from avocado peels was used to prepare several semi-synthetic derivatives of epicatechin by acid cleavage in the presence of phenol and thiol nucleophiles. The adducts formed by this reaction were successfully purified using one-step centrifugal partition chromatography (CPC) and identified by chromatographic and spectroscopic methods. The nine derivatives showed a concentration-dependent free radical scavenging activity in the DPPH assay. All compounds were also tested against a panel of pathogenic bacterial strains formed by (ATCC 7644 and 19115), (ATCC 9144), (ATCC 11775 and 25922), and (ATCC 13076). In addition, adducts were tested against two no-pathogenic strains, UCO-979C and UCO-25A. Overall, thiol-derived adducts displayed antimicrobial properties and, in some specific cases, inhibited biofilm formation, particularly in (ATCC 7644). Interestingly, phenolic adducts were inactive against all the strains and could not inhibit its biofilm formation. Moreover, depending on the structure, in specific cases, biofilm formation was strongly promoted. These findings contribute to demonstrating that CPC is a powerful tool to isolate new semi-synthetic molecules using avocado peels as starting material for PACc extraction. These compounds represent new lead molecules with antioxidant and antimicrobial activity.
Topics: Persea; Antioxidants; Proanthocyanidins; Catechin; Plant Extracts; Microbial Sensitivity Tests; Anti-Infective Agents; Sulfhydryl Compounds; Anti-Bacterial Agents; Phenols
PubMed: 38930937
DOI: 10.3390/molecules29122872 -
Molecules (Basel, Switzerland) Jun 2024The genus Strophantus belongs to the Apocynaceae family of flowering plants which grows primarily in tropical Africa. The plants are widely used in traditional herbal... (Review)
Review
The genus Strophantus belongs to the Apocynaceae family of flowering plants which grows primarily in tropical Africa. The plants are widely used in traditional herbal medicine. , in particular, is used for the treatment of, e.g., joint pain and rheumatoid arthritis, wound infections, head lice, diarrhea, snake bite, and eye conditions. Despite its widespread use, dedicated research characterizing its bioactive plant components is scarce. Investigations have focused mainly on its cardenolides because of their cardioactivity and historical use as cardiotonic. There are also studies concerning the antibacterial, antioxidant, and anti-inflammatory activity of plant extracts. This review summarizes the present knowledge surrounding the biochemical and analytical research on Strophantus, in general, and , in particular, and describes the current state of the field based on the available scientific literature.
Topics: Plant Extracts; Humans; Apocynaceae; Antioxidants; Animals; Anti-Inflammatory Agents; Phytochemicals; Anti-Bacterial Agents
PubMed: 38930911
DOI: 10.3390/molecules29122847 -
Molecules (Basel, Switzerland) Jun 2024(Pers.) B.L.Burtt & R.M.Sm is a perennial plant of the family widely distributed in the subtropical and tropical areas of South America, Oceania, and Asia. Multiple... (Review)
Review
(Pers.) B.L.Burtt & R.M.Sm is a perennial plant of the family widely distributed in the subtropical and tropical areas of South America, Oceania, and Asia. Multiple plant parts of have been traditionally used as medicinal sources, each with different clinical uses. These variations may arise from differences among the chemical components and/or accumulations of the active compounds in each part. Therefore, this review summarizes previous studies on the phytochemicals in and reveals the similarities and differences among the chemical constituents of its multiple medicinal parts, including the leaves, rhizomes, fruits, seeds, and flowers. The results contribute to the scientific validation of the traditional understanding that possesses different medicinal properties in each plant part. In addition, this review provides directions for further studies on the phytochemicals of this plant.
Topics: Alpinia; Phytochemicals; Plant Extracts; Humans; Plants, Medicinal
PubMed: 38930910
DOI: 10.3390/molecules29122845 -
Molecules (Basel, Switzerland) Jun 2024In this work, a group of ten sesquiterpene drimanes, including polygodial (), isopolygodial (), and drimenol () obtained from the bark of F. and seven synthetic...
In this work, a group of ten sesquiterpene drimanes, including polygodial (), isopolygodial (), and drimenol () obtained from the bark of F. and seven synthetic derivatives, were tested in vitro against a unique panel of bacteria, fungi, and oomycetes with standardized procedures against bacterial strains , , , and The minimum inhibitory concentrations and bactericidal activities were evaluated using standardized protocols. Polygodial () was the most active compound, with MBC 8 μg/mL and MIC 16 μg/mL in ; MBC 16 μg/mL and MIC 32 μg/mL in ; MBC 64 μg/mL and MIC 64 μg/mL in ; and MBC 8 μg/mL and MIC 16 μg/mL and MBC 32 μg/mL and MIC 64 μg/mL in , respectively. The observed high potency could be attributed to the presence of an aldehyde group at the C8-C9 position. The antifungal activity of from different microbial isolates has been evaluated. The results show that polygodial affects the growth of normal isolates and against filamentous fungi and oomycetes with MFC values ranging from 8 to 64 μg/mL. Sesquiterpene drimanes isolated from this plant have shown interesting antimicrobial properties.
Topics: Sesquiterpenes; Microbial Sensitivity Tests; Anti-Infective Agents; Drimys; Polycyclic Sesquiterpenes; Anti-Bacterial Agents; Plant Extracts; Escherichia coli; Fungi; Bacteria
PubMed: 38930909
DOI: 10.3390/molecules29122844 -
Molecules (Basel, Switzerland) Jun 2024Achyranthes bidentata (AR) is a traditional Chinese herb used for the treatment of hypertension and cerebral ischemia, but its pharmacological effects are not known.
Characterization of the Components and Metabolites of Achyranthes Bidentata in the Plasma and Brain Tissue of Rats Based on Ultrahigh Performance Liquid Chromatography-High-Resolution Mass Spectrometry (UHPLC-HR-MS).
BACKGROUND
Achyranthes bidentata (AR) is a traditional Chinese herb used for the treatment of hypertension and cerebral ischemia, but its pharmacological effects are not known.
AIM OF STUDY
We aimed to detect and accurately identify the components and metabolites of AR in the plasma and brain tissue of Sprague Dawley rats.
METHODS
We employed ultrahigh performance liquid chromatography-high-resolution mass spectrometry (UHPLC-HR-MS) to detect AR components in the plasma and brain tissue of rats. The absorption and metabolites in the plasma and brain tissue of normal control rats and rats that underwent middle cerebral artery occlusion (MCAO) were characterized and compared.
RESULTS
A total of 281 compounds, including alkaloids, flavonoids, terpenoids, phenylpropanes, sugars and glycosides, steroids, triterpenes, amino acids, and peptides, was identified in samples of Achyranthes bidentata (TCM-AR). Four types of absorbable prototype components and 48 kinds of metabolites were identified in rats in the normal control plasma group which were given AR (AR plasma group), and five kinds of metabolites were identified in rats of the normal control brain tissue group which were given AR (AR brain group). Three absorbed prototype components and 13 metabolites were identified in the plasma of rats which underwent MCAO and were given AR (MCAO + AR plasma group). Six absorbed prototype components and two metabolites were identified in the brain tissue of rats who underwent MCAO and were administered AR (MCAO + AR brain group). These results showed that, after the oral administration of AR, the number of identified components in plasma was more than that in brain tissue. The number of prototype components in the AR plasma group was higher than that in the MCAO + AR plasma group, which may indicate that metabolite absorption in rats undergoing MCAO was worse. The number of prototype components in the MCAO + AR brain group was higher than that in the AR brain group, indicating that the blood-brain barrier was destroyed after MCAO, resulting in more compounds entering brain tissue.
CONCLUSIONS
UHPLC-HR-MS was used to rapidly analyze the components and metabolites of AR in the blood and brain of rats under normal and pathologic conditions, and to comprehensively characterize the components of TCM-AR. We also analyzed and compared the absorbable components and metabolites of normal rats under cerebral ischemia-reperfusion injury to explore the potential mechanism of action. This method could be applied to various Chinese herbs and disease models, which could promote TCM modernization.
Topics: Animals; Achyranthes; Chromatography, High Pressure Liquid; Rats; Brain; Rats, Sprague-Dawley; Male; Mass Spectrometry; Drugs, Chinese Herbal; Infarction, Middle Cerebral Artery; Flavonoids; Alkaloids
PubMed: 38930905
DOI: 10.3390/molecules29122840 -
Molecules (Basel, Switzerland) Jun 2024The Equisetaceae family, commonly known as horsetails, has been of scientific interest for decades due to its status as one of the most ancient extant vascular plant...
The Equisetaceae family, commonly known as horsetails, has been of scientific interest for decades due to its status as one of the most ancient extant vascular plant families. Notably, the corresponding species have found their place in traditional medicine, offering a wide array of applications. This study presents a comprehensive phytochemical analysis of polar secondary metabolites within the sterile stems of five distinct species using HPLC-DAD-ESI-MS. For this purpose, fresh plant material was extracted with acetone/water, and the resulting crude extracts were fractionated using dichloromethane, ethyl acetate, and -butanol, respectively. The results reveal a complex array of compounds, including hydroxycinnamic acids, hydroxybenzoic acids, flavonoids, and other phenolic compounds. In addition, total phenolic contents (Folin-Ciocalteu assay) and antioxidant activities (DPPH assay) of the plant extracts were evaluated using spectrophotometric methods. The present comparative analysis across the five species highlights both shared and species-specific metabolites, providing valuable insights into their chemical diversity and potential pharmacological properties.
Topics: Antioxidants; Phytochemicals; Plant Extracts; Equisetum; Plant Stems; Chromatography, High Pressure Liquid; Phenols; Flavonoids
PubMed: 38930889
DOI: 10.3390/molecules29122821 -
Molecules (Basel, Switzerland) Jun 2024Anthocyanins, as the most critical water-soluble pigments in nature, are widely present in roots, stems, leaves, flowers, fruits, and fruit peels. Many studies have... (Review)
Review
Anthocyanins, as the most critical water-soluble pigments in nature, are widely present in roots, stems, leaves, flowers, fruits, and fruit peels. Many studies have indicated that anthocyanins exhibit various biological activities including antioxidant, anti-inflammatory, anti-tumor, hypoglycemic, vision protection, and anti-aging. Hence, anthocyanins are widely used in food, medicine, and cosmetics. The green and efficient extraction and purification of anthocyanins are an important prerequisite for their further development and utilization. However, the poor stability and low bioavailability of anthocyanins limit their application. Protein, one of the three essential nutrients for the human body, has good biocompatibility and biodegradability. Proteins are commonly used in food processing, but their functional properties need to be improved. Notably, anthocyanins can interact with proteins through covalent and non-covalent means during food processing, which can effectively improve the stability of anthocyanins and enhance their bioavailability. Moreover, the interactions between proteins and anthocyanins can also improve the functional characteristics and enhance the nutritional quality of proteins. Hence, this article systematically reviews the extraction and purification methods for anthocyanins. Moreover, this review also systematically summarizes the effect of the interactions between anthocyanins and proteins on the bioavailability of anthocyanins and their impact on protein properties. Furthermore, we also introduce the application of the interaction between anthocyanins and proteins. The findings can provide a theoretical reference for the application of anthocyanins and proteins in food deep processing.
Topics: Anthocyanins; Humans; Proteins; Antioxidants; Biological Availability; Plant Extracts
PubMed: 38930881
DOI: 10.3390/molecules29122815 -
Molecules (Basel, Switzerland) Jun 2024This research aimed to encapsulate the fruit extract to increase its stability for incorporation into food products such as jelly or jelly powder. After extraction, the...
This research aimed to encapsulate the fruit extract to increase its stability for incorporation into food products such as jelly or jelly powder. After extraction, the nanoliposomes containing the extract were prepared in ratios of 60-0, 50-10, 40-20, and 30-30 lecithin-to-cholesterol. The effects of lecithin-to-cholesterol concentrations on the related parameters were then evaluated. The results showed that the average particle size was in the range of 95.05 to 164.25 nm, and with an increasing cholesterol concentration, the particle size of the nanoliposomes increased. The addition of cholesterol increased the zeta potential from -60.40 to -68.55 millivolt. Furthermore, cholesterol led to an increase in encapsulation efficiency, and even improved the stability of phenolic compounds loaded in nanoliposomes during storage time. Fourier transform infrared (FTIR) spectroscopy confirmed the successful loading of the extract. Field emission scanning electron microscopy (FE-SEM) analysis revealed nano-sized spherical and almost-elliptical liposomes. For jelly powders, the water solubility index ranged from 39.5 to 43.7% ( > 0.05), and the hygroscopicity values ranged between 1.22 and 9.36 g/100 g ( < 0.05). In conclusion, nanoencapsulated extract displayed improved stability and can be used in jelly preparation without any challenge or unfavorable perception.
Topics: Liposomes; Plant Extracts; Capparis; Particle Size; Nanoparticles; Lecithins; Cholesterol; Drug Compounding; Spectroscopy, Fourier Transform Infrared; Solubility
PubMed: 38930869
DOI: 10.3390/molecules29122804 -
Molecules (Basel, Switzerland) Jun 2024Turmeric () contains curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC). Nevertheless, curcumin is the most researched active ingredient for its numerous...
Turmeric () contains curcumin, demethoxycurcumin (DMC), and bisdemethoxycurcumin (BDMC). Nevertheless, curcumin is the most researched active ingredient for its numerous pharmacological effects. We investigated the impact of these curcuminoids found in Ryudai gold, an approved cultivar of , on wound healing, inflammation, and diabetes. Sub-planter injections of carrageenan induced acute paw inflammation in rats. The wound-healing ability of 1% curcuminoids was examined by making a 6 mm round wound on the shaved dorsum of the mice with a biopsy punch. A single intraperitoneal injection of streptozotocin (50 mg/kg) was used to induce diabetes in mice. Curcuminoids at a dose rate of 100 mg/kg body weight were used with feed and as a gastric gavage to treat diabetes and inflammation in experimental animals. Paw thickness was measured at 1, 3, and 6 h following carrageenan injection. After three hours, mean paw volume was 58% in carrageenan-injected mice, which was 35%, 37%, and 31% in the curcumin, DMC, and BDMC groups, respectively. Histopathology of the paw tissue demonstrated severe infiltration of inflammatory cells and thickening of the dermis, which were remarkably improved by the curcuminoids. The wound-healing abilities were significantly higher in the curcumin- (95.0%), DMC- (93.17%), and BDMC-treated (89.0%) groups, in comparison to that of the control (65.09%) group at day nine. There were no significant differences in wound-healing activity among the groups treated with 1% curcuminoids throughout the study. Streptozotocin-induced diabetes was characterized by an increased blood glucose (552.2 mg/dL) and decreased body weight (31.2 g), compared to that of the control rats (145.6 mg/dL and 46.8 g blood glucose and body weight, respectively). It also caused an increase in serum alanine aminotransferase (ALT; 44.2 U/L) and aspartate aminotransferase (AST; 55.8 U/L) compared to that of the control group (18.6 U/L and 20.1 U/L, respectively). Histopathological examination of the liver showed that diabetes caused hepatic cellular necrosis, congestion of the central vein, and parenchymatous degeneration. However, all three curcuminoids significantly decreased blood glucose levels, ALT, and AST and improved the histopathological score of the liver. These results evidenced that not only curcumin but also DMC and BDMC have potent anti-inflammatory, wound healing, and anti-diabetic efficacy, and the Ryudai gold variety of turmeric could be used as a functional food supplement.
Topics: Animals; Curcuma; Wound Healing; Mice; Rats; Diabetes Mellitus, Experimental; Anti-Inflammatory Agents; Hypoglycemic Agents; Curcumin; Male; Plant Extracts; Carrageenan; Inflammation; Diarylheptanoids
PubMed: 38930859
DOI: 10.3390/molecules29122795