Pub Date : 2024-01-01DOI: 10.1177/1934578x231219560
Pawan K. Agrawal, Gerald Blunden, Claus Jacob
Isoquercetin, a naturally occurring dietary flavonoid glycoside, has shown many promising biological activities, such as antioxidant, anti-inflammatory, and anticancer. It also exhibits broad-spectrum antiviral activity, significantly reducing cell infection by influenza, Zika, Ebola, and dengue viruses, among others. Its beneficial effect for mitigating the disease of COVID-19 can be explained due to its inhibitory effects on several stages of the viral life cycle, from entry to replication and virus infectivity, and thus isoquercetin can be a promising anticoronaviral flavonoid to manage severe acute respiratory syndrome-coronavirus-2 (SARS-CoV-2) infection and warrants further investigation into its potential use in clinical settings.
{"title":"Antiviral Significance of Isoquercetin (Quercetin-3-O-Glucoside) With Special Reference to its Anti-Coronaviral Potential","authors":"Pawan K. Agrawal, Gerald Blunden, Claus Jacob","doi":"10.1177/1934578x231219560","DOIUrl":"https://doi.org/10.1177/1934578x231219560","url":null,"abstract":"Isoquercetin, a naturally occurring dietary flavonoid glycoside, has shown many promising biological activities, such as antioxidant, anti-inflammatory, and anticancer. It also exhibits broad-spectrum antiviral activity, significantly reducing cell infection by influenza, Zika, Ebola, and dengue viruses, among others. Its beneficial effect for mitigating the disease of COVID-19 can be explained due to its inhibitory effects on several stages of the viral life cycle, from entry to replication and virus infectivity, and thus isoquercetin can be a promising anticoronaviral flavonoid to manage severe acute respiratory syndrome-coronavirus-2 (SARS-CoV-2) infection and warrants further investigation into its potential use in clinical settings.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"103 20","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139454074","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x241227490
Eui-Joong Kim, Jiwon Park, Chang-hwan Yu, Jae-Woo Park, Kwan-il Kim, Hee-Jae Jung, Jang-Hoon Kim, Y. Bu, Beom-joon Lee
Background: A screening study investigated the effects of lung-moistening herbal medicines on a bleomycin-induced pulmonary fibrosis mouse model and reported that the efficacy of Adenophorae Radix (ADR) was higher than that of other remedies. Objectives: This study aimed to investigate the antifibrotic efficacy and mechanism of action of ADR in a mouse model of bleomycin-induced pulmonary fibrosis. Materials and Methods: ADR water extract was prepared and orally administered at doses of 30, 100, and 300 mg/kg for 10 days after intratracheal bleomycin instillation. Changes in the body weight and lung histology were assessed. In addition, the quantity of inflammatory cells in the bronchoalveolar lavage fluid (BALF) and the level of transforming growth factor-β and α-smooth muscle actin (α-SMA) were measured. Results: ADR treatment decreased the degree of histological fibrosis based on the Ashcroft score and the number of inflammatory cells in BALF. Moreover, α-SMA level in the lung tissue decreased. ADR at 300 mg/kg resulted in the most significant reduction in the measured indicators. Conclusion: The results indicate that the administration of 300 mg/kg ADR attenuates pulmonary fibrosis in an animal model of idiopathic pulmonary fibrosis; thus, ADR can be considered as a candidate treatment for lung fibrosis.
{"title":"Adenophorae Radix Reduces Fibrosis in a Bleomycin-Induced Pulmonary Fibrosis Mouse Model","authors":"Eui-Joong Kim, Jiwon Park, Chang-hwan Yu, Jae-Woo Park, Kwan-il Kim, Hee-Jae Jung, Jang-Hoon Kim, Y. Bu, Beom-joon Lee","doi":"10.1177/1934578x241227490","DOIUrl":"https://doi.org/10.1177/1934578x241227490","url":null,"abstract":"Background: A screening study investigated the effects of lung-moistening herbal medicines on a bleomycin-induced pulmonary fibrosis mouse model and reported that the efficacy of Adenophorae Radix (ADR) was higher than that of other remedies. Objectives: This study aimed to investigate the antifibrotic efficacy and mechanism of action of ADR in a mouse model of bleomycin-induced pulmonary fibrosis. Materials and Methods: ADR water extract was prepared and orally administered at doses of 30, 100, and 300 mg/kg for 10 days after intratracheal bleomycin instillation. Changes in the body weight and lung histology were assessed. In addition, the quantity of inflammatory cells in the bronchoalveolar lavage fluid (BALF) and the level of transforming growth factor-β and α-smooth muscle actin (α-SMA) were measured. Results: ADR treatment decreased the degree of histological fibrosis based on the Ashcroft score and the number of inflammatory cells in BALF. Moreover, α-SMA level in the lung tissue decreased. ADR at 300 mg/kg resulted in the most significant reduction in the measured indicators. Conclusion: The results indicate that the administration of 300 mg/kg ADR attenuates pulmonary fibrosis in an animal model of idiopathic pulmonary fibrosis; thus, ADR can be considered as a candidate treatment for lung fibrosis.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"158 3","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139636543","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x231224995
Duong Quang Huan, N. Luyen, Nguyen Xuan Ha, Do Ngoc Dai, Nguyen Quang Hop, Do Thi Lan Huong, N. Son
The Lauraceae plants comprised high amounts of essential oils, some of which established pharmacological potentials such as anticancer and antimicrobial activities. The Lauraceae essential oils are also used in cuisines and perfumes. The present study provides the chemical analysis of the leaf oils of Beilschmiedia tonkinensis and Lindera gracilipes, collected from Vietnam. Chemical components in the obtained oils were identified by the GC-FID/MS. The MTT and broth microdilution assays were used to evaluate cytotoxic and antimicrobial effects, respectively. The protein interactions were viewed by a docking study. Beilschmiedia tonkinensis leaf oil was characterized by sesquiterpene hydrocarbons (66.0%), in which bicyclogermacrene (23.3%), ( E)-caryophyllene (21.9%), caryophyllene oxide (9.9%), and spathulenol (6.0%) were the main components. The major chemical class in L gracilipes leaf oil was still sesquiterpene hydrocarbons (64.2%) with bicyclogermacrene (32.2%) being the principal component. Both 2 oil samples (IC50 41.2-44.12 µg/mL) were actively cytotoxic against the proliferation of A-549 cancer cells. In particular, B tonkinensis leaf oil strongly controlled Hep-G2 and MCF-7 cancerous cells with the IC50 values of 20.6 and 9.36 µg/mL, respectively. Beilschmiedia tonkinensis leaf oil also strongly inhibited the Gram (–) bacterium Pseudomonas aeruginosa and the fungus Aspergillus niger with the MIC values of 16 and 32 µg/mL, respectively. By molecular docking approach, bicyclogermacrene interacted with the p38α MAPK cancer protein (PDB ID: 4FA2) with a potential binding affinity of −8.019 kcal/mol, whereas ( E)-caryophyllene tends to bind 2 bacterial proteins P aeruginosa QS regulator (PDB ID: 6B8A) and glucosamine-6-phosphate synthase (GlmS) (PDB ID: 2VF5) with the better binding affinities of −6.740 and −6.521 kcal/mol, respectively. The most preferable binding mode was due to hydrophobic π-alkyl and alkyl interactions. The current result can be seen as a basic foundation in the applications of essential oils of B tonkinensis and L gracilipes for anticancer and antimicrobial treatments. Further phytochemical studies and mechanisms of action are needed.
{"title":"The Leaf Oils of Beilschmiedia tonkinensis (Lecomte) Ridl. and Lindera gracilipes H. W. Li: Chemical Composition, Cytotoxicity, Antimicrobial Activity, and Docking Study","authors":"Duong Quang Huan, N. Luyen, Nguyen Xuan Ha, Do Ngoc Dai, Nguyen Quang Hop, Do Thi Lan Huong, N. Son","doi":"10.1177/1934578x231224995","DOIUrl":"https://doi.org/10.1177/1934578x231224995","url":null,"abstract":"The Lauraceae plants comprised high amounts of essential oils, some of which established pharmacological potentials such as anticancer and antimicrobial activities. The Lauraceae essential oils are also used in cuisines and perfumes. The present study provides the chemical analysis of the leaf oils of Beilschmiedia tonkinensis and Lindera gracilipes, collected from Vietnam. Chemical components in the obtained oils were identified by the GC-FID/MS. The MTT and broth microdilution assays were used to evaluate cytotoxic and antimicrobial effects, respectively. The protein interactions were viewed by a docking study. Beilschmiedia tonkinensis leaf oil was characterized by sesquiterpene hydrocarbons (66.0%), in which bicyclogermacrene (23.3%), ( E)-caryophyllene (21.9%), caryophyllene oxide (9.9%), and spathulenol (6.0%) were the main components. The major chemical class in L gracilipes leaf oil was still sesquiterpene hydrocarbons (64.2%) with bicyclogermacrene (32.2%) being the principal component. Both 2 oil samples (IC50 41.2-44.12 µg/mL) were actively cytotoxic against the proliferation of A-549 cancer cells. In particular, B tonkinensis leaf oil strongly controlled Hep-G2 and MCF-7 cancerous cells with the IC50 values of 20.6 and 9.36 µg/mL, respectively. Beilschmiedia tonkinensis leaf oil also strongly inhibited the Gram (–) bacterium Pseudomonas aeruginosa and the fungus Aspergillus niger with the MIC values of 16 and 32 µg/mL, respectively. By molecular docking approach, bicyclogermacrene interacted with the p38α MAPK cancer protein (PDB ID: 4FA2) with a potential binding affinity of −8.019 kcal/mol, whereas ( E)-caryophyllene tends to bind 2 bacterial proteins P aeruginosa QS regulator (PDB ID: 6B8A) and glucosamine-6-phosphate synthase (GlmS) (PDB ID: 2VF5) with the better binding affinities of −6.740 and −6.521 kcal/mol, respectively. The most preferable binding mode was due to hydrophobic π-alkyl and alkyl interactions. The current result can be seen as a basic foundation in the applications of essential oils of B tonkinensis and L gracilipes for anticancer and antimicrobial treatments. Further phytochemical studies and mechanisms of action are needed.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"52 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139456327","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x231222096
Song Qian, Zuhua Wang, Xiuping Ma, Huiyi Ming, Jing Liu, Jing Yang, Teng Chen, Linli Liu, Jibian Ban, Jiangtao Guo
The ethnic drug Melastoma dodecandrum Lour. (MDL) is an important medicinal plant with potential antitumor properties, which have been proposed as promising anticancer agents, but the material basis for its therapeutic effect is still unclear and lacks in-depth research. In this study, the in vitro antitumor effects of different MDL extracts in different gynecological tumor cells were investigated by CCK-8 assay. The active components of 21 batches of MDL samples collected from different product areas and markets were determined and compared by the UPLC method. On this basis, the data was processed with the fingerprint similarity software, and the correlation between MDL fingerprint and antihuman cervical cancer activity was further analyzed by a multivariate statistical method. Five kinds of MDL extracts, including the aqueous extract, the crude polysaccharide, the total polyphenol, the ethyl acetate fraction of the aqueous extract and 50% ethanol extract, had inhibitory effects on human cervical cancer HeLa and SiHa cells, among which total polyphenols of MDL showed stronger inhibition effect on human cervical cancer cells. In addition, the fingerprint of the total polyphenols of MDL had sixteen common peaks, and six common peaks were checked by using diode array and UV spectra, among which peak 1 (gallic acid), peak 4 (protocatechuic acid), peak 12 (unknown), and peak 15 (ellagic acid) were negatively correlated with the IC50 value of the SiHa cells, and all variable importance values were greater than 1. Our data demonstrated that the main active components of MDL inhibiting human cervical cancer SiHa cells may be the synergistic effect of gallic acid, protocatechuic acid and ellagic acid, and the further spectrum-effect relationship analysis provides an important reference and basis for the quality control and the development of new anticervical cancer drug of MDL.
{"title":"Study on the Active Components and Inhibiting Effect of Melastoma dodecandrum Lour. on Human Cervical Cancer Cells Based on Spectrum–Effect Relationship Analysis","authors":"Song Qian, Zuhua Wang, Xiuping Ma, Huiyi Ming, Jing Liu, Jing Yang, Teng Chen, Linli Liu, Jibian Ban, Jiangtao Guo","doi":"10.1177/1934578x231222096","DOIUrl":"https://doi.org/10.1177/1934578x231222096","url":null,"abstract":"The ethnic drug Melastoma dodecandrum Lour. (MDL) is an important medicinal plant with potential antitumor properties, which have been proposed as promising anticancer agents, but the material basis for its therapeutic effect is still unclear and lacks in-depth research. In this study, the in vitro antitumor effects of different MDL extracts in different gynecological tumor cells were investigated by CCK-8 assay. The active components of 21 batches of MDL samples collected from different product areas and markets were determined and compared by the UPLC method. On this basis, the data was processed with the fingerprint similarity software, and the correlation between MDL fingerprint and antihuman cervical cancer activity was further analyzed by a multivariate statistical method. Five kinds of MDL extracts, including the aqueous extract, the crude polysaccharide, the total polyphenol, the ethyl acetate fraction of the aqueous extract and 50% ethanol extract, had inhibitory effects on human cervical cancer HeLa and SiHa cells, among which total polyphenols of MDL showed stronger inhibition effect on human cervical cancer cells. In addition, the fingerprint of the total polyphenols of MDL had sixteen common peaks, and six common peaks were checked by using diode array and UV spectra, among which peak 1 (gallic acid), peak 4 (protocatechuic acid), peak 12 (unknown), and peak 15 (ellagic acid) were negatively correlated with the IC50 value of the SiHa cells, and all variable importance values were greater than 1. Our data demonstrated that the main active components of MDL inhibiting human cervical cancer SiHa cells may be the synergistic effect of gallic acid, protocatechuic acid and ellagic acid, and the further spectrum-effect relationship analysis provides an important reference and basis for the quality control and the development of new anticervical cancer drug of MDL.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"44 47","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139634587","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x241228152
Lilia Chérigo, Dioxelis López, Carmenza Spadafora, Luis C. Mejia, Sergio Martínez-Luis
Objective: The objective of this study was to assess the biomedical potential of endophytic fungi isolated from Panamanian mangrove plants. This was achieved through the biological evaluation of organic extracts to determine their antiparasitic, anticancer, toxicity activity, and inhibition of the enzyme α-glucosidase. Methods: Leaves from various mangrove plant species in five different zones along the Pacific coast of Panama were collected using standard procedures. Endophytic fungi present on the leaves of each plant mangrove species collected were isolated using standard microbiological protocols. Organic extracts of each fungal isolate were prepared through maceration. The antiparasitic activity against Plasmodium falciparum, Trypanosoma cruzi, and Leishmania donovani, toxicity against Artemia salina, and anticancer activity in the MCF-7 cell line were investigated following protocols established by our institution. Finally, the ability to inhibit the enzymatic activity of α-glucosidase was evaluated by monitoring the hydrolysis of PNP-G. Results: Forty-three fungal isolates were isolated from the mangrove leaves analyzed. Organic extracts were prepared from each isolate for subsequent biological evaluation. It was found that twenty-one of the organic extracts showed activity in at least one of the performed bioassays. In the brine shrimp test, most samples were nontoxic or exhibited weak toxicity. Two fungal extracts showed anticancer activity, three showed antileishmanial activity, and one exhibited weak activity against P. falciparum. The most significant biological activity shown by the evaluated extracts was the inhibition of the α-glucosidase enzyme, where 44% of the fungal extracts were active. Conclusion: The most promising biomedical activity detected in the fungal isolates associated with mangrove plants is the inhibition of the α-glucosidase enzyme. Among the active samples, a high percentage belonged to fungi identified within the class Dothidiomycetes, revealing that this class is a potential new source of compounds with hypoglycemic activity.
{"title":"Exploring the Biomedical Potential of Endophytic Fungi Isolated from Panamanian Mangroves","authors":"Lilia Chérigo, Dioxelis López, Carmenza Spadafora, Luis C. Mejia, Sergio Martínez-Luis","doi":"10.1177/1934578x241228152","DOIUrl":"https://doi.org/10.1177/1934578x241228152","url":null,"abstract":"Objective: The objective of this study was to assess the biomedical potential of endophytic fungi isolated from Panamanian mangrove plants. This was achieved through the biological evaluation of organic extracts to determine their antiparasitic, anticancer, toxicity activity, and inhibition of the enzyme α-glucosidase. Methods: Leaves from various mangrove plant species in five different zones along the Pacific coast of Panama were collected using standard procedures. Endophytic fungi present on the leaves of each plant mangrove species collected were isolated using standard microbiological protocols. Organic extracts of each fungal isolate were prepared through maceration. The antiparasitic activity against Plasmodium falciparum, Trypanosoma cruzi, and Leishmania donovani, toxicity against Artemia salina, and anticancer activity in the MCF-7 cell line were investigated following protocols established by our institution. Finally, the ability to inhibit the enzymatic activity of α-glucosidase was evaluated by monitoring the hydrolysis of PNP-G. Results: Forty-three fungal isolates were isolated from the mangrove leaves analyzed. Organic extracts were prepared from each isolate for subsequent biological evaluation. It was found that twenty-one of the organic extracts showed activity in at least one of the performed bioassays. In the brine shrimp test, most samples were nontoxic or exhibited weak toxicity. Two fungal extracts showed anticancer activity, three showed antileishmanial activity, and one exhibited weak activity against P. falciparum. The most significant biological activity shown by the evaluated extracts was the inhibition of the α-glucosidase enzyme, where 44% of the fungal extracts were active. Conclusion: The most promising biomedical activity detected in the fungal isolates associated with mangrove plants is the inhibition of the α-glucosidase enzyme. Among the active samples, a high percentage belonged to fungi identified within the class Dothidiomycetes, revealing that this class is a potential new source of compounds with hypoglycemic activity.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"124 10","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139639576","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Fungi in the genus of Tolypocladium are often discovered as endophytes, soil inhabitants, and insect pathogens. Many biologically active secondary metabolites have been discovered from them in the past half-century, including medicinally important oligopeptide cyclosporine A, and other compounds like terpenes, polyketides, polyketide-non-ribosomal peptides. This review has summarized the chemistry and pharmacology of natural products discovered from Tolypocladium genus fungi, to provide a full record of all Tolypocladium secondary metabolites.
{"title":"Diversity of Secondary Metabolites from Fungi of the Ascomycete Genus Tolypocladium","authors":"Ting-Ting Niu, Wei-Qiong Chen, Wen-Xing Li, Li Zhang, Ying-Qiao Shan, Li-Wei Ren","doi":"10.1177/1934578x231225538","DOIUrl":"https://doi.org/10.1177/1934578x231225538","url":null,"abstract":"Fungi in the genus of Tolypocladium are often discovered as endophytes, soil inhabitants, and insect pathogens. Many biologically active secondary metabolites have been discovered from them in the past half-century, including medicinally important oligopeptide cyclosporine A, and other compounds like terpenes, polyketides, polyketide-non-ribosomal peptides. This review has summarized the chemistry and pharmacology of natural products discovered from Tolypocladium genus fungi, to provide a full record of all Tolypocladium secondary metabolites.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"21 36","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139631632","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x231222105
A. Christou, Constantina Stavrou, C. Michael, G. Botsaris, V. Goulas
Natural products are an inexhaustive reservoir of bioactive compounds with diverse effects protecting human health as components of nutrition and as active substances of drugs. The objective of the present study was to evaluate the bactericidal and carbohydrate digestive enzyme inhibitory activity of twelve native plants from Cyprus, that are consumed for medicinal and/ or culinary purposes. Each plant was sequentially extracted with solvents of increasing polarity, from non-polar to polar solvents. At first, the total phenolic (TPC) and flavonoid (TFC) content of the extracts were determined. The bactericidal potential of plant extracts was tested against six bacteria using the broth microdilution method. Furthermore, their inhibitory effects on digestive enzymes, namely α-glucosidase and α-amylase, were also determined. Results demonstrated a substantial diversity in TPC (2.3-483.5 mg gallic acid equivalent g−1) and TFC (4.1-394.6 mg catechin equivalent g−1) of the plant extracts; a great impact of solvent was found. Furthermore, potent antibacterial activity (minimum bactericidal concentration ≤ 500 µg ml−1) of capper, mountain oregano, rosemary, silver thistle, and vine leaf extracts against Gram-positive bacteria was determined. Regarding carbohydrate digestive enzyme inhibitory effects, the inhibition of α-glucosidase enzyme is higher than 80%, when rosemary, silver thistle, and vine leaf extracts are used at a concentration of 500 µg g−1. Overall, the present study describes the antibacterial and inhibitory effect against carbohydrate digestive enzymes of unstudied plant species or known plants from the unexplored island of Cyprus. It provides valuable data for the nutraceutical value of native edible plants as well as assesses these plants as potential sources of antibacterial and carbohydrate digestive enzyme inhibitory agents for drug discovery.
{"title":"Antibacterial and Carbohydrate Digestive Enzyme Inhibitory Effects of Native Plants Used for Medicinal and Culinary Purposes in Cyprus","authors":"A. Christou, Constantina Stavrou, C. Michael, G. Botsaris, V. Goulas","doi":"10.1177/1934578x231222105","DOIUrl":"https://doi.org/10.1177/1934578x231222105","url":null,"abstract":"Natural products are an inexhaustive reservoir of bioactive compounds with diverse effects protecting human health as components of nutrition and as active substances of drugs. The objective of the present study was to evaluate the bactericidal and carbohydrate digestive enzyme inhibitory activity of twelve native plants from Cyprus, that are consumed for medicinal and/ or culinary purposes. Each plant was sequentially extracted with solvents of increasing polarity, from non-polar to polar solvents. At first, the total phenolic (TPC) and flavonoid (TFC) content of the extracts were determined. The bactericidal potential of plant extracts was tested against six bacteria using the broth microdilution method. Furthermore, their inhibitory effects on digestive enzymes, namely α-glucosidase and α-amylase, were also determined. Results demonstrated a substantial diversity in TPC (2.3-483.5 mg gallic acid equivalent g−1) and TFC (4.1-394.6 mg catechin equivalent g−1) of the plant extracts; a great impact of solvent was found. Furthermore, potent antibacterial activity (minimum bactericidal concentration ≤ 500 µg ml−1) of capper, mountain oregano, rosemary, silver thistle, and vine leaf extracts against Gram-positive bacteria was determined. Regarding carbohydrate digestive enzyme inhibitory effects, the inhibition of α-glucosidase enzyme is higher than 80%, when rosemary, silver thistle, and vine leaf extracts are used at a concentration of 500 µg g−1. Overall, the present study describes the antibacterial and inhibitory effect against carbohydrate digestive enzymes of unstudied plant species or known plants from the unexplored island of Cyprus. It provides valuable data for the nutraceutical value of native edible plants as well as assesses these plants as potential sources of antibacterial and carbohydrate digestive enzyme inhibitory agents for drug discovery.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"6 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139634040","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x241227689
Luis Alberto González López, M. Andrés, W. Quiñones, Fernando Echeverri, A. González-Coloma
Objective: In this study, a series of synthetic hydroxylated (5-10) and prenylated (10-17) acetophenones, chalcones (18-20) and a flavone (21) have been synthesized and evaluated on the nematode Meloidogyne javanica. Additional phenolic compounds, including salicylic acid, isopropyl salicylate, thymol, carvacrol, cumic acid, eugenol, vanillin, and vanillic acid (22-29), were also tested. Methods: Compounds 5-21 have been synthesized by a sequence of reactions and were isolated and identified by 1H-NMR, 13C-NMR, and HRMS. The in vitro nematicidal effects of the compounds were tested on J2 juveniles. The nematicidal activity was confirmed by their egg hatching inhibition effects, tested at the minimum lethal concentration (minimum dose to give 100% J2 mortality). Results: Compounds 5-18 have been previously reported and 19-21 are described here for the first time. The 2´-hydroxylated acetophenones (5-9) showed strong nematicidal effects, being 7-9 the most active. Salicylic (22) and cumic (26) acids were effective compounds. Compounds 7, 12, 22-26, active on M. javanica J2 juveniles, were also egg hatching inhibitors. Conclusions: A C-2/C-4 dihydroxylation or C-2/C-4/C-3 trihydroxylation of the acetophenone moiety improved the activity, while introducing a hydrophilic isoprene chain (10-17) eliminated the effect, with only one prenylated acetophenone (12) being active. Among the additional phenolic compounds (22-29), these with a carboxyl group instead of the acyl side were better nematicides. These results generate molecular leads for developing new nematicidal phenolic compounds.
{"title":"Potential of 2-Hydroxyacetophenone Derivatives and Simple Phenol's for the control of Meloidogyne javanica","authors":"Luis Alberto González López, M. Andrés, W. Quiñones, Fernando Echeverri, A. González-Coloma","doi":"10.1177/1934578x241227689","DOIUrl":"https://doi.org/10.1177/1934578x241227689","url":null,"abstract":"Objective: In this study, a series of synthetic hydroxylated (5-10) and prenylated (10-17) acetophenones, chalcones (18-20) and a flavone (21) have been synthesized and evaluated on the nematode Meloidogyne javanica. Additional phenolic compounds, including salicylic acid, isopropyl salicylate, thymol, carvacrol, cumic acid, eugenol, vanillin, and vanillic acid (22-29), were also tested. Methods: Compounds 5-21 have been synthesized by a sequence of reactions and were isolated and identified by 1H-NMR, 13C-NMR, and HRMS. The in vitro nematicidal effects of the compounds were tested on J2 juveniles. The nematicidal activity was confirmed by their egg hatching inhibition effects, tested at the minimum lethal concentration (minimum dose to give 100% J2 mortality). Results: Compounds 5-18 have been previously reported and 19-21 are described here for the first time. The 2´-hydroxylated acetophenones (5-9) showed strong nematicidal effects, being 7-9 the most active. Salicylic (22) and cumic (26) acids were effective compounds. Compounds 7, 12, 22-26, active on M. javanica J2 juveniles, were also egg hatching inhibitors. Conclusions: A C-2/C-4 dihydroxylation or C-2/C-4/C-3 trihydroxylation of the acetophenone moiety improved the activity, while introducing a hydrophilic isoprene chain (10-17) eliminated the effect, with only one prenylated acetophenone (12) being active. Among the additional phenolic compounds (22-29), these with a carboxyl group instead of the acyl side were better nematicides. These results generate molecular leads for developing new nematicidal phenolic compounds.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"141 s1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139638369","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x231222764
David Calderón-Rangel, Hugo A. García-Gutiérrez, R. D. del Río, Christine Thomassigny
This study aims to convert cativic acid, which was isolated from Ageratina jocotepecana, into cistendiol (5), an analog of cistenolic acid isolated from Cistus symphytifolius. The position of hydroxyl at C-7 in compound 5 could be achieved by applying the Schenck reaction with singlet oxygen (1O2) through photooxidation reaction of 6. Additionally, epoxidation reaction of 1, followed by further reduction and acid treatment, can serve as another pathway to obtain compound 5. Cativic acid was isolated from Ageratina jocotepecana flowers, reduction methodology was realized with THF and LiAlH4, epoxidation reaction was carried out with mCPBA in CH2Cl2 and K2CO3, oxidation of alcohol with PCC in CH2Cl2 and MgSO4, photooxidation reaction was realized with blue and white light using singlet oxygen (1O2) and photosensitizers such as eosin, methylene blue and Ru(bpy)3(PF6)2 in acetonitrile. Geometry optimizations for transition states were performed using MMFF94 with Monte Carlo protocol, and GDFT was used B3LYP/DGDZVP level of theory with Gaussian 09. Cistendiol was synthesized by photooxidation reaction of 6 with Ru(bpy)3(PF6)2 and air such oxidant with a ratio of 8:1, while epoxidation of 1 further reduction and acid treatment afforded cistendiol with a ratio of 9:1, the ratio was determined by NMR, additionally the global minimum energy structures GDFT calculated values supports the results described by NMR ratio. The stereochemistry was also confirmed by NOESY experiment and the comparison is in agreement with literature data. Herein, we described the conversion of cativic acid isolated from Ageratina jocotepecana employing a new photooxidation methodology and classic epoxidation techniques, to produce an analog of cistenolic acid isolated from Cistus symphytifolius. The results, which include Supplemental material, enable comparison of stereochemistry, specifically the 13 S for C-13 of Ageratina jocotepecana with other compounds such as cistenolic or salvic acid, which had been the subject of study by researchers.
{"title":"Chemical Correlation of Cistendiol Obtained from Cativic Acid in Two Different Pathways","authors":"David Calderón-Rangel, Hugo A. García-Gutiérrez, R. D. del Río, Christine Thomassigny","doi":"10.1177/1934578x231222764","DOIUrl":"https://doi.org/10.1177/1934578x231222764","url":null,"abstract":"This study aims to convert cativic acid, which was isolated from Ageratina jocotepecana, into cistendiol (5), an analog of cistenolic acid isolated from Cistus symphytifolius. The position of hydroxyl at C-7 in compound 5 could be achieved by applying the Schenck reaction with singlet oxygen (1O2) through photooxidation reaction of 6. Additionally, epoxidation reaction of 1, followed by further reduction and acid treatment, can serve as another pathway to obtain compound 5. Cativic acid was isolated from Ageratina jocotepecana flowers, reduction methodology was realized with THF and LiAlH4, epoxidation reaction was carried out with mCPBA in CH2Cl2 and K2CO3, oxidation of alcohol with PCC in CH2Cl2 and MgSO4, photooxidation reaction was realized with blue and white light using singlet oxygen (1O2) and photosensitizers such as eosin, methylene blue and Ru(bpy)3(PF6)2 in acetonitrile. Geometry optimizations for transition states were performed using MMFF94 with Monte Carlo protocol, and GDFT was used B3LYP/DGDZVP level of theory with Gaussian 09. Cistendiol was synthesized by photooxidation reaction of 6 with Ru(bpy)3(PF6)2 and air such oxidant with a ratio of 8:1, while epoxidation of 1 further reduction and acid treatment afforded cistendiol with a ratio of 9:1, the ratio was determined by NMR, additionally the global minimum energy structures GDFT calculated values supports the results described by NMR ratio. The stereochemistry was also confirmed by NOESY experiment and the comparison is in agreement with literature data. Herein, we described the conversion of cativic acid isolated from Ageratina jocotepecana employing a new photooxidation methodology and classic epoxidation techniques, to produce an analog of cistenolic acid isolated from Cistus symphytifolius. The results, which include Supplemental material, enable comparison of stereochemistry, specifically the 13 S for C-13 of Ageratina jocotepecana with other compounds such as cistenolic or salvic acid, which had been the subject of study by researchers.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"6 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139457099","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-01DOI: 10.1177/1934578x231225842
Kathy Swor, P. Satyal, Ambika Poudel, W. Setzer
Background/Objective: Arrowleaf balsamroot ( Balsamorhiza sagittata (Pursh) Nutt., Asteraceae) is a conspicuous forb growing in open hillsides and prairies at mid to upper elevations in the Intermountain West and Rocky Mountain regions. The plant is important forage for deer and elk and several Native American tribes used arrowleaf balsamroot as food and medicine. The volatile phytochemicals of B. sagittata have not been previously examined. Methods/Results: Nine individual samples of B. sagittata were collected, the essential oils obtained by hydrodistillation using a Likens-Nickerson apparatus in yields of 0.069-0.956%, and the essential oils analyzed by gas chromatographic techniques (GC-MS, GC-FID, and chiral GC-MS). The major components in the leaf essential oil of B. sagittata were (−)-germacrene D (10.8-34.5%), (+)-β-phellandrene (6.4-19.4%), (−)-( E)-β-caryophyllene (1.4-15.0%), and ( E)-β-ocimene (3.1-8.4%). Conclusion: There was modest variation in composition or yield with respect to geographical location or elevation in the samples from southwestern Idaho, but comparison with essential oils from locations outside of Idaho should more completely define the volatile phytochemistry of this plant.
{"title":"The Essential Oil of Balsamorhiza sagittata from Southwestern Idaho: Chemical Composition and Enantiomeric Distribution","authors":"Kathy Swor, P. Satyal, Ambika Poudel, W. Setzer","doi":"10.1177/1934578x231225842","DOIUrl":"https://doi.org/10.1177/1934578x231225842","url":null,"abstract":"Background/Objective: Arrowleaf balsamroot ( Balsamorhiza sagittata (Pursh) Nutt., Asteraceae) is a conspicuous forb growing in open hillsides and prairies at mid to upper elevations in the Intermountain West and Rocky Mountain regions. The plant is important forage for deer and elk and several Native American tribes used arrowleaf balsamroot as food and medicine. The volatile phytochemicals of B. sagittata have not been previously examined. Methods/Results: Nine individual samples of B. sagittata were collected, the essential oils obtained by hydrodistillation using a Likens-Nickerson apparatus in yields of 0.069-0.956%, and the essential oils analyzed by gas chromatographic techniques (GC-MS, GC-FID, and chiral GC-MS). The major components in the leaf essential oil of B. sagittata were (−)-germacrene D (10.8-34.5%), (+)-β-phellandrene (6.4-19.4%), (−)-( E)-β-caryophyllene (1.4-15.0%), and ( E)-β-ocimene (3.1-8.4%). Conclusion: There was modest variation in composition or yield with respect to geographical location or elevation in the samples from southwestern Idaho, but comparison with essential oils from locations outside of Idaho should more completely define the volatile phytochemistry of this plant.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"89 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139639008","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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