Pub Date : 2024-02-01DOI: 10.1177/1934578x241232281
Hieu Tran-Trung, Duc Giang Le, Van Trung Hoang, Danh C. Vu, T. Thang, Hieu Nguyen-Ngoc, Chen Tran Van, Thanh Triet Nguyen, Nguyen Hoang Tuan, Trang H.D. Nguyen
The ginger family (Zingiberaceae) is one of the most diverse and abundant families in the plant kingdom in terms of number of species. In terms of chemistry, this is a family of plants containing much essential oil with mainly monoterpene and sesquiterpene derivatives, which has been widely used in medicine, food, and flavor industries. In our series of studies on ginger family plants, the two new species including Wurfbainia schmidtii (K. Schum.) Škorničk. & A.D. Poulsen and Zingiber atroporphyreus Škorničk. & Q.B. Nguyen has been investigated for the first time. This study aimed to identify the chemical compositions of essential oils extracted from the rhizomes and leaves of these two species using gas chromatography-mass spectrometry (GC/MS) analysis and evaluate their hypoglycemic effects through the α-glucosidase and α-amylase inhibitory assays. In terms of chemical composition, in general, the main compounds appearing in the essential oils of both leaves and rhizomes of each species are similar but they are differences in the percentage of the main components, for example, 1,8-cineole is a main component in leaves whereas fenchyl acetate is the main one in rhizomes of W. schmidtii. Several distinctive compounds, in comparison with other members in the genus Zingiber, namely β-pinene, α-pinene, β-elemene, and sabinene, were found in the essential oil of Z. atroporphyreus. Regarding hypoglycemic effects, the essential oils from the two species tested possessed weak α-glucosidase and α-amylase inhibitory effects. For the first time, this study was designed to investigate the chemical composition as well as the hypoglycemic effect of essential oils distilled from the rhizomes and leaves of two species W. schmidtii and Z. atroporphyreus have been reported, serving as a premise for further systematic research on their phytochemistry and pharmacological effects being conducted.
就物种数量而言，姜科（姜属）是植物王国中种类最多、最丰富的科之一。在化学方面，姜科植物含有大量以单萜烯和倍半萜衍生物为主的精油，被广泛应用于医药、食品和香料工业。在我们对姜科植物的一系列研究中，首次研究了两个新物种，包括 Wurfbainia schmidtii (K. Schum.) Škorničk. & A.D. Poulsen 和 Zingiber atroporphyreus Škorničk. & Q.B. Nguyen。本研究旨在利用气相色谱-质谱分析法（GC/MS）鉴定从这两种植物的根茎和叶中提取的精油的化学成分，并通过α-葡萄糖苷酶和α-淀粉酶抑制实验评估其降血糖作用。在化学成分方面，一般来说，每个物种的叶片和根茎精油中出现的主要化合物都很相似，但主要成分所占的比例有所不同，例如，1,8-蒎烯是叶片中的主要成分，而乙酸葑酯则是 W. schmidtii 根茎中的主要成分。与 Zingiber 属的其他成员相比，在 Z. atroporphyreus 的精油中发现了几种独特的化合物，即 β-蒎烯、α-蒎烯、β-榄香烯和沙比利烯。在降血糖作用方面，所测试的两个物种的精油都具有微弱的 α-葡萄糖苷酶和 α-淀粉酶抑制作用。本研究首次研究了从 W. schmidtii 和 Z. atroporphyreus 两种植物的根茎和叶中蒸馏出的精油的化学成分和降血糖作用，为进一步系统研究其植物化学和药理作用提供了前提。
{"title":"Essential Oils of Two Species of Zingiberaceae Family from Vietnam: Chemical Compositions and α-Glucosidase, α-Amylase Inhibitory Effects","authors":"Hieu Tran-Trung, Duc Giang Le, Van Trung Hoang, Danh C. Vu, T. Thang, Hieu Nguyen-Ngoc, Chen Tran Van, Thanh Triet Nguyen, Nguyen Hoang Tuan, Trang H.D. Nguyen","doi":"10.1177/1934578x241232281","DOIUrl":"https://doi.org/10.1177/1934578x241232281","url":null,"abstract":"The ginger family (Zingiberaceae) is one of the most diverse and abundant families in the plant kingdom in terms of number of species. In terms of chemistry, this is a family of plants containing much essential oil with mainly monoterpene and sesquiterpene derivatives, which has been widely used in medicine, food, and flavor industries. In our series of studies on ginger family plants, the two new species including Wurfbainia schmidtii (K. Schum.) Škorničk. & A.D. Poulsen and Zingiber atroporphyreus Škorničk. & Q.B. Nguyen has been investigated for the first time. This study aimed to identify the chemical compositions of essential oils extracted from the rhizomes and leaves of these two species using gas chromatography-mass spectrometry (GC/MS) analysis and evaluate their hypoglycemic effects through the α-glucosidase and α-amylase inhibitory assays. In terms of chemical composition, in general, the main compounds appearing in the essential oils of both leaves and rhizomes of each species are similar but they are differences in the percentage of the main components, for example, 1,8-cineole is a main component in leaves whereas fenchyl acetate is the main one in rhizomes of W. schmidtii. Several distinctive compounds, in comparison with other members in the genus Zingiber, namely β-pinene, α-pinene, β-elemene, and sabinene, were found in the essential oil of Z. atroporphyreus. Regarding hypoglycemic effects, the essential oils from the two species tested possessed weak α-glucosidase and α-amylase inhibitory effects. For the first time, this study was designed to investigate the chemical composition as well as the hypoglycemic effect of essential oils distilled from the rhizomes and leaves of two species W. schmidtii and Z. atroporphyreus have been reported, serving as a premise for further systematic research on their phytochemistry and pharmacological effects being conducted.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"37 17","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139881061","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 : 2024-02-01DOI: 10.1177/1934578x241230820
F. Maarouf, H. Rahman
Background: Carvacrol (CAR) is the active component in essential oils (EOs) of many fragrant plants, including oregano and thyme; however, its high toxicity restricts its usage in biomedical fields, and the self-nano-emulsifying drug delivery system (SNEDDS) was suggested to overcome this issue. Objective: To prepare and characterize the CAR-loaded SNEDDS and to assess its toxicity profile towards healthy rats using the in vivo sub-chronic study. Methods: SNEDDS was prepared from olive oil, dimethyl sulfoxide, Tween-80, and distilled water, then CAR-SNEDDS was prepared by adding 0.5% CAR to SNEDDS and both composites were gently agitated for 72 h at room temperature. Later on, both composites were physiochemically characterized for size/charge (Zetasizer), shape (TEM), crystallinity (XRAD), composition (FTIR), and quantitated (UV–Vis). Additionally, the sub-chronic toxicity of both composites at different doses was conducted by orally treating healthy Sprague Dawley for 4 weeks. Then, the treated rats were checked for toxicological symptoms, food/water intake, and behavioral abnormality. In addition, the blood samples were tested for hematologic/biochemical changes, while vital organs (liver and kidney) were assessed for histopathological alterations. Results: The average globule size, zeta potential, and polydispersity index of CAR-SNEDDS were 158.93 ± 22.18 nm, −22.56 ± 1.77 mV, 0.553 ± 0.31, respectively. All treated animal tissues, serum biochemical profiles, and total hemograms were normal. At 30-90 mg/kg oral doses, CAR-SNEDDS was not toxic and did not cause mortality. Conclusions: CAR-SNEDDS was successfully synthesized and characterized, and the results from sub-chronic oral toxicity studies showed that the CAR-SNEDDS were non-toxic and safe for biomedical fields.
{"title":"Preparation, Characterization, and Sub-Chronic Toxicity of Carvacrol-Self-Nano-Emulsifying Drug Delivery System Towards Healthy Sprague Dawley Rats","authors":"F. Maarouf, H. Rahman","doi":"10.1177/1934578x241230820","DOIUrl":"https://doi.org/10.1177/1934578x241230820","url":null,"abstract":"Background: Carvacrol (CAR) is the active component in essential oils (EOs) of many fragrant plants, including oregano and thyme; however, its high toxicity restricts its usage in biomedical fields, and the self-nano-emulsifying drug delivery system (SNEDDS) was suggested to overcome this issue. Objective: To prepare and characterize the CAR-loaded SNEDDS and to assess its toxicity profile towards healthy rats using the in vivo sub-chronic study. Methods: SNEDDS was prepared from olive oil, dimethyl sulfoxide, Tween-80, and distilled water, then CAR-SNEDDS was prepared by adding 0.5% CAR to SNEDDS and both composites were gently agitated for 72 h at room temperature. Later on, both composites were physiochemically characterized for size/charge (Zetasizer), shape (TEM), crystallinity (XRAD), composition (FTIR), and quantitated (UV–Vis). Additionally, the sub-chronic toxicity of both composites at different doses was conducted by orally treating healthy Sprague Dawley for 4 weeks. Then, the treated rats were checked for toxicological symptoms, food/water intake, and behavioral abnormality. In addition, the blood samples were tested for hematologic/biochemical changes, while vital organs (liver and kidney) were assessed for histopathological alterations. Results: The average globule size, zeta potential, and polydispersity index of CAR-SNEDDS were 158.93 ± 22.18 nm, −22.56 ± 1.77 mV, 0.553 ± 0.31, respectively. All treated animal tissues, serum biochemical profiles, and total hemograms were normal. At 30-90 mg/kg oral doses, CAR-SNEDDS was not toxic and did not cause mortality. Conclusions: CAR-SNEDDS was successfully synthesized and characterized, and the results from sub-chronic oral toxicity studies showed that the CAR-SNEDDS were non-toxic and safe for biomedical fields.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"59 8","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139823834","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 : 2024-02-01DOI: 10.1177/1934578x241226562
Zhiyuan Xu, Haixin Ding, Fu Xin, Xu Yan, Zhu Fadi, Huochun Ye, Zhang Yuan Yuan, Yongxia Guo, Zhang Jing, Feng Gang
Due to the urgent need to develop innovative, environmentally sustainable bactericides, we use the natural product isoquinoline as a lead compound to discover highly active bactericides from isoquinoline derivatives. In this paper, the antibacterial activity of 49 isoquinoline derivatives was evaluated against three plant bacteria in vitro. Among all the derivatives, isoquinoline-3-carboxylic acid (IQ3CA) demonstrated significant antibacterial activity against Ralstonia solanacearum ( Rs), Acidovorax citrulli ( Ac), X. oryzae pv. oryzicola ( Xoc), X. campestris pv. campestris ( Xcc), P. carotovorum subsp. carotovorum ( Pcc), and X. fragariae ( Xf), with EC50 values ranging from 8.38 to 17.35 μg/mL. Furthermore, IQ3CA exhibited a potent protective effect against Ac, with an efficacy of 68.56% at 200 μg/mL, which was not significantly different from that of the positive control kasugamycin (72.48%) and was superior to that of the positive control thiosen copper (64.62%). The scanning electron microscopy observations revealed that treatment of Ac cells with IQ3CA at a concentration of 25 μg/mL resulted in a curved and sunken cell morphology, along with destroyed cell membrane integrity. Additionally, the motility and exopolysaccharides production of Ac were inhibited, and biofilm formation was prevented. These results suggest that IQ3CA holds promise as a lead compound with antibacterial properties against plant diseases.
{"title":"Antibacterial Activity and Possibly Made of Action of Isoquinoline-3-Carboxylic Acid","authors":"Zhiyuan Xu, Haixin Ding, Fu Xin, Xu Yan, Zhu Fadi, Huochun Ye, Zhang Yuan Yuan, Yongxia Guo, Zhang Jing, Feng Gang","doi":"10.1177/1934578x241226562","DOIUrl":"https://doi.org/10.1177/1934578x241226562","url":null,"abstract":"Due to the urgent need to develop innovative, environmentally sustainable bactericides, we use the natural product isoquinoline as a lead compound to discover highly active bactericides from isoquinoline derivatives. In this paper, the antibacterial activity of 49 isoquinoline derivatives was evaluated against three plant bacteria in vitro. Among all the derivatives, isoquinoline-3-carboxylic acid (IQ3CA) demonstrated significant antibacterial activity against Ralstonia solanacearum ( Rs), Acidovorax citrulli ( Ac), X. oryzae pv. oryzicola ( Xoc), X. campestris pv. campestris ( Xcc), P. carotovorum subsp. carotovorum ( Pcc), and X. fragariae ( Xf), with EC50 values ranging from 8.38 to 17.35 μg/mL. Furthermore, IQ3CA exhibited a potent protective effect against Ac, with an efficacy of 68.56% at 200 μg/mL, which was not significantly different from that of the positive control kasugamycin (72.48%) and was superior to that of the positive control thiosen copper (64.62%). The scanning electron microscopy observations revealed that treatment of Ac cells with IQ3CA at a concentration of 25 μg/mL resulted in a curved and sunken cell morphology, along with destroyed cell membrane integrity. Additionally, the motility and exopolysaccharides production of Ac were inhibited, and biofilm formation was prevented. These results suggest that IQ3CA holds promise as a lead compound with antibacterial properties against plant diseases.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"132 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139886449","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 : 2024-02-01DOI: 10.1177/1934578x241232281
Hieu Tran-Trung, Duc Giang Le, Van Trung Hoang, Danh C. Vu, T. Thang, Hieu Nguyen-Ngoc, Chen Tran Van, Thanh Triet Nguyen, Nguyen Hoang Tuan, Trang H.D. Nguyen
The ginger family (Zingiberaceae) is one of the most diverse and abundant families in the plant kingdom in terms of number of species. In terms of chemistry, this is a family of plants containing much essential oil with mainly monoterpene and sesquiterpene derivatives, which has been widely used in medicine, food, and flavor industries. In our series of studies on ginger family plants, the two new species including Wurfbainia schmidtii (K. Schum.) Škorničk. & A.D. Poulsen and Zingiber atroporphyreus Škorničk. & Q.B. Nguyen has been investigated for the first time. This study aimed to identify the chemical compositions of essential oils extracted from the rhizomes and leaves of these two species using gas chromatography-mass spectrometry (GC/MS) analysis and evaluate their hypoglycemic effects through the α-glucosidase and α-amylase inhibitory assays. In terms of chemical composition, in general, the main compounds appearing in the essential oils of both leaves and rhizomes of each species are similar but they are differences in the percentage of the main components, for example, 1,8-cineole is a main component in leaves whereas fenchyl acetate is the main one in rhizomes of W. schmidtii. Several distinctive compounds, in comparison with other members in the genus Zingiber, namely β-pinene, α-pinene, β-elemene, and sabinene, were found in the essential oil of Z. atroporphyreus. Regarding hypoglycemic effects, the essential oils from the two species tested possessed weak α-glucosidase and α-amylase inhibitory effects. For the first time, this study was designed to investigate the chemical composition as well as the hypoglycemic effect of essential oils distilled from the rhizomes and leaves of two species W. schmidtii and Z. atroporphyreus have been reported, serving as a premise for further systematic research on their phytochemistry and pharmacological effects being conducted.
就物种数量而言，姜科（姜属）是植物王国中种类最多、最丰富的科之一。在化学方面，姜科植物含有大量以单萜烯和倍半萜衍生物为主的精油，被广泛应用于医药、食品和香料工业。在我们对姜科植物的一系列研究中，首次研究了两个新物种，包括 Wurfbainia schmidtii (K. Schum.) Škorničk. & A.D. Poulsen 和 Zingiber atroporphyreus Škorničk. & Q.B. Nguyen。本研究旨在利用气相色谱-质谱分析法（GC/MS）鉴定从这两种植物的根茎和叶中提取的精油的化学成分，并通过α-葡萄糖苷酶和α-淀粉酶抑制实验评估其降血糖作用。在化学成分方面，一般来说，每个物种的叶片和根茎精油中出现的主要化合物都很相似，但主要成分所占的比例有所不同，例如，1,8-蒎烯是叶片中的主要成分，而乙酸葑酯则是 W. schmidtii 根茎中的主要成分。与 Zingiber 属的其他成员相比，在 Z. atroporphyreus 的精油中发现了几种独特的化合物，即 β-蒎烯、α-蒎烯、β-榄香烯和沙比利烯。在降血糖作用方面，所测试的两个物种的精油都具有微弱的 α-葡萄糖苷酶和 α-淀粉酶抑制作用。本研究首次研究了从 W. schmidtii 和 Z. atroporphyreus 两种植物的根茎和叶中蒸馏出的精油的化学成分和降血糖作用，为进一步系统研究其植物化学和药理作用提供了前提。
{"title":"Essential Oils of Two Species of Zingiberaceae Family from Vietnam: Chemical Compositions and α-Glucosidase, α-Amylase Inhibitory Effects","authors":"Hieu Tran-Trung, Duc Giang Le, Van Trung Hoang, Danh C. Vu, T. Thang, Hieu Nguyen-Ngoc, Chen Tran Van, Thanh Triet Nguyen, Nguyen Hoang Tuan, Trang H.D. Nguyen","doi":"10.1177/1934578x241232281","DOIUrl":"https://doi.org/10.1177/1934578x241232281","url":null,"abstract":"The ginger family (Zingiberaceae) is one of the most diverse and abundant families in the plant kingdom in terms of number of species. In terms of chemistry, this is a family of plants containing much essential oil with mainly monoterpene and sesquiterpene derivatives, which has been widely used in medicine, food, and flavor industries. In our series of studies on ginger family plants, the two new species including Wurfbainia schmidtii (K. Schum.) Škorničk. & A.D. Poulsen and Zingiber atroporphyreus Škorničk. & Q.B. Nguyen has been investigated for the first time. This study aimed to identify the chemical compositions of essential oils extracted from the rhizomes and leaves of these two species using gas chromatography-mass spectrometry (GC/MS) analysis and evaluate their hypoglycemic effects through the α-glucosidase and α-amylase inhibitory assays. In terms of chemical composition, in general, the main compounds appearing in the essential oils of both leaves and rhizomes of each species are similar but they are differences in the percentage of the main components, for example, 1,8-cineole is a main component in leaves whereas fenchyl acetate is the main one in rhizomes of W. schmidtii. Several distinctive compounds, in comparison with other members in the genus Zingiber, namely β-pinene, α-pinene, β-elemene, and sabinene, were found in the essential oil of Z. atroporphyreus. Regarding hypoglycemic effects, the essential oils from the two species tested possessed weak α-glucosidase and α-amylase inhibitory effects. For the first time, this study was designed to investigate the chemical composition as well as the hypoglycemic effect of essential oils distilled from the rhizomes and leaves of two species W. schmidtii and Z. atroporphyreus have been reported, serving as a premise for further systematic research on their phytochemistry and pharmacological effects being conducted.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"203 ","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139821173","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: 10.1177/1934578x231171513
Danhong Lian, Xin Zhong, Lian Li, Li Gu, Yimei Zheng, Xin Liu
Background: The fruiting body of Ganoderma sinense Zhao, Xu et Zhang iscertified as an authoritative medical material in the Chinese Pharmacopoeia 2020 edition and has been used as a crude drug for a long time. G sinense spores are crucial part of the fruiting body of G sinense and exhibited antitumor and immune-enhancing activities according to our previous reports. However, there were few studies about the chemical composition of G sinense spores. This study was aimed at the structure determination and antitumor effect of the sterols isolated from G sinense spores. Methods: Modern chromatographic methods were applied to isolate compounds from the ruptured spores of G sinense. Their chemical structures were elucidated by analyses of one-dimensional and two-dimensional 1H nuclear magnetic resonance, and high-resolution electrospray ionization mass spectrometry data. The cytotoxicities of the isolated compounds against 3 tumor cell lines, human non-small cell lung cancer A549 and 95D cells, and human hepatocellular carcinoma HepG2 cells were measured by Cell Counting Kit-8. Results: A novel ergosterol derivative, (22 E,24 R)-3β,5β,6α,7α,14β-pentahydroxyergosta-8,22-dien-15-one (1), and 5 known sterols, (22 E,24 R)-3β,5α,9α,14β-tetrahydroxyergosta-7,22-dien-6-one (2), (22 E,24 R)-ergosta-7,9(11),22-triene-3β,5α,6β-triol (3), (22 E,24 R)-ergosta-7,9(11),22-triene-3β,5α,6β,14α-tetrol (4), β-daucosterine (5), and (22 E,24 R)-ergosta-7,22-diene-3β,5α,6β,9α-tetrol (6), were obtained from the ruptured spores of G sinense. Compound 1 exhibited cytotoxicity against A549 cells and HepG-2 cells with IC50 values of 65.12 ± 4.76 and 97.34 ± 6.36 μM, respectively. Compounds 1, 2, and 4 were obtained from G sinense for the first time. Conclusion: This paper is a continuation of an investigation of the chemical ingredients from G sinense spores and their antitumor effect. Only compound 1 showed weak cytotoxicities against A549 cells and HepG-2 cells.
{"title":"Polyhydroxy Sterols Isolated From Ganoderma sinense Spores and Their Cytotoxic Activities","authors":"Danhong Lian, Xin Zhong, Lian Li, Li Gu, Yimei Zheng, Xin Liu","doi":"10.1177/1934578x231171513","DOIUrl":"https://doi.org/10.1177/1934578x231171513","url":null,"abstract":"Background: The fruiting body of Ganoderma sinense Zhao, Xu et Zhang iscertified as an authoritative medical material in the Chinese Pharmacopoeia 2020 edition and has been used as a crude drug for a long time. G sinense spores are crucial part of the fruiting body of G sinense and exhibited antitumor and immune-enhancing activities according to our previous reports. However, there were few studies about the chemical composition of G sinense spores. This study was aimed at the structure determination and antitumor effect of the sterols isolated from G sinense spores. Methods: Modern chromatographic methods were applied to isolate compounds from the ruptured spores of G sinense. Their chemical structures were elucidated by analyses of one-dimensional and two-dimensional 1H nuclear magnetic resonance, and high-resolution electrospray ionization mass spectrometry data. The cytotoxicities of the isolated compounds against 3 tumor cell lines, human non-small cell lung cancer A549 and 95D cells, and human hepatocellular carcinoma HepG2 cells were measured by Cell Counting Kit-8. Results: A novel ergosterol derivative, (22 E,24 R)-3β,5β,6α,7α,14β-pentahydroxyergosta-8,22-dien-15-one (1), and 5 known sterols, (22 E,24 R)-3β,5α,9α,14β-tetrahydroxyergosta-7,22-dien-6-one (2), (22 E,24 R)-ergosta-7,9(11),22-triene-3β,5α,6β-triol (3), (22 E,24 R)-ergosta-7,9(11),22-triene-3β,5α,6β,14α-tetrol (4), β-daucosterine (5), and (22 E,24 R)-ergosta-7,22-diene-3β,5α,6β,9α-tetrol (6), were obtained from the ruptured spores of G sinense. Compound 1 exhibited cytotoxicity against A549 cells and HepG-2 cells with IC50 values of 65.12 ± 4.76 and 97.34 ± 6.36 μM, respectively. Compounds 1, 2, and 4 were obtained from G sinense for the first time. Conclusion: This paper is a continuation of an investigation of the chemical ingredients from G sinense spores and their antitumor effect. Only compound 1 showed weak cytotoxicities against A549 cells and HepG-2 cells.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"36 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139635660","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: 10.1177/1934578x231222106
Mohammed Helmy Faris Shalayel, G. Al-Mazaideh, Majed Meshal Almutairi, W. A. Alsubhi, Abdullah K. Althaiban
Many vitamin D analogs and sterols-related compounds have been identified and extracted from several plants including Solanaceae species. The aim of our study was to evaluate the antifungal potential of 15 vitamin D, D3 analogs, and some sterols-related compounds that have been detected in some plants along with 3 standard antifungal drugs, Isavuconazole, Fluconazole, and Voriconazole, on the Mucormycosis-sterol 14-alpha demethylase (CYP51) enzyme by in silico study. In this work, the molecular simulation was used to prepare the specific enzyme and the antifungal profiles utilized for the molecular docking of the contemplated compounds and subsequent prediction for the mechanism of binding within the catalytic site of Sterol 14-Demethylase (CYP51) to speculate their binding affinities. Anti-fungal medications, Fluconazole and Voriconazole revealed drugs bound distant from the binding sites, but Isavuconazole bound close to the binding site. In this context, the 15 vitamin D and D3 compounds were somewhat seen in binding proximity, especially for Alfacalcidol, Eldecalcitol, and Inecalcitol. Seocalcitol and Isavuconazole had the lowest binding energies and were the closest ones connected to the binding cavities with the best binding free energies equal −13.21 ± 0.24 and −15.29 ± 0.25, respectively. Isavuconazole and Seocalcitol could potentially be further assessed to be adjuvantly used as drugs to inhibit the fungal activity by targeting CYP51, a significant target for anti-fungal as well as anti-protozoan drugs, and hence could be efficient against mucormycosis.
{"title":"The Computational Interaction Analyses of Some Vitamin D-Related Compounds with Sterol 14-Demethylase (CYP51) – Could It Be a Glimmer of Hope to Find New Anti-Mucormycotic Drugs Extracted from Plants-Derived Sterols?","authors":"Mohammed Helmy Faris Shalayel, G. Al-Mazaideh, Majed Meshal Almutairi, W. A. Alsubhi, Abdullah K. Althaiban","doi":"10.1177/1934578x231222106","DOIUrl":"https://doi.org/10.1177/1934578x231222106","url":null,"abstract":"Many vitamin D analogs and sterols-related compounds have been identified and extracted from several plants including Solanaceae species. The aim of our study was to evaluate the antifungal potential of 15 vitamin D, D3 analogs, and some sterols-related compounds that have been detected in some plants along with 3 standard antifungal drugs, Isavuconazole, Fluconazole, and Voriconazole, on the Mucormycosis-sterol 14-alpha demethylase (CYP51) enzyme by in silico study. In this work, the molecular simulation was used to prepare the specific enzyme and the antifungal profiles utilized for the molecular docking of the contemplated compounds and subsequent prediction for the mechanism of binding within the catalytic site of Sterol 14-Demethylase (CYP51) to speculate their binding affinities. Anti-fungal medications, Fluconazole and Voriconazole revealed drugs bound distant from the binding sites, but Isavuconazole bound close to the binding site. In this context, the 15 vitamin D and D3 compounds were somewhat seen in binding proximity, especially for Alfacalcidol, Eldecalcitol, and Inecalcitol. Seocalcitol and Isavuconazole had the lowest binding energies and were the closest ones connected to the binding cavities with the best binding free energies equal −13.21 ± 0.24 and −15.29 ± 0.25, respectively. Isavuconazole and Seocalcitol could potentially be further assessed to be adjuvantly used as drugs to inhibit the fungal activity by targeting CYP51, a significant target for anti-fungal as well as anti-protozoan drugs, and hence could be efficient against mucormycosis.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"77 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139639929","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}
Background: Garcinia kola is recommended in African folk medicine for the treatment of diabetes and its associated complications. In this study, we investigated the effects of Garcinia biflavonoid 1 (GB1), an active chemical component of Garcinia kola, on blood glucose and lipid in db/db mice with type 2 diabetes. Methods: Db/db mice were divided into 4 groups: vehicle, low-dose GB1 (50 mg/kg), high-dose GB1 (100 mg/kg), and rosiglitazone, and treated for 4 weeks. Body weight, fasting blood glucose (FBG), fasting insulin, oral glucose tolerance test (OGTT), insulin tolerance test (ITT), hepatic glycogen, serum and liver biochemical parameters, and histological morphology of the pancreas, heart, and kidneys were evaluated. Results: GB1 significantly reduced FBG, the area under the curve value of OGTT and ITT, and the homeostasis model assessment of insulin resistance, increased the homeostasis model assessment of β-cell function, quantitative insulin sensitivity check index, and the level of hepatic glycogen. Lower triglyceride and free fatty acid level, and a lower triglyceride-glucose index were also observed in the GB1 groups. In addition, no significant changes in alanine aminotransferase and aspartate aminotransferase levels, or in the histopathology of the pancreas, heart, or kidney were observed after GB1 treatment. Conclusion: These findings indicate that GB1 exerts an antidiabetic effect in db/db mice, by improving hyperglycemia, insulin resistance, and lipid dysregulation without evidence of adverse reactions.
{"title":"Garcinia Biflavonoid 1 from Garcinia kola Ameliorates Glycolipid Metabolism Disorder in Type 2 Diabetic db/db Mice","authors":"Ting-Dan Fu, Wen-Li Zhang, Ying Zhang, Chang-Sheng Deng, Wang Qi, Qin Xu, Jian-Ping Song, Wen-Feng Guo, Rui-Yi Yang, Xin-An Huang","doi":"10.1177/1934578x231224993","DOIUrl":"https://doi.org/10.1177/1934578x231224993","url":null,"abstract":"Background: Garcinia kola is recommended in African folk medicine for the treatment of diabetes and its associated complications. In this study, we investigated the effects of Garcinia biflavonoid 1 (GB1), an active chemical component of Garcinia kola, on blood glucose and lipid in db/db mice with type 2 diabetes. Methods: Db/db mice were divided into 4 groups: vehicle, low-dose GB1 (50 mg/kg), high-dose GB1 (100 mg/kg), and rosiglitazone, and treated for 4 weeks. Body weight, fasting blood glucose (FBG), fasting insulin, oral glucose tolerance test (OGTT), insulin tolerance test (ITT), hepatic glycogen, serum and liver biochemical parameters, and histological morphology of the pancreas, heart, and kidneys were evaluated. Results: GB1 significantly reduced FBG, the area under the curve value of OGTT and ITT, and the homeostasis model assessment of insulin resistance, increased the homeostasis model assessment of β-cell function, quantitative insulin sensitivity check index, and the level of hepatic glycogen. Lower triglyceride and free fatty acid level, and a lower triglyceride-glucose index were also observed in the GB1 groups. In addition, no significant changes in alanine aminotransferase and aspartate aminotransferase levels, or in the histopathology of the pancreas, heart, or kidney were observed after GB1 treatment. Conclusion: These findings indicate that GB1 exerts an antidiabetic effect in db/db mice, by improving hyperglycemia, insulin resistance, and lipid dysregulation without evidence of adverse reactions.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"20 4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139455342","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: 10.1177/1934578x231224994
Ni Thi Ngoc Huynh, Ninh Thi Pham, Chien Van Tran, Dung Thi Nguyen, Mai Thi Ngoc Dinh, Van Thi Nguyen, Minh Hong Nguyen, Hieu Van Ngo, Anh Ngoc Ho, Jinhua Cheng, Joo-Won Suh, Sung Van Tran, Thao Kim Nu Nguyen, Thao Thi Phuong Tran
Actinomycetes have been known to be the great natural sources to explore antibiotics for the treatment of tuberculosis (TB). The isolation of actinomycetes from the samples in Vietnam followed by the screening of their antimycobacterial activity was performed in this study. The metabolites isolated from the most active strain were further evaluated for their antimycobacterial, antimicrobial and cytotoxic activity. Actinomycetes were growth in culture media, isolated and identified by colony, spore chain morphology and 16S rRNA gene sequencing. Agar diffusion assay was used for the screening of the isolated strains against Mycobacterium smegmatis, a safety surrogate for Mycobacterium tuberculosis. The metabolites produced from the most active strain were investigated by actinomycete fermentation, extraction and isolation from biomass and cultures. The structures of the isolated compound were elucidated by spectral data and comparison with the reported literatures. 181 strains were isolated from nine regions along the north to central Vietnam. The five most active strains against Mycobacterium smegmatis were detected. Following the bioassay-guided result, the strain A121 ( Streptomyces alboniger) was selected for further isolation of the bioactive metabolites. As a result, obscurolide B2β (1) and chartreusin (2) were obtained and evaluated for their antimycobacterial activity against M. smegmatis. Compound 2 displayed potential antimycobacterial activity, antimicrobial effect against the Gram positive bacteria Staphylococcus aureus, Bacillus subtilis, Lactobacillus fermentum and cytotoxicity against four cancer cell lines KB, HepG-2, Lu-1 and MCF-7. Five strains possessing potential antimycobacterial activity were identified from the samples collected in Vietnam. Two compounds including obscurolide B2β (1) and chartreusin (2) were isolated from the most active strain A121 ( Streptomyces alboniger). This is the first time these compounds have been isolated from this strain. Chartreusin (2) exhibited notable antimycobacterial, antimicrobial and cytotoxic activity, making its worthy attention for further drug development, particularly for antituberculosis therapeutic agents.
{"title":"Screening for Antimycobacterial Activity of Actinomycetes Collected in Vietnam – Isolation and Activity of Metabolites from Streptomyces alboniger (A121)","authors":"Ni Thi Ngoc Huynh, Ninh Thi Pham, Chien Van Tran, Dung Thi Nguyen, Mai Thi Ngoc Dinh, Van Thi Nguyen, Minh Hong Nguyen, Hieu Van Ngo, Anh Ngoc Ho, Jinhua Cheng, Joo-Won Suh, Sung Van Tran, Thao Kim Nu Nguyen, Thao Thi Phuong Tran","doi":"10.1177/1934578x231224994","DOIUrl":"https://doi.org/10.1177/1934578x231224994","url":null,"abstract":"Actinomycetes have been known to be the great natural sources to explore antibiotics for the treatment of tuberculosis (TB). The isolation of actinomycetes from the samples in Vietnam followed by the screening of their antimycobacterial activity was performed in this study. The metabolites isolated from the most active strain were further evaluated for their antimycobacterial, antimicrobial and cytotoxic activity. Actinomycetes were growth in culture media, isolated and identified by colony, spore chain morphology and 16S rRNA gene sequencing. Agar diffusion assay was used for the screening of the isolated strains against Mycobacterium smegmatis, a safety surrogate for Mycobacterium tuberculosis. The metabolites produced from the most active strain were investigated by actinomycete fermentation, extraction and isolation from biomass and cultures. The structures of the isolated compound were elucidated by spectral data and comparison with the reported literatures. 181 strains were isolated from nine regions along the north to central Vietnam. The five most active strains against Mycobacterium smegmatis were detected. Following the bioassay-guided result, the strain A121 ( Streptomyces alboniger) was selected for further isolation of the bioactive metabolites. As a result, obscurolide B2β (1) and chartreusin (2) were obtained and evaluated for their antimycobacterial activity against M. smegmatis. Compound 2 displayed potential antimycobacterial activity, antimicrobial effect against the Gram positive bacteria Staphylococcus aureus, Bacillus subtilis, Lactobacillus fermentum and cytotoxicity against four cancer cell lines KB, HepG-2, Lu-1 and MCF-7. Five strains possessing potential antimycobacterial activity were identified from the samples collected in Vietnam. Two compounds including obscurolide B2β (1) and chartreusin (2) were isolated from the most active strain A121 ( Streptomyces alboniger). This is the first time these compounds have been isolated from this strain. Chartreusin (2) exhibited notable antimycobacterial, antimicrobial and cytotoxic activity, making its worthy attention for further drug development, particularly for antituberculosis therapeutic agents.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"19 7","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139455349","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: 10.1177/1934578x241226825
Nong Thi Anh Thu, Lo Huyen Linh, Dao Anh Hoang, Nguyen Tu Oanh, Vu Mai Thao, Nguyen Thi Minh Hang, N. X. Nhiem
Objectives: The aim of the project was the isolation, structure elucidation, and anti-inflammatory evaluation of compounds from the leaves of Ligustrum sinense Lour. Methods: Chromatographic techniques were used to isolate anti-inflammatory compounds from the methanol extract of L sinense leaves. The structures of compounds were elucidated by analyses of mass spectra, nuclear magnetic resonance data, and Circular dichroism spectra. Compounds were evaluated using anti-inflammatory assays. Results: One new neolignane glucoside, neoligustrume A (1), along with eleven known compounds, ligujaponoside A (2), ligujaponoside B (3), ligustroside (4), oleuropein (5), ligustaloside A dimethyl acetal (6), ligustaloside B dimethyl acetal (7), olivil (8), (+)-cycloolivil (9), kaempferol 3- O-β-D-glucopyranoside-7- O-α-L-rhamnopyranoside (10), oleanoic acid (11), and hydroxytyrosol (12) were isolated from the methanol extract of L sinense leaves. Compounds 2, 3, and 12 showed significant inhibitory NO production with IC50 values of 16.3 ± 0.5, 18.2 ± 1.1, and 15.7 ± 1.9 μM, respectively. Compounds 4-7 and 11 showed moderate inhibitory NO production with IC50 values ranging from 21.4 to 45.0 µM. Moreover, compound 12 showed the most TNF-α inhibition with 58.1 ± 5.7% at a concentration of 50 μM. Conclusions: One new and 11 known compounds were isolated from L sinense. This is the first report of compounds 2-9 from L sinense. Compounds 2, 3, and 12 showed significant inhibitory NO production with IC50 values of 16.3 ± 0.5, 18.2 ± 1.1, and 15.7 ± 1.9 μM, respectively. Compound 12 could be the anti-inflammatory source.
{"title":"Neolignan Glycoside and Other Constituents From the Leaves of Ligustrum sinense and Their Anti-Inflammatory Activity","authors":"Nong Thi Anh Thu, Lo Huyen Linh, Dao Anh Hoang, Nguyen Tu Oanh, Vu Mai Thao, Nguyen Thi Minh Hang, N. X. Nhiem","doi":"10.1177/1934578x241226825","DOIUrl":"https://doi.org/10.1177/1934578x241226825","url":null,"abstract":"Objectives: The aim of the project was the isolation, structure elucidation, and anti-inflammatory evaluation of compounds from the leaves of Ligustrum sinense Lour. Methods: Chromatographic techniques were used to isolate anti-inflammatory compounds from the methanol extract of L sinense leaves. The structures of compounds were elucidated by analyses of mass spectra, nuclear magnetic resonance data, and Circular dichroism spectra. Compounds were evaluated using anti-inflammatory assays. Results: One new neolignane glucoside, neoligustrume A (1), along with eleven known compounds, ligujaponoside A (2), ligujaponoside B (3), ligustroside (4), oleuropein (5), ligustaloside A dimethyl acetal (6), ligustaloside B dimethyl acetal (7), olivil (8), (+)-cycloolivil (9), kaempferol 3- O-β-D-glucopyranoside-7- O-α-L-rhamnopyranoside (10), oleanoic acid (11), and hydroxytyrosol (12) were isolated from the methanol extract of L sinense leaves. Compounds 2, 3, and 12 showed significant inhibitory NO production with IC50 values of 16.3 ± 0.5, 18.2 ± 1.1, and 15.7 ± 1.9 μM, respectively. Compounds 4-7 and 11 showed moderate inhibitory NO production with IC50 values ranging from 21.4 to 45.0 µM. Moreover, compound 12 showed the most TNF-α inhibition with 58.1 ± 5.7% at a concentration of 50 μM. Conclusions: One new and 11 known compounds were isolated from L sinense. This is the first report of compounds 2-9 from L sinense. Compounds 2, 3, and 12 showed significant inhibitory NO production with IC50 values of 16.3 ± 0.5, 18.2 ± 1.1, and 15.7 ± 1.9 μM, respectively. Compound 12 could be the anti-inflammatory source.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"5 11","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139634012","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: 10.1177/1934578x221111036
Meng S. Cheong, L. Nahar, S. Sarker, Hui Cao, Wai S. Cheang, Jia-Qi Xiao
Piceatannol is a stilbenoid, which has shown bioactivities in various cell culture models. However, its stability in cell culture medium is not clear. Here, UPLC-MS/MS was applied in situ to analyze the degradation products of piceatannol in Dulbecco's Modified Eagle's Medium (DMEM) and cell culture to investigate the compound's stability in DMEM. During the incubation with cell culture medium (at 4 and 37 °C), several piceatannol derivatives, such as an oxidation product ( m/z 243.06), a reduction product ( m/z 247.09), dimers ( m/z 485.12 and 487.14) and trimers ( m/z 727.18) were detected, which demonstrated the instability of piceatannol in cell culture conditions. To confirm if the new products during the incubation were generated due to the instability of piceatannol, ascorbic acid was added. The presence of ascorbic acid could significantly slow the degradation rate of piceatannol and the generation of piceatannol derivatives, which proved that the new products were generated by the degradation of piceatannol and indicated that the instability of piceatannol might be related to its antioxidant activity.
{"title":"Stability of Piceatannol in Dulbecco's Modified Eagle's Medium by In Situ UPLC-MS/MS Analysis","authors":"Meng S. Cheong, L. Nahar, S. Sarker, Hui Cao, Wai S. Cheang, Jia-Qi Xiao","doi":"10.1177/1934578x221111036","DOIUrl":"https://doi.org/10.1177/1934578x221111036","url":null,"abstract":"Piceatannol is a stilbenoid, which has shown bioactivities in various cell culture models. However, its stability in cell culture medium is not clear. Here, UPLC-MS/MS was applied in situ to analyze the degradation products of piceatannol in Dulbecco's Modified Eagle's Medium (DMEM) and cell culture to investigate the compound's stability in DMEM. During the incubation with cell culture medium (at 4 and 37 °C), several piceatannol derivatives, such as an oxidation product ( m/z 243.06), a reduction product ( m/z 247.09), dimers ( m/z 485.12 and 487.14) and trimers ( m/z 727.18) were detected, which demonstrated the instability of piceatannol in cell culture conditions. To confirm if the new products during the incubation were generated due to the instability of piceatannol, ascorbic acid was added. The presence of ascorbic acid could significantly slow the degradation rate of piceatannol and the generation of piceatannol derivatives, which proved that the new products were generated by the degradation of piceatannol and indicated that the instability of piceatannol might be related to its antioxidant activity.","PeriodicalId":509851,"journal":{"name":"Natural Product Communications","volume":"346 13‐15","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139632094","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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