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Keywords = alphitolic acid

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16 pages, 3361 KB  
Article
Comparative Analysis of the Sedative and Hypnotic Effects among Various Parts of Zizyphus spinosus Hu and Their Chemical Analysis
by Baojian Li, Yuangui Yang, Zhongxing Song and Zhishu Tang
Pharmaceuticals 2024, 17(4), 413; https://doi.org/10.3390/ph17040413 - 25 Mar 2024
Cited by 2 | Viewed by 2640
Abstract
Zizyphus spinosus Hu (ZS), as a “medicinal and food-homologous” plant, has been used for a long history. The study was to assess the sedative and hypnotic effects among various parts of ZS. The model, diazepam (DZP), ZS kernel (ZSS), ZS flesh (ZSF), and [...] Read more.
Zizyphus spinosus Hu (ZS), as a “medicinal and food-homologous” plant, has been used for a long history. The study was to assess the sedative and hypnotic effects among various parts of ZS. The model, diazepam (DZP), ZS kernel (ZSS), ZS flesh (ZSF), and ZS husk (ZSKS) group occurred subsequent to the successful establishment of the para-chlorophenylalanine induced insomnia model via intraperitoneal injection. The latency and duration of sleep in mice in each group were recorded. The substance basis of various parts of ZS was analyzed by the UPLC-QTOF-MS technique. The results showed that relative to the model group, DZP, ZSS, ZSF, and ZSKS groups demonstrated shortened sleep latency (p < 0.05) and extended sleep duration (p < 0.01). The GABA, 5-HT, and BDNF levels were significantly upregulated in the brain tissues of the mice in the DZP, ZSF, and ZSS groups (p < 0.01). However, the improvement in ZSKS was non-significant. Additionally, the mRNA and protein expression levels of 5-HT1AR, GABAARα1, and BDNF in mice in the DZP, ZSS, and ZSF groups were significantly enhanced (p < 0.01). However, the improvement in the ZSKS group was insignificant (p < 0.05). The examination of the substance composition across different parts revealed that the shared chemical basis contributing to the sedative and hypnotic potency of different parts of ZS may involve the presence of compounds such as (1) magnoflorine, (8) betulinic acid, (9) ceanothic acid, and (10) alphitolic acid. It provides a basis for further elucidation of the substance basis responsible for the functional and medicinal effects of ZS. Full article
(This article belongs to the Section Natural Products)
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13 pages, 4369 KB  
Article
Anti-Inflammatory Effects of Alphitolic Acid Isolated from Agrimonia coreana Nakai Extracts Are Mediated via the Inhibition of ICRAC Activity in T Cells
by Su Jin Park, Jin Seok Lee, Yu Ran Nam, Ji Min Lee, Dae-Won Ki, Bong-Sik Yun, Seong Woo Choi, Nhung Thi Hong Van, Joo Hyun Nam, Hyun Jong Kim and Woo Kyung Kim
Int. J. Mol. Sci. 2023, 24(24), 17309; https://doi.org/10.3390/ijms242417309 - 9 Dec 2023
Cited by 2 | Viewed by 2022
Abstract
Agrimonia pilosa Ledeb., an important medicinal herb in traditional East Asian medicine, is primarily used to treat abdominal pain, dysentery, and hemostasis. There are ten other reported species of Agrimonia plants, including Agrimonia coreana Nakai—a naturally growing species in South Korea—and Agrimonia eupatoria [...] Read more.
Agrimonia pilosa Ledeb., an important medicinal herb in traditional East Asian medicine, is primarily used to treat abdominal pain, dysentery, and hemostasis. There are ten other reported species of Agrimonia plants, including Agrimonia coreana Nakai—a naturally growing species in South Korea—and Agrimonia eupatoria Linn. Although recent studies have isolated numerous active constituents and investigated their effects, the medicinal utility of this herb is not yet fully explored. Through patch-clamp recording, a previous study reported that Agrimonia plant extracts inhibit the function of Ca2+ release-activated Ca2+ channels (CRACs). Herein, we aimed to identify and isolate the main compounds in A. coreana responsible for CRAC inhibition while assessing the anti-inflammatory effects mediated by this inhibition. We demonstrated for the first time that alphitolic acid isolated from A. coreana has a dose-dependent inhibitory effect on CRAC activity and, thus, an inhibitory effect on intracellular calcium increase. Furthermore, analysis of human CD4+ T cell proliferation via the carboxyfluorescein diacetate succinimidyl ester method revealed that alphitolic acid inhibited T cell proliferation in a concentration-dependent manner. Our findings provide a theoretical basis for the potential therapeutic use of alphitolic acid in the treatment of inflammatory diseases. Full article
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25 pages, 2113 KB  
Review
Triterpenoids in Jujube: A Review of Composition, Content Diversity, Pharmacological Effects, Synthetic Pathway, and Variation during Domestication
by Fuxu Pan, Xuan Zhao, Fawei Liu, Zhi Luo, Shuangjiang Chen, Zhiguo Liu, Zhihui Zhao, Mengjun Liu and Lili Wang
Plants 2023, 12(7), 1501; https://doi.org/10.3390/plants12071501 - 29 Mar 2023
Cited by 23 | Viewed by 4707
Abstract
Chinese jujube (Ziziphus jujuba Mill.) and its wild ancestor, sour jujube (Z. acidojujuba C.Y. Cheng & M.J. Liu), is a Ziziphus genus in the Rhamnaceae family. ZJ and ZA are rich in a variety of active ingredients, with triterpenoids being a [...] Read more.
Chinese jujube (Ziziphus jujuba Mill.) and its wild ancestor, sour jujube (Z. acidojujuba C.Y. Cheng & M.J. Liu), is a Ziziphus genus in the Rhamnaceae family. ZJ and ZA are rich in a variety of active ingredients, with triterpenoids being a unique active ingredient, which are present in the fruit, leaves, branches, and roots. More than 120 triterpenoids have been identified in ZJ and ZA, and have various biological activities. For example, betulinic and ursolic acids have anticancer, antioxidant, antibacterial and antiviral activities. ceanothic, alphitolic, and zizyberanalic acids possess anti-inflammatory activities. The MVA pathway is a synthetic pathway for triterpenoids in ZJ and ZA, and 23 genes of the MVA pathway are known to regulate triterpene synthesis in ZJ and ZA. In order to better understand the basic situation of triterpenoids in ZJ and ZA, this paper reviews the types, content dynamic changes, activities, pharmacokinetics, triterpenoid synthesis pathways, and the effects of domestication on triterpenoids in ZJ and ZA, and provides some ideas for the future research of triterpenoids in ZJ and ZA. In addition, there are many types of ZJ and ZA triterpenoids, and most of the studies on their activities are on lupane- and ursane-type triterpenes, while the activities of the ceanothane-type and saponin are less studied and need additional research. Full article
(This article belongs to the Special Issue Advances in Jujube Research)
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7 pages, 760 KB  
Proceeding Paper
In Silico Comparison of Drug-Likeness of Phytochemicals from Nine Herbal Plants against Asthma
by Tharindra Weerakoon, Nisshaptha Nadarajah, Ramlah Rizwan, Rithmi Ranathunga and Janani Vithanage
Chem. Proc. 2022, 12(1), 93; https://doi.org/10.3390/ecsoc-26-13527 - 14 Nov 2022
Viewed by 1950
Abstract
Asthma is a chronic obstructive pulmonary disease, affecting approximately 300 million people worldwide. Current therapies have disadvantages such as side effects and high costs. Alternatively, herbal plants have been used for decades as focal medicine to cure asthma. The goal of this research [...] Read more.
Asthma is a chronic obstructive pulmonary disease, affecting approximately 300 million people worldwide. Current therapies have disadvantages such as side effects and high costs. Alternatively, herbal plants have been used for decades as focal medicine to cure asthma. The goal of this research was to make use of molinspiration and pkCSM in silico tools to determine the drug-likeness of nine phytochemicals (mangiferonic acid, withaferin A, stigmasterol, 6-shogaol, rosmarinic acid, glycyrrhizin, alphitolic acid, oleanic acid, and kalambroside A) present in nine distinct herbal plants. These phytochemicals have been reported to have anti-asthmatic properties. The currently available fluticasone propionate drug was used as the positive control. Molinspiration findings showed that except for glycyrrhizin and kamabroside A, all other phytochemicals obeyed Lipinski’s and Verber’s rules. Furthermore, all phytochemicals except for glycyrrhizin and kalambroside A exhibited considerable bioactivity for nuclear receptors (NRs) with bioactivity scores ranging from 0.20 to 0.96. The pkCSM results indicated that mangiferonic acid, withaferin A, 6-shogaol, and stigmasterol exhibit high intestinal absorption (>80%), high Caco-2 permeability (log Papp > 0.90 × 10−6 cm/s), high lethal dose (LD50 = 2.081 to 3.201 mol/kg), non-mutagenicity, and non-hepatotoxicity. Furthermore, these phytochemicals were non-inhibitors of cytochrome P450 enzymes. In conclusion, mangiferonic acid abundantly available in Pericampylus glaucus is regarded as the best phytochemical that can be developed into a drug against asthma, since it has good bioavailability, considerable bioactivity towards NRs, and higher LD50 than the control drug. However, further wet lab experiments are required to develop mangiferonic acid as a potent anti-asthmatic drug. Full article
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50 pages, 4475 KB  
Review
Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants
by Karma Yeshi, Gerry Turpin, Tenzin Jamtsho and Phurpa Wangchuk
Molecules 2022, 27(12), 3849; https://doi.org/10.3390/molecules27123849 - 15 Jun 2022
Cited by 33 | Viewed by 12188
Abstract
Australian tropical plants have been a rich source of food (bush food) and medicine to the first Australians (Aboriginal people), who are believed to have lived for more than 50,000 years. Plants such as spreading sneezeweed (Centipeda minima), goat’s foot ( [...] Read more.
Australian tropical plants have been a rich source of food (bush food) and medicine to the first Australians (Aboriginal people), who are believed to have lived for more than 50,000 years. Plants such as spreading sneezeweed (Centipeda minima), goat’s foot (Ipomoea pes-caprae), and hop bush (Dodonaea viscosa and D. polyandra) are a few popular Aboriginal medicinal plants. Thus far, more than 900 medicinal plants have been recorded in the tropical region alone, and many of them are associated with diverse ethnomedicinal uses that belong to the traditional owners of Aboriginal people. In our effort to find anti-inflammatory lead compounds in collaboration with Aboriginal communities from their medicinal plants, we reviewed 78 medicinal plants used against various inflammation and inflammatory-related conditions by Aboriginal people. Out of those 78 species, we have included only 45 species whose crude extracts or isolated pure compounds showed anti-inflammatory properties. Upon investigating compounds isolated from 40 species (for five species, only crude extracts were studied), 83 compounds were associated with various anti-inflammatory properties. Alphitolic acid, Betulinic acid, Malabaric acid, and Hispidulin reduced proinflammatory cytokines and cyclooxygenase enzymes (COX-1 and 2) with IC50 values ranging from 11.5 to 46.9 uM. Other promising anti-inflammatory compounds are Brevilin A (from Centipeda minima), Eupalestin, and 5′-methoxy nobiletin (from Ageratum conyzoides), Calophyllolide (from Calophyllum inophyllum), and Brusatol (from Brucea javanica). D. polyandra is one example of an Aboriginal medicinal plant from which a novel anti-inflammatory benzoyl ester clerodane diterpenoid compound was obtained (compound name not disclosed), and it is in the development of topical medicines for inflammatory skin diseases. Medicinal plants in the tropics and those associated with indigenous knowledge of Aboriginal people could be a potential alternative source of novel anti-inflammatory therapeutics. Full article
(This article belongs to the Special Issue Bioactive Molecules and Drug Lead Compounds)
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12 pages, 2740 KB  
Article
New Terpenoids from Potentilla freyniana Bornm. and Their Cytotoxic Activities
by Jia Wu, Zai-Qi Zhang, Xu-Dong Zhou, Qing-Ying Yao, Zhu-Liang Chen, Ling-Ling Chu, Huang-He Yu, Yu-Pei Yang, Bin Li and Wei Wang
Molecules 2022, 27(12), 3665; https://doi.org/10.3390/molecules27123665 - 7 Jun 2022
Cited by 13 | Viewed by 2991
Abstract
Two new A-ring contracted triterpenoids, madengaisu A and madengaisu B, and one undescribed ent-kaurane diterpenoid, madengaisu C, along with 20 known compounds were isolated from the roots of Potentilla freyniana Bornm. The structures were elucidated using extensive spectroscopic techniques, including 1D and [...] Read more.
Two new A-ring contracted triterpenoids, madengaisu A and madengaisu B, and one undescribed ent-kaurane diterpenoid, madengaisu C, along with 20 known compounds were isolated from the roots of Potentilla freyniana Bornm. The structures were elucidated using extensive spectroscopic techniques, including 1D and 2D-NMR, HR-ESI-MS, ECD spectra, IR, and UV analysis. Moreover, all isolated constituents were evaluated for their anti-proliferative activity against RA-FLS cells and cytotoxic activities against the human cancer cell lines Hep-G2, HCT-116, BGC-823, and MCF-7. Ursolic acid and pomolic acid displayed moderate inhibitory activity in RA-FLS cells with IC50 values of 24.63 ± 1.96 and 25.12 ± 1.97 μM, respectively. Hyptadienic acid and 2α,3β-dihydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranoside exhibited good cytotoxicity against Hep-G2 cells with IC50 values of 25.16 ± 2.55 and 17.66 ± 1.82 μM, respectively. In addition, 2α,3β-dihydroxyolean-13(18)-en-28-oic acid and alphitolic acid were observed to inhibit HCT-116 cells (13.25 ± 1.65 and 21.62 ± 0.33 μM, respectively), while madengaisu B and 2α,3β-dihydroxyolean-13(18)-en-28-oic acid showed cytotoxic activities against BGC-823 cells with IC50 values of 24.76 ± 0.94 and 26.83 ± 2.52 μM, respectively, which demonstrated that triterpenes from P. freyniana may serve as therapeutic agents for RA and cancer treatment. Full article
(This article belongs to the Section Natural Products Chemistry)
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12 pages, 6155 KB  
Article
Anticancer Activity of 2-O-caffeoyl Alphitolic Acid Extracted from the Lichen, Usnea barbata 2017-KL-10
by Hae-Jung Chae, Geum-Jin Kim, Barsha Deshar, Hyun-Jin Kim, Min-Ji Shin, Hyukbean Kwon, Ui-Joung Youn, Joo-Won Nam, Sung-Hak Kim, Hyukjae Choi and Sung-Suk Suh
Molecules 2021, 26(13), 3937; https://doi.org/10.3390/molecules26133937 - 28 Jun 2021
Cited by 14 | Viewed by 3710
Abstract
Colorectal cancer is one of the life-threatening ailments causing high mortality and morbidity worldwide. Despite the innovation in medical genetics, the prognosis for metastatic colorectal cancer in patients remains unsatisfactory. Recently, lichens have attracted the attention of researchers in the search for targets [...] Read more.
Colorectal cancer is one of the life-threatening ailments causing high mortality and morbidity worldwide. Despite the innovation in medical genetics, the prognosis for metastatic colorectal cancer in patients remains unsatisfactory. Recently, lichens have attracted the attention of researchers in the search for targets to fight against cancer. Lichens are considered mines of thousands of metabolites. Researchers have reported that lichen-derived metabolites demonstrated biological effects, such as anticancer, antiviral, anti-inflammatory, antibacterial, analgesic, antipyretic, antiproliferative, and cytotoxic, on various cell lines. However, the exploration of the biological activities of lichens’ metabolites is limited. Thus, the main objective of our study was to evaluate the anticancer effect of secondary metabolites isolated from lichen (Usnea barbata 2017-KL-10) on the human colorectal cancer cell line HCT116. In this study, 2OCAA exhibited concentration-dependent anticancer activities by suppressing antiapoptotic genes, such as MCL-1, and inducing apoptotic genes, such as BAX, TP53, and CDKN1A(p21). Moreover, 2OCAA inhibited the migration and invasion of colorectal cancer cells in a concentration-dependent manner. Taken together, these data suggest that 2OCAA is a better therapeutic candidate for colorectal cancer. Full article
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16 pages, 2184 KB  
Article
Optimized Extraction of Total Triterpenoids from Jujube (Ziziphus jujuba Mill.) and Comprehensive Analysis of Triterpenic Acids in Different Cultivars
by Lijun Song, Li Zhang, Long Xu, Yunjian Ma, Weishuai Lian, Yongguo Liu and Yonghua Wang
Plants 2020, 9(4), 412; https://doi.org/10.3390/plants9040412 - 27 Mar 2020
Cited by 34 | Viewed by 5931
Abstract
Triterpenoid compounds are one of the main functional components in jujube fruit. In this study, the optimal process for ultrasound-assisted extraction (UAE) of total triterpenoids from jujube fruit was determined using response surface methodology (RSM). The optimal conditions were as follows: temperature of [...] Read more.
Triterpenoid compounds are one of the main functional components in jujube fruit. In this study, the optimal process for ultrasound-assisted extraction (UAE) of total triterpenoids from jujube fruit was determined using response surface methodology (RSM). The optimal conditions were as follows: temperature of 55.14 °C, ethanol concentration of 86.57%, time of 34.41 min, and liquid-to-solid ratio of 39.33 mL/g. The triterpenoid yield was 19.21 ± 0.25 mg/g under optimal conditions. The triterpenoid profiles and antioxidant activity were further analyzed. Betulinic acid, alphitolic acid, maslinic acid, oleanolic acid, and ursolic acid were the dominant triterpenoid acids in jujube fruits. Correlation analysis revealed a significant positive correlation between the major triterpenic acids and antioxidant activities. The variations of triterpenoid profiles and antioxidant activity within the jujube fruits and the degree of variation were evaluated by hierarchical cluster analysis (HCA) and principal component analysis (PCA), respectively. The results provide important guidance for the quality evaluation and industrial application of jujube fruit. Full article
(This article belongs to the Special Issue Structural and Functional Analysis of Extracts in Plants)
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13 pages, 2669 KB  
Article
Pharmacokinetic Comparisons of Multiple Triterpenic Acids from Jujubae Fructus Extract Following Oral Delivery in Normal and Acute Liver Injury Rats
by Yao Li, Sheng Guo, Quanjin Ren, Dandan Wei, Ming Zhao, Shulan Su, Zhishu Tang and Jin-Ao Duan
Int. J. Mol. Sci. 2018, 19(7), 2047; https://doi.org/10.3390/ijms19072047 - 13 Jul 2018
Cited by 16 | Viewed by 4178
Abstract
Jujubae Fructus, the dried fruit of Ziziphus jujuba, has been used as Chinese medicine and food for centuries. Triterpenic acids have been found to be the major bioactive constituents in Jujubae Fructus responsible for their hepatoprotective activity in previous phytochemical and [...] Read more.
Jujubae Fructus, the dried fruit of Ziziphus jujuba, has been used as Chinese medicine and food for centuries. Triterpenic acids have been found to be the major bioactive constituents in Jujubae Fructus responsible for their hepatoprotective activity in previous phytochemical and biological studies, while few pharmacokinetic studies have been conducted. To reveal the kinetics of the triterpenic acids under the pathological liver injury state, an established ultra-performance liquid chromatography coupled with a mass spectrometry method was applied for the simultaneous quantitation of seven triterpenic acids (ceanothic acid, epiceanothic acid, pomonic acid, alphitolic acid, maslinic acid, betulinic acid, and betulonic acid) in plasma samples of normal and acute liver injury rats induced by CCl4. The results showed that there were significant differences (p < 0.05) in the pharmacokinetic parameters of seven triterpenic acids between model and normal groups. The AUC0–t and AUC0–∞ of epiceanothic acid (5227 ± 334 μg⋅h/L vs. 1478 ± 255 μg⋅h/L and 6127 ± 423 μg⋅h/L vs. 1482 ± 255 μg⋅h/L, respectively) and pomonic acid (4654 ± 349 μg⋅h/L vs. 1834 ± 225 μg⋅h/L and 4776 ± 322 μg⋅h/L vs. 1859 ± 230 μg⋅h/L, respectively) in model rats were significantly higher than those in normal rats, and the CLz/F of them were significantly decreased (0.28 ± 0.02 L/h/kg vs. 1.36 ± 0.18 L/h/kg and 19.96 ± 1.30 L/h/kg vs. 53.15 ± 5.60 L/h/kg, respectively). In contrast, the above parameters for alphitolic acid, betulinic acid and betulonic acid exhibited the quite different trend. This pharmacokinetic research might provide useful information for the clinical usage of triterpenic acids from Jujubae Fructus. Full article
(This article belongs to the Special Issue Plant Natural Products for Human Health)
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7 pages, 406 KB  
Short Note
Anti-Inflammatory Chemical Profiling of the Australian Rainforest Tree Alphitonia petriei (Rhamnaceae)
by Ritesh Raju, Dhanushka Gunawardena, Most Afia Ahktar, Mitchell Low, Paul Reddell and Gerald Münch
Molecules 2016, 21(11), 1521; https://doi.org/10.3390/molecules21111521 - 11 Nov 2016
Cited by 29 | Viewed by 7747
Abstract
Chronic inflammation is an important pathological condition in many human diseases, and due to the side effects of the currently used non-steroidal anti-inflammatory drugs, discovery of novel anti-inflammatory drugs is of general interest. Anti-inflammatory activity guided compound isolation from the plant Alphitonia petriei [...] Read more.
Chronic inflammation is an important pathological condition in many human diseases, and due to the side effects of the currently used non-steroidal anti-inflammatory drugs, discovery of novel anti-inflammatory drugs is of general interest. Anti-inflammatory activity guided compound isolation from the plant Alphitonia petriei led to the isolation of the known plant sterols emmolic acid (1), alphitolic acid (2), trans- and cis-coumaroyl esters of alphitolic acid (3 and 4) and betulinic acid (5). A detailed spectroscopic analysis led to the structure elucidation of the alphitolic acid derivatives (15), and the semi-synthetic emmolic acid acetate (6). When tested in LPS (Lipopolysaccharides) + IFN-γ (Interferon gamma) activated RAW 264.7 macrophages, all compounds except (1) exhibited potent anti-inflammatory activity (IC50 values as low as 1.7 μM) in terms of downregulation of NO and TNF-α production, but also demonstrated some considerable cytotoxicity. Full article
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