| Reference | [1]. Planta Med. 2013 Jan;79(2):181-8. doi: 10.1055/s-0032-1328089. Epub 2013 Jan 8.<br />
Simultaneous determination and characterization of tannins and triterpene saponins from the fruits of various species of Terminalia and Phyllantus emblica using a UHPLC-UV-MS method: application to triphala.<br />
Avula B(1), Wang YH, Wang M, Shen YH, Khan IA.<br />
Author information: (1)National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA.<br />
Terminalia species are a rich source of tannins. Many preparations of these species are used in traditional medicine and have many different ethnobotanical applications. A simple UHPLC method was developed for the simultaneous analysis of such hydrolysable tannins and triterpene saponins from the fruit rinds of different species of Terminalia (T. chebula, T. arjuna, T. bellirica) and Phyllantus emblica. A separation by LC was achieved using a reversed-phase column and a water/acetonitrile mobile phase, both containing formic acid, using a gradient system and a temperature of 40°C. Eight hydrolysable tannins (gallic acid, gallic acid methyl ester, corilagin, chebulagic acid, 1,2,3,6-tetra-O-galloyl-β-D-glucose, ellagic acid, chebulinic acid, and 1,2,3,4,6-penta-O-galloyl-β-D-glucose) and six triterpene saponins (arjunglucoside-I, arjunglucoside-III, chebuloside II, bellericoside, arjunetin, and arjunglucoside-II) could be separated within 20 minutes. The wavelength used for detection with the diode array detector was 254 and 275 nm for tannins and 205 nm for triterpene saponins. The method was validated for linearity, repeatability, limits of detection, and limits of quantification. The developed method is economical, fast, and especially suitable for quality control analysis of tannins and triterpene saponins in various plant samples and commercial products of Terminalia. Georg Thieme Verlag KG Stuttgart · New York.<br />
DOI: 10.1055/s-0032-1328089 PMID: 23299756 [Indexed for MEDLINE]<br />
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[2]. J Ethnopharmacol. 2021 Mar 1;267:113624. doi: 10.1016/j.jep.2020.113624. Epub 2020 Nov 25.<br />
Bioassay-guided isolation of antiplasmodial and antimicrobial constituents from the roots of Terminalia albida.<br />
Baldé MA(1), Tuenter E(1), Matheeussen A(2), Traoré MS(3), Cos P(2), Maes L(2), Camara A(4), Diallo MST(4), Baldé ES(5), Balde AM(3), Pieters L(6), Foubert K(1).<br />
Author information: (1)Natural Products & Food Research and Analysis (NatuRA), Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610, Antwerp, Belgium. (2)Laboratory of Microbiology, Parasitology and Hygiene (LMPH), Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, Universiteitsplein 1, B-2610, Antwerp, Belgium. (3)Department of Pharmacy, University Gamal Abdel Nasser of Conakry, BP, 1017, Guinea; Research and Valorization Center on Medicinal Plants Dubreka, BP, 6411, Conakry, Guinea. (4)Research and Valorization Center on Medicinal Plants Dubreka, BP, 6411, Conakry, Guinea. (5)Department of Pharmacy, University Gamal Abdel Nasser of Conakry, BP, 1017, Guinea. (6)Natural Products & Food Research and Analysis (NatuRA), Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B-2610, Antwerp, Belgium. Electronic address: [email protected].<br />
ETHNOPHARMACOLOGICAL RELEVANCE: Terminalia albida (Combretaceae), widely used in Guinean traditional medicine, showed promising activity against Plasmodium falciparum and Candida albicans in previous studies. Bioassay-guided fractionation was carried out in order to isolate the compounds responsible for these activities. MATERIALS AND METHODS: Fractionation and isolation were performed by flash chromatography, followed by semi-preparative HPLC-DAD-MS. The structural elucidation of the isolated compounds was carried out by 1D and 2D NMR as well as HR-ESI-MS. Isolated compounds were evaluated against Plasmodium falciparum, Candida albicans, Staphylococcus aureus and Escherichia coli, and their cytotoxicity against MRC-5 cells was determined. RESULTS: Bioassay-guided fractionation of Terminalia albida root resulted in the isolation of 14 compounds (1-14), and their antimicrobial properties were evaluated. Pantolactone (1) (IC50 0.60 ± 0.03 μM) demonstrated significant activity against P. falciparum. Other compounds, including 3,4,3'-tri-O-methyl-ellagic acid (3), the triterpenes arjunolic acid (5), arjungenin (6), arjunic acid (7) and arjunglucoside II (10), and the phenol glycoside calophymembranside-B (14), were less active and showed IC50 values in the range 5-15 μM. None of the tested compound showed antibacterial or antifungal activity. CONCLUSION: These results may explain at least in part the activity of the root extract of T. albida against P. falciparum.<br />
DOI: 10.1016/j.jep.2020.113624 PMID: 33246123 [Indexed for MEDLINE]<br />
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[3]. Medicines (Basel). 2017 Jan 24;4(1):6. doi: 10.3390/medicines4010006.<br />
Compounds from Terminalia mantaly L. (Combretaceae) Stem Bark Exhibit Potent Inhibition against Some Pathogenic Yeasts and Enzymes of Metabolic Significance.<br />
Tchuente Tchuenmogne MA(1), Kammalac TN(2), Gohlke S(3), Kouipou RMT(4), Aslan A(5), Kuzu M(6), Comakli V(7), Demirdag R(8), Ngouela SA(9), Tsamo E(10), Sewald N(11), Lenta BN(12), Boyom FF(13).<br />
Author information: (1)Laboratory of Natural Products and Organic Synthesis, Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon. [email protected]. (2)Antimicrobial & Biocontrol Agents Unit, Laboratory for Phytobiochemistry and Medicinal Plants Studies, Department of Biochemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon. [email protected]. (3)Chemistry Department, Organic and Bioorganic Chemistry, Bielefeld University, P.O. Box 100131, D-33501 Bielefeld, Germany. [email protected]. (4)Antimicrobial & Biocontrol Agents Unit, Laboratory for Phytobiochemistry and Medicinal Plants Studies, Department of Biochemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon. [email protected]. (5)Faculty of Engineering, Department of Industrial Engineering, Giresun University, 28200 Giresun, Turkey. [email protected]. (6)Faculty of Pharmacy, Department of Basic Pharmaceutical Sciences, Agrı Ibrahim Cecen University, 04100 Agri, Turkey. [email protected]. (7)School of Health, Department of Nutrition and Dietetics, Agrı Ibrahim Cecen University, 04100 Agri, Turkey. [email protected]. (8)School of Health, Department of Nutrition and Dietetics, Agrı Ibrahim Cecen University, 04100 Agri, Turkey. [email protected]. (9)Laboratory of Natural Products and Organic Synthesis, Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon. [email protected]. (10)Laboratory of Natural Products and Organic Synthesis, Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon. [email protected]. (11)Chemistry Department, Organic and Bioorganic Chemistry, Bielefeld University, P.O. Box 100131, D-33501 Bielefeld, Germany. [email protected]. (12)Department of Chemistry, Higher Teacher Training College, University of Yaoundé 1, Yaoundé, Cameroon. [email protected]. (13)Antimicrobial & Biocontrol Agents Unit, Laboratory for Phytobiochemistry and Medicinal Plants Studies, Department of Biochemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon. [email protected].<br />
Background: Pathogenic yeasts resistance to current drugs emphasizes the need for new, safe, and cost-effective drugs. Also, new inhibitors are needed to control the effects of enzymes that are implicated in metabolic dysfunctions such as cancer, obesity, and epilepsy. Methods: The anti-yeast extract from Terminalia mantaly (Combretaceae) was fractionated and the structures of the isolated compounds established by means of spectroscopic analysis and comparison with literature data. Activity was assessed against Candida albicans, C. parapsilosis and C. krusei using the microdilution method, and against four enzymes of metabolic significance: glucose-6-phosphate dehydrogenase, human erythrocyte carbonic anhydrase I and II, and glutathione S-transferase. Results: Seven compounds, 3,3'-di-O-methylellagic acid 4'-O-α-rhamnopyranoside; 3-O-methylellagic acid; arjungenin or 2,3,19,23-tetrahydroxyolean-12-en-28-oïc acid; arjunglucoside or 2,3,19,23-tetrahydroxyolean-12-en-28-oïc acid glucopyranoside; 2α,3α,24-trihydroxyolean-11,13(18)-dien-28-oïc acid; stigmasterol; and stigmasterol 3-O-β-d-glucopyranoside were isolated from the extract. Among those, 3,3'-di-O-methylellagic acid 4'-O-α-rhamnopyranoside, 3-O-methylellagic acid, and arjunglucoside showed anti-yeast activity comparable to that of reference fluconazole with minimal inhibitory concentrations (MIC) below 32 µg/mL. Besides, Arjunglucoside potently inhibited the tested enzymes with 50% inhibitory concentrations (IC50) below 4 µM and inhibitory constant (Ki) <3 µM. Conclusions: The results achieved indicate that further SAR studies will likely identify potent hit derivatives that should subsequently enter the drug development pipeline.<br />
DOI: 10.3390/medicines4010006 PMCID: PMC5597071 PMID: 28930221<br />
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[4]. Phytomedicine. 2005 May;12(5):391-3. doi: 10.1016/j.phymed.2003.11.007.<br />
Effect of oleanane triterpenoids from Terminalia arjuna–a cardioprotective drug on the process of respiratory oxyburst.<br />
Pawar RS(1), Bhutani KK.<br />
Author information: (1)Department of Natural Products, National Institute of Pharmaceutical Education and Research, Sect. 67, S.A.S. Nagar, Phase X, (Mohali), Punjab, India.<br />
The oleanane triterpenes arjunic acid, arjungenin and their glucosides, arjunetin and arjunglucoside II, were isolated from the bark of Terminalia arjuna. Arjungenin and its glucoside exhibited a moderate free radical scavenging activity while all the compounds showed no effect on the superoxide release from PMN cells. Further arjungenin also exhibited greater inhibitory action on the hypochlorous acid production from human neutrophils.<br />
DOI: 10.1016/j.phymed.2003.11.007 PMID: 15957375 [Indexed for MEDLINE]<br />
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[5]. Ethiop Med J. 2005 Jan;43(1):15-20.<br />
Anti-HIV activity against immunodeficiency virus type 1 (HIV-I) and type II (HIV-II) of compounds isolated from the stem bark of Combretum molle.<br />
Asres K(1), Bucar F.<br />
Author information: (1)Department of Pharmacognosy, School of Pharmacy, Addis Ababa University, P.O. Box 1176, Addis Ababa, Ethiopia.<br />
In vitro anti-HIV activity of various extracts prepared from the stem bark of Combretum molle (R. Br. Ex. G. Don.) Engl & Diels (Combretaceae), a plant widely used in Ethiopian traditional medicine for the treatment of liver diseases, malaria and tuberculosis has been assessed against human imnmuunodeficiencvy virus type 1 (HIV-1) and type 2 (HIV-2). The total extract was prepared by percolation with 80% methanol whilst the petroleum ether, chloroform, acetone and 100% methanol fractions were obtained by successive hot extraction using Soxhlet apparatus. Selective inhibition of viral growth was assessed by the simultaneous determination of the in vitro cytotoxicity of each of the extracts against MT-4 cells. Results obtained in this study indicate that the acetone fraction possessed the highest selective inhibition of HIV-1 replicatuon. Phytochemical investigation of the acetone fraction resulted in the isolation of two tannins and two oleanane-type pentacyclic triterpene glycosides. One of the tannins was identified as puncalagin (an ellagitannin), whilst the structure of the other (CM-A) has not yet been fully elucidated. The saponins that were characterized as arjunglucoside (also called 4-epi-sericoside) and sericoside did not inhibit replication of either HIV-1 or HIV-2. On the other hand, both punicalgin and CM-A displayed selective inhibition of HIV-1 replication with selectrvitv indices (ratio of 50% cytotoxic concentration to 50% effective antiviral concentration) of 16 and 25, respectivelvy and afforded cell protection of viral induced cytopathic effect of 100% when compared with control samples. Neither of the tannins exhibited a selective inhibition to HIV-2 replication at nontoxic doses.<br />
PMID: 16370525 [Indexed for MEDLINE]
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