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      Isolation, characterization, and antimicrobial activity of communic acid from Juniperus phoenicea

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          Abstract

          Objectives

          A mixture of Z and E communic acid is isolated for the first time from the cones of Juniperus phoenicea. Its biological activity was studied.

          Methods

          The plant material was extracted in a Soxhlet apparatus with n-hexane, the resulting extract was subjected to column chromatography (CC) on silica gel. The structure elucidation of the constituents of the isolated fraction was identified by comparison of its spectroscopic properties 1H and 13C NMR data with those reported in the literature. The antimicrobial assay of hexanic extract and isolated compounds was carried out by the disc diffusion and micro-dilution methods.

          Results

          A mixture of two diterpene acids isomers was isolated, with a high yield (68%). Their chemical structures were confirmed after comparing their spectral data with published reports. These natural products exhibited a significant antibacterial and antifungal activity against the tested strains. Indeed, for Bacillus cereus, Staphylococcus aureus, and Pseudomonas aeruginosa, the inhibition zone diameters (36–37 mm) was better than penicillin, novobiocin, and amoxicillin. For Candida albicans activity, it show that the mixture possess an activity similar to that of Metrazol. Against Escherichia coli, the inhibitory activity was found less than Amoxicillin. This is the first report of isolation of communic acid from J. phoenicea.

          Conclusions

          These results showed that the cones of J. phoenicea were an important source of communic acid, and its hexanic extract had the greatest potential antibacterial activity against both Gram-negative and Gram-positive bacteria and C. albicans.

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          Most cited references12

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          Traditional plant treatments for diabetes. Studies in normal and streptozotocin diabetic mice.

          The effects on glucose homeostasis of eleven plants used as traditional treatments for diabetes mellitus were evaluated in normal and streptozotocin diabetic mice. Dried leaves of agrimony (Agrimonia eupatoria), alfalfa (Medicago sativa), blackberry (Rubus fructicosus), celandine (Chelidonium majus), eucalyptus (Eucalyptus globulus), lady's mantle (Alchemilla vulgaris), and lily of the valley (Convallaria majalis); seeds of coriander (Coriandrum sativum); dried berries of juniper (Juniperus communis); bulbs of garlic (Allium sativum) and roots of liquorice (Glycyrhizza glabra) were studied. Each plant material was supplied in the diet (6.25% by weight) and some plants were additionally supplied as decoctions or infusions (1 g/400 ml) in place of drinking water to coincide with the traditional method of preparation. Food and fluid intake, body weight gain, plasma glucose and insulin concentrations in normal mice were not altered by 12 days of treatment with any of the plants. After administration of streptozotocin (200 mg/kg i.p.) on day 12 the development of hyperphagia, polydipsia, body weight loss, hyperglycaemia and hypoinsulinaemia were not affected by blackberry, celandine, lady's mantle or lily of the valley. Garlic and liquorice reduced the hyperphagia and polydipsia but did not significantly alter the hyperglycaemia or hypoinsulinaemia. Treatment with agrimony, alfalfa, coriander, eucalyptus and juniper reduced the level of hyperglycaemia during the development of streptozotocin diabetes. This was associated with reduced polydipsia (except coriander) and a reduced rate of body weight loss (except agrimony). Alfalfa initially countered the hypoinsulinaemic effect of streptozotocin, but the other treatments did not affect the fall in plasma insulin. The results suggest that certain traditional plant treatments for diabetes, namely agrimony, alfalfa, coriander, eucalyptus and juniper, can retard the development of streptozotocin diabetes in mice.
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            Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae).

            Juniperus communis is a plant which has been reported as a traditional cure for tuberculosis (TB) and other respiratory diseases. The aim of this study was to isolate and identify the constituents responsible for the activity of the n-hexane extract of Juniperus communis roots against Mycobacterium tuberculosis H(37)Rv and Juniperus communis aerial parts against Mycobacterium aurum. Subsequently, it was to evaluate the activity of the pure isolated compounds against (i) drug-resistant Mycobacterium tuberculosis variants, (ii) non-replicating Mycobacterium tuberculosis and (iii) a range of non-tuberculous mycobacteria (NTM). The antimycobacterial activity of Juniperus communis extracts, fractions and constituents was determined against Mycobacterium tuberculosis H(37)Rv, and against rifampicin-, isoniazid-, streptomycin- and moxifloxacin-resistant variants, using the microplate broth Alamar Blue assay (MABA) method. Isolated constituents were tested against non-replicating Mycobacterium tuberculosis H(37)Rv, using the low oxygen recovery assay (LORA), and against NTM (Mycobacterium aurum, Mycobacterium phlei, Mycobacterium fortuitum and Mycobacterium smegmatis), using a broth microdilution method. Cytotoxicity studies were performed using mammalian Vero cells. The antimycobacterial activity of Juniperus communis was attributed to a sesquiterpene identified as longifolene (1) and two diterpenes, characterised as totarol (2) and trans-communic acid (3). All compounds were identified following analysis of their spectroscopic data (1D- and 2D-NMR, MS) and by comparison with the literature and commercial authentic standards when available. Revised assignments for 3 are reported. Totarol showed the best activity against Mycobacterium tuberculosis H(37)Rv (MIC of 73.7 microM). It was also most active against the isoniazid-, streptomycin-, and moxifloxacin-resistant variants (MIC of 38.4, 83.4 and 60 microM, respectively). Longifolene and totarol were most active against the rifampicin-resistant variant (MICs of 24 and 20.2 microM, respectively). Totarol showed the best activity in the LORA assay (MIC of 81.3 microM) and against all NTM species (MICs in the range of 7-14 microM). Trans-communic acid showed good activity against Mycobacterium aurum (MIC of 13.2 microM). The low selectivity indices (SI) obtained following cytotoxicity studies indicated that the isolated terpenoids were relatively toxic towards mammalian cells. This is the first report of the isolation of (1) and (2) from Juniperus communis roots, and of (3) from the aerial parts. The antimycobacterial activity of (1) and (3), and the activity of (2) against Mycobacterium aurum, Mycobacterium fortuitum and Mycobacterium phlei, is reported for the first time. The effect of totarol on drug-resistant variants and non-replicating Mycobacterium tuberculosis has never been published. The presence of antimycobacterial terpenoids in Juniperus communis aerial parts and roots justifies, to some extent, the ethnomedicinal use of this species as a traditional anti-TB remedy.
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              Diterpenes from the berries of Juniperus excelsa.

              From the hexane extract of berries of Juniperus excelsa, one new and four known diterpenes were isolated besides a known sesquiterpene. The structures of the known diterpenes were identified as isopimaric, isocommunic, (-)ent-trans communic and sandracopimaric acids, along with the sesquiterpene 4a-hydroxycedrol and the new compound which was elucidated as 3 alpha-acetoxylabda-8(17),13(16),14-trien-19-oic acid (juniperexcelsic acid). Cytotoxic activity of the hexane extract was investigated against a panel of cell line and found highly active against LNCaP, KB-V (+VLB) and KB-V (-VLB) cell lines. Furthermore, the hexane and methanol extracts, and the new compound were found to be moderately active against Mycobacterium tuberculosis.
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                Author and article information

                Contributors
                (View ORCID Profile)
                Journal
                Journal of Complementary and Integrative Medicine
                Walter de Gruyter GmbH
                2194-6329
                1553-3840
                September 21 2022
                July 29 2021
                June 01 2022
                September 21 2022
                July 29 2021
                June 01 2022
                : 19
                : 2
                : 467-470
                Affiliations
                [1 ]Laboratory of Organic Synthesis, Extraction and Valorisation, Faculty of Sciences Aïn Chock, Hassan II University of Casablanca , BP. 20000 , Casablanca , Morocco
                [2 ]Laboratoire de Santé et Environnement, Faculty of Sciences Aïn Chock, Hassan II University of Casablanca , Casablanca , Morocco
                [3 ]Laboratoire de microbiologie et de pharmacologie et environnement, Faculty of Sciences Aïn Chock, Hassan II University of Casablanca , Casablanca , Morocco
                Article
                10.1515/jcim-2019-0319
                75b1895e-9717-4ef5-b097-82aa409e97e8
                © 2022
                History

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