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      Two new phenolic compounds from the leaves of Alnus sibirica Fisch. ex Turcz.

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          Abstract

          Two new phenolic compounds, 4- O-glucopyranosyl-5- O-caffeoylshikimic acid ( 1) and 2,3-digalloyl oregonin ( 2), were isolated along with eight known phenolic compounds ( 310) from an 80% acetone extract of Alnus sibirica leaves. The chemical structures of these compounds were elucidated using 1D/2D nuclear magnetic resonance and high resolution-MS. The anti-oxidative activities of these compounds were determined by assaying their 1,1-diphenyl-2-picrylhydrazyl radical and nitroblue tetrazolium superoxide anion scavenging activity. All of the isolated phenolic compounds ( 110) exhibited potent anti-oxidative activities. In particular, 2 and 4, which are diarylheptanoids, and 10 which is ellagitannin exhibited excellent anti-oxidative activities with almost the same potency as that of the positive controls L-ascorbic acid and allopurinol.

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          Identification of phenolics in the fruit of emblica (Phyllanthus emblica L.) and their antioxidant activities.

          An activity-directed fractionation and purification process was used to identify the antioxidative components of emblica fruit. Dried fruit of emblica was extracted with methanol and then partitioned by ethyl ether, ethyl acetate, butanol and water. The ethyl acetate fraction showed the strongest 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity among four fractions. The ethyl acetate fraction was then subjected to separation and purification using Sephadex LH-20 chromatography and reverse-phase high-performance liquid chromatography (HPLC). Six compounds were identified to be geraniin (1), quercetin 3-β-d-glucopyranoside (2), kaempferol 3-β-d-glucopyranoside (3), isocorilagin (4), quercetin (5), and kaempferol (6), respectively, by spectral methods, (1)H and (13)C nuclear magnetic resonance (NMR) spectroscopy, ultraviolet-visible (UV-Vis) spectrophotometry and mass spectroscopy (MS), and comparison with literatures. Compounds 2-4 and 6 were identified from emblica fruit for the first time. Furthermore, the antioxidant activities of purified compounds were screened for their antioxidative potential using lipid peroxidation and DPPH systems. All the purified compounds showed strong antioxidant and radical scavenging activities. Amongst, geraniin showed the highest antioxidant activity (4.7 and 65.7μM of IC50 values for DPPH and lipid peroxidation assay, respectively) than other purified compounds.
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            Antithrombotic flavonoids from the faeces of Trogopterus xanthipes.

            Chemical investigation of Trogopterus faeces has led to the isolation of seven flavonoids. Their structures were elucidated by chemical and spectral analyses. In an anticoagulative assay, three kaempferol coumaroyl rhamnosides had significant antithrombin activity. This is the first report on the occurrence of flavonoid glycosides in Trogopterus faeces.
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              New diarylheptanoids from Alnus japonica and their antioxidative activity.

              In the course of research on the bioactive constituents of woody plants in the Cyugoku area of Japan, a methanol extract of the leaves of Alnus japonica were found to have strong antioxidative activity. Ethyl acetate soluble and n-buthanol soluble fractions of the methanol extract had a potent antioxidative effect. Both fractions were purified by silica gel column chromatography and HPLC using an ODS column to give four new diarylheptanoids along with known diarylheptanoids and flavonoids. These new compounds were elucidated to be 7-(3,4-dihydroxyphenyl)-5-hydroxy-1-(4-hydroxyphenyl)-3-heptanone-5-O-beta-D-xylopyranoside (1), 1-(3,4-dihydroxyphenyl)-5-hydroxy-7-(4-hydroxyphenyl)-3-heptanone-5-O-beta-D-xylopyranoside (2), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxy-3-heptanone-5-O-[2-(2-methylbutenoyl)]-beta-D-xylopyranoside (3) and 1,7-bis-(3,4-dihydroxyphenyl)-5-methoxy-3-heptanone (4) using spectral methods and especially 1H-, 13C-NMR and 2D-NMR measurements. The isolated compounds including their main constituent, oregonin (5), were tested for antioxidative activity. Some of these compounds having two catechol structures showed potent antioxidative activity. Compounds having one catechol structure showed moderate antioxidative activity, but a peracetate of 5 having no catechol structure exhibited no antioxidative activity. Thus the catechol structure of the diarylheptanoids is indispensable for antioxidative activity.
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                Author and article information

                Journal
                Nat Prod Res
                Nat. Prod. Res
                GNPL
                gnpl20
                Natural Product Research
                Taylor & Francis
                1478-6419
                1478-6427
                17 January 2016
                27 July 2015
                : 30
                : 2
                : 206-213
                Affiliations
                [ a ]Laboratory of Pharmacognosy and Natural Product Derived Medicine, College of Pharmacy, Chung-Ang University , Seoul 156-756, Republic of Korea
                Author notes
                [* ]Corresponding author. Email: mwlee@ 123456cau.ac.kr
                Article
                1053087
                10.1080/14786419.2015.1053087
                4699475
                26211877
                abcb30c6-c741-4172-a250-5c547412d2f9
                © 2015 The Author(s). Published by Taylor & Francis.

                This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License ( http://creativecommons.org/licenses/by-nc-nd/4.0/), which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited, and is not altered, transformed, or built upon in any way.

                History
                : 7 March 2015
                : 11 May 2015
                : 13 May 2015
                Page count
                Figures: 2, Tables: 1, Equations: 0, References: 18, Pages: 8
                Funding
                This study was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology [grant number 2010-0022929].
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                Articles

                alnus sibirica,caffeoylshikimic acid,galloyl-diarylheptanoid,anti-oxidant activity

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