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      Isoleojaponin, a New Halimane Diterpene Isolated from Leonurus japonicus

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          Abstract

          Leojaponin ( 2), a labdane diterpene, was isolated from the EtOH extract of the herb of Leonurus japonicus together with a new halimane diterpene named isoleojaponin ( 1). Isoleojaponin has a new diterpene skeleton with a unique cross-conjugated α,β-unsaturated ketone system, Their structures were elucidated by physical and spectroscopic analysis, and the relative configuration of the chiral C-9 carbon was determined by a computational method, and analysis of its possible biogenesis pathways.

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          Chemical Composition and Antibacterial Activity of Essential Oils from Different Parts of Leonurus japonicus Houtt.

          The herb and fruits of Leonurus japonicus Houtt., named “Yimucao” and “Chongweizi”, respectively, in Chinese, have been widely used in China as gynecological medicines. The components of the essential oils obtained by hydrodistillation were investigated by GC-MS. The antibacterial activity of the essential oils was determined by micro-dilution assay. The results showed large variations in the chemical composition and antibacterial activity of the oils. The oil of “Yimucao” showed antibacterial activity against various Gram-positive bacteria and consisted mainly of sesquiterpenes and diterpenes, with phytone, phytol, caryophyllene oxide and β-caryophyllene being the most significant constituents, whereas the oil of “Chongweizi”, mainly made up of bornyl acetate and aliphatic hydrocarbons, was inactive in the antibacterial assay. Further study of the main compounds in “Yimucao oil” showed that β-caryophyllene had wide-spectrum activity against Gram-positive bacteria.
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            Labdane Diterpenoids from Leonotis leonurus

            Three known (leoleorins A-C) and eight hitherto unknown (leoleorins D-J and 16-epi-leoleorin F) labdane diterpenoids, were isolated from leaves of Leonotis leonurus. The absolute configurations of leoleorins A and D were established by X-ray crystallographic analyses. In a competitive binding assay, all isolated compounds showed inhibition in excess of 50% at various CNS receptors. Leoleorin C showed moderate binding affinity (Ki=2.9 μM) for the Sigma 1 receptor.
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              Sesquiterpenoids from the Herb of Leonurus japonicus

              Two new sesquiterpenoids, (−)-(1S*,2S*,3R*)-3-ethoxycupar-5-ene-1,2-diol (1) and (−)-(1S*,4S*,9S*)-1,9-epoxybisabola-2,10-diene-4-ol (2), along with six known compounds 3−8, were isolated from the EtOH extract of the herb of Leonurus japonicus. Their structures were elucidated by physical and spectroscopic analysis. In the in vitro assays, compounds 7 and 8 showed obvious antibacterial activity against several bacteria strains, while compound 3 significantly inhibited abnormal increase of platelet aggregation induced by ADP.
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                Author and article information

                Contributors
                Role: Academic Editor
                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                07 January 2015
                January 2015
                : 20
                : 1
                : 839-845
                Affiliations
                College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000, Henan, China; E-Mails: wssn2006@ 123456163.com (S.W.); xzytyyl1314@ 123456hotmail.com (Z.X.); sssaynu@ 123456163.com (S.S.); liuaynu@ 123456163.com (H.L.); wangaynu@ 123456163.com (J.W.); yanaynu@ 123456163.com (Y.E.); lvaynu@ 123456163.com (Y.L.); dongaynu@ 123456163.com (X.D.); lpzhang70@ 123456163.com (L.Z.)
                Author notes
                [* ]Authors to whom correspondence should be addressed; E-Mails: hkwu@ 123456aynu.edu.cn (H.W.); lgorgchem@ 123456126.com (G.L.); yfshi@ 123456aliyun.com (Y.S.); Tel: +86-372-290-004 (H.W.).
                Article
                molecules-20-00839
                10.3390/molecules20010839
                6272656
                25574824
                1708e491-f493-423b-9aee-676a3c5ee23c
                © 2015 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 06 November 2014
                : 06 January 2015
                Categories
                Communication

                leonurus japonicus,labdane diterpenoid,isoleojaponin,halimane

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