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      Secondary Metabolites from Rubiaceae Species

      review-article
      , *
      Molecules
      MDPI
      Rubiaceae, Rubioideae, Cinchonoideae, Ixoroideae, iridoids, alkaloid, anthraquinones, triterpenes

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          Abstract

          This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion.

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          A revised system of classification of the angiosperms

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              Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa.

              The leaves of a tropical plant, Mitragyna speciosa KORTH (Rubiaceae), have been traditionally used as a substitute for opium. Phytochemical studies of the constituents of the plant growing in Thailand and Malaysia have led to the isolation of several 9-methoxy-Corynanthe-type monoterpenoid indole alkaloids, including new natural products. The structures of the new compounds were elucidated by spectroscopic and/or synthetic methods. The potent opioid agonistic activities of mitragynine, the major constituent of this plant, and its analogues were found in in vitro and in vivo experiments and the mechanisms underlying the analgesic activity were clarified. The essential structural features of mitragynines, which differ from those of morphine and are responsible for the analgesic activity, were elucidated by pharmacological evaluation of the natural and synthetic derivatives. Among the mitragynine derivatives, 7-hydroxymitragynine, a minor constituent of M. speciosa, was found to exhibit potent antinociceptive activity in mice.
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                Author and article information

                Contributors
                Role: Academic Editor
                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                22 July 2015
                July 2015
                : 20
                : 7
                : 13422-13495
                Affiliations
                Bioprospection and Biotechnology Laboratory, Technology and Innovation Coordenation, National Research Institute of Amazonia, Av. André Araújo, 2936, Petrópolis, Manaus, AM 69067-375, Brazil
                Author notes
                [* ]Author to whom correspondence should be addressed; E-Mail: cecilia@ 123456inpa.gov.br ; Tel.: +55-092-3643-3654.
                Article
                molecules-20-13422
                10.3390/molecules200713422
                6331836
                26205062
                6b2ef0c0-0b43-429d-9f6e-f256895169e1
                © 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
                : 13 June 2015
                : 13 July 2015
                Categories
                Review

                rubiaceae,rubioideae,cinchonoideae,ixoroideae,iridoids,alkaloid,anthraquinones,triterpenes

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