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      The Occurrence and Biological Activity of Tormentic Acid—A Review

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          Abstract

          This review focuses on the natural sources and pharmacological activity of tormentic acid (TA; 2α,3β,19α-trihydroxyurs-2-en-28-oic acid). The current knowledge of its occurrence in various plant species and families is summarized. Biological activity (e.g., anti-inflammatory, antidiabetic, antihyperlipidemic, hepatoprotective, cardioprotective, neuroprotective, anti-cancer, anti-osteoarthritic, antinociceptive, antioxidative, anti-melanogenic, cytotoxic, antimicrobial, and antiparasitic) confirmed in in vitro and in vivo studies is compiled and described. Biochemical mechanisms affected by TA are indicated. Moreover, issues related to the biotechnological methods of production, effective eluents, and TA derivatives are presented.

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          Pentacyclic Triterpene Distribution in Various Plants – Rich Sources for a New Group of Multi-Potent Plant Extracts

          Sebastian Jäger, Holger Trojan, Thomas Kopp … (2009)
          Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 ‑ 90%. Depending on the plant material, betulin (birch bark), betulinic acid (plane bark), oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers), ursolic acid (apple pomace) or an equal mixture of the three triterpene acids (rosemary leaves) are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations.
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            Anti-HIV triterpene acids from Geum japonicum.

            M Wan, Q. Zeng, Sam Sim … (1996)
            The methanol extract from the whole plant of Geum japonicum was found to inhibit the human immunodeficiency virus (HIV-1) protease. Through bioassay-directed fractionation of the extract, a new triterpene acid along with five known triterpene acids, ursolic acid, epipomolic acid, maslinic acid, euscaphic acid, and tormentic acid, were isolated. The structure of the new compound was determined by spectral means including 1H-1H COSY, HMQC, HMBC, and NOE experiments to be 2 alpha, 19 alpha-dihydroxy-3-oxo-12-ursen-28-oic acid (1). Of these compounds, 1, ursolic acid, and maslinic acid showed potent inhibitory activity against HIV-1 protease.
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              Triterpene acids from the leaves of Perilla frutescens and their anti-inflammatory and antitumor-promoting effects.

              Norihiro Banno, Toshihiro Akihisa, Harukuni Tokuda … (2004)
              Nine triterpene acids, viz., six of the ursane type, ursolic acid (1), corosolic acid (2), 3-epicorosolic acid (3), pomolic acid (4), tormentic acid (5) and hyptadienic acid (6), and three of the oleanane type, oleanolic acid (7), augustic acid (8) and 3-epimaslinic acid (9), among which 1 constituted the most predominant triterpene acid, were isolated and identified from ethanol extracts of the leaves of red perilla [Perilla frutescens (L.) Britton var. acuta Kudo] and green perilla [P. frutescens (L.) Britton var. acuta Kudo forma viridis Makino]. These eight compounds, 1, 2, 4-9, were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice. All the compounds tested showed a marked anti-inflammatory effect, with a 50% inhibitory dose (ID50) of 0.09-0.3 mg per ear. In addition, an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA showed five compounds, 1-3, 5 and 9, with a potent inhibitory effect on EBV-EA induction (91-93% inhibition at 1x10(3) mol ratio/TPA). Furthermore, compound 5 exhibited strong antitumor-promoting activity in an in vivo two-stage carcinogenesis test of mouse tumor by using 7,12-dimethylbenz(a)anthracene (DMBA) as an initiator and TPA as a promoter.
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                Author and article information

                Contributors
                Valeria Patricia Sülsen: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 22 June 2021
                Publication date Collection: July 2021
                Volume: 26
                Issue: 13
                Electronic Location Identifier: 3797
                Affiliations
                Chair and Department of Pharmaceutical Botany, Medical University of Lublin, 1 Chodźki Street, 20-093 Lublin, Poland; zimiwoj@ 123456gmail.com (W.Z.); natalia.nowacka@ 123456umlub.pl (N.N.-J.)
                Author notes
                [* ]Correspondence: marta.olech@ 123456umlub.pl ; Tel.: +48-814-487-060
                Author information
                https://orcid.org/0000-0002-2838-550X
                https://orcid.org/0000-0003-1133-2150
                Article
                Publisher ID: molecules-26-03797
                DOI: 10.3390/molecules26133797
                PMC ID: 8270333
                PubMed ID: 34206442
                SO-VID: 44da81d0-f44e-4ee0-b07c-e641ca798a8a
                Copyright © © 2021 by the authors.
                License:

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

                History
                Date received : 16 May 2021
                Date accepted : 18 June 2021
                Categories
                Subject: Review

                Keywords: tormentic acid,triterpenes,pentacyclic triterpene,cas 13850-16-3,bioactivity,plant metabolite,tormentic acid derivatives
                Data availability:
                Keywords: tormentic acid, triterpenes, pentacyclic triterpene, cas 13850-16-3, bioactivity, plant metabolite, tormentic acid derivatives

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