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UNIVERSIDADE DE LISBOA FACULDADE DE FARMÁCIA PHYTOCHEMICAL STUDY AND BIOLOGICAL ACTIVITIES OF DITERPENES AND DERIVATIVES FROM PLECTRANTHUS SPECIES Patrícia Dias de Mendonça Rijo DOUTORAMENTO EM FARMÁCIA (QUÍMICA FARMACÊUTICA E TERAPÊUTICA) 2010 UNIVERSIDADE DE LISBOA FACULDADE DE FARMÁCIA PHYTOCHEMICAL STUDY AND BIOLOGICAL ACTIVITIES OF DITERPENES AND DERIVATIVES FROM PLECTRANTHUS SPECIES Patrícia Dias de Mendonça Rijo Tese orientada por: Professora Doutora Maria de Fátima Alfaiate Simões e co-orientada por: Professora Doutora Lídia Maria Veloso Pinheiro DOUTORAMENTO EM FARMÁCIA (QUÍMICA FARMACÊUTICA E TERAPÊUTICA) 2010 The research work was performed, mostly, in the Faculdade de Farmácia da Universidade de Lisboa at the Medicinal Chemistry Group (former Centro de Estudos de Ciências Farmacêuticas – CECF) of the Institute for Medicines and Pharmaceutical Sciences (iMed.UL). Funding to these research centres and the attribution of a Doctoral degree grant (SFRH/BD/19250/2004) were provided by the Fundação para a Ciência e a Tecnologia - Ministério da Ciência, Tecnologia e Ensino Superior (FCT-MCTES). ABSTRACT This study focused on the research of new bioactive constituents from four species of the Plectranthus plants. Previous works on plants of the genus Plectranthus (Lamiaceæ) evidenced that some of their constituents possess interesting biological activities. The antimicrobial activity of the plant extracts and of the isolated metabolites was thoroughly searched. Antioxidant, anticholinesterase and anti-inflammatory properties of some compounds were also screened. The phytochemical study of the acetone extracts of Plectranthus ornatus Codd., P. ecklonii Benth., P. porcatus Winter & Van Jaarsv and P. saccatus Benth. rendered several terpenoid constituents mostly diterpenes. From P. ornatus three new forskolin-like labdane diterpenes (6-O-acetylforskolin, 1,6-di-O-acetylforskolin and 1,6-di-O-acetyl-9-deoxyforskolin), a new diterpene with the rare halimane skeleton (11R*-acetoxyhalima-5,13E-dien-15-oic acid), and two known labdane diterpenes were isolated; the rhinocerotinoic acid which was found in Plectranthus species for the first time, and plectrornatin C. Six known triterpenoids were also identified as mixtures. The study of P. ecklonii led to the isolation of two known abietanes, sugiol and parvifloron D. Sugiol was obtained from Plectranthus species for the first time. Four known triterpenoids were also identified as mixtures. P. porcatus, a plant not hitherto studied, yield a new spiro-abietane diterpene [(13S,15S)- 6β,7α,12α,19-tetrahydroxy-13β,16-cyclo-8-abietene-11,14-dione]. A new beyerane diterpene (ent-7α-acetoxy-15-beyeren-18-oic acid) was isolated from P. saccatus. Attempting to find novel bioactive prototypes from the more potent antibacterial diterpenes, isolated in higher yields, some diterpene derivatives were prepared. Nine new derivatives were obtained from (11R*,13E)-11-acetoxyhalima- 5,13-dien-15-oic acid (P. ornatus). A new 2β-(4-hydroxy)benzoyloxy derivative of microstegiol was prepared from parvifloron D (P. ecklonii). From the 7α-acetoxy-6β- hydroxyroyleanone (isolated in the past from P. grandidentatus) thirteen ester derivatives were synthesized, whereof ten were new compounds. The unequivocal chemical structures of pure compounds (natural and derivatives) were deduced from their spectroscopic (IR, MS, 1D and 2D NMR experiments) and physico-chemical data, as well as from literature information. The preliminary antimicrobial activity screenings of all the isolated metabolites showed that several diterpenes inhibited the growth of the Gram positive bacteria tested. In addition, the minimum inhibitory concentration against standard and clinical isolates of sensitive and resistant Staphylococcus and Enterococcus strains was determined for the antibacterial metabolites and their synthesized derivatives. The (11R*,13E)-11-acetoxyhalima-5,13-dien-15-oic acid and its (11R*,13E)- halima-5,13-diene-11,15-diol derivative were the more active halimanes. Parvifloron D was less active than its microstegiol 2β-(4-hydroxy)benzoate derivative, but both showed more potent antibacterial activities than the halimane diterpenoids. The three 12-O-benzoyl esters derivatives of the 7α-acetoxy-6β- hydroxyroyleanone prototype revealed to be more potent growth inhibitors against Staphylococcus and Enterococcus strains than the prototype. The 6β-propionyloxy-12- O-propionyl derivative also showed to be more active against Enterococcus than the vii prototype. Generally, the 12-esters and the 6,12-diesters were more active against Enterococcus than Staphylococcus strains. The hydrophobic extra-interactions with the bacterial targets seem to play an important role on the activity of royleanones derivatives prepared. Taking into account the IC50 values which expressed the scavenging DPPH radical ability, the isolated metabolite parvifloron D as well as 7α-acetoxy-6β- hydroxyroyleanone showed in vitro antioxidant activity. The in vitro acetylcholinesterase assay did not detect any activity for all the newly isolated diterpenes and 7α-acetoxy-6β-hydroxyroyleanone. The COX inhibitor screening assay was tested on 6-O-acetylforskolin, rhinocerotinoic acid, plectrornatin C, (11R*,13E)-halima-5,13-diene-11,15- diol, 11R*- acetoxyhalima-5,13E-dien-15-oic acid and on its methyl ester, for their ability to inhibit COX-2. The preliminary results encourage further studies aiming to confirm and to examine its potential anti-inflammatory activity in a more robust approach. Keywords: Lamiaceae, Plectranthus, Plectranthus ornatus, Plectranthus ecklonii, Plectranthus saccatus, Plectranthus porcatus, diterpenes, abietane, halimane, forskolin-like diterpenoids, labdane, beyerane, antimicrobial activity, antioxidant activity, anticholinesterase activity and anti-inflammatory activity. viii RESUMO Este estudo teve como objectivo a pesquisa de novos constituintes bioactivos de quatro espécies de plantas do género Plectranthus. A actividade antimicrobiana dos extractos obtidos e dos metabolitos isolados foi realizada e foram testadas as propriedades anti-oxidante, anti-colinesterase e anti- inflamatória de alguns compostos. O estudo fitoquímico dos extractos de acetona de Plectranthus ornatus Codd., P. ecklonii Benth., P. porcatus Winter & Van Jaarsv. e P. saccatus Benth. originou diversos constituintes terpénicos, principalmente diterpenos. Três novos diterpenos do tipo forskolina (6-O-acetilforskolina; 1,6-di-O- acetilforskolina e 1,6-di-O-acetil-9-deoxiforskolina) foram isolados de P. ornatus. Foram também identificados um novo diterpeno com o raro esqueleto de halimano (ácido 11R*-acetoxihalima-5,13E-dien-15-óico), dois diterpenos labdânicos conhecidos; o ácido rinocerotinóico encontrado pela primeira vez em espécies do género Plectranthus, e a plectrornatina C. Seis triterpenos já conhecidos foram igualmente identificados na forma de misturas. O estudo de P. ecklonii originou o isolamento de dois abietanos conhecidos: o sugiol e a parviflorona D. O sugiol foi isolado pela primeira vez de espécies Plectranthus. Outros quatro triterpenos conhecidos foram identificados também como misturas. A planta P. porcatus, até à data não estudada, originou um novo diterpeno spiro-abietânico [(13S,15S)- 6β,7α,12α,19-tetrahidroxi-13β,16-ciclo-8-abietene-11,14-diona]. Um novo diterpeno com esqueleto de beierano (ácido ent-7α-acetoxi-15-beieren-18-óico) foi isolado de P. saccatus. Na tentativa de obter novos protótipos bioactivos, vários derivados foram preparados, a partir dos diterpenos antibacterianos mais potentes e isolados em maior quantidade. Nove novos derivados foram obtidos do ácido (11R*,13E)-11- acetoxihalima-5,13-dien-15-óico (P. ornatus). Um novo derivado 2β-(4- hidroxi)benzoilado do microstegiol, foi preparado a partir da parviflorona D (P. ecklonii). Treze ésteres derivados da 7α-acetoxi-6β-hidroxiroyleanona (isolada anteriormente de P. grandidentatus) foram sintetizados, sendo de assinalar que dez dos derivados são compostos novos. A determinação estrutural dos compostos puros (naturais e derivados) foi deduzida por espectroscopia (IV, EM, RMN 1D e 2D), propriedades físico-químicas e com base na informação obtida da literatura. O estudo preliminar da actividade antimicrobiana de todos os metabolitos isolados, mostrou que diversos diterpenos inibem o crescimento de bactérias de Gram positivo. A concentração mínima inibitória (CMI) dos metabolitos e seus derivados foi determinada em estirpes de Staphylococcus e Enterococcus, tanto em bactérias padrão como em isolados clínicos resistentes e sensíveis a antibióticos. O ácido (11R*,13E)-11- acetoxihalima-5,13-dien-15-óico e o seu derivado (11R*,13E)-halima-5,13-diene-11,15- diol foram os halimanos mais activos. A parviflorona D foi menos activa do que o seu correspondente derivado 2β-(4-hidroxi)benzoilado, mas ambos apresentaram uma actividade antibacteriana mais potente do que os diterpenos com esqueleto de halimano. ix Os três 12-O-benzoil-ésteres derivados do protótipo 7α-acetoxi-6β- hidroxiroyleanona revelaram ser inibidores mais potentes do que a royleanona- protótipo, contra as estirpes testadas de Staphylococcus e Enterococcus. O derivado 6β-propioniloxi-12-O-propionilo mostrou ser o mais activo contra as estirpes testadas de Enterococcus do que o protótipo. De um modo geral, os derivados 12-ésteres e os 6,12-diésteres foram mais activos contra as estirpes de Enterococcus do que as estirpes de Staphylococcus testadas. As interacções hidrofóbicas com os alvos bacterianos parecem ter um papel
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  • Plectranthus (Labiatae) and Allied Genera in Southern Africa

    Plectranthus (Labiatae) and Allied Genera in Southern Africa

    Bothalia 11, 4:371-442 (1975) Plectranthus (Labiatae) and allied genera in Southern Africa L. E. CODD* ABSTRACT A revision is presented of the 40 species of Plectranthus, 1 species of Rabdosia and 3 species of Solenostemon which are indigenous, semi-naturalized or widely cultivated in Southern Africa. Descriptions, illustrations, keys and distribution data are provided. The following new names are published: P. mutabilis Codd, P. psammo- philus Codd, P. rubropunctatus Codd, P. unguentarius Codd, P. ornatus Codd (nom. nov. for Coleus comosus Hochst. ex Guerke), P. zatarhendi (Forsk.) E. A. Bruce var. tomentosus (Benth.) Codd, —var. woodii (Guerke) Codd, P. madagascariensis (Pers.) Benth. var. aliciae Codd, Solenostemon scutellarioides (L.) Codd and S. shirensis (Guerke) Codd. CONTENTS Page Page Introduction ...............................................................372 20. P. mutabilis Codd ....................................... 404 History .........................................................................372 21. P. psammophilus Codd .............................. 405 References ..................................................................441 Sect. Plectranthus ................................................ 406 Key to Genera ..................................................... ...374 22. P. verticillatus (L.f.) Druce ...................... 407 Plectranthus ..........................................................374 23. P. strigosus Benth............................................ 409 Key to Species .........................................................374
  • Plectranthus: a Plant for the Future? ⁎ L.J

    Plectranthus: a Plant for the Future? ⁎ L.J

    Available online at www.sciencedirect.com South African Journal of Botany 77 (2011) 947–959 www.elsevier.com/locate/sajb Plectranthus: A plant for the future? ⁎ L.J. Rice a, G.J. Brits b, C.J. Potgieter c, J. Van Staden a, a Research Centre for Plant Growth and Development, School of Biological and Conservation Sciences, University of KwaZulu-Natal Pietermaritzburg, Private Bag X01, Scottsville 3209, South Africa b Brits Nursery, 28 Flamingo Road, Stellenbosch 7600, South Africa c Bews Herbarium, School of Biological and Conservation Sciences, University of KwaZulu-Natal Pietermaritzburg, Private Bag X01, Scottsville 3209, South Africa Abstract The genus Plectranthus (Lamiaceae) is a significant, prolific and extensively used genus in southern Africa. It plays a dominant role in both horticulture and traditional medicine. Some 12 species are documented for their use in treating ailments by various indigenous peoples of southern Africa. It is a firm favourite in gardens and Plectranthus has been bred to further utilise the remarkable diversity of indigenous South African wildflowers with amenity horticultural potential. Although previously subjected to both horticultural (Van Jaarsveld, 2006) and ethnobotanical (Lukhoba et al., 2006) review, Plectranthus is a genus with economic potential in various sectors, and this article aims to review this potential of southern African species. © 2011 SAAB. Published by Elsevier B.V. All rights reserved. Keywords: Ethnobotany; Flow cytometry; Flowering pot plants; Genetic resources; Plant Breeders' Rights; Plectranthus; Triploid breeding; Wildflowers 1. Introduction home to the species with most promise for horticulture (Van Jaarsveld, 2006). Other prominent areas of diversity are The genus Plectranthus L'Hér.
  • Weed Categories for Natural and Agricultural Ecosystem Management

    Weed Categories for Natural and Agricultural Ecosystem Management

    Weed Categories for Natural and Agricultural Ecosystem Management R.H. Groves (Convenor), J.R. Hosking, G.N. Batianoff, D.A. Cooke, I.D. Cowie, R.W. Johnson, G.J. Keighery, B.J. Lepschi, A.A. Mitchell, M. Moerkerk, R.P. Randall, A.C. Rozefelds, N.G. Walsh and B.M. Waterhouse DEPARTMENT OF AGRICULTURE, FISHERIES AND FORESTRY Weed categories for natural and agricultural ecosystem management R.H. Groves1 (Convenor), J.R. Hosking2, G.N. Batianoff3, D.A. Cooke4, I.D. Cowie5, R.W. Johnson3, G.J. Keighery6, B.J. Lepschi7, A.A. Mitchell8, M. Moerkerk9, R.P. Randall10, A.C. Rozefelds11, N.G. Walsh12 and B.M. Waterhouse13 1 CSIRO Plant Industry & CRC for Australian Weed Management, GPO Box 1600, Canberra, ACT 2601 2 NSW Agriculture & CRC for Australian Weed Management, RMB 944, Tamworth, NSW 2340 3 Queensland Herbarium, Mt Coot-tha Road, Toowong, Qld 4066 4 Animal & Plant Control Commission, Department of Water, Land and Biodiversity Conservation, GPO Box 2834, Adelaide, SA 5001 5 NT Herbarium, Department of Primary Industries & Fisheries, GPO Box 990, Darwin, NT 0801 6 Department of Conservation & Land Management, PO Box 51, Wanneroo, WA 6065 7 Australian National Herbarium, GPO Box 1600, Canberra, ACT 2601 8 Northern Australia Quarantine Strategy, AQIS & CRC for Australian Weed Management, c/- NT Department of Primary Industries & Fisheries, GPO Box 3000, Darwin, NT 0801 9 Victorian Institute for Dryland Agriculture, NRE & CRC for Australian Weed Management, Private Bag 260, Horsham, Vic. 3401 10 Department of Agriculture Western Australia & CRC for Australian Weed Management, Locked Bag No. 4, Bentley, WA 6983 11 Tasmanian Museum and Art Gallery, GPO Box 1164, Hobart, Tas.
  • Anti-Microbial Activity of Hydro-Alcoholic Extracts of Some Traditionally Important Medicinal Plants Research Article

    Anti-Microbial Activity of Hydro-Alcoholic Extracts of Some Traditionally Important Medicinal Plants Research Article

    Int. J. Pharm. Sci. Rev. Res., 62(2), May - June 2020; Article No. 24, Pages: 148-156 ISSN 0976 – 044X Research Article Anti-microbial Activity of Hydro-alcoholic Extracts of Some Traditionally Important Medicinal Plants 1*S.K.Gunavathy, 2H.Benita Sherine, 3N.Muruganantham, 4R.Govindharaju 1* Assistant Professor, Department of Chemistry, Srimad Andavan Arts and Science College (Autonomous), (Affiliated to Bharathidasan University) Tiruchirappalli - 620 005, Tamil Nadu, India. 2Assistant Professor, PG & Research Department Chemistry, Periyar E.V.R. College (Autonomous), (Affiliated to Bharathidasan University) Tiruchirappalli - 620 023, Tamil Nadu, India. 3,4PG & Research Department of Chemistry, Thanthai Hans Roever College (Autonomous), (Affiliated to Bharathidasan University), Perambalur - 621 220, Tamil Nadu, India. *Corresponding author’s E-mail: [email protected] Received: 06-03-2020; Revised: 24-05-2020; Accepted: 30-05-2020. ABSTRACT Plants are the rich natural source of bioactive compounds. The more diversified composition of the plants makes their role as biomedicine. These bioactive molecules are often lethal to both plants and animals. Based on ethnomedical use, the leaves Plectranthus mollis, Elaeagnus conferta and Grewia tilaefolia leaf extracts were extracted successively with organic solvents. These plants are reported to exhibit relaxant activity on smooth and skeletal muscles, and has cytotoxic and anti-tumour promoting activity, and can be used in the treatment of cancer. These crude extracts were screened for their toxic potential against three Gram- positive bacteria, five Gram- negative bacteria and two fungus by using disc diffusion method. The hydro alcoholic extracts of the plant possessed significant antimicrobial activities on both Gram- positive and Gram- negative bacteria.