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Secondary Metabolites from Mozambican Plants

Monjane, Julião LU (2017)
Abstract (Swedish)
Produkter som härrör från olika naturliga källor har använts i tusentals år av människor för deras vardagliga behov. Av dessa naturliga källor var växterna det mest prisvärda. Växtbaserade produkter användes för skydd, mat och som läkemedel. De medicinska egenskaperna hos växtbaserade produkter spelade en viktig roll i forntida civilisationer, och även i dagens dagar är de användbara på grund av deras medicinska egenskaper.
Baserat på erfarenheterna från människor över åren genom att utnyttja växtbaserade produkter eller sekundära metaboliter, syftade denna uppsats till att analysera de kemiska komponenterna hos vissa växter från den moçambikiska floran som används i traditionell medicin för behandling av olika sjukdomar. Extrakt av... (More)
Produkter som härrör från olika naturliga källor har använts i tusentals år av människor för deras vardagliga behov. Av dessa naturliga källor var växterna det mest prisvärda. Växtbaserade produkter användes för skydd, mat och som läkemedel. De medicinska egenskaperna hos växtbaserade produkter spelade en viktig roll i forntida civilisationer, och även i dagens dagar är de användbara på grund av deras medicinska egenskaper.
Baserat på erfarenheterna från människor över åren genom att utnyttja växtbaserade produkter eller sekundära metaboliter, syftade denna uppsats till att analysera de kemiska komponenterna hos vissa växter från den moçambikiska floran som används i traditionell medicin för behandling av olika sjukdomar. Extrakt av växtarterna Cadaba natalensis (Capparaceae), Clematis viridiflora (Ranunculaceae), Brachylaena discolor (Asteraceae) och Senna spectabilis (Fabaceae) växtarter undersöktes för deras kemiska beståndsdelar.
Genom fraktionering baserat på olika kromatografiska metoder isolerades 40 metaboliter och deras kemiska strukturer bestämdes. Av dessa konstaterades tre nya metaboliter. Totalt sett isolerades 40 sekundära metaboliter som hör till de tre huvudklassen av sekundära metaboliter och deras strukturer bestämdes genom högupplösande NMR- och MS-tekniker. Den makrocykliska dibensodiazocyklododekanedionen (134), (S) -2-etyl-2-metyloxazolidin-5-on (139a) och 4-metoxi-3-metyl-2- (metyltio) -lindol (141) var de tre nya metaboliter, medan (R) -5-etyl-5-metyloxazolidin-2-on (140) isolerades som naturlig produkt för första gången. Strukturerna på dessa metaboliter bestämdes genom omfattande användning av
spektroskopiska tekniker för NMR (1D- och 2D-NMR), IR, såväl som MS-data. Strukturerna av de kända föreningarna bestämdes med samma tekniker och bekräftades genom jämförelse av deras spektroskopiska
data med de som rapporterats i litteraturen.
Isolerade metaboliter med intressanta strukturella egenskaper analyserades för in vitro antiprotozoal aktivitet mot två Leishmania stam, Leishmania amazonensis clon 1 och L. braziliensis. Kinonmetidtriterpenoid (29a) uppvisade en potent antileishmaniell aktivitet mot båda stammen med ICso-värdena 4,2 respektive 2,8 μM jämfört med den positiva kontrollmeltfonen med ICso-värdena 5,1 respektive 4,9 μM. Miltefone är ett aktuellt läkemedel som används för att behandla Leishmania. 141 med IC50-värdena 25,0 respektive 13,2 μM respektive onopordopicrin (153) med ICso-värdena 13,8 respektive 9,7 μM hade även intressant antileishmaniell aktivitet, även om germacranolidepoxidderivatet 154, härlett från 153, var inaktivt mot båda stammen testas (Less)
Abstract
Products derived from different natural sources have been used for thousands of years by human beings for their everyday needs. Out of these natural sources, plants were the most affordable. Plant-derived products were used for shelter, food, and as medicines. The medicinal properties of plant-derived products played an important role in ancient civilizations, and even in the present days they are useful due to their medicinal properties.
Based on the experience acquired by humans over the years by exploiting plant-derived products or secondary metabolites, this thesis was aimed to analyse the chemical components of some plants from the Mozambican flora used in the traditional medicine for the treatment of various ailments. Extracts of... (More)
Products derived from different natural sources have been used for thousands of years by human beings for their everyday needs. Out of these natural sources, plants were the most affordable. Plant-derived products were used for shelter, food, and as medicines. The medicinal properties of plant-derived products played an important role in ancient civilizations, and even in the present days they are useful due to their medicinal properties.
Based on the experience acquired by humans over the years by exploiting plant-derived products or secondary metabolites, this thesis was aimed to analyse the chemical components of some plants from the Mozambican flora used in the traditional medicine for the treatment of various ailments. Extracts of Cadaba natalensis (Capparaceae), Clematis viridiflora (Ranunculaceae), Brachylaena discolor (Asteraceae) and Senna spectabilis (Fabaceae) plant species were investigated for their chemical constituents.
By fractionation based on various chromatographic methods, forty metabolites were isolated and their chemical structures were determined. Out of these, three were found to be novel metabolites, All in all, 40 secondary metabolites belonging to the three main classes of secondary metabolites were isolated and their structures were determined by high resolution NMR and MS techniques. The macrocyclic dibenzo-diazocyclododecanedione (134), (S)-2-ethyl-2-methyloxazolidin-5-one (139a), and 4-methoxy-3-methyl-2-(methylthio)-1Hindole (141) were the three novel metabolites, while the (R)-5-ethyl-5-methyloxazolidin-2-one (140) was isolated as natural product for the first time. The structures on these metabolites were determined by extensive use of
the spectroscopic techniques of NMR (1D- and 2D-NMR), IR, as well as MS data. The structures of the known compounds were determined by the same techniques, and confirmed by the comparison of their spectroscopic
data with those reported in the literature.
Isolated metabolites with interesting structural features were assayed for in vitro antiprotozoal activity towards two Leishmania strain, Leishmania amazonensis clon 1 and L. braziliensis. The quinone methide triterpenoid (29a) showed a potent antileishmanial activity against both strain with the IC50 values 4.2 and 2.8 μM, respectively compared to the positive controle miltefone with the IC50 values 5.1 and 4.9 μM, respectively. Miltefone is a current used drug to treat Leishmania. 141 with the IC50 values 25.0 and 13.2 μM, respectively, and onopordopicrin (153) with the IC50 values 13.8 and 9.7 μM, respectively, also possessed interesting antileishmanial activity, although the germacranolide epoxy derivative 154, derived from 153, was inactive against both strain tested. (Less)
Please use this url to cite or link to this publication:
author
supervisor
opponent
  • Associate Professor Vik, Anders, Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, Norway
organization
publishing date
type
Thesis
publication status
published
subject
keywords
Secondary metabolites, Mozambique, Medicinal plants, Isolation, Structural elucidation, Antileishmanial activity
pages
70 pages
publisher
Lund University, Faculty of Science, Department of Chemistry, Centre for Analysis and Synthesis
defense location
Lecture hall F, Center for chemistry and chemical engineering, Naturvetarvägen 14, Lund
defense date
2017-12-21 09:30
ISBN
978-91-7422-553-2
978-91-7422-554-9
language
English
LU publication?
yes
id
fa81367d-7a87-4293-98db-fd2bf576b277
date added to LUP
2017-11-27 08:43:17
date last changed
2017-12-06 11:58:55
@phdthesis{fa81367d-7a87-4293-98db-fd2bf576b277,
  abstract     = {Products derived from different natural sources have been used for thousands of years by human beings for their everyday needs. Out of these natural sources, plants were the most affordable. Plant-derived products were used for shelter, food, and as medicines. The medicinal properties of plant-derived products played an important role in ancient civilizations, and even in the present days they are useful due to their medicinal properties.<br/>Based on the experience acquired by humans over the years by exploiting plant-derived products or secondary metabolites, this thesis was aimed to analyse the chemical components of some plants from the Mozambican flora used in the traditional medicine for the treatment of various ailments. Extracts of Cadaba natalensis (Capparaceae), Clematis viridiflora (Ranunculaceae), Brachylaena discolor (Asteraceae) and Senna spectabilis (Fabaceae) plant species were investigated for their chemical constituents.<br/>By fractionation based on various chromatographic methods, forty metabolites were isolated and their chemical structures were determined. Out of these, three were found to be novel metabolites, All in all, 40 secondary metabolites belonging to the three main classes of secondary metabolites were isolated and their structures were determined by high resolution NMR and MS techniques. The macrocyclic dibenzo-diazocyclododecanedione (134), (S)-2-ethyl-2-methyloxazolidin-5-one (139a), and 4-methoxy-3-methyl-2-(methylthio)-1Hindole (141) were the three novel metabolites, while the (R)-5-ethyl-5-methyloxazolidin-2-one (140) was isolated as natural product for the first time. The structures on these metabolites were determined by extensive use of<br/>the spectroscopic techniques of NMR (1D- and 2D-NMR), IR, as well as MS data. The structures of the known compounds were determined by the same techniques, and confirmed by the comparison of their spectroscopic<br/>data with those reported in the literature.<br/>Isolated metabolites with interesting structural features were assayed for in vitro antiprotozoal activity towards two Leishmania strain, Leishmania amazonensis clon 1 and L. braziliensis. The quinone methide triterpenoid (29a) showed a potent antileishmanial activity against both strain with the IC50 values 4.2 and 2.8 μM, respectively compared to the positive controle miltefone with the IC50 values 5.1 and 4.9 μM, respectively. Miltefone is a current used drug to treat Leishmania. 141 with the IC50 values 25.0 and 13.2 μM, respectively, and onopordopicrin (153) with the IC50 values 13.8 and 9.7 μM, respectively, also possessed interesting antileishmanial activity, although the germacranolide epoxy derivative 154, derived from 153, was inactive against both strain tested.},
  author       = {Monjane, Julião},
  isbn         = {978-91-7422-553-2},
  keyword      = {Secondary metabolites,Mozambique,Medicinal plants,Isolation,Structural elucidation,Antileishmanial activity},
  language     = {eng},
  pages        = {70},
  publisher    = {Lund University, Faculty of Science, Department of Chemistry, Centre for Analysis and Synthesis},
  school       = {Lund University},
  title        = {Secondary Metabolites from Mozambican Plants},
  year         = {2017},
}