Volatile constituents of <i>Artemisia annua</i> L. (Asteraceae)

Woerdenbag, Herman J.; Bos, Rein; Salomons, M. C.; Hendriks, H.; Pras, Niesko; Malingré, Theo M.

doi:10.1002/ffj.2730080303

Cited by 69 publications

(42 citation statements)

References 15 publications

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“…The components of the oils were fully unambiguously identified by their mass spectral fragmentation patterns with those reported in computerized MS-data bank spectral libraries (NIST and WILEY) 10 or reported in the literature. [11][12] The compounds are arranged in order to GC elution on SLB-5ms capillary column. Relative percentages were calculated based on the GC-FID peak areas without the use of correction factors and are compiled.…”

Section: Gas Chromatography Analysis (Gc-fid)mentioning

confidence: 99%

GC/MS Analysis and Potential Cytotoxic Activity of Haplophyllum tuberculatum Essential Oils Against Lung and Liver Cancer Cells

Sabry¹,

Sayed²,

Alshalmani³

2015

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Background: Haplophyllum tuberculatum is a plant belongs to family rutacee. It is rich in volatile oils, fixed oils, alkaloids, and furanocoumarins. It is well known for the huge number of folkloric uses in middle east. Objective: The aim of this study is to establish the chemical composition of the essential oils of Libyan H. tuberculatum and to investigate their cytotoxic potentialities.Materials and Methods: The essential oils of the aerial parts and flowers of H. tuberculatum growing in Libya were prepared by hydrodistillation. GC/MS analyses were performed on a Shimaduz capillary gas chromatograph (GC 17A ver.3) instrument directly coupled to mass spectrometer-MS QP5050A. Oil A and F of H. tuberculatum at different concentrations (0-50 µg/ml) in DMSO were tested for cytotoxicity against human tumor cell lines. Results: Oil yield was found 0.4 and 1.5 (v/w %) on dry weight basis respectively. GC/MS analysis resulted in identification of total 35 compounds. 15 compounds were common to both oils. oil A of H. tuberculatum exhibited antitumor activities against. liver carcinoma

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Section: Gas Chromatography Analysis (Gc-fid)mentioning

confidence: 99%

GC/MS Analysis and Potential Cytotoxic Activity of Haplophyllum tuberculatum Essential Oils Against Lung and Liver Cancer Cells

Sabry¹,

Sayed²,

Alshalmani³

2015

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“…The first likely step is the cytochrome-P450-catalysed hydroxylation at C12 of amorpha-4,11-diene yielding artemisinic alcohol. This compound has not been reported in A. annua shoot essential-oil extracts, but was tentatively identified in the roots (Woerdenbag et al 1993). Subsequently, the alcohol could be oxidized two additional times at C12 by either cytochrome P450 enzymes or dehydrogenases, yielding the corresponding acid, artemisinic acid (Funk and Croteau 1994;De Kraker et al 2001;Sangwan et al 1993b;West 1980 Compounds: 1, -copaene;2, -caryophyllene;3, trans--farnesene;5, selina-4,11-diene;6, germacrene D;9, bicyclogermacrene;10, germacrene A;14, amorpha-4,11-diene.…”

Section: Biosynthetic Pathway Beyond Amorpha-411-dienementioning

confidence: 84%

“…Several authors have analysed hydrocarbon sesquiterpenes in A. annua tissues, but a compound that could be the olefinic sesquiterpene intermediate in the biosynthesis of artemisinin was never identified (Ahmad and Misra 1994;Charles et al 1991;Woerdenbag et al 1993). In leaf extracts of A. annua we detected 14 sesquiterpene olefins, of which ten could be identified using GC-MS libraries (Wiley and personal library of W.A.…”

Section: Identification Of Olefinic Sesquiterpenes In a Annua Leavesmentioning

confidence: 99%

“…Artemisinic and dihydroartemisinic acid were reported by many authors, as well as many olefinic mono-and sesquiterpenes and putative intermediates en route from dihydroartemisinic acid to artemisinin (Brown 1994;Jung et al 1990;Ranasinghe et al 1993;Wallaart et al 1999b;Woerdenbag et al 1993). However, none of the reported olefinic sesquiterpenes seemed to fit in the biosynthetic pathway, nor was a possible intermediate between the sesquiterpene olefin and artemisinic acid ever detected, with the exception of artemisinic alcohol, which was tentatively identified in the roots of A. annua (Woerdenbag et al 1993).…”

Section: Introductionmentioning

confidence: 97%

“…annua is a cosmopolitan species, growing wild in many countries, e.g. in China and Vietnam, the Balkan, the former Soviet Union, Argentina and Southern Europe (Van Geldre et al 1997), and large differences exist in artemisinin content between different varieties of A. annua (Delabays et al 1993;Woerdenbag et al 1993). A substantial increase in the content of artemisinin would be required to make artemisinin available on a large scale also to the people in the Third World.…”

Section: Introductionmentioning

confidence: 99%

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Research to Improve Artemisinin Production for use in the Preparation of Anti-Malarial Drugs

Bouwmeester

Bertea²,

Kraker³

et al.

Medicinal and Aromatic Plants

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Abstract. An important group of antimalarial drugs consists of the endoperoxide sesquiterpene lactone artemisinin and its semi-synthetically prepared derivatives. Because of the development of resistance against other malarial drugs, the demand for artemisinin has rapidly increased during the past decade. However, the supply of artemisinin is troublesome as neither total nor semi-synthesis are economically feasible and the only plant species known to produce artemisinin, Artemisia annua L., contains only low amounts of this compound. For a directed strategy to improve artemisinin production, one of the first requirements is to have insight into the regulation of its biosynthesis. Surprisingly, until some years ago hardly anything was known about the biosynthesis of artemisinin, particularly about the early enzymatic steps leading to (dihydro)artemisinic acid. To elucidate this important missing part in the pathway, we have analysed the terpenoids in A. annua leaves and the presence of sesquiterpene synthases, the enzyme class that should theoretically catalyse the first step in the formation of artemisinin. This led to the discovery of amorpha-4,11-diene synthase, which indeed catalyses the first step in artemisinin biosynthesis and for which the corresponding gene was cloned shortly afterwards. A subsequent search for oxidized derivatives of amorpha-4,11-diene -which could be postulated to be intermediates en route to artemisinin -revealed the presence of artemisinic alcohol, dihydroartemisinic alcohol, artemisinic aldehyde, dihydroartemisinic aldehyde and dihydroartemisinic acid. We also demonstrated the presence of the biosynthetic enzymes amorpha-4,11-diene hydroxylase, artemisinic alcohol dehydrogenase, artemisinic aldehyde reductase and dihydroartemisinic aldehyde dehydrogenase in A. annua. From these results, we conclude that the early steps in artemisinin biosynthesis involve: cyclization of farnesyl diphosphate by amorpha-4,11-diene synthase to amorpha-4,11-diene, hydroxylation of amorpha-4,11-diene to artemisinic alcohol, oxidation of artemisinic alcohol to artemisinic aldehyde, reduction of the C11-C13 double bond yielding dihydroartemisinic aldehyde, and oxidation of dihydroartemisinic aldehyde to dihydroartemisinic acid. During this biochemical research we have also managed to develop a trichome isolation protocol which has not only accelerated our biochemical work but also enables us to clone -in a very directed way -the genes that encode the enzymes responsible for artemisinin production. This should in the next few years result in several approaches to boost artemisinin production. 276H. BOUWMEESTER ET AL.

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Variation in the essential oil composition ofArtemisia annua L. of different origin cultivated in Finland

et al. 1997

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Seven batches of seeds of Artemisia annua L. (Asteraceae) of dierent origin were grown in Finland. The leaf essential oils were obtained by hydrodistillation in yields of 0.4±0.9% (v/w). About 30 compounds were identi®ed and 19 key compounds, representing 87±96% of the total oil, are listed. There was a large variability in the essential oil composition in plants of dierent seed origin. Camphor, artemisia ketone, germacrene-D and b-caryophyllene were detected as the major compounds. One oil had an exceptionally high content of -a-pinene. Cluster analysis grouped the oils according to their origin, which shows that the essential oil composition is under strict genetic control. During the growing period the essential oil content and the amounts of artemisia ketone and 1,8-cineole reached a maximum about 2 weeks before budding. Camphor reached its maximum 2±3 weeks earlier. The enantiomeric ratios of À-camphene/-camphene and À-a-pinene/-a-pinene were determined for the ®rst time in an A. annua oil and studied during a growing period.

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Volatile constituents of Artemisia annua L. (Asteraceae)

Cited by 69 publications

References 15 publications

GC/MS Analysis and Potential Cytotoxic Activity of Haplophyllum tuberculatum Essential Oils Against Lung and Liver Cancer Cells

GC/MS Analysis and Potential Cytotoxic Activity of Haplophyllum tuberculatum Essential Oils Against Lung and Liver Cancer Cells

Research to Improve Artemisinin Production for use in the Preparation of Anti-Malarial Drugs

Variation in the essential oil composition ofArtemisia annua L. of different origin cultivated in Finland

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