Biosynthesis of the isoprene units of chamomile sesquiterpenes

Adam, Klaus-Peter; Zapp, Josef

doi:10.1016/s0031-9422(97)00992-8

Cited by 126 publications

(69 citation statements)

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“…5,12,[16][17][18][19][20][21][22][23] The prenylation of the phydroxybenzoic acid involved in the formation of the chromenes 1 and 2 occurred via MEP pathway, suggesting that it is compartmentalized in the plastid. On the other hand, the second prenylation step would be occurred in the cytosol by MVA pathway.…”

Section: Resultsmentioning

confidence: 99%

Biosynthetic origin of the isoprene units in chromenes of Piper aduncum (Piperaceae)

Leite¹,

Lopes²,

Kato

et al. 2007

J. Braz. Chem. Soc.

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Estudos metabólicos envolvendo a incorporação de D-glicose-[1-13 C] em folhas dePiper aduncum (Piperaceae) mostraram que as vias do mevalonato (MVA) e da triose-piruvato (MEP) estão envolvidas na biossíntese da unidade isoprênica presente no 2,2-dimetil-2H-1-cromeno-6-carboxilato de metila (1) e no 2,2-dimetil-8-(3'-metil-2'-butenil)-2H-1-cromeno-6-carboxilato de metila (2). O padrão de incorporação dos carbonos marcados com D-glicose-[1-13 C] destes cromenos foram determinados através de espectroscopia de RMN de 13 C quantitativo. Os resultados confirmaram que o compartimento biossintético de 1 e 2 pode ser o plastídio e/ou citosol, ou possivelmente um compartimento adicional, como o espaço entre a membrana e o plastídio.Metabolic studies involving the incorporation of [1-13 C]-D-glucose into intact leaves of Piper aduncum (Piperaceae) have indicated that both the mevalonate (MVA) and the pyruvate-triose (MEP) non-mevalonate pathways are implicated in the biosynthesis of isoprene moieties present in methyl 2,2-dimethyl-2H-1-chromene-6-carboxylate (1) and methyl 2,2-dimethyl-8-(3'-methyl-2'-butenyl)-2H-1-chromene-6-carboxylate (2). The pattern of incorporation of label from [1- 13C]-D-glucose into these chromenes was determined by quantitative 13 C NMR spectroscopy. The results confirmed that biosynthetic compartment of 1 and 2 could either be the plastid and/ or the cytosol or, possibly, an additional compartment such as the plastid inter-membrane space. Keywords:Piper aduncum, chromenes, [1-13 C]-D-glucose, mevalonate pathway, 2-C-methyl-D-erythritol-4-phosphate pathway IntroductionThe isoprenoids constitute a large class of natural products comprising more than 29,000 compounds. 1 In higher plants, isoprenoids play essential roles in membrane structure (sterols), redox chemistry (plastoquinones, ubiquinones), growth regulation (gibberellins, cytokinins, brassinosteroids and abscisic acid), defence mechanisms (phytoalexins) and free radical scavenging (carotenoids and tocopherols). 2 The common building blocks of all isoprenoids, the so-called 'isoprene units', is derived from isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). The biosynthesis of IPP can proceed via two different pathways, namely the longestablished mevalonic acid (MVA) and the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathways, the reaction sequence of which has been characterized. 3 In plants, the MEP pathway appears generally operative for formation of monoterpenoids, diterpenoids, phytols and carotenoids. [4][5][6] The key regulatory step of the MVA pathway involves reduction of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) to mevalonate, with this being catalysed by the cytosolic enzyme HMG-CoA reductase (HMGR). Plastidic IPP is derived, however, from MEP formed via the condensation of pyruvate and glyceraldehyde-3-phosphate (G3P) catalysed by 1-deoxy-D-xylulose-5-phosphate synthase (DXS). 2,6 The two pathways to IPP are thus compartmentalized in the cytosol and the plastid, respectively. However, they may function in the for...

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Section: Resultsmentioning

confidence: 99%

Biosynthetic origin of the isoprene units in chromenes of Piper aduncum (Piperaceae)

Leite¹,

Lopes²,

Kato

et al. 2007

J. Braz. Chem. Soc.

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“…Then DOXP can form IPP through a series of reactions (Adam and Zapp, 1998). IPP is isomerized to the other isoprene unit, DMAPP, by isopentenyldiphosphate-D-isomerase (EC 5.3.3.2).…”

Section: Terpenoid Biosynthesismentioning

confidence: 99%

Medicinal chemistry and pharmacology of genus Tripterygium (Celastraceae)

et al. 2007

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Plants in the genus Tripterygium, such as Tripterygium wilfordii Hook. f., have a long history of use in traditional Chinese medicine. In recent years there has been considerable interest in the use of Tripterygium extracts and of the main bioactive constituent, the diterpene triepoxide triptolide (1), to treat a variety of autoimmune and inflammation-related conditions. The main mode of action of the Tripterygium extracts and triptolide (1) is the inhibition of expression of proinflammatory genes such as those for interleukin-2 (IL-2), inducible nitric oxide synthase (iNOS), tumor necrosis factor-α (TNF-α), cyclooxygenase-2 (COX-2) and interferon-gamma (IFN-γ). The efficacy and safety of certain types of Tripterygium extracts were confirmed in human clinical trials in the US and abroad. Over 300 compounds have been identified in the genus Tripterygium, and many of these have been evaluated for biological activity. The overall activity of the extract is based on the interaction between its components. Therefore, the safety and efficacy of the extract cannot be fully mimicked by any individual constituent. This review discusses the biochemical composition and biological and pharmacological activities of Tripterygium extracts, and their main bioactive components.

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“…Furthermore, in snapdragon, IPP precursors destined for both mono-and sesquiterpene assembly were derived from the MEP pathway [66]. The two biosynthetic pathways can operate in concert, as studies of sesquiterpene production in chamomile, for example, have shown that isoprenoid precursors were derived from both the plastidial and cytosolic terpenoid biosynthetic pathways [67]. In a series of elegant experiments using tobacco cell cultures, radiolabeled precursor metabolites, and protein biochemistry techniques, Hemmerlin et al [68] described the considerable cross-talk between the MVA and MEP metabolic pathways in vivo.…”

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confidence: 99%