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Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae).
Phytochemistry. 2007 Aug; 68(15):2053-8.P

Abstract

The biosynthesis of (2S)-2-methyl-2-(4'-methyl-3'-pentenyl)-8-(3''-methyl-2-butenyl)-2H-1-benzopyran-6-carboxylic acid (gaudichaudianic acid), the major metabolite in leaves and roots of Piper gaudichaudianum Kunth (Piperaceae), has been investigated employing [1-(13)C]-D-glucose as precursor. The labelling pattern in the isolated gaudichaudianic acid was determined by quantitative (13)C NMR spectroscopy analysis and was consistent with involvement of both mevalonic acid and 2-C-methyl-D-erythritol-4-phosphate pathways in the formation of the dimethylallyl- and geranyl-derived moieties. The results confirmed that both plastidic and cytoplasmic pathways are able to provide isopentenyl diphosphate units for prenylation of p-hydroxybenzoic acid.

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Authors+Show Affiliations

Lopes AA
Instituto de Química, Universidade Estadual Paulista, C.P. 355, CEP 14801-970 Araraquara, SP, Brazil.
Baldoqui DC
No affiliation info available
López SN
No affiliation info available
Kato MJ
No affiliation info available
Bolzani Vda S
No affiliation info available
Furlan M
No affiliation info available

MeSH

BenzoatesErythritolGlucoseHemiterpenesMevalonic AcidMolecular StructureNuclear Magnetic Resonance, BiomolecularOrganophosphorus CompoundsPiperPlant LeavesPlant RootsSugar PhosphatesTerpenes

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17574633

Citation

Lopes, Adriana A., et al. "Biosynthetic Origins of the Isoprene Units of Gaudichaudianic Acid in Piper Gaudichaudianum (Piperaceae)." Phytochemistry, vol. 68, no. 15, 2007, pp. 2053-8.
Lopes AA, Baldoqui DC, López SN, et al. Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae). Phytochemistry. 2007;68(15):2053-8.
Lopes, A. A., Baldoqui, D. C., López, S. N., Kato, M. J., Bolzani, V. d. a. . S., & Furlan, M. (2007). Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae). Phytochemistry, 68(15), 2053-8.
Lopes AA, et al. Biosynthetic Origins of the Isoprene Units of Gaudichaudianic Acid in Piper Gaudichaudianum (Piperaceae). Phytochemistry. 2007;68(15):2053-8. PubMed PMID: 17574633.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae). AU - Lopes,Adriana A, AU - Baldoqui,Debora C, AU - López,Silvia N, AU - Kato,Massuo J, AU - Bolzani,Vanderlan da S, AU - Furlan,Maysa, Y1 - 2007/06/14/ PY - 2006/10/19/received PY - 2007/04/13/revised PY - 2007/04/23/accepted PY - 2007/6/19/pubmed PY - 2007/10/5/medline PY - 2007/6/19/entrez SP - 2053 EP - 8 JF - Phytochemistry JO - Phytochemistry VL - 68 IS - 15 N2 - The biosynthesis of (2S)-2-methyl-2-(4'-methyl-3'-pentenyl)-8-(3''-methyl-2-butenyl)-2H-1-benzopyran-6-carboxylic acid (gaudichaudianic acid), the major metabolite in leaves and roots of Piper gaudichaudianum Kunth (Piperaceae), has been investigated employing [1-(13)C]-D-glucose as precursor. The labelling pattern in the isolated gaudichaudianic acid was determined by quantitative (13)C NMR spectroscopy analysis and was consistent with involvement of both mevalonic acid and 2-C-methyl-D-erythritol-4-phosphate pathways in the formation of the dimethylallyl- and geranyl-derived moieties. The results confirmed that both plastidic and cytoplasmic pathways are able to provide isopentenyl diphosphate units for prenylation of p-hydroxybenzoic acid. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/17574633/Biosynthetic_origins_of_the_isoprene_units_of_gaudichaudianic_acid_in_Piper_gaudichaudianum__Piperaceae__ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(07)00283-X DB - PRIME DP - Unbound Medicine ER -