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Topic

Diterpene

About: Diterpene is a(n) research topic. Over the lifetime, 2586 publication(s) have been published within this topic receiving 48162 citation(s). The topic is also known as: C20 isoprenoids & diterpenes.
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Journal ArticleDOI
S Trapp1, Rodney Croteau1Institutions (1)
01 Jun 2001-Genetics
TL;DR: A model presented for the evolutionary history of plant terpenoid synthases suggests that this superfamily of genes responsible for natural products biosynthesis derived from terpene synthase genes involved in primary metabolism by duplication and divergence in structural and functional specialization.
Abstract: Terpenoids are the largest, most diverse class of plant natural products and they play numerous functional roles in primary metabolism and in ecological interactions. The first committed step in the formation of the various terpenoid classes is the transformation of the prenyl diphosphate precursors, geranyl diphosphate, farnesyl diphosphate, and geranylgeranyl diphosphate, to the parent structures of each type catalyzed by the respective monoterpene (C(10)), sesquiterpene (C(15)), and diterpene synthases (C(20)). Over 30 cDNAs encoding plant terpenoid synthases involved in primary and secondary metabolism have been cloned and characterized. Here we describe the isolation and analysis of six genomic clones encoding terpene synthases of conifers, [(-)-pinene (C(10)), (-)-limonene (C(10)), (E)-alpha-bisabolene (C(15)), delta-selinene (C(15)), and abietadiene synthase (C(20)) from Abies grandis and taxadiene synthase (C(20)) from Taxus brevifolia], all of which are involved in natural products biosynthesis. Genome organization (intron number, size, placement and phase, and exon size) of these gymnosperm terpene synthases was compared to eight previously characterized angiosperm terpene synthase genes and to six putative terpene synthase genomic sequences from Arabidopsis thaliana. Three distinct classes of terpene synthase genes were discerned, from which assumed patterns of sequential intron loss and the loss of an unusual internal sequence element suggest that the ancestral terpenoid synthase gene resembled a contemporary conifer diterpene synthase gene in containing at least 12 introns and 13 exons of conserved size. A model presented for the evolutionary history of plant terpene synthases suggests that this superfamily of genes responsible for natural products biosynthesis derived from terpene synthase genes involved in primary metabolism by duplication and divergence in structural and functional specialization. This novel molecular evolutionary approach focused on genes of secondary metabolism may have broad implications for the origins of natural products and for plant phylogenetics in general.

432 citations


Book ChapterDOI
Edward M. Davis1, Rodney Croteau1Institutions (1)
10 Nov 2000
Abstract: Terpene synthases catalyze the first committed steps in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes. An overview is presented of the enzymology and mechanism of these terpene synthases, and their molecular cloning, expression, and sequence analysis. Detailed structural and functional evaluation of four representative monoterpene, sesquiterpene, and diterpene synthases is also presented.

421 citations


Journal ArticleDOI
Mark R. Wildung1, Rodney CroteauInstitutions (1)
TL;DR: Sequence comparisons with monoterpene, sesquiterpenes, and diterpene cyclases of plant origin indicate a significant degree of similarity between these enzymes; the taxadiene synthase most closely resembles (46% identity, 67% similarity) abietadienes synthase, a diterPene cyclase from grand fir.
Abstract: The committed step of taxol (paclitaxel) biosynthesis is catalyzed by taxa-4(5),11(12)-diene synthase, a diterpene cyclase responsible for transforming the ubiquitous isoprenoid intermediate geranylgeranyl diphosphate to the parent olefin with a taxane skeleton. To obtain the corresponding cDNA clone, a set of degenerate primers was constructed based on consensus sequences of related monoterpene, sesquiterpene, and diterpene cyclases. Two of these primers amplified a 83-base pair fragment that was cyclase-like in sequence and that was employed as a hybridization probe to screen a cDNA library constructed from poly(A) RNA extracted from Pacific yew (Taxus brevifolia) stems. Twelve independent clones with insert size in excess of 2 kilobase pairs were isolated and partially sequenced. One of these cDNA isolates was functionally expressed in Escherichia coli, yielding a protein that was catalytically active in converting geranylgeranyl diphosphate to a diterpene olefin that was confirmed to be taxa-4(5),11(12)-diene by combined capillary gas chromatography-mass spectrometry. The sequence specifies an open reading frame of 2586 nucleotides, and the complete deduced polypeptide, including a long presumptive plastidial targeting peptide, contains 862 amino acid residues and has a molecular weight of 98,303, compared with about 79,000 previously determined for the mature native enzyme. Sequence comparisons with monoterpene, sesquiterpene, and diterpene cyclases of plant origin indicate a significant degree of similarity between these enzymes; the taxadiene synthase most closely resembles (46% identity, 67% similarity) abietadiene synthase, a diterpene cyclase from grand fir.

276 citations


Journal ArticleDOI
TL;DR: The methanol extract of the aerial part of Andrographis paniculata Nees showed potent cell differentiation-inducing activity on mouse myeloid leukemia (M1) cells and four new diterpene dimers were isolated along with six known compounds.
Abstract: The methanol extract of the aerial part of Andrographis paniculata Nees showed potent cell differentiation-inducing activity on mouse myeloid leukemia (M1) cells. From the ethyl acetate-soluble fraction of the methanol extract, six new diterpenoids of ent-labdane type, 14-epi-andrographolide (3), isoandrographolide (4), 14-deoxy-12-methoxyandrographolide (7), 12-epi-14-deoxy-12-methoxyandrographolide (8), 14-deoxy-12-hydroxyandrographolide (9) and 14-deoxy-11-hydroxyandrographolide (10) as well as two new diterpene glucosides, 14-deoxy-11,12-didehydroandrographi-side (12) and 6'-acetylneoandrographolide (14), and four new diterpene dimers, bis-andrograpolides A (15), B (16), C (17) and D (18), were isolated along with six known compounds. The structures of the diterpenoids were determined by means of spectral methods. Some of these compounds showed potent cell differentiation-inducing activity towards M1 cells.

263 citations


Journal ArticleDOI
Abstract: A high-performance liquid chromatography method for analyzing the phenolic diterpenes present in rosemary (Rosmarinus officinalis L.) and commercial rosemary extracts is reported. Carnosic acid was the major phenolic diterpene present in rosemary leaves, with lesser amounts of 12-methoxycarnosic acid and carnosol. Several commercial rosemary extracts also were analyzed by this method, and in addition to these three compounds other phenolic diterpenes, such as 7-methoxyrosmanol, 7-methoxy-epirosmanol, and rosmanol, were found in some samples. These latter three compounds seem to be artifacts, produced from carnosic acid by oxidation and cyclization. The major phenolic diterpenes were isolated, and their relative antioxidatn activities in soybean oil were measured by the Rancimat. The potency of carnosic acid was more than twice that of any other compound. The antioxidant activity of pure carnosic acid was compared to butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), and tertiary butylhydroquinone (TBHQ) and was several times greater than BHT and BHA but less than TBHQ. Nuclear magnetic resonance data for several of the compounds that were incompletely characterized in previous literature are reported.

224 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202146
202043
201959
201855
201772
201658