Literature DB >> 9614092

Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase.

M L Wise1, T J Savage, E Katahira, R Croteau.   

Abstract

Common sage (Salvia officinalis) produces an extremely broad range of cyclic monoterpenes bearing diverse carbon skeletons, including members of the p-menthane (1,8-cineole), pinane (alpha- and beta-pinene), thujane (isothujone), camphane (camphene), and bornane (camphor) families. An homology-based polymerase chain reaction cloning strategy was developed and used to isolate the cDNAs encoding three multiproduct monoterpene synthases from this species that were functionally expressed in Escherichia coli. The heterologously expressed synthases produce (+)-bornyl diphosphate, 1, 8-cineole, and (+)-sabinene, respectively, as their major products from geranyl diphosphate. The bornyl diphosphate synthase also produces significant amounts of (+)-alpha-pinene, (+)-camphene, and (+/-)-limonene. The 1,8-cineole synthase produces significant amounts of (+)- and (-)-alpha-pinene, (+)- and (-)-beta-pinene, myrcene and (+)-sabinene, and the (+)-sabinene synthase produces significant quantities of gamma-terpinene and terpinolene. All three enzymes appear to be translated as preproteins bearing an amino-terminal plastid targeting sequence, consistent with the plastidial origin of monoterpenes in plants. Deduced sequence analysis and size exclusion chromatography indicate that the recombinant bornyl diphosphate synthase is a homodimer, whereas the other two recombinant enzymes are monomeric, consistent with the size and subunit architecture of their native enzyme counterparts. The distribution and stereochemistry of the products generated by the recombinant (+)-bornyl diphosphate synthase suggest that this enzyme might represent both (+)-bornyl diphosphate synthase and (+)-pinene synthase which were previously assumed to be distinct enzymes.

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Year:  1998        PMID: 9614092     DOI: 10.1074/jbc.273.24.14891

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  64 in total

1.  Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase.

Authors:  Douglas A Whittington; Mitchell L Wise; Marek Urbansky; Robert M Coates; Rodney B Croteau; David W Christianson
Journal:  Proc Natl Acad Sci U S A       Date:  2002-11-13       Impact factor: 11.205

2.  A biochemical interpretation of terpene chemotypes in Melaleuca alternifolia.

Authors:  Andras Keszei; Yasmin Hassan; William J Foley
Journal:  J Chem Ecol       Date:  2010-05-29       Impact factor: 2.626

3.  The effects of water deficit on the expression of monoterpene synthases and essential oils composition in Salvia ecotypes.

Authors:  Sadrollah Ramezani; Alireza Abbasi; Sajjad Sobhanverdi; Abdolali Shojaeiyan; Nima Ahmadi
Journal:  Physiol Mol Biol Plants       Date:  2020-11-12

Review 4.  Two rings in them all: the labdane-related diterpenoids.

Authors:  Reuben J Peters
Journal:  Nat Prod Rep       Date:  2010-10-01       Impact factor: 13.423

5.  Cloning, functional characterization and genomic organization of 1,8-cineole synthases from Lavandula.

Authors:  Zerihun A Demissie; Monica A Cella; Lukman S Sarker; Travis J Thompson; Mark R Rheault; Soheil S Mahmoud
Journal:  Plant Mol Biol       Date:  2012-05-17       Impact factor: 4.076

6.  EST analysis and annotation of transcripts derived from a trichome-specific cDNA library from Salvia fruticosa.

Authors:  Fani M Chatzopoulou; Antonios M Makris; Anagnostis Argiriou; Jörg Degenhardt; Angelos K Kanellis
Journal:  Plant Cell Rep       Date:  2010-03-24       Impact factor: 4.570

7.  Predicting Productive Binding Modes for Substrates and Carbocation Intermediates in Terpene Synthases-Bornyl Diphosphate Synthase as a Representative Case.

Authors:  Terrence E O'Brien; Steven J Bertolani; Yue Zhang; Justin B Siegel; Dean J Tantillo
Journal:  ACS Catal       Date:  2018-03-08       Impact factor: 13.084

Review 8.  Diversifying carotenoid biosynthetic pathways by directed evolution.

Authors:  Daisuke Umeno; Alexander V Tobias; Frances H Arnold
Journal:  Microbiol Mol Biol Rev       Date:  2005-03       Impact factor: 11.056

9.  Biochemistry and molecular genetics of the biosynthesis of the earthy odorant methylisoborneol in Streptomyces coelicolor.

Authors:  Chieh-Mei Wang; David E Cane
Journal:  J Am Chem Soc       Date:  2008-06-19       Impact factor: 15.419

10.  The variability of sesquiterpenes emitted from two Zea mays cultivars is controlled by allelic variation of two terpene synthase genes encoding stereoselective multiple product enzymes.

Authors:  Tobias G Köllner; Christiane Schnee; Jonathan Gershenzon; Jörg Degenhardt
Journal:  Plant Cell       Date:  2004-04-09       Impact factor: 11.277

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