Isolation of new acyclic C25-isoprenyl alcohol from potato leaves.

Toyoda, Masanobu; Asahina, Masako; Fukawa, Hideaki; Shimizu, Toru

doi:10.1016/s0040-4039(01)88836-5

Cited by 23 publications

(12 citation statements)

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“…Sesterterpenes have been identified in nature largely in marine sponges, where they have anti‐bacterial, anti‐mollusk and fish‐deterrent activities, and thus probably serve in defense against predators and pathogens (Ebada et al ., ). Their presence has also been shown in insects (Rios et al ., ; Veloz et al ., ; Kusumi et al ., ), fungi (Wang et al ., , ; Cueto et al ., ; Nihashi et al ., ; Chiba et al ., ), bacteria (Sato et al ., ; Shinozaki et al ., ) and plants of the Solanaceae (Toyoda et al ., ; McDowell et al ., ) and Lamiaceae (Dal Piaz et al ., ; Luo et al ., ), as well as in Gossypium hirsutum (Malvaceae; Stipanovic et al ., ), Croton hieronymi (Euphorbiaceae; Catalan et al ., ) and Aletris farinosa (Liliaceae; Challinor et al ., ). When the roles of these sesterterpenes were investigated, they were also shown to function in protection against predators and pathogens.…”

Section: Discussionmentioning

confidence: 98%

“…2002; Chiba et al, 2013), bacteria (Sato et al, 2013;Shinozaki et al, 2013) and plants of the Solanaceae (Toyoda et al, 1969;McDowell et al, 2011) and Lamiaceae (Dal Piaz et al, 2010;Luo et al, 2010), as well as in Gossypium hirsutum (Malvaceae; Stipanovic et al, 1977), Croton hieronymi (Euphorbiaceae; Catalan et al, 2003) and Aletris farinosa (Liliaceae; Challinor et al, 2013). When the roles of these sesterterpenes were investigated, they were also shown to function in protection against predators and pathogens.…”

Section: Gfdp Synthases Are Likely To Be Involved In Sesterterpene Fomentioning

confidence: 99%

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Arabidopsis thaliana isoprenyl diphosphate synthases produce the C₂₅ intermediate geranylfarnesyl diphosphate

et al. 2015

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Isoprenyl diphosphate synthases (IDSs) catalyze some of the most basic steps in terpene biosynthesis by producing the prenyl diphosphate precursors of each of the various terpenoid classes. Most plants investigated have distinct enzymes that produce the short-chain all-trans (E) prenyl diphosphates geranyl diphosphate (GDP, C10 ), farnesyl diphosphate (FDP, C15 ) or geranylgeranyl diphosphate (GGDP, C20 ). In the genome of Arabidopsis thaliana, 15 trans-product-forming IDSs are present. Ten of these have recently been shown to produce GGDP by genetic complementation of a carotenoid pathway engineered into Escherichia coli. When verifying the product pattern of IDSs producing GGDP by a new LC-MS/MS procedure, we found that five of these IDSs produce geranylfarnesyl diphosphate (GFDP, C25 ) instead of GGDP as their major product in enzyme assays performed in vitro. Over-expression of one of the GFDP synthases in A. thaliana confirmed the production of GFDP in vivo. Enzyme assays with A. thaliana protein extracts from roots but not other organs showed formation of GFDP. Furthermore, GFDP itself was detected in root extracts. Subcellular localization studies in leaves indicated that four of the GFDP synthases were targeted to the plastoglobules of the chloroplast and one was targeted to the mitochondria. Sequence comparison and mutational studies showed that the size of the R group of the 5th amino acid residue N-terminal to the first aspartate-rich motif is responsible for C25 versus C20 product formation, with smaller R groups (Ala and Ser) resulting in GGDP (C20 ) as a product and a larger R group (Met) resulting in GFDP (C25 ).

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Section: Discussionmentioning

confidence: 98%

Section: Gfdp Synthases Are Likely To Be Involved In Sesterterpene Fomentioning

confidence: 99%

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C₂₅ intermediate geranylfarnesyl diphosphate

et al. 2015

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“…Acyclic poly-cis prenol (C 25 ), with one cis-isoprene unit attached to phytyl group, was isolated from potato (Solanum tuberosum) leaves in 1969 [34]. Poly-cis prenol (glycinoprenol C 45 , C 50 , and C 55 ) from the leaves of soy bean (Glycine max Merill) possesses a phytyl residue, 4 to 6 internal cis-isoprene residues, and a cis α-terminal residue aligned in that order [35].…”

Section: Poly-cis Prenolmentioning

confidence: 99%

The history and recent advances in research of polyprenol and its derivatives

Sagami

Świeżewska

Shidoji

2018

Bioscience, Biotechnology, and Biochemistry

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The reduction pathway leading to the formation of dolichol was clarified in 2010 with the identification of SRD5A3, which is the polyprenol reductase. The finding inspired us to reanalyze the length of the major chain of polyprenol and dolichol from several plant leaves, including mangrove plants, as well as from animal and fish livers by 2D-TLC. Polyprenol- and dolichol-derived metabolites such as polyprenylacetone and epoxydolichol were found together with rubber-like prenol. This review focuses on analyses of polyprenol and its derivatives, including recently found epoxypolyprenol and polyprenylacetone. Attention has also been paid to the chromatographic behavior of rubber-like prenol on TLC.

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“…Even though sesterterpenoid structures occur mainly in marine organisms, they can also be found in the wax of insects (Rios and Colunga, 1965), higher plants (Toyoda et al, 1969) and terrestrial fungi (Lauer et al, 1989). Although they are by definition strictly C 25 compounds, there are a large number of nor-and alkylated derivatives.…”

Section: Marine Sesterterpenes [C 25 ]: Frequently Encountered Structmentioning

confidence: 99%

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

2006

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Marine organisms produce a wide array of fascinating terpenoid structures distinguished by characteristic structural features. Certain structural classes, e.g. cembrane, chamigrene, amphilectane skeletons, and unusual functional groups such as isonitrile, isothiocyanate, isocyanate, dichloroimine and halogenated functionalities occur predominantly in marine metabolites. Especially striking is the frequent occurrence of sesterterpenes in marine organisms, and sponges must be considered as one of the prime sources of these C 25 terpenoid compounds. In most cases however, these structural features are not strictly unique for marine natural products. The prominent biological activity of marine terpenes is evident in their ecological role in the marine environment, and makes them interesting as potential drugs. Several terpenoid compounds, e.g. eleutherobin, sarcodictyin, contignasterol derivatives, are in preclinical or clinical development. Despite the many structures known and their ecological and pharmacological importance, only a few biosynthetic studies on marine terpenoid compounds have been performed.

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Isolation of new acyclic C25-isoprenyl alcohol from potato leaves.

Cited by 23 publications

References 2 publications

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C₂₅ intermediate geranylfarnesyl diphosphate

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C₂₅ intermediate geranylfarnesyl diphosphate

The history and recent advances in research of polyprenol and its derivatives

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

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Isolation of new acyclic C25-isoprenyl alcohol from potato leaves.

Cited by 23 publications

References 2 publications

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C25 intermediate geranylfarnesyl diphosphate

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C25 intermediate geranylfarnesyl diphosphate

The history and recent advances in research of polyprenol and its derivatives

Terpenoids from Marine Organisms: Unique Structures and their Pharmacological Potential

Contact Info

Product

Resources

About

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C₂₅ intermediate geranylfarnesyl diphosphate

Arabidopsis thaliana isoprenyl diphosphate synthases produce the C₂₅ intermediate geranylfarnesyl diphosphate