Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris

Suga, Takayuki; Ohta, Shigeru; Munesada, Kiyotaka; Ide, Nagatoshi; Kurokawa, Masako; Shimizu, Masahiro; Ohta, Emi

doi:10.1016/0031-9422(93)85098-c

Cited by 97 publications

(69 citation statements)

References 19 publications

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“…In addition to chemopreventive activity, methylated resveratrols, such as desoxyrhapontigenin (4Ј-O-methylresveratrol) and pinostilbene (1k: 3-O-methyl-resveratrol), exhibit higher CYP1A1 inhibitory activity than resveratrol (2f) [52]. Furthermore, a pinosylvin monomethyl ether (1k) as a nematicidal agent from Pinus massoniana shows a tentimes smaller LC 50 value than pinosylvin (1f) [53]. These observations show usefulness of methylated stilbenes as bioactive substances.…”

Section: -2 Production Of Stilbene Methyl Ethersmentioning

confidence: 85%

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

Horinouchi

2008

J Antibiot

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One of the approaches of combinatorial biosynthesis is combining genes from different organisms and designing a new set of gene clusters to produce bioactive compounds, leading to diversification of both chemical and natural product libraries. This makes efficient use of the potential of the host organisms, especially when microorganisms are used. An Escherichia coli system, in which artificial biosynthetic pathways for production of plant-specific medicinal polyketides, such as flavonoids, stilbenoids, isoflavonoids, and curcuminoids, are assembled, has been designed and expressed. Starting with amino acids tyrosine and phenylalanine as substrates, this system yields naringenin, resveratrol, genistein, and curcumin, for example, all of which are beneficial to human health because of their wide variety of biological activities. Supplementation of unnatural carboxylic acids to the recombinant E. coli cells carrying the artificial pathways by precursor-directed biosynthesis results in production of unnatural compounds. Addition of decorating or modification enzymes to the artificial pathway leads to production of natural and unnatural flavonols, flavones, and methylated resveratrols. This microbial system is promising for construction of larger libraries by employing other polyketide synthases and decorating enzymes of various origins. In addition, the concept of building and expressing artificial biosynthetic pathways for production of non-bacterial and unnatural compounds in microorganisms should be successfully applied to production of not only plant-specific polyketides but also many other useful compound classes.

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Section: -2 Production Of Stilbene Methyl Ethersmentioning

confidence: 85%

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

Horinouchi

2008

J Antibiot

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“…[2][3][4][5][6][7][8][9][10][11][12][13][14] C]Malonyl-CoA (2.04 GBq͞mmol) was purchased from Amersham Pharmacia. Cinnamoyl-CoA and pAbbreviations: STS, stilbene synthase; CHS, chalcone synthase; PDSTS1, STS1 from P. densiflora; PDSTS2, STS2 from P. densiflora; PDSTS3, STS3 from P. densiflora; PDCHSX, CHSX from P. densiflora; PSSTS2, STS2 from P. strobus.…”

Section: Methodsmentioning

confidence: 99%

“…Japanese pines (Pinus densiflora and Pinus thunbergii) have been under severe biotic stress over the past 10 decades from pine-wilt diseases, mainly caused by exotic pinewood nematodes (2). In the genus Pinus, the stilbenoids, pinosylvin and its monomethyl ether, are key metabolites that can kill nematodes (3). Stilbenoid phytoalexin formation is controlled by stilbene synthase (STS), which comprises a small gene family in most species examined.…”

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confidence: 99%

A stilbene synthase from Japanese red pine ( Pinus densiflora ): Implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis

Kodan

Kuroda²,

Sakai³

2002

Proc. Natl. Acad. Sci. U.S.A.

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Stilbene synthase (STS) and chalcone synthase (CHS) are plantspecific polyketide synthases that play key roles in the stilbenoid and flavonoid biosyntheses, respectively. We have recently isolated from Pinus densiflora three STS cDNAs (PDSTS1, PDSTS2, and PDSTS3) and one CHS cDNA (PDCHSX). We then heterologously expressed these cDNAs in Escherichia coli and characterized their properties. An unusual STS isozyme, PDSTS3, lacks the common C-terminal extension of STS because of a frame-shift mutation and shows the highest pinosylvin-forming activity among the STSs tested. Pinosylvin was shown to be a potent inhibitor of PDCHSX (K i ‫؍‬ 6 M) as well as PDSTS2 (Ki ‫؍‬ 13 M), which presumably maintains the balance between the stilbenoid and flavonoid biosyntheses. PDSTS3 was insensitive to product inhibition. We identified PDSTS3 in the pine seedlings as well as full-length STS. The data provide evidence that PDSTS3 is involved in the potential regulation of the stilbenoid and flavonoid biosynthetic pathways in pine trees.

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“…Stilbenoids (e.g., pinosylvin monomethyl ether and 3-O-methyldihydropinosylvin) were specifically detected in resistant pine species (e.g., P. massoniana, P. strobus, and P. palustris) in previous studies [23,24]. These compounds showed acute nematicidal activity against PWN.…”

Section: Introductionmentioning

confidence: 77%

Metabolites from Resistant and Susceptible <i>Pinus thunbergii</i> after Inoculation with Pine Wood Nematode

Fujia¹,

Kajiwara²,

Mori³

et al. 2013

AJPS

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Pine wilt disease (PWD), which is caused by pine wood nematodes (PWN), is one of the most serious forest diseases worldwide. To clarify the mechanism of resistance to PWD, we compared metabolites from resistant and susceptible Japanese black pine (Pinus thunbergii) families after inoculation with PWN. After 2 weeks to 1 month post inoculation, the number of PWN dramatically increased in susceptible plants, but not in resistant plants. At this PWN-proliferation phase, ethyl acetate soluble fractions extracted from PWN-inoculated plants were analyzed by gas chromatogramphymass spectrometry (GC-MS). Although most compounds were qualitatively and quantitatively similar between resistant and susceptible plants, resistant plants accumulated 2.0-fold more linoleic acid (LA) than susceptible plants. On the other hand, benzoic acid (BA) was barely detected in resistant plants, but it accumulated in susceptible plants as the number of PWN increased. Susceptible plants contained greater levels of the nematicidal compounds pinosylvin and pinosylvin monomethyl ether, compared with resistant plants. These results suggested that LA is involved in the resistance reaction against PWN-proliferation, and that BA could be a good biomarker for PWD.

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Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris

Cited by 97 publications

References 19 publications

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

A stilbene synthase from Japanese red pine ( Pinus densiflora ): Implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis

Metabolites from Resistant and Susceptible <i>Pinus thunbergii</i> after Inoculation with Pine Wood Nematode

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Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris

Cited by 97 publications

References 19 publications

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

A stilbene synthase from Japanese red pine ( Pinus densiflora ): Implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis

Metabolites from Resistant and Susceptible &lt;i&gt;Pinus thunbergii&lt;/i&gt; after Inoculation with Pine Wood Nematode

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Metabolites from Resistant and Susceptible <i>Pinus thunbergii</i> after Inoculation with Pine Wood Nematode