Conversion of [19-2H2]fusicocca-2,10(14)-diene into its 8β-ol and fusicoccins by Phomopsis (Fusicoccum) amygdali

Sassa, Takeshi; Zhang, Chang-Shan; Sato, Mitsuyoshi; Tajima, Naoto; Kato, Nobuo; Mori, Akira

doi:10.1016/s0040-4039(00)00173-8

Cited by 15 publications

(14 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3) is a biosynthetic intermediate of fusicoccins. [41][42][43] We sought to isolate the gene encoding the diterpene cyclase responsible for fusicoccin biosynthesis. In fungi, the diterpene cyclase gene was first isolated from the new GA-producing fungus Phaeosphaeria sp.…”

Section: Labdane-related Diterpene Cyclase Gene Family In Ricementioning

confidence: 99%

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Toyomasu

2008

Bioscience, Biotechnology, and Biochemistry

100

View full text Add to dashboard Cite

Cyclic diterpenoids are commonly biosynthesized from geranylgeranyl diphosphate (GGDP) through the formation of carbon skeletons by specific cyclases and subsequent chemical modifications, such as oxidation, reduction, methylation, and glucosidation. A variety of diterpenoids are produced in higher plants and fungi. Rice produces four classes of diterpene phytoalexins, phytocassanes A to E, oryzalexins A to F, oryzalexin S, and momilactones A and B. The six diterpene cyclase genes involved in the biosynthesis of these phytoalexins were identified and characterized. Fusicoccin A was produced by the phytopathogenic Phomopsis amygdali and served as a plant H þ -ATPase activator. A PaFS, encoding a fungal diterpene synthase responsible for fusicoccin biosynthesis, was isolated. The PaFS is an unusual chimeric diterpene synthase that possesses not only terpene cyclase activity (the formation of fusicoccadiene, a biosynthetic precursor of fusicoccin A), but also prenyltransferase activity (the formation of GGDP). Thus, we identified a unique multifunctional diterpene synthase family in fungi.

show abstract

Section: Labdane-related Diterpene Cyclase Gene Family In Ricementioning

confidence: 99%

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Toyomasu

2008

Bioscience, Biotechnology, and Biochemistry

100

View full text Add to dashboard Cite

show abstract

“…An additional new shunt metabolic pathway generating 16-O-demethyl-3-epi-FC J from 3-epi-FC H is also suggested in this paper. On the other hand, the biosynthetic intermediates in the early stage of the FC-aglycon biosynthesis have been investigated in detail by us, and (+)-fusicocca-2,10(14)-diene 14) and its 8b-ol 15) (Fig. 3) were determined as common intermediates in the biosynthesis of FCs J and A.…”

Section: )mentioning

confidence: 99%

Fusicoccins P and Q, and 3-Epifusicoccins H and Q, New Polar Fusicoccins from Isolate Niigata 2-A of a Peach Fusicoccum Canker Fungus

Sassa

Tajima

Sato

et al. 2002

Bioscience, Biotechnology, and Biochemistry

Self Cite

View full text Add to dashboard Cite

“…The isolation of phomopsiol, one of the fusicoccin aglycons, from the culture filtrate of this fungus was done for the first time, although related metabolites of (þ)-fusicocca-2,10(14)-diene and its 8 -ol have been isolated as biosynthetic intermediates of FC A from its mycelial extract. 4) The germination-stimulating activity of the newly isolated fusicoccins toward lettuce seeds in the presence of (AE)-abscisic acid (10 g/ml) was examined ( Table 2). FC R and 3 -hydroxy-FC J, these being 16-O-methylated fusicoccins, respectively induced the germination at low concentrations of 1 and 3 g/ml, 3 -Hydroxy-FC J had high activity similar to that of FC J.…”

Section: Methodsmentioning

confidence: 99%

“…3). Figure 3 illustrates two biosynthetic routes from (þ)-fusicocca-2,10(14)-dien-8 -ol 4) to FC S as 3 -hydroxy fusicoccin and FC R as 3 -hydroxyfusicoccin; the 3 -and 3 -hydroxyfusicoccins seem to be formed from the corresponding 3,16-epoxides derived from a fusicoccatriene of the common intermediate. …”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Novel Fusicoccins R and S, and the Fusicoccin S Aglycon (Phomopsiol) fromPhomopsis amygdaliNiigata 2-A, and Their Seed Germination-stimulating Activity in the Presence of Abscisic Acid

Tajima

Nukina

Kato

et al. 2004

Bioscience, Biotechnology, and Biochemistry

Self Cite

View full text Add to dashboard Cite

Our search for new 3-hydroxyfusicoccins structurally related to cotylenin A from a culture of Phomopsis amygdali Niigata 2-A resulted in the isolation of novel 3-hydroxy fusicoccins, called fusicoccins R and S, and the fusicoccin S aglycon, called phomopsiol, together with known 3 -hydroxyfusicoccin J. The structure of phomopsiol was identified as that of O-demethyl-3-epicotylenol based on spectroscopic evidence. The structures of fusicoccins R and S were also determined to be those of 3 0 -deacetyl-3 -hydroxyfusicoccin A and 3 -hydroxy-3-epifusicoccin H. The lettuce seed germination-stimulating activity of fusicoccins R and S, phomopsiol and 3 -hydroxyfusicoccin J was examined in the presence of ABA; fusicoccin R and 3 -hydroxyfusicoccin J were highly active, while fusicoccin S and phomopsiol were inactive. The possible biosynthetic relationships among these novel fusicoccins having a 3 -or 3 -hydroxy group in their diterpene moiety are briefly discussed.

show abstract

Conversion of [19-2H2]fusicocca-2,10(14)-diene into its 8β-ol and fusicoccins by Phomopsis (Fusicoccum) amygdali

Cited by 15 publications

References 16 publications

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Fusicoccins P and Q, and 3-Epifusicoccins H and Q, New Polar Fusicoccins from Isolate Niigata 2-A of a Peach Fusicoccum Canker Fungus

Novel Fusicoccins R and S, and the Fusicoccin S Aglycon (Phomopsiol) fromPhomopsis amygdaliNiigata 2-A, and Their Seed Germination-stimulating Activity in the Presence of Abscisic Acid

Contact Info

Product

Resources

About