Cyclopentane fatty acids from Gibberella fujikuroi

Miersch, Otto; Brückner, B.; Schmidt, Jürgen; Sembdner, G.

doi:10.1016/s0031-9422(00)97537-x

Cited by 44 publications

(22 citation statements)

References 15 publications

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“…javtrs responses to Me JA, and their pleiotropic nature, suggests that MeJA may act as a growth regulator in this fungus. At least two species of fungi, both plant pathogens, produce jasmonates (Aldridge et a/., 1971 ;Miersch et a/., 1992), and many others produce the fatty acid precursor alinolenate (Staswick, 1992 (Fernando & Bean, 1986 Inhibition of fungal spore germination by jasmonates has been previously reported for two other fungi, both plant pathogens (Neto et al, 1991;Cohen e t al., 1993). In addition, growth of other structures of plant symbiotic or pathogenic fungi is inhibited (Gogala, 1991 ;Net0 et al, 1991 ;Schweizer et al, 1993) or stimulated (Cohen e t al., 1993) by jasmonates.…”

Section: Jasmonate Production By Fungimentioning

confidence: 91%

The plant growth regulator methyl jasmonate inhibits aflatoxin production by Aspergillus flavus

1995

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Aflatoxins are highly toxic and carcinogenic compounds produced by certain Aspergillus species on agricultural commodities. The presence of fatty acid hydroperoxides, which can form in plant material either preharvest under stress or postharvest under improper storage conditions, correlates with high levels of aflatoxin production. Effects on fungal growth and aflatoxin production are known for only a few of the numerous plant metabolites of fatty acid hydroperoxides. Jasmonic acid (JA), a plant growth regulator, is a metabolite of 13-hydroperoxylinolenic acid, derived from a-linolenic acid. The volatile methyl ester of JA, methyl jasmonate (MeJA), is also a plant growth regulator. In this study we report the effect of MeJA on aflatoxin production and growth of Aspergillus flaws. MeJA a t concentrations of 10-3-10-8 M in the growth medium inhibited aflatoxin production, by as much as 96%. Exposure of cultures to MeJA vapour similarly inhibited af latoxin production. The amount of aflatoxin produced depended on the timing of the exposure. MeJA treatment also delayed spore germination and inhibited the production of a mycelial pigment. These fungal responses resemble plant jasmonate responses.

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Section: Jasmonate Production By Fungimentioning

confidence: 91%

The plant growth regulator methyl jasmonate inhibits aflatoxin production by Aspergillus flavus

1995

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“…The isoleucine derivative of (-)-jasmonic acid was also reported in pollen of Pinus mugo [8]. In addition, conjugates of JA and 9,10-dihydro-JA with amino acids could be isolated from Gibberella fujikuroi demonstrating that fungi are able to synthesize this type of conjugates too [9,10].…”

Section: Introductionmentioning

confidence: 71%

Partial purification and characterization of a jasmonic acid conjugate cleaving amidohydrolase from the fungus Botryodiplodia theobromae

et al. 1997

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A protein preparation from the mycelium of the tropical pathogenic fungus Botryodiplodia theobromae revealed a novel peptidase activity. This enzyme was capable of cleaving conjugates of jasmonic acid with a-amino acids. The protein was enriched 108-fold by gel filtration, ion exchange and hydrophobic interaction chromatography. The enzyme was found to be a glycoprotein with a molecular mass of about 107 kDa. The amidohydrolase seems to be very specific with regard to (-)-jasmonic acid and a-amino acids with (5)-configuration.

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“…The fungus shows the presence of enzymes involved in the biosynthetic pathway of such type of diterpenoids which might be responsible for the chemical modification of the gibberellin structure (Tudzynski et al 2003;Malonek et al 2004;Tudzynski, 2005). Also described has been the ability of this fungus for producing the plant hormone jasmonic acid in small amounts and mainly being detected in the supernatant of the mediaculture (Miersch et al 1992). This suggests the occurrence of enzymatic activities allowing JA production and a potential machinery able for transforming the chemical structure of this molecule.…”

Section: Biotransformation Experiments and Chemical Analysismentioning

confidence: 99%

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

Carvajal¹,

Espinoza²,

Caggia³

et al. 2011

Electro Journal of Biotech

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Background: Several studies have shown that (-)-Jasmonic acid, (+)-7-iso-Jasmonic acid and its methyl ester, methyl jasmonate, have anti-cancer activity in vitro and in vivo, exhibiting selective cytotoxicity towards cancer cells. The degree of activity of these molecules is strongly related to their stereochemistry. The biotransformation of known compounds, natural or synthesized, related to interesting biological activities, generates new molecules displaying new improved properties compared with the original ones, increasing its value and providing new more effective products. Therefore, based on the above rationales and observations, in this work a biotransformation protocol to modify the chemical structure of the plant hormone jasmonic acid by using the fungus Gibberella fujikuroi was established. Results: The three jasmonic acid derivatives obtained, 3(S)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (1), 3(R)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (2), 3-Hydroxy-2(S)-(2Z-pentenyl)-cyclopentane-1(S)-acetic acid (3), were tested for cell-growth inhibition activity towards the human cancer epithelial cell line, the oral squamous carcinoma cells (KB). The results obtained show that jasmonic acid derivatives (1-3) are active on human cancer cells examined in different concentration ranges, with IC50 value less than of 25 µM. The compound 3, with the same molecular structure of compounds 1 and 2, but with different stereochemistry, was more active confirming that the activity of jasmonate compounds is related to their stereochemistry and to substituents in the cyclopentane ring. In this study, we also tested the potential proapoptotic activity of compound 3, and our data suggest that it, as other jasmonate compounds, is able to trigger apoptotic death in cancer cells. This event may be correlated at an elevation of reactive oxygen species (ROS). Administration of N-acetylcysteine (NAC) prevented compound 3 cytotoxicity. Conclusions: This work shows for the by first time the production of hydroxylated derivatives of JA by biotransformation. The activity observed of these compounds in cancer cells is higher than the observed with JA and is strongly related to its stereochemistry.

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Cyclopentane fatty acids from Gibberella fujikuroi

Cited by 44 publications

References 15 publications

The plant growth regulator methyl jasmonate inhibits aflatoxin production by Aspergillus flavus

The plant growth regulator methyl jasmonate inhibits aflatoxin production by Aspergillus flavus

Partial purification and characterization of a jasmonic acid conjugate cleaving amidohydrolase from the fungus Botryodiplodia theobromae

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

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