CAF-603: A New Antifungal Carotane Sesquiterpene. Isolation and Structure Elucidation

Watanabe, Naoharu; Yamagishi, Masaaki; Mizutani, Taku; Kondoh, Hideaki; Omura, Sadafumi; Hanada, Kazunori; Kushida, Katsuhiko

doi:10.1021/np50071a006

Cited by 36 publications

(17 citation statements)

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“…On the other hand, clear NOE effects between signals of the isopropyl group and H-3R and H-5R and between H-3R and H-2R were observed. The relative stereochemistry was in agreement with the previously isolated fungal carotanes, 19 and the structure of trichocarane A (1) was assigned as 8R,9R-epoxy-3 ,4 -dihydroxycarotane.…”

Section: Resultssupporting

confidence: 85%

Bioactive Carotanes from Trichoderma virens

et al. 2000

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Section: Resultssupporting

confidence: 85%

Bioactive Carotanes from Trichoderma virens

et al. 2000

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“…1S,7R,9R,10S)-carot-4-en-9,10-diol (see Table S1 and Fig. S2 to S4 in the supplemental material), which is identical to those of a carotane-type sesquiterpene, CAF-603, isolated from another strain of Trichoderma virens (24).…”

Section: Resultsmentioning

confidence: 67%

Carot-4-en-9,10-Diol, a Conidiation-Inducing Sesquiterpene Diol Produced by Trichoderma virens PS1-7 upon Exposure to Chemical Stress from Highly Active Iron Chelators

Wang

Hashimoto

Hashidoko

2013

Appl Environ Microbiol

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To screen biocontrol agents against Burkholderia plantarii, the causative agent of rice seedling blight, we employed catechol, an analog of the virulence factor tropolone, to obtain chemical stress-resistant microorganisms. The fungal isolate PS1-7, identified as a strain of Trichoderma virens, showed the highest resistance to catechol (20 mM) and exhibited efficacy as a biocontrol agent for rice seedling blight. During investigation of metabolic traits of T. virens PS1-7 exposed to catechol, we found a secondary metabolite that was released extracellularly and uniquely accumulated in the culture. The compound induced by chemical stress due to catechol was subsequently isolated and identified as a sesquiterpene diol, carot-4-en-9,10-diol, based on spectroscopic analyses. T. virens PS1-7 produced carot-4-en-9,10-diol as a metabolic response to tropolone at concentrations from 0.05 to 0.2 mM, and the response was enhanced in a dose-dependent manner, similar to its response to catechol at concentrations from 0.1 to 1 mM. Some iron chelators, such as pyrogallol, gallic acid, salicylic acid, and citric acid, at 0.5 mM also showed activation of T. virens PS1-7 production of carot-4-en-9,10-diol. This sesquiterpene diol, formed in response to chemical stress, promoted conidiation of T. virens PS1-7, suggesting that it is involved in an autoregulatory signaling system. In a bioassay of the metabolic and morphological responses of T. virens PS1-7, conidiation in hyphae grown on potato dextrose agar (PDA) plates was either promoted or induced by carot-4-en-9,10-diol. Carot-4-en-9,10-diol can thus be regarded as an autoregulatory signal in T. virens, and our findings demonstrate that intrinsic intracellular signaling regulates conidiation of T. virens.

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“…During the course of a screening program for antifungal compounds, a strain of T. virens was found to produce a novel bioactive carotane-type metabolite (8) (Fig. 3) exhibiting antifungal activity against various yeast and dermatophytes and having a remarkable effect on Candida albicans (Watanabe et al 1990). Lee et al (1995a) isolated an oleic ester derivative of 8 named L-735,334 (9) (Fig.…”

Section: Daucanesmentioning

confidence: 99%

Secondary metabolites from species of the biocontrol agent Trichoderma

et al. 2007

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Trichoderma species are free-living fungi that are highly interactive in root, soil and foliar environments and have been used successfully in field trials to control many crop pathogens. Structural and biological studies of the metabolites isolated from Trichoderma species are reviewed. This review, encompassing all the literature in this field up to the present and in which 269 references are cited, also includes a detailed study of the biological activity of the metabolites, especially the role of these metabolites in biological control mechanisms. Some aspects of the biosynthesis of these metabolites and related compounds are likewise discussed.

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CAF-603: A New Antifungal Carotane Sesquiterpene. Isolation and Structure Elucidation

Cited by 36 publications

References 1 publication

Bioactive Carotanes from Trichoderma virens

Bioactive Carotanes from Trichoderma virens

Carot-4-en-9,10-Diol, a Conidiation-Inducing Sesquiterpene Diol Produced by Trichoderma virens PS1-7 upon Exposure to Chemical Stress from Highly Active Iron Chelators

Secondary metabolites from species of the biocontrol agent Trichoderma

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