Mycoepoxydiene represents a novel class of fungal metabolites

Cai, Ping; McPhail, Andrew T.; Krainer, Eduardo; Katz, Barry; Pearce, Cedric J.; Boros, Christie; Caceres, Bernardo; Smith, David F.; Houck, David R.

doi:10.1016/s0040-4039(98)02700-2

Cited by 38 publications

(35 citation statements)

References 4 publications

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“…With respect to solid supports, the fact that cellulose paper gave the best mycoepoxydiene production without fungal attachment indicated that adherence to a solid support was not essential for the mycoepoxydiene synthesis but that fungal growth near the liquid surface was more important. It is not known why surface cultivation could signiWcantly enhance mycoepoxydiene productivity in this fungus, since mycoepoxydiene represents a new class of fungal metabolites [2] and its biosynthetic pathway is presently totally uncharacterized. But if a hypothesis is to be made to explain this phenomenon, we would speculate that the process of mycoepoxydiene biosynthesis, particularly the step(s) involving the formation of the 'epoxy' moiety of the molecule, might require the presence of high oxygen concentration, the condition that exists at the liquid/ air interface zone.…”

Section: Evect Of Solid Supports On Mycoepoxydiene Productionmentioning

confidence: 99%

“…1) was Wrst isolated in 1999 from solid-state fermentation culture of a sterile dematiaceous fungus isolated from twig litter collected in a Brazilian forest and designated OS-F66617 [2]. Because the compound contained a rare oxygen-bridged cyclooctadiene and a functional -lactone, it was a novel fungal secondary metabolite, but there was no report of its biological activity at that time.…”

Section: Introductionmentioning

confidence: 99%

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Optimization of culture conditions for mycoepoxydiene production by Phomopsis sp. Hant25

Thammajaruk

Sriubolmas

Israngkul

et al. 2010

J Ind Microbiol Biotechnol

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Culture media and fermentation conditions for cultivation of an endophytic fungus Phomopsis sp. Hant25 were investigated in order to improve the yield of mycoepoxydiene, a novel fungal metabolite having potent cytotoxic activity against many cancer cell lines. Mycoepoxydiene accumulated in the culture broth during the stationary phase of fungal growth. Modified M1D medium was superior to malt Czapek, and Czapek yeast autolysate broths in supporting mycoepoxydiene production. Pellet growth was the morphological form that favored biosynthesis of mycoepoxydiene. This could be achieved by incubating the culture statically for 6 days before shaking at 120 rpm. Incorporation of a cellulose paper disc into the culture flask promoted fungal growth at the liquid surface, which accelerated mycoepoxydiene production and maximized the final yield to a level of 354 mg l⁻¹, though fungal attachment to the solid support was not required. Since the peak concentration of mycoepoxydiene in the culture broth was followed by a steeply declining phase, the harvest time had to be precisely determined for maximum product yield. Understanding the factor(s) involved in rapid degradation of mycoepoxydiene could lead to improved final yields.

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Section: Evect Of Solid Supports On Mycoepoxydiene Productionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Optimization of culture conditions for mycoepoxydiene production by Phomopsis sp. Hant25

Thammajaruk

Sriubolmas

Israngkul

et al. 2010

J Ind Microbiol Biotechnol

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“…To a stirred solution of 10 (11.0 mg, 31.4 m mol) in DMF containing 1% water (1 ml) were added PdCl 2 (MeCN) 2 (16 mM solution in DMF containing 1% water, 0.1 ml, 1.6 mmol) and CuCl 2 (79 mM solution in DMF containing 1% water, 0.1 ml, 7.9 mmol). The mixture was stirred for 4 days and concentrated in vacuo.…”

Section: G G-lactone Formation Preparation Of 11mentioning

confidence: 99%

“…1893A (1) and 1893B (2) were isolated in 2003 during the course of antitumor natural products searching from a marine endophytic fungus designated as No. 1893, which exists in mangroves ( Fig.…”

Section: Introductionmentioning

confidence: 99%

“…The structure of 1 was elucidated by extensive spectroscopic studies and finally determined by X-ray crystallographic analysis. As structurally related natural product, (ϩ)-mycoepoxydiene (3) was isolated in 1999 [2,3]. We already reported the total syntheses of 1 and 3, which were characterized by a sequential ringopening/cross/ring-closing metathesis strategy [4,5].…”

Section: Introductionmentioning

confidence: 99%

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Total Syntheses of (+)-1893B and Its Three Diastereomers and Evaluation of Their Biological Activities

et al. 2006

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The total syntheses of natural (ϩ)-1893B (2) and three other diastereomers 14, 18, and 21 were accomplished. Starting from the sequential metathesis product 5 prepared in turn from a 7-oxanorbornene derivative (ϩ)-4, 2 was synthesized by means of an epoxyring opening of 9a with trimethylsilylacetylide followed by Wacker-type oxidation of the resulting alkyne 10 for the construction of the g-lactone moiety. By applying the same synthetic sequence, three additional diastereomers of 2, 14, 18, and 21 were also synthesized. The biological activities of previously synthesized 1893A (1), 1893B (2), and the diastereomers of 1893B 14, 18, and 21 were investigated. Introduction1893A (1) and 1893B (2) were isolated in 2003 during the course of antitumor natural products searching from a marine endophytic fungus designated as No. 1893, which exists in mangroves (Fig. 1) [1]. Lin and Chen reported that the extract mixture of No. 1893 appeared to exhibit cytotoxic and insecticidal activities. However, the biological activity of the pure metabolites 1 and 2 has not reported. The structure of 1 was elucidated by extensive spectroscopic studies and finally determined by X-ray crystallographic analysis. As structurally related natural product, (ϩ)-mycoepoxydiene (3) was isolated in 1999 [2,3]. We already reported the total syntheses of 1 and 3, which were characterized by a sequential ringopening/cross/ring-closing metathesis strategy [4,5]. Although the stereostructures of 1 and 3 were confirmed by our synthetic studies, the stereochemistry of 2 was not unambiguously established at that time. Later, we were concerned with the stereochemically defined total synthesis of 2 through the total syntheses of all four possible stereoisomers regarding the vicinal diol moiety in 2. The first total synthesis of natural (ϩ)-2 was reported as a preliminary communication [6]. Herein, we describe in detail the total syntheses of 2 and three additional diastereomers. The evaluation of their biological activities is also presented. Results and DiscussionAccording to our previous report [5], we converted the enantioenriched 7-oxanorbornene derivative (ϩ)-4 (Ͼ95% ee) into the cyclooctadiene 5 through a one-pot ring-expansion metathesis strategy (Scheme 1). The

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Applications in the Synthesis of Natural and Biologically Active Molecules

Cossy

2014

Olefin Metathesis

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Mycoepoxydiene represents a novel class of fungal metabolites

Cited by 38 publications

References 4 publications

Optimization of culture conditions for mycoepoxydiene production by Phomopsis sp. Hant25

Optimization of culture conditions for mycoepoxydiene production by Phomopsis sp. Hant25

Total Syntheses of (+)-1893B and Its Three Diastereomers and Evaluation of Their Biological Activities

Applications in the Synthesis of Natural and Biologically Active Molecules

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