1H NMR conformational study of fusicoccin and related compounds: molecular conformation and biological activity

Ballio, A.; Castellano, S.; Cerrini, S.; Evidente, Antonio; Randazzo, G.; Segre, Anna Laura

doi:10.1016/0031-9422(91)84114-8

Cited by 26 publications

(18 citation statements)

References 28 publications

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“…The new 3-epi-FC isolated as a metabolite less polar than FC H had the same molecular formula of C26H42O8 as that of FC H from its HR-FABMS data. Its 1 H-and 13 C-NMR spectra (Tables 1 and 2) showed similar signals to those of FC H. The slight diŠerence in chemical shifts of C-1 and C-3 in the 13 C-NMR signals suggested that this new 3-epi-FC was the 3-epimer of FC H. This was conˆrmed by the results of NOE experiments: irradiation of H-17 (d0.89) markedly enhanced the signal of H-3 at d2.39 and that of H-9 at d3.88. The structure of this new 3-epi-FC was thus assigned as that of 3-epi-FC H.…”

Section: )mentioning

confidence: 70%

“…The 1 H-NMR spectrum showed many signals characteristic of those of FC J (isopropyl, H-13 and H-8 methine, H-1 vinyl, H?-1 anomeric and 16-O-methyl protons) in the absence of typical signals of the isopentenyl group (two t-methyl and three vinyl protons) 13) ( Table 1). Furthermore its 13 C-NMR data clearly indicated that FC P was deisopentenyl-FC J (Table 2). …”

Section: Resultsmentioning

confidence: 99%

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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

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Section: )mentioning

confidence: 70%

Section: Resultsmentioning

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

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“…Distance geometry computation started from a fully extended open chain and obtained ring closures through the use of appropriate angle and bond constraints [11]. With regard to the geometry of the five-member ring, the structural information reported by Tsuboi et al [12] for the 3-(2'-chloro vinyl)-2-hydroxy-2-cyclopentenone was used.…”

Section: Resultsmentioning

confidence: 99%

Determination of the structure of fusaproliferin by1H-NMR and distance geometry

et al. 1995

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The absolute configuration of fusaproliferin, a toxic metabolite produced by Fusarium proliferaturn, was determined by the combined use of 1H NMR and distance geometry. The configuration of double bonds has been determined in agreement with NOESY buildup data. An R configuration for C10 was determined using Mosher's method. Processing the constraints obtained from NOESY experiments with a distance geometry program, a limited number (80) of possible structures was derived. An agglomerative nonhierarchical method of clustering was used in order to place these structures into classes suggested by the data, and not previously defined in any way. This statistical method showed that indeed the structures could be grouped in four classes. One of these classes is represented by a single structure, with the highest sum of violations and was discarded. All other structures have the same chirality; respectively S for C14 and R for C15. In solution the overall conformation is quite well defined in the region of the five-member ring and the planes of double bonds C2--C3 and C11--C12, while near to C8 and C9 internal flexibility appears evident.

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“…7,9-epiDeacetylfusicoccin was obtained as previously reported (8); in a recent paper (11), it was shown that epimerization involves C-7 and C-9, and not C-9 only as previously reported (8). Cotylenins A and G were kind gifts of Dr. T. Sassa, Yamagata University, Japan.…”

Section: Chemicalsmentioning

confidence: 99%

Some Properties of a Functional Reconstituted Plasmalemma H⁺-ATPase Activated by Fusicoccin

Marra¹,

Ballio²,

Fullone³

et al. 1992

Plant Physiol.

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Fusicoccin was shown to stimulate the ATP-driven, intravesicular acidification of liposomes reconstituted with crude fusicoccin receptors and the H -translocating ATPase, both solubilized from maize (Zea mays L.) plasma membrane. The present paper reports optimal conditions for dual reconstitution and fusicoccin activation as well as the biochemical characterization of the effect of fusicoccin on this system. Fusicoccin stimulation of proton pumping was dependent on pH and fusicoccin concentration. Its specificity was demonstrated by the positive effect of two cotylenins that have a high affinity for fusicoccin receptors and by the negative response to 7,9-epideacetylfusicoccin, an inactive fusicoccin derivative. Kinetic measurements at different ATP concentrations showed that fusicoccin increases the V",, of the enzyme. Fusicoccin stimulation of maize H+-ATPase was also maintained when receptors from maize were substituted by those from spinach (Spinacia oleracea L.).The fungal metabolite FC2 is known to affect several physiological processes in all higher plants so far examined (19 (12, 21). In particular, this evidence was stressed by demonstrating that FC efficiently stimulates ATP-driven H+-pumping into proteoliposomes in which both maize H+-ATPase and FC receptors had been incorporated (4).In this paper, we report a more detailed biochemical characterization of the reconstituted system in view of its possible use as a tool for the elucidation ofthe molecular events linking FC receptors to H+-ATPase. In fact, the nature of the signal transduction pathway following the primary interaction ofFC with its receptors is still unknown. MATERIALS AND METHODS ChemicalsFC was prepared as described by Ballio et al. (7). 7,9-epiDeacetylfusicoccin was obtained as previously reported (8); in a recent paper (11), it was shown that epimerization involves C-7 and C-9, and not C-9 only as previously reported (8). Cotylenins A and G were kind gifts of Dr. T. Sassa, Yamagata University, Japan. The dye ACMA was purchased from Sigma Chemical Company. All other products were of analytical grade.

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1H NMR conformational study of fusicoccin and related compounds: molecular conformation and biological activity

Cited by 26 publications

References 28 publications

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

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

Determination of the structure of fusaproliferin by1H-NMR and distance geometry

Some Properties of a Functional Reconstituted Plasmalemma H⁺-ATPase Activated by Fusicoccin

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1H NMR conformational study of fusicoccin and related compounds: molecular conformation and biological activity

Cited by 26 publications

References 28 publications

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

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

Determination of the structure of fusaproliferin by1H-NMR and distance geometry

Some Properties of a Functional Reconstituted Plasmalemma H+-ATPase Activated by Fusicoccin

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Some Properties of a Functional Reconstituted Plasmalemma H⁺-ATPase Activated by Fusicoccin