Fungerin, a New Antifungal Alkaloid from<i>Fusarium</i>sp.

Kato, Yumiko; Koshino, Hiroyuki; Uzawa, Jun; Anzai, Kentaro

doi:10.1271/bbb.60.2081

Cited by 27 publications

(20 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fungerin (1) was originally isolated as an antifungal antibiotic from a Fusarium sp., and subsequently reported [9]. As shown in this paper, 1 was also produced by a different fungus a Metarhisium sp.…”

Section: Discussionsupporting

confidence: 62%

“…from morphogical characteristics. Compounds 2 and 3 were structurally related to 1, previously reported antifungal antibiotic active against Penicillium chrysogenum, Colletorichum langenarium, Altenaria mali and Pyricularia oryzae [9]. In this paper, the taxonomy of the producing fungus and the fermentation, isolation, structure elucidation and biological properties of hydroxyfungerins are described.…”

Section: Introductionmentioning

confidence: 79%

“…These data indicated that these compounds are structurally related. Compound 1 was identified as the known compound fungerin previously reported as an antifungal antibiotic [9].…”

Section: Physico-chemical Propertiesmentioning

confidence: 99%

“…In the course of our screening program for insecticidal antibiotics, we found that a fungal strain FKI-1079, which was isolated from soil collected at Yakushima, Kagoshima Prefecture, Japan, produced two new insecticidal antibiotics, named hydroxyfungerins A (2) and B (3), along with the known compound, fungerin (1) [9] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

New Insecticidal Antibiotics, Hydroxyfungerins A and B, Produced by Metarhizium sp. FKI-1079

et al. 2005

View full text Add to dashboard Cite

New insecticidal antibiotics designated hydroxyfungerins A and B were isolated from the culture broth of a fungal strain Metarhizium sp. FKI-1079 together with a known compound, fungerin. The structures of hydroxyfungerins A and B were elucidated by spectroscopic studies including various NMR experiments. Hydroxyfungerins A and B showed growth inhibitory activity against brine shrimps, Artemia salina.Keywords fungerin, insecticidal, brine shrimp, fungi, Metarhizium sp. IntroductionOur research group has focused on discovery of biological active compounds from microbial metabolites [1ϳ8]. In the course of our screening program for insecticidal antibiotics, we found that a fungal strain FKI-1079, which was isolated from soil collected at Yakushima, Kagoshima Prefecture, Japan, produced two new insecticidal antibiotics, named hydroxyfungerins A (2) and B (3), along with the known compound, fungerin (1) [9] (Fig. 1). The strain was identified as Metarhizium sp. from morphogical characteristics. Compounds 2 and 3 were structurally related to 1, previously reported antifungal antibiotic active against Penicillium chrysogenum, Colletorichum langenarium, Altenaria mali and Pyricularia oryzae [9]. In this paper, the taxonomy of the producing fungus and the fermentation, isolation, structure elucidation and biological properties of hydroxyfungerins are described. Furthermore, biological activities of 1 previously reported to have antifungal activity are also described.

show abstract

Section: Discussionsupporting

confidence: 62%

Section: Introductionmentioning

confidence: 79%

“…These data indicated that these compounds are structurally related. Compound 1 was identified as the known compound fungerin previously reported as an antifungal antibiotic [9].…”

Section: Physico-chemical Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

New Insecticidal Antibiotics, Hydroxyfungerins A and B, Produced by Metarhizium sp. FKI-1079

et al. 2005

View full text Add to dashboard Cite

show abstract

“…5 However, the measurement of 1 H-15 N long-range coupling constants without enrichment is still difficult because of the insufficient sensitivity caused by the low natural abundance of 15 N. 5 The measurement of this coupling constant was also attempted by the use of conventional HMBC with PFG. 6 But the limited coupling constant having the value of more than 7 -8 Hz was observed in this method. We thought that J-HMBC 2D method is applicable to the determination of 1 H-15 N long-range coupling at natural abundance by optimization of sample concentration and measurement parameters.…”

mentioning

confidence: 77%

PFG J-HMBC 2D NMR Spectroscopic Observation of the Natural Abundance 1H-15N Long-Range Coupling

et al. 1999

View full text Add to dashboard Cite

Perturbations of15N chemical shifts followingN-oxidation of the alkaloid cryptolepinone determined by1H-15N GHSQC and GHMBC at natural abundance

Martin¹,

Hadden²,

Blinn³

et al. 1999

Magn. Reson. Chem.

View full text Add to dashboard Cite

Direct and long‐range 1H–15N correlations for cryptolepinone and its N5‐oxide as a mixture in DMSO‐d6 were determined using a combination of 1H–15N GHSQC and GHMBC experiments. The 15N chemical shifts of cryptolepinone in the mixture were comparable to those reported previously for a pure sample of the alkaloid. Following N‐oxidation, the N‐5 resonance shifted from 103.4 ppm in cryptolepinone to 188.1 ppm (+84.7 ppm) in the N5‐oxide. The N‐10 resonance is also shifted from 111.4 ppm downfield by +23.9 ppm to 135.3 ppm in the N‐oxide. The downfield shift observed for N‐10 is attributed to a transfer of electronic effects via the intervening C‐5a—C‐10a carbon–carbon double bond in a manner comparable to that observed for fully aromatic diazines and their corresponding N‐oxides, although the shift of N‐10 is in the opposite direction of that observed for diazine systems and their N‐oxides. The downfield shift of N‐10 is consistent with the calculated partial charges at N‐10 before and after oxidation, which are identical in sense with the partial charges at N‐5, the actual site of oxidation, although much smaller in magnitude. © 1999 John Wiley & Sons, Ltd.

show abstract

Fungerin, a New Antifungal Alkaloid fromFusariumsp.

Cited by 27 publications

References 2 publications

New Insecticidal Antibiotics, Hydroxyfungerins A and B, Produced by Metarhizium sp. FKI-1079

New Insecticidal Antibiotics, Hydroxyfungerins A and B, Produced by Metarhizium sp. FKI-1079

PFG J-HMBC 2D NMR Spectroscopic Observation of the Natural Abundance 1H-15N Long-Range Coupling

Perturbations of15N chemical shifts followingN-oxidation of the alkaloid cryptolepinone determined by1H-15N GHSQC and GHMBC at natural abundance

Contact Info

Product

Resources

About