Synthesis of visoltricin and fungerin: imidazole derivatives of Fusarium sp.

Rieder, Johann M.; Lepschy, J.

doi:10.1016/s0040-4039(02)00298-8

Cited by 9 publications

(4 citation statements)

References 5 publications

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“…salina activity and cholinesterase inhibitory activities [14,15]. However, a recent synthetic study resulted in a revised structure identical to 1 [16]. In this sense, we only confirmed the anti-A.…”

Section: Discussionmentioning

confidence: 52%

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

et al. 2005

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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.

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Section: Discussionmentioning

confidence: 52%

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

et al. 2005

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“…The syntheses of two imidazole derivatives, fungerin 119 and its isomer 120 have been described. 45 As a result, it has been concluded that visoltricin, isolated from the strain of Fusarium tricinctum and previously thought to have structure 120, is in fact identical to fungerin.…”

Section: Zhong Jin 2 Muscarine Alkaloidsmentioning

confidence: 99%

Muscarine, imidazole, oxazole, and thiazole alkaloids

Jin

2003

Nat. Prod. Rep.

132

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“…Its structure was successively and slightly revised because it is identical to Fungerin ( 6 , FU), which is an antifungal metabolite independently isolated from a culture of a strain of Fusarium sp. [ 32 ]. Recently, Fungerin has been reported to inhibit the polymerization of microtubules interrupting the cell cycle in the M-phase [ 33 ].…”

Section: Introductionmentioning

confidence: 99%

Natural Scaffolds with Multi-Target Activity for the Potential Treatment of Alzheimer’s Disease

et al. 2018

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A few symptomatic drugs are currently available for Alzheimer’s Disease (AD) therapy, but these molecules are only able to temporary improve the cognitive capacity of the patients if administered in the first stages of the pathology. Recently, important advances have been achieved about the knowledge of this complex condition, which is now considered a multi-factorial disease. Researchers are, thus, more oriented toward the preparation of molecules being able to contemporaneously act on different pathological features. To date, the inhibition of acetylcholinesterase (AChE) and of β-amyloid (Aβ) aggregation as well as the antioxidant activity and the removal and/or redistribution of metal ions at the level of the nervous system are the most common investigated targets for the treatment of AD. Since many natural compounds show multiple biological properties, a series of secondary metabolites of plants or fungi with suitable structural characteristics have been selected and assayed in order to evaluate their potential role in the preparation of multi-target agents. Out of six compounds evaluated, 1 showed the best activity as an antioxidant (EC50 = 2.6 ± 0.2 μmol/µmol of DPPH) while compound 2 proved to be effective in the inhibition of AChE (IC50 = 6.86 ± 0.67 μM) and Aβ1–40 aggregation (IC50 = 74 ± 1 μM). Furthermore, compound 6 inhibited BChE (IC50 = 1.75 ± 0.59 μM) with a good selectivity toward AChE (IC50 = 86.0 ± 15.0 μM). Moreover, preliminary tests on metal chelation suggested a possible interaction between compounds 1, 3 and 4 and copper (II). Molecules with the best multi-target profiles will be used as starting hit compounds to appropriately address future studies of Structure-Activity Relationships (SARs).

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Synthesis of visoltricin and fungerin: imidazole derivatives of Fusarium sp.

Cited by 9 publications

References 5 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

Muscarine, imidazole, oxazole, and thiazole alkaloids

Natural Scaffolds with Multi-Target Activity for the Potential Treatment of Alzheimer’s Disease

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