Structures of marcfortine B and C (X-ray analysis), alkaloids from

Prangé, T.; Billion, Marie-Annick; Vuilhorgne, Marc; Pascard, Claudine; Polonsky, Judith; Moreau, Serge

doi:10.1016/s0040-4039(01)92883-7

Cited by 88 publications

(44 citation statements)

References 6 publications

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“…Among them, paraherquamide was the most potent with an LD 50 value of 2.5 g mL -1 [8]. From another strain of Penicillium, IMI332995, paraherquamide and its seven novel analogues VM55594 (8), VM54158 (9), VM54159 (10), VM55595 (11), VM55596 (12), VM55597 (13) and VM55599 (14) were found [10,11]. The nematicidal activities of compounds 1 and 8-10 were assayed against both Haemonchus contortus larvae and Trichostrongylus colubriformis adults in vitro.…”

Section: Alkaloidsmentioning

confidence: 99%

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Nematicidal Substances from Fungi

Zhang²,

Xu³

et al. 2007

BIOT

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This review summarizes the 179 compounds from fungi that have shown to possess nematicidal activities. These compounds belong to diverse chemical groups and they are mainly isolated from a variety of deuteromycete, ascomycete and basidiomycete fungi. Some of them have been patented as nematicidal agents. We review and classify these compounds based on their structural types. Their nematicidal activities are described and their potential roles in natural environments and in the biocontrol of nematodes are discussed.

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Section: Alkaloidsmentioning

confidence: 99%

“…Three new alkaloids marcfortine A (19), B (20) and C (21) were obtained from the mycelium of Penicillium roqueforti [13,14]. The chemical structures of marcfortine A and C were established by Xray analysis.…”

Section: Alkaloidsmentioning

confidence: 99%

Nematicidal Substances from Fungi

Zhang²,

Xu³

et al. 2007

BIOT

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“…In particular, various prenylated indole alkaloids have been discovered, including the brevianamides, 1–7 marcfortines, 8,9 paraherquamides, 10–14 penicimutamides, 15 sclerotiamide, 16 asperparalines, 17 avrainvillamide, 18,19 stephacidins, 20 malbrancheamides, 21–23 notoamides, 24–27 versicolamide B, 28 chrysogenamide, 29 and recently the taichunamides (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

et al. 2018

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Various fungi of the genera Aspergillus, Penicillium, and Malbranchea produce prenylated indole alkaloids possessing a bicyclo[2.2.2]diazaoctane ring system. After the discovery of distinct enantiomers of the natural alkaloids stephacidin A and notoamide B, from A. protuberus MF297-2 and A. amoenus NRRL 35660, another fungi, A. taichungensis, was found to produce their diastereomers, 6-epi-stephacidin A and versicolamide B, as major metabolites. Distinct enantiomers of stephacidin A and 6-epi-stephacidin A may be derived from a common precursor, notoamide S, by enzymes that form a bicyclo[2.2.2] diazaoctane core via a putative intramolecular hetero-Diels–Alder cycloaddition. This review provides our current understanding of the structural and stereochemical homologies and disparities of these alkaloids. Through the deployment of biomimetic syntheses, whole-genome sequencing, and biochemical studies, a unified biogenesis of both the dioxopiperazine and the monooxopiperazine families of prenylated indole alkaloids constituted of bicyclo[2.2.2]diazaoctane ring systems is presented.

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“…Spectral properties matched known characterization. 1b,17a 1 H NMR (600 MHz, CDCl 3 ): δ 9.02 (bs, 1H), 6.89 (d, J = 8.2 Hz, 1H), 6.47 (bs, 1H), 6.44 (d, J = 8.2 Hz, 1H), 6.39 (d, J = 9.8 Hz, 1H), 5.81 (d, J = 9.8 Hz, 1H), 3.70 (d, J = 11.7 Hz, 1H), 3.08 (t, J = 10.7 Hz, 1H), 2.68 (br d, J = 10.5 Hz, 1H), 2.48-2.42 (m, 2H), 2.15 (d, J = 15.1 Hz, 1H), 2.14 (br d, J = 13.0 Hz, 1H), 1.96 (d, J = 15.1 Hz, 1H), 1.55–1.85 (m, 7H), 1.46 (s, 3H), 1.44 (s, 3H), 1.09 (s, 3H), 0.83 (s, 3H). 13 C NMR (125 MHz, CDCl 3 ): δ 185.2, 177.2, 153.4, 137.8, 131.6, 125.9, 121.4, 116.5, 110.0, 105.8, 76.7, 62.8, 61.3, 61.1, 61.0, 54.9, 54.5, 46.7, 40.3, 31.3, 30.9, 28.3, 28.2, 25.7, 24.1, 20.9, 20.8.…”

Section: Methodsmentioning

confidence: 99%

“…1 Structurally, they are complex heptacyclic molecules with densely functionalized cores containing four quaternary centers. Characterized by the presence of a bicyclo[2.2.2]diazaoctane and a fused spirooxindole, they are related to several families of prenylated indole alkaloids, including paraherquamides, 2,3,4 sclerotiamide, 5 notoamides, 6 brevianamides 7 and versicolamide B.…”

Section: Introductionmentioning

confidence: 99%

Rapid Access to Spirocyclic Oxindole Alkaloids: Application of the Asymmetric Palladium-Catalyzed [3 + 2] Trimethylenemethane Cycloaddition

et al. 2013

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The marcfortines are complex secondary metabolites that show potent anthelmintic activity and are characterized by the presence of a bicyclo[2.2.2]diazaoctane fused to a spirooxindole. Herein, we report the synthesis of two members of this family. The synthesis of marcfortine B utilizes a carboxylative TMM cycloaddition to establish the spirocyclic core, followed by an intramolecular Michael addition and oxidative radical cyclization to access the strained bicyclic ring system. In addition, the first asymmetric synthesis of (–)-marcfortine C is described. The key step involves a cyano-substituted TMM cycloaddition, which proceeds in nearly quantitative yield with high diastereo- and enantioselectivity. The resulting chiral center was used to establish all remaining stereocenters in the natural product.

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Structures of marcfortine B and C (X-ray analysis), alkaloids from

Cited by 88 publications

References 6 publications

Nematicidal Substances from Fungi

Nematicidal Substances from Fungi

Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

Rapid Access to Spirocyclic Oxindole Alkaloids: Application of the Asymmetric Palladium-Catalyzed [3 + 2] Trimethylenemethane Cycloaddition

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