Synthesis of [phenyl‐13C6]lachnanthocarpone and other 13C‐labelled phenylphenalenones

Otálvaro, Felipe; Quiñones, Winston; Echeverri, Fernándo; Schneider, Bernd

doi:10.1002/jlcr.808

Cited by 16 publications

(15 citation statements)

References 20 publications

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“…However, we were unable to obtain 8 using this reaction sequence, which previously had been used successfully to prepare hydroxyanigorufone [13]. Similar findings were also reported by Otálvaro et al in the synthesis of lachnanthocarpone [14]. Subsequently, several other hydroxylation conditions were screened for the formation of 8. process catalyzed by p-toluenesulfonic acid (PTSA) to afford 8 smoothly in moderate yield (60%) (Scheme 2).…”

Section: Resultssupporting

confidence: 59%

Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

et al. 2019

Zeitschrift Für Naturforschung B

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The total synthesis of the natural phytoalexin 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one (3) isolated from Eichhornia crassipes was accomplished in seven steps. The synthetic strategy included a Friedel–Crafts acylation and a Jacobsen–Katsuki epoxidation as the key reactions to obtain the target compound. Based on a comparison of the NMR data and a crystal structure of 3, the previously proposed structure of 2,5-dimethoxy-4-phenyl-benzoindenone (2) isolated from the same plant has been revised.

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Section: Resultssupporting

confidence: 59%

Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

et al. 2019

Zeitschrift Für Naturforschung B

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“…9‐Phenylphenalenone was synthesized according to the protocol reported by Otálvaro et al (Otálvaro et al . ), extensively purified by chromatographic techniques (column chromatography, preparative thin‐layer chromatography, semipreparative HPLC) up to a purity >98% (UV 254 and 280 nm) and used as internal standard for quantification of phenylphenalenones. A total of 25 mg of the infected dried and ground tissue was transferred into 0.8 mL methanol with 0.2 mL phosphate buffer and 0.1 mL of a 9‐phenylphenalenone solution (final concentration: 0.05 mg mL −1 ) for extraction and cleaning procedures as described in the preceding text, except that an SPE cartridge of 200 mg was used instead of a 500 mg SPE cartridge.…”

Section: Methodsmentioning

confidence: 80%

Phenylphenalenones protect banana plants from infection by Mycosphaerella fijiensis and are deactivated by metabolic conversion

Hidalgo

Chandran

Menezes

et al. 2015

Plant Cell & Environment

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Phenylphenalenones, polycyclic aromatic natural products from some monocotyledonous plants, are known as phytoalexins in banana (Musa spp.). In this study, 1H nuclear magnetic resonance (NMR)‐based metabolomics along with liquid chromatography and mass spectrometry were used to explore the chemical responses of the susceptible ‘Williams’ and the resistant ‘Khai Thong Ruang’ Musa varieties to the ascomycete fungus Mycosphaerella fijiensis, the agent of the black leaf Sigatoka disease. Principal component analysis discriminated strongly between infected and non‐infected plant tissue, mainly because of specialized metabolism induced in response to the fungus. Phenylphenalenones are among the major induced compounds, and the resistance level of the plants was correlated with the progress of the disease. However, a virulent strain of M. fijiensis was able to overcome plant resistance by converting phenylphenalenones to sulfate conjugates. Here, we report the first metabolic detoxification of fungitoxic phenylphenalenones to evade the chemical defence of Musa plants.

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“…A biosynthetic exper- iment to understand the production of phytoalexins in plants was carried out using methyl jasmonate as inductor and applying acetate, phenylalanine and SAM (S-adenosylmethionine) 13 C-labeled. After 5 days of induction with jasmonate and addition of labeled precursors, compounds were isolated and then identified by means of 13 C NMR (Otalvaro et al 2004). These experiments and the structure of the compounds previously isolated showed a putative biosynthesic pathway (Fig.…”

Section: Phenylphenalenone Biosynthesismentioning

confidence: 99%

Phenylphenalenone phytoalexins, will they be a new type of fungicide?

et al. 2010

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Phenylphenalenones represent a kind of phytoalexins produced in leaves and rhyzomes of banana and plantains (Musaceae), as well as in species of other families. These compounds are synthesized in plants by induction with aminoglycosides, or in the first stages of attack by the pathogenic fungus Mycosphaerella fijensis, a causal agent of the disease known as Black Sigatoka, which reduces banana production. In this paper we report the biosynthesis, synthesis and antifungal activities of these kinds of compounds and discus the possibility to use phytoalexins inductors as plant protectants.

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Synthesis of [phenyl‐¹³C₆]lachnanthocarpone and other ¹³C‐labelled phenylphenalenones

Cited by 16 publications

References 20 publications

Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

Phenylphenalenones protect banana plants from infection by Mycosphaerella fijiensis and are deactivated by metabolic conversion

Phenylphenalenone phytoalexins, will they be a new type of fungicide?

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