Phenylphenalenonic phytoanticipins. New acenaphtylene and dimeric phenylphenalenones from the resistant Musa selected hybrid SH-3481

Luis, Javier G.; Lahlou, El Hassane; Andrés, Lucía S.; Echeverri, Fernándo; Fletcher, Winston Q.

doi:10.1016/s0040-4020(97)00490-0

Cited by 22 publications

(14 citation statements)

References 7 publications

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“…Following the electronic excitation of PN, 3 n-heptane, the former reaction is dominant as the quantum of singlet oxygen production is closesuggests a high efficiency of singlet oxygen production ( Figure 5). Nonetheless, Φ deg is 5-fold 357 higher in the wax compared to n-heptane.…”

Section: Singlet Oxygen Production 314mentioning

confidence: 99%

Perinaphthenone phototransformation in a model of leaf epicuticular waxes

Trivella

Monadjemi

Worrall

et al. 2014

Journal of Photochemistry and Photobiology B: Biology

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Perinaphthenone (1H-phenalen-1-one, PN) is a reference photosensitizer producing singlet 20 oxygen with a quantum yield close to one in a large variety of solvents. It is also the basic 21 structure of a class of phototoxic phytoalexins. In this work, the PN photoreactivity was studied 22for the first time in a paraffinic wax, used as model of leaf epicuticular waxes. The PN 23 photodegradation was monitored by UV-Vis spectroscopy. The triplet excited state, singlet 24 oxygen and the hydroxyperinaphthenyl radical were detected by diffuse reflectance laser flash 25 photolysis, near infrared phosphorescence and by EPR spectroscopy, respectively. The PN 26 phototransformation was found to be five-fold faster in the wax than in n-heptane under steady-27 state irradiation. The hydroxyperinaphthenyl radical formation was observed in aerated irradiated 28 paraffin wax while in n-heptane solution the radical was observed only in the absence of oxygen. 29These results show that under continuous irradiation, PN is much more easily phototransformed 30 in a solid environment than in solution. Several photoproducts were identified, in particular 31 phenalanone, PN dimers, and oxidized PN-alkanes adducts. Finally, when pyrethrum extract is 32 added into the wax, the radical concentration was increased by a factor of 2.4. Such 33 photochemical reactions may occur when systemic pesticides enter the plant cuticle. 34 35

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Section: Singlet Oxygen Production 314mentioning

confidence: 99%

Perinaphthenone phototransformation in a model of leaf epicuticular waxes

Trivella

Monadjemi

Worrall

et al. 2014

Journal of Photochemistry and Photobiology B: Biology

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“…Many natural products based on the phenalenone (PN) skeleton have been isolated from plants and fungi (1–6). There is sufficient evidence to indicate that such compounds play a significant role in the protection of plants against potentially harmful microorganisms (4–7). One can speculate that the mode of action in these protective mechanisms involves a photooxidation component, because PN is arguably one of the most useful photosensitizers discovered thus far for the production of singlet molecular oxygen, O 2 (a 1 Δ g ).…”

Section: Introductionmentioning

confidence: 99%

Phototoxic Phytoalexins. Processes that Compete with the Photosensitized Production of Singlet Oxygen by 9-Phenylphenalenones†

Flors

Ogilby

Luis

et al. 2006

Photochem Photobiol

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Experiments were performed to elucidate the excited-state behavior of 9-phenylphenalenones, which are phototoxic plant secondary metabolites involved in mechanisms of light-mediated plant defense. Using a combination of time-resolved and steady-state UV/visible spectroscopies, time-resolved IR absorption spectroscopy, time-resolved singlet oxygen phosphorescence measurements and cyclic voltammetry, we provide evidence of an intramolecular charge-transfer process in the excited singlet and the triplet states of 9-phenylphenalenones that modulates the photosensitized production of singlet oxygen.

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“…2) (Luis et al 1996b;Binks et al 1997;Kamo et al 1998;Hölscher and Schneider 1999;Kamo et al 2001;Otalvaro et al 2002aOtalvaro et al , b, c, 2007.…”

Section: The Bases Of Banana Phytoalexin Inductionmentioning

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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Phenylphenalenonic phytoanticipins. New acenaphtylene and dimeric phenylphenalenones from the resistant Musa selected hybrid SH-3481

Cited by 22 publications

References 7 publications

Perinaphthenone phototransformation in a model of leaf epicuticular waxes

Perinaphthenone phototransformation in a model of leaf epicuticular waxes

Phototoxic Phytoalexins. Processes that Compete with the Photosensitized Production of Singlet Oxygen by 9-Phenylphenalenones†

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

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