Botrylactone: new interest in an old molecule—review of its absolute configuration and related compounds

Abstract

a b s t r a c tThe absolute configuration of botrylactone, a unique compound with an interesting polyketide lactone skeleton with two oxirane bridges previously isolated from Botrytis cinerea and described as a powerful antibiotic, has been reviewed on the basis of sign of the optical rotation, NOE experiments and NMR method. The isolation of 7-deoxybotrylactone and 5-hydroxy-7-(4-hydroxydec-2(3)-enoyl) botrylactone enables us to characterize an intriguing new family of compounds with this interesting polyketide skeleton. A common biosynthetic origin with botcinin derivatives is proposed.

Botrydial and botcinins produced by Botrytis cinerea regulate the expression of Trichoderma arundinaceum genes involved in trichothecene biosynthesis

“…In previous studies, the analysis of the bcbot2Δ metabolome led to the conclusion that BcBOT2 disruption abolishes BOT biosynthesis, but also results in the overproduction of botcinolides BotcA and BotcB, which are polyketide compounds also produced by the wild‐type strain, but at a much lower level (Moraga et al ., ; Pinedo et al ., ). Thus, the effect of addition of Botcs to Ta37 cultures grown alone or in confrontation with B05.10 was analysed to determine their effect in tri gene regulation.…”

“…Furthermore, there are several elements that are clearly involved in this interaction. These include BOT exogenously added or produced by B05.10, Botcs added to the medium or produced by bcbot2Δ , HA produced by Ta37, other SMs produced by B05.10 (botcinic acid, Moraga et al ., ; botrylactones, Massaroli et al ., ) and Ta37 (aspinolides, Malmierca et al ., ), and the hydrolytic enzymes and signalling molecules generated in the interaction zone that can act as signals even far away from the confrontation region. The cross‐pathway interactions established between these SMs, together with the hydrolytic enzyme activity, observed in the present work, and with the ability of HA to inhibit the germination of B. cinerea spores (Malmierca et al ., ), contribute to explain why T. arundinaceum is able to overcome and suppress the virulence mechanisms exhibited by the pathogen.…”

“…by the wild-type strain, but at a much lower level (Moraga et al, 2011;Pinedo et al, 2008). Thus, the effect of addition of Botcs to Ta37 cultures grown alone or in confrontation with B05.10 was analysed to determine their effect in tri gene regulation.…”

“…S1a). Botrytis cinerea also produces the polyketide botrylactones, whose biological activities have not been evaluated (Bruns et al, 1995;Massaroli et al, 2013;Moraga et al, 2011). In addition to these toxins, Botrytis produces other virulence factors involved in plant cutin and cell wall degradation, host colonization, host cell death and/or protection against oxidative bursts and defences (Choquer et al, 2007;Nakajima and Akutsu, 2014) which, together with the toxins, make B. cinerea a highly virulent pathogen.…”

Micro-organismos de interesse farmacêutico e agrícola: estudo químico e biossintético

“…Na infecção acometida por este fungo necrotrófico, a planta hospedeira é bombardeada por numerosas enzimas extracelulares e metabólitos secundários, importantes para o fungo durante o processo de infecção, induzindo a clorose e/ou rompimento da parede celular (COLMENARES et al, 2002;ELAD et al, 2004;CHOQUER et al, 2007 (FEHLHABER et al, 1974;BREITMAIER, 1979;COLMENARES et al, 2002;TANI et al, 2005TANI et al, , 2006REINO et al, 2006;MORAGA et al, 2011). Durante doze dias foi realizado o acompanhamento da produção de sesquiterpenos da classe dos aristoloquenos nos extratos obtidos da biomassa micelial e do líquido fermentado.…”