Novel Fusicoccins R and S, and the Fusicoccin S Aglycon (Phomopsiol) fromPhomopsis amygdaliNiigata 2-A, and Their Seed Germination-stimulating Activity in the Presence of Abscisic Acid

Abstract

Our search for new 3-hydroxyfusicoccins structurally related to cotylenin A from a culture of Phomopsis amygdali Niigata 2-A resulted in the isolation of novel 3-hydroxy fusicoccins, called fusicoccins R and S, and the fusicoccin S aglycon, called phomopsiol, together with known 3 -hydroxyfusicoccin J. The structure of phomopsiol was identified as that of O-demethyl-3-epicotylenol based on spectroscopic evidence. The structures of fusicoccins R and S were also determined to be those of 3 0 -deacetyl-3 -hydroxyfusicoccin A and 3 -hydroxy-3-epifusicoccin H. The lettuce seed germination-stimulating activity of fusicoccins R and S, phomopsiol and 3 -hydroxyfusicoccin J was examined in the presence of ABA; fusicoccin R and 3 -hydroxyfusicoccin J were highly active, while fusicoccin S and phomopsiol were inactive. The possible biosynthetic relationships among these novel fusicoccins having a 3 -or 3 -hydroxy group in their diterpene moiety are briefly discussed.

Genome of Diaporthe sp. provides insights into the potential inter-phylum transfer of a fungal sesquiterpenoid biosynthetic pathway

“…Furthermore, fungal endophytes such as the Ascomycete Diaporthe ( Phomopsis ) sp. produce a diversity of interesting and bioactive sesquiterpene scaffolds, such as cadinanes (Silva et al, 2006), drimanes (Zang le et al, 2012) and meroterpenoids (Hemtasin et al, 2011; Ma et al, 2015; Tajima et al, 2004) and as we have shown here, trans -humulane scaffolds. Diaporthe ( Phomopsis ) sp.…”

A new sesquiterpene from the entomogenous fungusPhomopsis amygdali

“…Compounds 2 -6 were identified as abscisic acid (2) (Jadulco et al 2002;Zheng et al 2002;del Refugio Ramos et al 2004), fusicoccin J (3) (Tajima et al 2004), 3a-hydroxyfusicoccin J (4) (Tajima et al 2004), 5-hydroxymethylmellein (5) (Kokubun et al 2003) and 4-hydroxyphenethyl acetate (6) Compounds 1 -6 were tested for antimicrobial activity against three plant pathogenic fungi: Gibberella zeae, Verticillium albo-atrum and Fusarium nivale, and two bacteria: Escherichia coli and Pseudomonas aeruginosa 2033E. The positive controls were carbendazim and gentamicin, respectively.…”

Using Jasplakinolide to Turn on Pathways that Enable the Isolation of New Chaetoglobosins from Phomospis asparagi

“…The untreated cultures appeared to be rich in polyketides of masses below 400 amu. While an exhaustive dereplication was not undertaken, examples of these compounds were provisionally identified as 4,6-dihydroxymellein (t R = 21.0 min), 20 patulolide C (t R = 21.5 min), 21 convolvulopyrone (t R = 24.0 min), 22 culpin (t R = 24.5 min), 23 phompsiol (t R = 28.0 min), 24 To obtain milligram quantities of the new metabolites, scale-up cultures were grown (5 × 1 L) using methods and conditions outlined in the Experimental Section. The immediate goal was to characterize the new compounds and evaluate their biological properties.…”