Sphaeropsidin A: A Pimarane Diterpene with Interesting Biological Activities and Promising Practical Applications

Abstract

Sphaeropsidin A (SphA) is a tetracyclic pimarane diterpene, first isolated as the main phytotoxin produced by Diplodia cupressi the causal agent of a severe canker disease of Italian cypress (Cupressus sempervirens L.). It was also produced, together with several analogues, by different pathogenic Diplodia species and other fungi and showed a broad array of biological activities suggesting its promising application in agriculture and medicine. The anticancer activity of SphA is very potent and cell specific. Recent studies have revealed its unique mode of action. This minireview reports the structures of SphA and its family of natural analogues, their biosynthetic origins, their fungal sources, and biological activities. The preparation of various SphA derivatives is also described as well as the results of structure-activity relationship (SAR) studies and on their potential practical applications.

Comparative Analysis of Secondary Metabolites in Diplodia corticola Strains with Different Virulence Degrees Associated with Canker and Dieback of Quercus spp.

“…Interestingly, Sphs A, B and C were detected in all the investigated crude extracts. Considering that Sph A and its analogues are already known to be the main phytotoxins produced by Diplodia species [24], we conjectured that these members of the family of tetracyclic pimarane diterpenes could also be involved in the different virulence degrees observed in the strains of D. corticola from oaks investigated in this study. For this reason, Sphs A and B were selected to evaluate quantitative differences among the strains.…”

“…During a study on Botryosphaeriaceae species associated with oak decline in Tunisia, Linaldeddu et al reported the existence of two distinct lineages within D. corticola (i.e., A and B) [22,23]. Diplodia corticola is able to produce many bioactive secondary metabolites, which could be involved as virulence factors in host-pathogen interactions [24][25][26][27]. Considering that virulence of D. corticola is strain dependent [28], we selected three strains of D. corticola associated with holm (Q. ilex) and cork (Q. suber) oak trees exhibiting dieback symptoms and cankers in Algeria [15] to investigate the production of secondary metabolites.…”

The incredible story of ophiobolin A and sphaeropsidin A: two fungal terpenes from wilt-inducing phytotoxins to promising anticancer compounds

“…The preparation of some hemisynthetic derivatives of SphA and the results of SAR studies were also discussed. 13…”

“…The preparation of some hemisynthetic derivatives of SphA and the results of SAR studies were also discussed. 13 All the compounds, their source, biological activities and corresponding literature illustrated in the present review are reported in Tables 1 and 2 in the ESI. ‡…”

Secondary Metabolites, including a New 5,6-Dihydropyran-2-One, Produced by the Fungus Diplodia corticola. Aphicidal Activity of the Main Metabolite, Sphaeropsidin A

“…It is frequently associated with dieback and canker diseases of oaks in many Mediterranean countries [ 11 , 12 , 13 ]. Among the metabolites frequently isolated from in vitro cultures of D. corticola , sphaeropsidin A is particularly promising for practical applications in agriculture and medicine due to its exciting biological properties, including antimicrobial, insecticidal, herbicidal, and anticancer activities [ 14 ]. Besides potential applications, the documented antimicrobial and insecticidal effects of sphaeropsidin A [ 15 , 16 , 17 , 18 ] are relevant for further consideration of the ecological role of the fungus.…”