Chcl3

Solvents such as EtOAc, n-hexane MeOH, i-PrOH, CHCl₃, and CH₂Cl₂ were purchased from Panreac AppliChem (Barcelona, Spain). Colletochlorin A, orcinol, and tyrosol were isolated from in vitro cultures of Colletotrichum gloeosporioides [31 (link)]; colletochlorins E and F, colletopyrone, higginsianin A, and higginsianin B were isolated from in vitro cultures of C. higginsianum [32 (link),33 (link)]; (R)-mellein was isolated from in vitro cultures of Neofusicoccum parvum [34 (link)]; 6-hydroxymellein were isolated from in vitro cultures of Phoma chenopodiicola [35 (link)]; resorcinol was isolated from in vitro cultures of Dothiorella vidmadera [36 (link)]; and 4-hydroxybenzaldehyde and 2-(4-hydroxyphenyl) acetic acid were isolated from in vitro cultures of Spencermartinsia viticola [37 (link)]. The identity and purity of all standard metabolites were checked using NMR analysis at the Department of Chemical Sciences of the University of Naples Federico II. As an internal standard (IS) for the UHPLC-QTOF-HRMS analysis, (±)-naringenin analytical standard, purchased from Sigma-Aldrich, Milan, Italy, was used.

Analytical and preparative TLCs were carried out on silica gel (Merck, Kieselgel 60, F254, 0.25, and 0.5 mm) and reverse phase (Merck, Kieselgel 60 RP-18, F254, 0.20 mm) plates. The spots were visualized by exposure to UV radiation (254 and/or 312 nm) or by spraying first with 10% H₂SO₄ in MeOH, and then with 5% phosphomolybdic acid in EtOH, followed by heating at 110 °C for 10 min on a hot plate. Column chromatography was performed using silica gel (Merck, Kieselgel 60, 0.063–0.200 mm). Solvents n-hexane MeOH, i-PrOH, CHCl₃, and CH₂Cl₂ were purchased from Panreac AppliChem (Barcelona, Spain). Unless otherwise noted, optical rotation was measured in MeOH on a Jasco (Tokyo, Japan) polarimeter, whereas the CD spectrum was recorded on a JASCO J-815 CD in MeOH. ¹H and ¹³C NMR and 2D NMR spectra were recorded at 400 or 500, and 100 or 125 MHz in CDCl₃ on Bruker and Varian instruments. The same solvent was used as an internal standard. HR-ESIMS analyses were performed using the LC/MS TOF system (AGILENT 6230B, HPLC 1260 Infinity) column Phenomenex LUNA (C18 (2) 5 µm 150 × 4.6 mm). ¹H-NMR and ESI/MS (+) spectra of the identified compounds are reported in the Supplementary Figures S1–S14.