Four New Insecticidal Xanthene Derivatives from the Mangrove-Derived Fungus Penicillium sp. JY246

Abstract

Four new xanthene derivatives, penicixanthenes A–D (1–4), and one known compound 5 were isolated from a marine mangrove endophytic fungus Penicillium sp. JY246 that was obtained from the stem of Ceriops tagal. Their structures were determined by detailed NMR, MS spectroscopic data, modified Mosher’s method, and calculated electronic circular dichroism data. All of the isolated compounds were examined for insecticidal activity. Compounds 2 and 3 showed growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner with the IC50 values 100 and 200 μg/mL, respectively, and compounds 1, 3, and 4 showed insecticidal activity against newly hatched larvae of Culex quinquefasciatus with LC50 values of 38.5 (±1.16), 11.6 (±0.58), and 20.5 (±1) μg/mL, respectively. The four xanthene derivatives have the potential to be developed as new biopesticides.

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

“…The Penicillium strains were the source of xanthones, including 15 monomers 497–511 , 108,181,231–235 such as mangrovamides J ( 497 ) and K ( 498 ), 108 penixanthones C ( 499 ) and D ( 500 ), 181 penixanthones A ( 505 ) and B ( 506 ), 231 chlorinated xanthone 507 , 232 and the insecticidal penicixanthenes A–D ( 508–511 ). 233 The genus Phomopsis yielded 14 new xanthone derivatives, including the cytotoxic xanthones 512–514 , 236–238 phomoxanthones G–K ( 515–519 ), which are the first report of a C6- O -C12 bridge in xanthone-derived, 93 and six xanthone dimers 520–525 . 239,240 The genus Aspergillus also yielded a number of new xanthone polyketides, including four monomers versicones E–H ( 526–529 ), 241 six cytotoxic xanthone–chromanone dimers versixanthones A–F ( 530–535 ), 242 five tetrahydroxanthones dimers 536–540 as potential topoisomerase I inhibitors, 243 and three cytotoxic tetrahydroxanthone dimers 5- epi -asperdichrome ( 541 ), versixanthones N ( 542 ) and O ( 543 ).…”

“…This family of polyketides with 79 members is characterized from mangrove-associated fungi. The Penicillium strains were the source of xanthones, including 15 monomers 497-511, 108,181,[231][232][233][234][235] such as mangrovamides J (497) and K (498), 108 penixanthones C (499) and D (500), 181 penixanthones A (505) and B (506), 231 chlorinated xanthone 507, 232 and the insecticidal penicixanthenes A-D (508-511). 233 The genus Phomopsis yielded 14 new xanthone derivatives, including the cytotoxic xanthones 512-514, [236][237][238] phomoxanthones G-K (515-519), which are the rst report of a C6-O-C12 bridge in xanthone-derived, 93 and six xanthone dimers 520-525.…”

The Chemical Ecology Approach to Reveal Fungal Metabolites for Arthropod Pest Management

“…For instance, the study of insecticidal metabolites of marine species (e.g., Acremonium , Beauveria , Penicillium , etc.) successfully has begun [ 240 , 241 , 242 ].…”

Marine Natural Products: The Important Resource of Biological Insecticide

“…JY246 and identified via NMR, MS and ECD technique. Three of them exhibited potent insecticidal activity against larvae of Culex quinquefasciatus [120] …”