Isoprenylated Chromone Derivatives from the Plant Endophytic Fungus Pestalotiopsis fici

Abstract

Pestaloficiols F-L (1-7), new isoprenylated chromone derivatives including one heterodimer (7), have been isolated from a scale-up fermentation extract of the plant endophytic fungus Pestalotiopsis fici. The structures of these compounds were elucidated primarily by NMR and MS methods. The absolute configurations of 1 and 4 were assigned using the modified Mosher method. Compounds 1-3, 5, and 6 displayed inhibitory effects on HIV-1 replication in C8166 cells, whereas 4-7 showed cytotoxic activity against the human tumor cell lines HeLa and MCF7.

Phthalide derivatives with antifungal activities against the plant pathogens isolated from the liquid culture of Pestalotiopsis photiniae

“…Comparison of the physicochemical properties with reported data allowed identifying the compounds (4-9) as 5-(3¢,3¢-dimethylallyloxy)-3-methoxy-4-methylphthalide (4), 14 zinnimidine (5), 14 5-(3¢,3¢-dimethyl allyloxy)-3-methoxy-4-methylphthalide (6), 14 5-(3¢,3¢-dimethylallyloxy)-3-methoxy-4-methylphthalic acid (7), 15 zinniol anhydride (8) 16 and porriolide (9). 17 …”

“…Up to date, about 300 species of the genus Pestalotiopsis have been recorded in China, but only about 10% of these species referred to chemical investigation led to the isolation of a variety of bioactive metabolites. [4][5][6][7][8][9] Our previous investigation of Pestalotiopsis photiniae grown in the liquid culture has led to the isolation of several compounds, such as dihydroberkleasmin A, 10 10-norparvulenone 11 and zinniol-related phytotoxins. 12 Further to search for the minor active components, the fungus P. photiniae was refermented in a larger scale using the liquid fermentation culture.…”

Tandem Claisen Rearrangement/6‐endo Cyclization Approach to Allylated and Pren­ylated Chromones

“…[56,57] Both the crude extracts of fermentation cultures and isolated pestaloficiol J display moderate inhibitory activity against HIV-1 cells. [58] This natural product has, to the best of our knowledge, not been synthesized previously. Following the general tandem approach outlined in Scheme 1 and taking into account the results presented in Table 1, its synthesis would require dimethylallyl ether 3, appropriately protected at 6-OH (Scheme 2).…”

Chloropupukeanolides C–E: Cytotoxic Pupukeanane Chlorides with a Spiroketal Skeleton from Pestalotiopsis fici

“…In an initial step, chloropupukeananin (1) had been depleted in order to readily isolate the minor components, and subsequent fractionation of the extract led to the isolation of a variety of bioactive metabolites. [17][18][19][20] Representative compounds include chloropestolide A (4; Figure 1), [18] a spiroketal with an unprecedented skeleton derived from a chlorinated bicyclo-[2.2.2]-oct-2-en-5-one moiety and a 2,6-dihydroxy-4-methylbenzoic acid unit, chloropupukeanolides A and B (5 and 6; Figure 1), [19] two novel spiroketal peroxides, and chloropupukeanone A (7; Figure 1), [19] an analogue of chloropupukeananin (1) with the C8 ketone functionality. The aboveAbstract: Chloropupukeanolides C-E (8-10), three highly functionalized secondary metabolites featuring a novel spiroketal skeleton derived from the chlorinated tricyclo-[4.3.1.0 3,7 ]-decane (pupukeanane) and the 2,6-dihydroxy-4-methylbenzoic acid moieties, were isolated from the scale-up fermentation extract of the plant endophytic fungus Pestalotiopsis fici.…”