Purpurogemutantin and Purpurogemutantidin, New Drimenyl Cyclohexenone Derivatives Produced by a Mutant Obtained by Diethyl Sulfate Mutagenesis of a Marine-Derived Penicillium purpurogenum G59

Abstract

Two new drimenyl cyclohexenone derivatives, named purpurogemutantin (1) and purpurogemutantidin (2), and the known macrophorin A (3) were isolated from a bioactive mutant BD-1-6 obtained by random diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. Structures and absolute configurations of 1 and 2 were determined by extensive spectroscopic methods, especially 2D NMR and electronic circular dichroism (ECD) analysis. Possible biosynthetic pathways for 1–3 were also proposed and discussed. Compounds 1 and 2 significantly inhibited human cancer K562, HL-60, HeLa, BGC-823 and MCF-7 cells, and compound 3 also inhibited the K562 and HL-60 cells. Both bioassay and chemical analysis (HPLC, LC-ESIMS) demonstrated that the parent strain G59 did not produce 1–3, and that DES-induced mutation(s) in the mutant BD-1-6 activated some silent biosynthetic pathways in the parent strain G59, including one set for 1–3 production.

Paraconfuranones A–H, eight new furanone analogs from the insect‐associated fungus Paraconiothyrium brasiliense MZ‐1

“…To our best knowledge, the strain can produce some novel terpenoid derivatives. [8][9][10][11] When this fungus was cultured under the rice medium in our preliminary experiments, a few terpenoids could be detected. When the culture medium was guided by the one strain-many compounds approach, [12] the secondary metabolites thereby changed.…”

New Metabolites Produced by Cylindrocarpon sp. SY‐39 from a Driftwood

“…To the best of our knowledge, as chlorinated phenolic sesquiterpenoids related with 3 , dihydroxyneogrifolic acid has been isolated from leafhopper pathogenic fungus Microcera sp., ilicicolins A, C, E and F from fungus Cylindrocladium ilicicola, and deacetylchloronectrin from Necrtia coccinea, too. The biosynthetic pathways of 1 , 2 , 4 , and 5 are derived from polyketides, which is different from the biosynthetic pathway of 3 that is derived from a farnesyl pyrophosphate and a gentisyl alcohol . In fact, derivative of the gentisyl alcohols have been isolated from metabolites of fungi, which was biosynthesized via polyketide pathway .…”

“…The biosynthetic pathways of 1, 2, 4, and 5 are derived from polyketides, which is different from the biosynthetic pathway of 3 that is derived from a farnesyl pyrophosphate and a gentisyl alcohol. [17] In fact, derivative of the gentisyl alcohols have been isolated from metabolites of fungi, which was biosynthesized via polyketide pathway. [18] In addition, with respect to this meroterpene 3, ilicicolinic acid D was isolated from Neonectria discophora isolated from a termite nest.…”

Penicillium purpurogenumexerts antitumor effects and ameliorates inflammations in Erlich mice model

“…Importantly, tumor-animals groups treated with the extract showed 100% survival rate in all doses, being significantly different when compared to controls (Figure 5b). Tang et al [32], Fang et al [29]. and He et al [33].…”