ChemInform Abstract: Biologically Active Metabolites from Fungi. Part 4. Palmarumycins CP1‐ CP4 from Coniothyrium palmarum: Isolation, Structure Elucidation, and Biological Activity.

Abstract

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Structural and Stereochemical Studies of Hydroxyanthraquinone Derivatives from the Endophytic Fungus Coniothyrium sp

“…1 Isolation and structural elucidation afforded a series of naphthalene derivatives, including palmarumycins, [2][3][4] nitronaphthalenes, 5 and a-methylene-glactone derivatives belonging to the group of massarilactones. 6,7 These metabolites demonstrated antifungal, 3,5 antibacterial, 3,5 and antialgal activities 3 in bioassays in vitro. In addition, several benzofuranones and derivatives have also been isolated from the fungus, showing similar antimicrobial activities.…”

“…In the course of our ongoing investigations to search for new biologically active secondary metabolites from fungi, we have repeatedly analyzed the culture extracts of Coniothyrium species, a very creative genus with respect to secondary metabolism . Isolation and structural elucidation afforded a series of naphthalene derivatives, including palmarumycins, nitronaphthalenes, and α ‐methylene‐ γ ‐lactone derivatives belonging to the group of massarilactones . These metabolites demonstrated antifungal, antibacterial, and antialgal activities in bioassays in vitro.…”

“…This is the first report of anthraquinones and their derivatives from an isolate of the genus Coniothyrium. The absolute configurations of coniothyrinones A (5), B (6), and D (8) were determined on the basis of TDDFT calculations of ECD spectra, allowing the determination of absolute configuration of coniothyrinones C (7). Herein we report the isolation, structural elucidation, and bioactivities of these compounds.…”

Spirobisnaphthalenes effectively inhibit carbonic anhydrase

“…Spirobisnaphthalenes derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were all determined to inhibit hCA I, with K i values ranging of 1.60-460.42 mM for spirobisnaphthalenes derivatives. Spirobisnaphthalenes derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were all found to inhibit hCA II, with K i values ranging of 0.39-419.42 mM for spirobisnaphthalenes derivatives.…”

“…The spirobisnaphthalenes exhibit a wide range of biological effects such as antifungal and antibacterial [1][2][3][4] , antimitotic 5 , antileishmanial 6 and antitumor 5,7 activities. The antitumor and antimitotic effect may result from the phospholipase D [8][9][10] , DNA gyrase 11 or thioredoxin-reductase [12][13][14] inhibition.…”