Novel anthraquinone derivatives produced by Phoma sorghina, an endophyte found in association with the medicinal plant Tithonia diversifolia (Asteraceae)

Abstract

Três antraquinonas conhecidas (1,7-diidroxi-3-metil-9,10-antraquinona, 1,6-diidroxi-3-metil-9,10-antraquinona e 1-hidroxi-3-metil-9,10-antraquinona), uma nova antraquinona (1,7-diidroxi-3-hidroximetil-9,10-antraquinona), e dois novos derivados hexaidroantraquinônicos, dendrióis E e F, foram isolados da cultura do fungo endofítico Phoma sorghina, associado a Tithonia diversifolia (Asteraceae). Suas estruturas foram identificadas com base em dados espectroscópicos, principalmente RMN 1D e 2D. Three known anthraquinones (1,7-dihydroxy-3-methyl-9,10-anthraquinone, 1,6-dihydroxy-3-methyl-9,10-anthraquinone and 1-hydroxy-3-methyl-9,10-anthraquinone), one new anthraquinone (1,7-dihydroxy-3-hydroxymethyl-9,10-anthraquinone), and two new hexahydroanthraquinone derivatives, dendryols E and F, were isolated from the culture of the endophytic fungus Phoma sorghina, found in association with Tithonia diversifolia (Asteraceae). Their structures were identified on the basis of spectroscopic data, mainly 1D and 2D NMR.

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

“…On the basis of detailed spectroscopic analysis and by comparison with reported data, four known hydroxyanthraquinone analogues ( 1 , 2 , 3 , 4 ) were readily determined as 1‐hydroxy‐3‐methyl‐9,10‐anthraquinone (pachybasin, 1 ), 1,7‐dihydroxy‐3‐methyl‐9,10‐anthraquinone ( 2 ), 1,6‐dihydroxy‐3‐methyl‐9,10‐anthraquinone (phomarin, 3 ), and 1‐hydroxy‐3‐hydroxymethyl‐9,10‐anthraquinone ( 4 ) . The major metabolite pachybasin ( 1 ) was purified from the fungus Trichoderma harzianum ETS 323 with much higher yield and is mainly used as a yellow pigment.…”

Plant Bioactive Metabolites and Drugs Produced by Endophytic Fungi of Spermatophyta

“…This strain also produces the biosynthetically related chromone derivative eugenitin, previously extracted as a secondary metabolite of clove (Syzygium aromaticum), and its analog 6-hydroxymethyleugenitin [179]. A strain of Phoma sorghina endophytic in the medicinal plant Tithonia diversifolia [180] has been found to produce pachybasin and phomarin, known as secondary metabolites of species in the Scrophulariaceae, such as Digitalis spp. [181] and Isoplexis isabelliana [182], and 1,7-dihydroxy-3-methylanthraquinone, first extracted from leaves of Digitalis viridiflora [183].…”

High-performance liquid chromatography–off line mass spectrometry analysis of anthraquinones produced by Geosmithia lavendula

“…In general, good separation without significant peak tailing is achieved in mobile phases consisting of water and organic modifier only for anthraquinones having a lower number of substituents (2)(3)(4) [21][22][23]. In the case of anthraquinones harboring four or more hydroxyl groups it was necessary to add acid to the mobile phase to reach both sufficient solubility and separation.…”