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Funiculosone, a substituted dihydroxanthene-1,9-dione with two of its analogues produced by an endolichenic fungus Talaromyces funiculosus and their antimicrobial activity
Phytochemistry ( IF 3.8 ) Pub Date : 2019-01-01 , DOI: 10.1016/j.phytochem.2018.10.031
Srichanadan Padhi , Marco Masi , Alessio Cimmino , Angela Tuzi , Subhrakanta Jena , Kumananda Tayung , Antonio Evidente

An undescribed substituted dihydroxanthene-1,9-dione, named funiculosone, was isolated together with its two analogues identified as mangrovamide J and ravenelin, from the culture filtrates of Talaromyces funiculosus (Thom) Samson, Yilmaz, Frisvad & Seifert (Trichocomaceae), an endolichenic fungus isolated from lichen thallus of Diorygma hieroglyphicum (Pers.) Staiger & Kalb (Graphidaceae), in India. Funiculosone was characterized, essentially by spectroscopic methods, as 4,8,9a-trihydroxy-3,4a-dimethyl-4a,9a-dihydro-4H-xanthene-1,9-dione. Its relative stereochemistry was deduced by single crystal X-ray analysis while the absolute configuration was assigned as 4S,4aS,9aS by ECD spectra in comparison to that of the closely related mangrovamide J. This latter, to which, not being an amide, an inappropriate common name was given, was only recently isolated, together with undescribed and known prenylatedindole alkaloids and chromone derivatives from an unidentified Penicillium sp. X-ray structural analysis of the isolated mangrovamide J, for which no biological activity was previously reported, revealed polymorphism and a new crystalline phase is described. All the compounds displayed antibacterial activity with an IC50 range 23-104 μg/mL when assayed against Escherichia coli Escherich and Staphylococcus aureus Ogston. Funiculosone also showed anticandidal activity against Candida albicans Berkhout with an IC50 35 μg/mL.

中文翻译:

绳索酮,一种取代的二氢氧杂蒽-1,9-二酮及其两种由内生真菌 Talaromyces funiculosus 产生的类似物及其抗菌活性

从 Talaromyces funiculosus (Thom) Samson、Yilmaz、Frisvad & Seifert (Trichocomaceae) 的培养滤液中分离出一种未描述的取代二氢氧杂蒽-1,9-二酮,命名为绳索酮,连同其两种类似物,被鉴定为 mangrovamide J 和 ravenelin从 Diorygma hieroglyphicum (Pers.) Staiger & Kalb (Graphidaceae) 的地衣菌体中分离出的内生真菌,在印度。绳索酮主要通过光谱方法表征为 4,8,9a-三羟基-3,4a-二甲基-4a,9a-二氢-4H-呫吨-1,9-二酮。其相对立体化学由单晶 X 射线分析推导出,而绝对构型通过 ECD 光谱指定为 4S、4aS、9aS,与密切相关的 mangrovamide J 相比。后者,不是酰胺,是给出了不恰当的通用名称,直到最近才从一种未鉴定的青霉菌中分离出未描述和已知的异戊二烯化吲哚生物碱和色酮衍生物。先前未报道过其生物活性的分离的 mangrovamide J 的 X 射线结构分析揭示了多态性并描述了新的结晶相。当对大肠杆菌和金黄色葡萄球菌 Ogston 进行测定时,所有化合物均显示出抗菌活性,IC50 范围为 23-104 μg/mL。Funiculosone 还显示出对白色念珠菌 Berkhout 的抗念珠菌活性,IC50 为 35 μg/mL。揭示了多晶型现象,并描述了新的结晶相。当对大肠杆菌和金黄色葡萄球菌 Ogston 进行测定时,所有化合物均显示出抗菌活性,IC50 范围为 23-104 μg/mL。Funiculosone 还显示出对白色念珠菌 Berkhout 的抗念珠菌活性,IC50 为 35 μg/mL。揭示了多晶型现象,并描述了新的结晶相。当对大肠杆菌和金黄色葡萄球菌 Ogston 进行测定时,所有化合物均显示出抗菌活性,IC50 范围为 23-104 μg/mL。Funiculosone 还显示出对白色念珠菌 Berkhout 的抗念珠菌活性,IC50 为 35 μg/mL。
更新日期:2019-01-01
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