Sporormiellin A, the first tetrahydrofuran-fused furochromone with an unprecedented tetracyclic skeleton from Sporormiella minima

Abstract

Sporormiellin A (1), the first tetrahydrofuran-fused furochromone with an unprecedented tetracyclic skeleton, has been obtained from the fungal strain Sporormiella minima.

Natural Compounds with Oxepinochromene Scaffold. Structure, Source, Biological Activity and Synthesis

“…66-3-4-2), where it plays the role of biosynthetic precursor of furochromene derivatives sporormiellins. [38] Xanthepinone 17 was isolated also by Liermann et al [39] by fermentation and extraction from a soil fungus of Phoma sp. (IBWF 132-98).…”

“…Microsphaeropsone A 10 was also obtained from the endolichenic fungus Sporormiella minima (No. 66‐3‐4‐2), where it plays the role of biosynthetic precursor of furochromene derivatives sporormiellins [38] …”

A New Xanthone Glycoside from the Endolichenic Fungus Sporormiella irregularis

“…Some species of the genus are saprobes, and others are endophytic in living plants, fungi, and lichens [5,6,7,8]. Previous chemical investigation of this genus led to isolation of polyketides (such as xanthones (sporormiellins A–C, sporormiellones A, B, microsphaeropsone A, brocaenol B) [5,9], chromones (corymbiferone C, corymbiferan lactone E, corymbiferone) [5], macrocyclic lactone (sporostatin) [10], organic acids (including zaragozic acid B, L731-127, L731-128, sporovexins A, B, and sporminarins A, B) [11,12,13]), triterpenoids (including FR171456, FR173945 [14,15], and (2a R ,2a 1 R ,3 S ,5a R ,6b S ,9 S ,10a R ,12b S )-9-hydroxy-2a 1 ,3,6b,10,10,12b-hexamethyl-1,2,2a,2a 1 ,3,5a,6,6b,7,8,9,10,10a,11,12,12b-hexadecahydro-4 H -cyclopenta[ de ]naphtho[2,1- g ]chromen-4-one [16]), steroids (including 22 E -3,7-epoxy-5,10:8,9-disecoergosta-9(10),22-diene-5,8-dione, 22 E -5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol, 22 E -5α,6α-epoxyergosta-8(9),22-diene-3β,7α-diol, 22 E -7 α -methoxy-5 α ,6 α -epoxyergosta-8(14),22-dien-3β-ol, 22 E -3β-hydroxy-5α,6α-epoxyergosta-22-en-7-one, 22 E -ergosta-7,22-diene-3β,5α,6β-triol, 22 E -6β-methoxyergosta-7,22-diene-3β,5α-diol, 22 E -5α,8α-epidioxyergosta-6,22-dien-3β-ol and 22 E -ergosta-4,6,8(14),22-tetraen-3-one [17]), and the nitrogenous compounds (including terezines A–D [18], similin B [19], sporovexin C [12], and (2 Z ,4 E ,6 E )-3-hydroxy- N -(1,11a,11b-trihydroxy-3,6,9-trioxodecahydro-1 H -pyrazino[1,2- a ]pyrrolo[2,1- c ]pyrazin-10-yl)octadeca-2,4,6-trienamide [20]).…”

“…In our previous chemical investigation of this genus Sporormiella , a series of xanthones (sporormiellins A–C, sporormiellones A, B, and microsphaeropsone A) were isolated from S. minima (No. 66-3-4-2) [9]. Notably, sporormiellin A is the first discovered tetrahydrofuran-fused furochromone with an unprecedented tetracyclic skeleton.…”

Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

“…During our ongoing research on bioactive secondary metabolites from fungi 5 6 7 8 9 10 11 12 13 , a chemical investigation on metabolites from Periconia sp. (No.…”