UV-Guided Isolation of Alantrypinone, a Novel Penicillium Alkaloid

Abstract

Fumiquinazoline F (1) and alantrypinone (2) have been isolated as the two major metabolites of Penicillium thymicola. The structure of 2, which contains a new ring structure, was elucidated by analysis of spectroscopic data including 2D NMR. The absolute configuration of 2 was established by a single-crystal X-ray diffraction study.

The spiroquinazoline family of alkaloids: a review

“…The structure of alantrypinone was established by X-ray crystallography (Figure 4). 6 Alantrypinone co-crystallized with DMSO and acetonitrile and thus, it was possible to determine its absolute configuration using the anomalous dispersion technique. Finally, the CD spectrum of 7 was essentially the mirror image (opposite Cotton effect) of the CD spectrum of lapatin A 2 (vide supra).…”

Syntheses of Quinazoline-2,4-dione Alkaloids and Analogues from Mexican Zanthoxylum Species †

“…Quinazolinone and quinazolinedione derivatives are of considerable interest because of their wide array of pharmacological properties [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. We have been specifically interested in the synthesis of novel heterocycles containing the quinazoline-2,4-dione backbone, which are known to exhibit potential anti-hypertensive properties [16][17][18][19][20].…”

A Novel Alkaloid Serantrypinone and the Spiro Azaphilone Daldinin D from Penicillium thymicola

“…This latter group included the isolate of P. thymicola recently studied by our group. 2 In addition to displaying different morphological characteristics the three species can be distinguished by differences in production of quinazoline and other secondary metabolites. 1 P. verrucosum produces verrucines, 3 P. nordicum produces anacines, 1 while P. thymicola produces anacine, fumiquinazoline F, and the related spiroquinazoline alantrypinone.…”

“…1 P. verrucosum produces verrucines, 3 P. nordicum produces anacines, 1 while P. thymicola produces anacine, fumiquinazoline F, and the related spiroquinazoline alantrypinone. 1,2 From previous work with UV-guided isolation of secondary metabolites from P. thymicola 2 we knew that the fungus often produces a minor compound with UV data almost identical to those seen for a major component, alantrypinone (4). 2 The present report describes the isolation and structure elucidation of this minor and novel quinazoline compound, serantrypinone (1), together with a new azaphilone derivative, daldinin D (2), from P. thymicola (IBT 5891 and a quinazoline moiety derived from anthranilic acid.…”

“…1,2 From previous work with UV-guided isolation of secondary metabolites from P. thymicola 2 we knew that the fungus often produces a minor compound with UV data almost identical to those seen for a major component, alantrypinone (4). 2 The present report describes the isolation and structure elucidation of this minor and novel quinazoline compound, serantrypinone (1), together with a new azaphilone derivative, daldinin D (2), from P. thymicola (IBT 5891 and a quinazoline moiety derived from anthranilic acid. HMBC experiments predicted the linkage between C-3 in the oxopiperazine ring and C-17 in the tryptophane-derived oxindole as in 4.…”