Structure of Wortmin, a new Metabolite from Penicillium wortmanni

Abstract

(Dedicated to Prof. Dr. M. Viscontini for his 501h birthday) (31. X. 72)Suwnzary. Thc structure of ester of 2-hydroxy-4-mcthoxy-6-methylbenzoic acid with 6-acetoxy-7-hydroxy-7-methyl-3-propenyl-3,4,5,6,7, 265 (E 16,800) and 305 nm (t 5,500)). These features, together with the presence in the NMK. 5pectrum of 1 (see below) of an Aryl-Me, one OMe, two aromatic meta protons, and one clielated OH, suggested the presence of an orsellinic acid-type moiety.Methanolysis of 1 with sodium methoxide afforded methyl 2-hydroxy-4-niethoxy-6-methylbenzoate (3) and a mixture of two products, 2 and 5. Treatment of this mixture with CH,N, gave 3 and methyl 2,4-dimethoxy-O-niethylbenzoate (4), thus making the isolation of 5 easier. The compound 5 has formula C,,H,,O, (m.w. = 238), and its IR. spectrum shows only one CO band at 6.00 ,IL; the UV. absorption at 239 nm ( E = 8,100). Comparison of the NMR. and mass spectra of 1 and 5 shows that in the methanolysis atlso an acetoxy group has been hydrolyzed. Confirmation of this result was obtained by acid hydrolysis of 1 with dil. HCI, that gave deacetylwortmin (6) (m.w. = 402), which, by methanolysis, gave again 5. Thus I must be a diester of the diol 5 with acetic acid and with 2-hydroxy-4-methoxg--6-methylbenzoic acid (2).Rcetylation of 5 gave diacetyl-5 (7) (m.w. = 322). The analysis of the NMR. spectra of 1, 4, 5, 6, together with double and triple resonance experiments gave information on all the H atoms of the compound 1 (see l) Centro Idel C.N.R. per lo Studio dellc Sostanzc Organichc Naturali.

Antibiotically active metabolites from Talaromyces wortmannii, an endophyte of Aloe vera

“…Compound 3-11 were identified on the basis of their 1 H and 13 C NMR, mass spectrometric data, [a] D values and comparison with published data as amino adduct 3a (3), 14 wortmannin-diol (VIII) (4), 15 wortmannin (5), 15 wortmin (6), 16 emodic acid (7), 17 skyrin (8), 13 Scheme 1 Structures of isolated compounds.…”

Structure and absolute configuration of acetosellin, a new polyketide from a phytotoxic strain of Cercosporella acetosella

“…The remaining C 4 H 8 O 2 fragment of compound 2 must be part of the dihydropyran ring C in which the C(4)H 2 group is linked at C-5, since the 4-H 2 protons presented a mutual NOE with H-1% (see Data). The similarity of the aliphatic portion of acetosellin with that of wortmin 9, a metabolite isolated by us in Penicillium wortmanni, 4 justified these assignments.…”

The Chemical Constituents of Endophytic Fungus Trichoderma sp. MFF‐1

“…Accordingly, compound 1 was determined to be (3S*,6R*,7R*)-3,4,5,6,7,8-hexahydro-7-hydroxy-7-methyl-8-oxo-3-[(E)-prop-1-enyl]-1H-isochromen-6-yl 2,4-dihydroxy-6-methylbenzoate (Fig.). The position of 6-methylbenzoyloxy moiety in compound 1 was different from that in deacetylwortmin [10], so compound 1 was named deacetylisowortmin. Me(5') correlated with C(4'), C(3'), C(2'), and C(1'), and the H-atoms HÀC(3') and HÀC(4') with C(5'), C(1'), and C(2') (w), and CH 2 (1') with C(1), C(2'), C(3'), and C(4').…”

“…2 , and six CH groups, as well as to nine quaternary Catoms. According to the NMR data, compound 1 was a mitorubrin derivative [10] [11]. The detailed structure was established by 2D-NMR ( Table 1).…”

“…Mitorubrin and derivatives are a subclass of azaphilones and have been isolated from a variety of sources [10] [11] [14] [15]. Mitorubrin and derivatives display diverse biological activities [16] [17].…”