Synthesis and chemistry of N-benzoyl-O- [N'-benzoyl-l-phenylalanyl]-l-phenylalaninol, the major mycelial metabolite of penicillium canadense

Chemical diversity from the Tibetan Plateau fungi Penicillium kongii and P. brasilianum

“…The absolute configuration of 6 was determined by the ECD spectrum, which showed the similar Cotton effect with asperphenamate. Furthermore, the specific rotation of 5 was similar to that of asperphenamate, which was consistent with asperphenamate (McCorkindale et al 1978). Thus, the 3D configurations of 2 and 2′ position are same between compound 6 and asperphenamate, and compound 6 was defined as N-p-phydroxybenzoyl-phenylalanine-2-benzoylamino-3-phenyl propyl ester.…”

“…The partial structure of N-benzoyl-phenylalaninol was defined by the HMBC correlations from H-2′ to C-1′ ( δ 65.5) and C-10′ ( δ 167.6), and from H-3′ to C-1′ (δ 65.5), C-5′ (δ 129.4), and C-9′ (δ 129.4) and from H-1′ to C-2′ (δ 50.5) and C-3′ (δ 37.4), and from H-12′/H-16′ to C-10′ (δ 167.6) (Figure 3). In addition, its absolute configuration was established from the negative Cotton effect at 234 nm in the ECD spectrum, which was consistent with a known compound asperphenamate (McCorkindale et al 1978). Furthermore, the specific rotation of 5 was similar to that of asperphenamate.…”

“…13 C NMR and heteronuclear singular quantum correlation (HSQC) spectra showed a total of 22 carbon signals that could be classified into 2 carbonyl, 6 olefinic carbons, 3 sp 3 quaternary carbon, 5 sp 3 methines (including 2 oxymethines), 4 sp 3 methylenes, and 2 methyls (Table 1). Analysing the 1 H and 13 C NMR spectra indicated that 1 possessed the drimane-type sesquiterpenoid skeleton, which showed signals similar to those for 1-deoxypebrolide (McCorkindale et al 1978). The sole difference was that one acetyl group is replaced by a hydroxyl group at C-14 in 1 .…”

“…The other known compounds isolated from P. kongii including pebrolide (Mccorkindale et al 1981) ( 2 ), 1-deoxypebrolide (Mccorkindale et al 1981) ( 3 ), asperphenamate (McCorkindale et al 1978) ( 4 ), N-benzoyl-phenylalaninol (McCorkindale et al 1978) ( 8 ), orsellinic acid (Fang et al 2012) ( 9 ), mycophenolic acid (Makara et al 1996) ( 10 ), and 5, 7-dihydroxy-4-methylphthalide (Fujimoto et al 1999) ( 11 ), and the other known compounds isolated from P. brasilianum including 12, 13-dihydroxyfumitremorgin C (Inokoshi et al 2013) ( 12 ), verruculogen (Afiyatullov et al 2004) ( 13 ), viridicatumtoxin (Inokoshi et al 2013) ( 14 ), dehydroaustin (Hayashi et al 1994) ( 15 ), austinolide (Lo et al 2012) ( 16 ), neoaustin (Hayashi et al 1994) ( 17 ), brasiliamide A (Fujita et al 2002) ( 18 ), brasiliamide C (Fujita & Hayashi 2004) ( 19 ), and aspterric acid (Shimada et al 2002) ( 20 ), were determined by comparison of those reported spectroscopic data. Among these, aspterric acid is reported from P. brasilianum for the first time.…”

New Antioxidant Phenolic Glycosides from Walsura yunnanensis

“…The aglycone of 1 was found to correspond to isolariciresinol, based on a comparison of the experimental 1 H-and 13 C-NMR data with those published for isolariciresinol derivatives [6] [7]. This assumption was further supported by inspection of the HMBC, HMQC, and 1 H, 1 H-COSY spectra of 1.…”