The structure and chemistry of pebrolide, desacetylpebrolide and 1-deoxypebrolide, sesquiterpene benzoates from penicillium brevicompactum

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

“…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.…”

Drimane Sesquiterpene Lactones from Peniophora polygonia

“…Peniopholide contains no olefinic carbons (13C nmr) indicating that it is tricyclic. The 'H-nmr spectrum showed three Me groups as singlets, which together with the characteristic high field signal at 0.98 ppm (H-5, dd,J= 13.8, 2.0 Hz) suggeted a drimane sesquiterpenoid skeleton (4,5). The presence of the fragment CO-0-CH2-CH was indicated by chemical shifts and the coupling pattern in the 'H-nmr spectrum (see Table 1).…”

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Several new drimane sesquiterpenes, peniopholide [1],3 ß-hydroxypeniopholide [2], 3<x-hydroxypeniopholide [3], 3 ß-hydroxydihydroconfertifolin [5], 6ß-hydroxycinnamolide [8], 6a-hydroxycinnamolide [10], and 7 -hydroxyconfertifolin [11], have been isolated from Peniophora polygonia, a fungus associated with aspen. The structures were established by spectroscopic methods.

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Occurrence, biological activity and synthesis of drimane sesquiterpenoids

“…54 When cultivated in solid or liquid medium Aspergillus sp., 55- 57 Kuehneromyces sp., 58 Trichopezizella barbata, 59 Mniopetalum sp. and Panus sp., 60 Penicillium brevicom-pactum, 61 Lactarius uvidus, 62 Polyporus ciliatus, 63 and P. arcularius, 63,64 Pestalotiopsis spp., endophytic fungi of the yew tree, and Lepista glaucocana 65 afforded novel biologically active drimanes. A series of structurally related dimeric drimanes were isolated from Cryptoporus volvatus fruit bodies, 66 Ganoderma neo-japonicum, 67 Cryptoporus volvatus infected by Paecylomyces varioti, 68 Haploporus odorus, 69 and from Roseoformes subflexibilis.…”