Three new natural furanones, pulvinulin A (1), graminin C (2), and cis-gregatin B (3), together with the known fungal metabolites, graminin B (4) and 10-norparvulenone (5), were isolated from Pulvinula sp. 11120, an endophytic fungal strain occurring in healthy foliage of Cupressus arizonica (Arizona cypress). The structures of 1 and 2 were elucidated by the analysis of their spectroscopic data and chemical interconversions, and that of 3 was determined by comparison with data for synthetic cis-gregatin B. Comparison of spectroscopic data of 4 and 5 with those reported identified them as graminin B and 10-norparvulenone, respectively. Metabolites 1–4 exhibited antibacterial activity against E. coli.
Studies on arid lands plants and microorganisms, Part 28. For Part 27, see BashyalBP, WellensiekBP, RamakrishnanR, FaethSH, AhmadN, GunatilakaAAL. (2014) Altertoxins with potent anti-HIV activity from Alternaria tenuissima, a fungal endophyte of Quercus emoryi. Bioorganic & Medicinal Chemistry, 22, 6112–6116.
2.
FukamiA, NakamuraT, KimY-P, ShiomiK, HayashiM, NagaiT, YamadaH, KomiyamaK, OmuraS. (2000) A new anti-influenza virus antibiotic, 10-norparvulenone from Microsphaeropsis sp. FO-5050. Journal of Antibiotics, 53, 1215–1218.
3.
LiK-K, LuY-J, SongX-H, ShiZ-G, WuX-W, AnL-K, YeC-X, LinY-C. (2010) The metabolites of mangrove endophytic fungus Zh6-B1 from the South China Sea. Bioorganic & Medicinal Chemistry Letters, 20, 3326–3328.
4.
AnkeH, SchwabH, AchenbachH. (1980) Tetronic acid derivatives from Aspergillus panamensis. Production, isolation, characterization and biological activity. Journal of Antibiotics, 33, 931–939.
5.
KobayashiK, UiT. (1977) Graminin A, a new toxic metabolite from Cephalosporium gramineum Nisikado & Ikata. Journal of the Chemical Society, Chemical Communications, 774.
6.
BallantineJA, FerritoV, HassallCH, JonesVIP. (1969) Aspertetronin A and B, two novel tetronic acid derivatives produced by a blocked mutant of Aspergillus rugulosus. Journal of the Chemical Society C: Organic, 56–61.
7.
KimuraT, TakeuchiT, Kumamoto-YonezawaY, OhashiE, OhmoriH, MasutaniC, HanaokaF, SugawaraF, YoshidaH, MizushinaY. (2009) Penicilliols A and B, novel inhibitors specific to mammalian Y-family DNA polymerases. Bioorganic & Medicinal Chemistry, 17, 1811–1816.
8.
KobayashiK, UiT. (1975) Isolation of phytotoxic substances produced by Cephalosporium chamberlain Allington & Chamberlain. Tetrahedron Letters, 47, 4119–4122.
9.
KobayashiK, UiT. (1977) Wilt-inducing antibiotic compounds produced by Cephalosposium gregatum. Physiological Plant Pathology, 11, 55–60.
10.
ClemoNG, PattendenG. (1982) Vinylic carbanions in synthesis. Novel synthesis of iso-gregatin B, iso-aspertetronin A and related O-methyltetronic acids. Tetrahedron Letters, 23, 585–588
11.
ClemoNG, PattendenG. (1985) Synthesis of isoaspertetronin, iso-gregatin and related O-methyltetronic acids. Reassignment of 5-methoxyfuran-3(2H)-one structures to the aspertetronin group of natural products. Journal of the Chemical Society, Perkin Transactions1, 2407–2411.
12.
Burghart-StollH, BrücknerR. (2012) Total synthesis of the gregatins A–D and aspertetronin A: Structure revisions of these compounds and of aspertetronin B, together with plausible structure revisions of gregatin E, cyclogregatin, graminin A, the penicilliols A and B, and the huaspenones A and B. European Journal of Organic Chemistry, 3978–4017.
13.
KobayashiK, UiT. (1979) Phytotoxicity and anti-microbial activity of graminin A produced by Cephalosporium gramineum, the causal agent of Cephalosporium stripe disease of wheat. Physiological Plant Pathology, 14, 129–133.
14.
AlmeidaC, AouadNE, MartinJ, Perez-VictoriaI, Gonzalea-MenendezV, PlatesG, De La CruzM, MonteiroMC, de PedroN, BillsGF, VicenteF, GenilloudO, ReyesF. (2014) Graminin B, a furanone from the fungus Paraconiothyrium sp. Journal of Antibiotics, 67, 421–423.
15.
KirmizigulS, AnilH.UcarF.AkdemirK (1996) Antimicrobial and antifungal activities of three new triterpenoid glycosides. Phytotherapy Research, 10, 274–276.
16.
HoffmanMT, ArnoldAE. (2010). Diverse bacteria inhabit living hyphae of phylogenetically diverse foliar endophytes. Applied and Environmental Microbiology, 76, 4063–4075.
17.
AltschulSF, GishW, MillerW, MyersEW, LipmanDJ. (1990) Basic local alignment search tool. Journal of Molecular Biology, 215, 403–410.
18.
PerryBA, HansenK, PfisterDH. (2007). A phylogenetic overview of the family Pyronemataceae. Mycological Research, 111, 549–571.
ZwicklDJ. (2008) Genetic algorithm approaches for the phylogenetic analysis of large biological sequence datasets under the maximum likelihood criterion. Ph.D. Dissertation, The University of Texas at Austin, Austin, TX, pp. 1–114.
22.
PosadaD, CrandallKA. (1998) MODELTEST: testing the model of DNA substitution, Bioinformatics, 14, 817–818.
23.
U'RenJM, LutzoniF, MiadlikowskaJ, LaetschAD, ArnoldAE. (2012) Host and geographic structure of endophytic and endolichenic fungi at a continental scale. American Journal of Botany, 99, 898–914.
