A new ascochlorin, 10′-deoxy-10′α-hydroxyascochlorin (1), together with ascofuranone (2), ascochlorin (3), and 4′,5′-dihydro-4′β-hydroxyascochlorin (4) were isolated from Acremonium sp. LG0808, an endophytic fungal strain occurring in the stem tissue of the medicinal plant, Ephedra trifurca. The structure of 1 was elucidated on the basis of its high-resolution mass spectrometric, and 1D and 2D NMR spectroscopic data. Compounds 1 and 3 inhibited migration of metastatic prostate cancer cells, PC-3M. In addition, 3 exhibited moderately selective cytotoxicity against the NCI-H460 (non-small cell lung cancer) cell line, but its dimethyl ether (6) showed selective activity against PC-3M, MCF-7 (breast cancer), and MDA-MB-231 (metastatic breast cancer) cell lines.
Studies on Arid Lands Plants and Microorganisms, Part 24. For Part 23, see WijeratneEMK, BashyalBP, LiuMX, RochaDD, GunaherathGMKB, U'RenJM, GunatilakaMK, ArnoldAE, GunatilakaAAL (2012) Geopyxins A-E, ent-kaurane diterpenoids from endolichenic fungal strain Geopyxis aff. majalis and Geopyxis sp. AZ0066: Structure-activity relationships of geopyxins and their analogues. Journal of Natural Products, 75, 361–369.
2.
ZhangP, BaoB, DangHT, HongJ, LeeHJ, YooES, BaeKS. (2009) Anti-inflammatory sesquiterpenoids from a sponge-derived fungus Acremonium sp. Journal of Natural Products, 72, 270–275.
3.
SasakiH, HosokawaT, SawadaM, AndoK., (1973) Isolation and structure of ascofuranone and ascofuranol, antibiotics with hypolipidemic activity. The Journal of Antibiotics, 25, 676–680.
4.
SasakiH, HosokawaT, NawataY, AndoK., (1974) Isolation and structure of ascochlorin and its analogs. Agricultural and Biological Chemistry, 38, 1463–1466.
5.
SeeponkaiP, IsakaM, KitakoopP, BoonudomlapU, ThebtaranonthY., (2004) A novel ascochlorin glycoside from the insect pathogenic fungus Verticillium hemipterigenum BCC2370. The Journal of Antibiotics, 57, 10–16.
6.
O'BrienJ, WilsonI, OrtonT, PognanF., (2000) Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. European Journal of Biochemistry, 267, 5421–5426.
7.
ZhanJ, BurnsAM, LiuMX, FaethSH, GunatilakaAAL. (2007) Search for cell motility and angiogenesis inhibitors with potential anticancer activity: beauvericin and other constituents of two endophytic strains of Fusarium oxysporum, Journal of Natural Products, 70, 227–232.
8.
GakuzoT, SeikichiS, AkiraT, KunioA, KeiA., (1968) Antiviral and antitumor antibiotics. I. Ascochlorin, a new antibiotic found by the paper-disk, agar-diffusion method. 1. Isolation and biological and chemical properties of ascochlorin. The Journal of Antibiotics, 21, 539–544.
9.
EllestadGA, EvansRH, KunstmannMP. (1969) Some new terpenoid metabolites from an unidentified Fusarium species. Tetrahedron, 25, 1323–1334.
10.
KosugeY, SuzukiA, HirotaS, TamuraS. (1973) Structure of collectochlorin from Collectotrichum nicotianae. Agricultural and Biological Chemistry, 37, 455–456.
11.
SinghSBR, BallRG, BillsGF, CascalesC, GibbsJB, GoetzMA, HoogsteenK, JenkinsRG, LieschJM, LinghamRB, SilvermanKC, ZinkDL. (1996) Chemistry and biology of cylindrols: Novel inhibitors of Ras farnesyl-protein transferase from Cylindrocarpon lucidum. Journal of Organic Chemistry, 61, 7727–7737.
12.
KatoA, AndoK, TamuraG, ArimaK., (1970) Cylindrochlorin, a new antibiotic produced by Cylindrocladium. The Journal of Antibiotics, 23, 168–169.
13.
HayakawaS, MinatoH, KatagiriK., (1971) The ilicicolins, antibiotics from Cylindrocladium ilicicola. The Journal of Antibiotics, 24, 653–654.
14.
AldridgeDC, BorrowA, FosterRG, LargeMS, SpencerH, TurnerWB. (1972) Metabolites of Nectria coccinea. Journal of the Chemical Society Perkin Transactions I. 2136–2141.
TakamatsuS, RhoM–C, MasumaR, HayashiM, KomiyamaK, TanakaH, OmuraS. (1994) A novel testosterone 5α-reductase inhibitor, 8′,9′-dehydroascochlorin produced by Verticillium sp. FO-2787. Chemical and Pharmaceutical Bulletin, 42, 953–956.
17.
NawataY, AndoK, TamuraG, ArimaK, IitakaY., (1969) Molecular structure of ascochlorin. The Journal of Antibiotics, 22, 511–512.
18.
TakatsukiA, TamuraG, ArimaK., (1969) Antiviral and antitumor antibiotics. XIV. Effects of ascochlorin and other respiration inhibitors on multiplication of Newcastle disease virus in cultured cells. Applied Microbiology, 17, 825–829.
19.
SawadaM, HosokawaT, OkutomiT, AndoK., (1973) Isolation and structure of ascofuranone and ascofranol, antibiotics with hypolipidemic activity. The Journal of Antibiotics, 26, 681–686.
20.
HosokawaT, OkutomiT, SawadaM, AndoK, TamuraG., (1982) An ascochlorin derivative, AS-6, potentiates insulin action in streptozotocin diabetic mice and rats. Agricultural and Biological Chemistry, 46, 2865–2869.
21.
HosokawaT, AndoK, TamuraG., (1985) An ascochlorin derivative, AS-6, reduces insulin resistance in the genetically obese diabetic mouse, db/db. Diabetes, 34, 267–274.
22.
MagaeJ, TsurugaM, MaruyamaA, FurukawaC, KojimaS, ShimizuH, AndoK., (2009) Relationship between peroxisome proliferator-activated receptor-gamma activation and the ameliorative effects of ascochlorin derivatives on type II diabetes. The Journal of Antibiotics, 62, 365–369.
23.
TsurugaM, NakajimaH., MagaeJ. (2007) Immunosuppressive activity of 4-O-methylascochlorin. The Journal of Antibiotics, 60, 20–26.
24.
MagaeJ, HisokawaT, AndoK, NagaiK, TamuraG., (1982) Antitumor protective property of an isoprenoid antibiotic, ascofuranone. The Journal of Antibiotics, 35, 1547–1552.
25.
KitaK. (2004) Drug development at global level. Farumashia, 40, 909–913.
26.
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.
27.
EwingB, GreenP., (1998) Base-calling of automated sequencer traces using Phred. II. Error–probabilities. Genome Research, 8, 186–194.
28.
EwingB, HillierL, WendlMC, GreenP., (1998) Base-calling of automated sequencer traces using Phred. I. Accuracy assessment. Genome Research, 8, 175–185.
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.
34.
PosadaD, CrandallKA. (1998) MODEL TEST: testing the model of DNA substitution. Bioinformatics, 14, 817–818.
35.
KolaríkM, FreelandE, UtleyC, TisseratN., (2011) Geosmithia morbida sp. nov., a new phytopathogenic species living in symbiosis with the walnut twig beetle (Pityophthorus juglandis) on Juglans in USA. Mycologia, 103, 325–332.
36.
SummerbellR, GueidanC, SchroersH-J, de HoogGS, StarinkM, Arocha-RoseteY, GuarroJ, ScottJA. (2011) Acremonium phylogenetic overview and revision of Gliomastix, Sarocladium, and Trichothecium. Studies in Mycology, 68, 139–162.
