The saltwater culture of an Arthrinium sp. derived from a marine sediment collected at −550 meters was a source of tyrosol (1) and a new compound, tyrosol carbamate (2). This is only the third report of novel secondary metabolites discovered from the saltwater culture of a deep-water marine-derived fungus.
ChengX-C, VarogluM, AbrellLM, CrewsP, LobkovskyE, ClardyJ. (1994) Chloriolins A-C, chlorinated sesquiterpenes produced by fungal cultures separated from a Jaspis marine sponge. Journal of Organic Chemistry, 59, 6344–6348.
2.
KobayashiM, UeharaH, MatsunamiK, AokiS, KitagawaI. (1993) Trichoharzin, a new polyketide produced by the imperfect fungus Trichoderma harzianum separated from the marine sponge Micale cecilia.Tetrahedron Letters, 34, 7925–7928.
3.
selected highlights include (a) Chlorocarolides A-B from Aspergillus: AbrellLM, BorgesonB, CrewsP. (1996) A new polyketide, secocurvularin, from the salt water culture of a sponge derived fungus. Tetrahedron Letters, 37, 8983–8984
4.
(b) Asperazine from Aspergillus: isolVarogluM, CorbettTH, ValerioteFA, CrewsP. (1997) Asperazine, a selective cytotoxic alkaloid from a sponge-derived culture of Aspergillus niger.Journal of Organic Chemistry, 62, 7078–7079; synGovekSP, OvermanLE. (2001) Total synthesis of asperazine. Journal of the American Chemical Society, 123, 9468–9469
5.
(c) epoxysorbicillinol derived from Trichoderma longibrachiatum: isolSperryS, SamuelsGJ, CrewsP. (1998) Vertinoid polyketides from the saltwater culture of the fungus Trichoderma longibrachiatum separated from a Haliclona marine sponge. Journal of Organic Chemistry, 63, 10011–10014
6.
synWoodJL, ThompsonBD, YusuffN, PflumDA, MatthäusMSP. (2001) Total synthesis of (±)-epoxysorbicillinol. Journal of the American Chemical Society, 123, 2097–2098
7.
(d) ChristianOE, ComptonJ, ChristianKR, MooberrySL, ValerioteFA, CrewsP. (2005) Using jasplakinolide to turn on pathways that enable the isolation of new chaetoglobosins from Phomospis asparagi.Journal of Natural Products, 68, 1592–1597
8.
(e) BootCM, TenneyK, ValerioteFA, CrewsP. (2006) Highly N-methylated linear peptides produced by an atypical sponge-derived Acremonium sp. Journal of Natural Products, 69, 83–92.
9.
selected highlights include (a) gymnastatins from Gymnacella dankaliensis: isolAmagataT, DoiM, OhtaT, MinouraK, NumataA. (1998) Absolute stereostructures of novel cytotoxic metabolites, gymnastatins A-E, from a Gymnacella species separated from a Halichondria sponge. Journal of the Chemical Society. Perkin Transactions. I, 21, 3585–3599; synGurjarMK, BhaketP. (2000) Total synthesis of a novel cytotoxic metabolite gymnastatin A. Heterocycles, 53, 143–149
10.
(b) petrosifungins from a Penicillium: BringmannG, LangG, SteffensS, SchaumannK. (2004) Petrosifungins A and B, novel cyclodepsipeptides from a sponge-derived strain of Penicillium brevicompactum.Journal of Natural Products, 67, 311–315
11.
(c) aspernigrins from Aspergillus: HiortJ, MaksimenkaK, ReichertM, Perovic-OttstadtS, LinWH, WrayV, SteubeK, SchaumannK, WeberH, ProkschP, EbelR, MullerWEG, BringmannG. (2004) New natural products from the sponge-derived fungus Aspergillus niger.Journal of Natural Products, 67, 1532–1543
12.
(d) gliotide from Gliocladium:LangG, MitovaMI, EllisG, Van der SarS, PhippsRK, BluntJW, CummingsNJ, ColeALJ, MunroMHG. (2006) Bioactivity profiling using HPLC/microtiter-plate analysis: application to a New Zealand marine alga-derived fungus, Gliocladium sp. Journal of Natural Products, 69, 621–624.
13.
BugniTS, IrelandCM. (2004) Marine-derived fungi: a chemically and biologically diverse group of microorganisms. Natural Product Reports, 21, 143–163 (273 compounds discovered to 2002).
14.
(a) GautschiJT, AmagataT, AmagataA, ValerioteFA, MooberrySL, CrewsP. (2004) Expanding the strategies in natural product studies of marine-derived fungi: a chemical investigation of Penicillium obtained from deep water sediment. Journal of Natural Products, 67, 362–367
There is no general agreement on the use of the term “deep water,” however, we prefer the definition of - 90 m or greater below sea level based on the limitations of non-decompression, non-rebreather, scientific diving procedures, and to be consistent with current literature on marine natural products from deep water organisms.
17.
The first report of fungal metabolites from a deep water fungal strain (Aspergillus fumigatus, sediment, −695 m) involved non-saltwater culture conditions: CuiC-B, KakeyaH, OsadaH. (1996) Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase. Tetrahedron, 52, 12651–12666.
18.
ParkYC, GunasekeraSP, LopezJV, McCarthyPJ, WrightAE. (2006) Metabolites from the marine-derived fungus Chromocleista sp. isolated from a deep-water sediment sample collected in the Gulf of Mexico. Journal of Natural Products, 69, 580–584.
19.
(a) KohlmeyerJ, KohlemeyerE. (1979) Marine Mycology The Higher Fungi. Academic Press, New York, USA, 41–44
20.
(b) JohnsonT, SparrowF. (1970) Fungi in Oceans and Estuaries. Verlag von J. Cramer, New York, USA, 9–12.
21.
The sparse literature of deep-water fungi includes: (a) RaghukumarC, RaghukumarS, SharmaS, ChandramohanD. (1992) Diversity and adaptations of deep sea microorganisms. Oceanographaphic Indian Oceanography, 1, 3–9
22.
(b) LorenzR, MolitorisH. (1997) Cultivation of fungi under simulated deep-sea conditions. Mycological Research, 101, 1355–1365
23.
(c) NagahamaT, HamamotoM, NakaseT, TakamiH, HorikoshiK. (2001) Distribution and identification of red yeasts in deep-sea environments around the northwest Pacific Ocean. Antonie van Leeuwenhoek, 80, 101–110
24.
(d) ChandramohanD. (1997) Recent advances in marine microbiology: the Indian scenario. Journal of Marine Biotechnology, 5, 73–81
25.
(e) NagahamaT. (2001) Rhodotorula lamellibrachii sp. nov., a new yeast species from a tubeworm collected at the deep-sea floor in Sagami Bay and its phylogenetic analysis. Antonie van Leeuwenhoek, 80, 317–323
26.
(f) RaghukumarC, RaghukumarS. (1998) Barotolerance of fungi isolated from deep sea sediments of the Indian ocean. Aquatic Microbial Ecology, 15, 153–163
27.
(g) AbeF, HorikoshiK. (1998) Analysis of intracellular pH in the yeast Saccharomyces cerevisiae under elevated hydrostatic pressure: a study in baro- (piezo-) physiology. Extremophiles, 2, 223–228
28.
(h) GondaK, JendrossekD, MolitorisH. (2000) Fungal degradation of the thermoplastic polymer poly-β-hydroxybutyric acid (PHB) under simulated deep sea pressure. Hydrobiologia, 426, 173–183.
29.
(a) SperryS, ValerioteFA, CorbettTH, CrewsP. (1998) Isolation and cytotoxic evaluation of marine sponge-derived norterpene peroxides. Journal of Natural Products, 61, 241–247
30.
(b) ValerioteF, GrieshaberC, MediaJ, PietraszkewicsH, HoffmanJ, PanM, McLaughlinS. (2002) Discovery and development of anticancer agents from plants. Journal of Experimental Therapeutics and Oncolology, 2, 228–236.
31.
For similar strategies, see (a) StessmanC, EbelR, CorvinoA, CrewsP. (2002) Employing dereplication and gradient 1D NMR methods to rapidly characterize sponge-derived sesterterpenes. Journal of Natural Products, 65, 1183–1186
32.
(b) EdradaR, HeubesM, BrauersG, WrayV, BergA, GräfeU, WohlfarthM, MühlbacherJ, SchaumannK, SudarsonoBringmann G, ProkschP. (2002) Online analysis of Xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua.Journal of Natural Products, 65, 1598–1604
33.
(c) OsterageC, SchwibbeM, KönigG, WrightA. (2000) Differences between marine and terrestrial Phoma species as determined by HPLC-DAD and HPLC-MS. Phytochemical Analysis, 11, 288–294
databases known to accurately identify Arthrinium phaeospermumHallL, WohlfielS, RobertsGD. (2004) Experience with the MicroSeq D2 large-subunit ribosomal DNA sequencing kit for identification of filamentous fungi encountered in the clinical laboratory. Journal of Clinical Microbiology, 42, 622–626.
36.
(a) arthrinoneQian-CutroneJ, GaoQ, HuangS, KlohrSE, VeitchJA, Yue-ZhongS. (1994) Arthrinone, a novel fungal metabolite from Arthrinium sp. FA 1744. Journal of Natural Products, 57, 1656–1660
(c) bostrycin strucNodaT, TakeT, WatanabeT, AbeJ. (1970) The structure of bostrycin. Tetrahedron, 26, 1339–1346.
39.
(a) maxikdiolOndeykaJG, BallRG, GarciaML, DombrowskiAW, SabnisG, KaczorowskiGJ, ZinkDL, BillsGF, GoetzMA, SchmalhoferWA, SinghSB. (1995) A carotane sesquiterpene as a potent modulator of the Maxi-K channel from Arthrinium phaesospermum.Bioorganic & Medicinal Chemistry Letters, 5, 733–734
40.
(b) arundifunginCabelloMA, PlatasG, ColladoJ, DíezMT, MartínI, VicenteF, MeinzM, OnishiJC, DouglasC, ThompsonJ, KurtzMB, SchwartzRE, BillsGF, GiacobbeRA, AbruzzoGK, FlatteryAM, KongL, PeláezF. (2001) Arundifungin, a novel antifungal compound produced by fungi: biological activity and taxonomy of the producing organisms. International Microbiology, 4, 93–102
41.
(c) terpestacinIimuraS, OkaM, NaritaY, KonishiM, KakisawaH, GaoQ, OkiT. (1993) Terpestacin, a novel syncytium formation inhibitor, isolated from Arthrinium species. Journal of Antibiotics, 46, 367–373.
42.
arthrichitinVijayakumarEKS, RoyK, ChatterjeeS, DeshmukhSK, GanguliBN, FehlhaberH-W, KoglerH. (1996) Arthrichitin, a new cell wall active metabolite from Arthrinium phaeospermum.Journal of Organic Chemistry, 61, 6591–6593.
43.
TsukamotoS, YoshidaT, HosonoH, OhtaT, YokosawabH. (2006) Hexylitaconic acid: a new inhibitor of p53-HDM2 interaction isolated from a marine-derived fungus, Arthrinium sp. Bioorganic & Medicinal Chemistry Letters, 16, 69–71.
44.
(a) ChenH, FujitaM, FengQ, ClardyJ, FinkGR. (2004) Tyrosol is a quorum-sensing molecule in Candida albicans.Proceedings of the National Academy of Sciences of the United States of America, 101, 5048–5052
45.
(b) isolAyerWA, HoyanoY, PedrasMS, VanaltenaI. (1986) The chemistry of the blue stain fungi. Part 1. Some metabolites of Ceratocystis species associated with mountain pine beetle infected lodgepole pine. Canadian Journal of Chemistry, 64, 904–909
46.
(c) isolCrossBE, GroveJF, HansonJR, MorrisonA, CurtisPJ, GaltRHB. (1963) New metabolites of Giberrella fukikuroi.Journal of the Chemical Society, 2937–2943.
47.
66 analogs of tyrosol have been reported from natural sources: Dictionary of Natural Products2004, Web Version (2), Chapman & Hall/CRC Press (www.chemnetbase.com).
48.
Aldrich Library of 13C and 1H FT NMR Spectra (1992) 2, 409.
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EspinoCG, DuBoisJ. (2001) A Rh-catalyzed C-H insertion reaction for the oxidative conversion of carbamates to oxazolidinones. Angewandt Chemie International Edition, 40, 598–601.
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KoguchiY, AsaiY, SuzukiS-I, NishioM, YanakaN, OmoriK, OhnukiT, KomatsubaraS. (1998) TMC-49A, a novel transcriptional up-regulator of low density lipoprotein receptor, produced by Streptomyces sp. AS1345. Journal of Antibiotics, 51, 107–111.
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LitaudonM, HartJB, BluntJW, LakeRJ, MunroMHG. (1994) Isohomohalichondrin B, a new antitumour polyether macrolide from the New Zealand deep-water sponge Lissodendoryx sp. Tetrahedron Letters, 35, 9435–9438.
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PhuwapraisirisanP, MatsunagaS, van SoestRWM, FusetaniN. (2004) Shinsonefuran, a cytotoxic furanosesterterpene with a novel carbon skeleton, from the deep-sea sponge Stoeba extensa.Tetrahedron Letters, 45, 2125–2128.
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KichaAA, KalinovskyAI, IvanchinaNV, StonikVA. (1999) New steroid glycosides from the deep-water starfish Mediaster murrayi.Journal of Natural Products, 62, 279–282.
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PiñaIC, GautschiJT, WangG-Y-S, SandersML, SchmitzFJ, FranceD, Cornell-KennonS, SambucettiLC, RemiszewskiSW, PerezLB, BairKW, CrewsP. (2003) Psammaplins from the sponge Pseudoceratina purpurea: inhibition of both histone deacetylase and DNA methyltransferase. Journal of Organic Chemistry, 68, 3866–3873.
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UCSC deep water, marine-derived fungal libraries hold over 70 viable saltwater strains from 6 distinct geographic collections ranging in depths between −90 and −1830 m.
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