Two antifouling compounds, aureobasidin (1), a new ester with an unusual 4,6-dihydroxydecanoic acid residue, and (3R,5S)-3,5-dihydroxydecanoic acid (2), were isolated from the marine-derived fungus Aureobasidium sp., in addition to (5R,3Z)-5-hydroxydec-3-enoic acid (3) and (R)-3-hydroxydecanoic acid (4). The structures were unambiguously established by IR, 1D and 2D NMR spectroscopic and mass spectral data. Compounds 1-3 were found to be active against Bacillus subtilis, Escherichia coli and Staphyllococcus aureus. Compound 3 showed fungistatic activity against Candida albicans.
BugniT, AbbanatD, BernanVS, MaieseWM, GreensteinM, Van WagonerRM, IrelandCM. (2000) Yanuthones: Novel metabolites from a marine isolate of Aspergillus niger. Journal of Organic Chemistry, 65, 7195–7200.
5.
McDonaldLA, AbbanatDR, BarbieriLR, BernanVS, DiscafaniCM, GreensteinM, JosephK, KorshallaD, LassotaP, CarterMT. (1999) Spiroxins, DNA cleaving antitumor antibiotics from a marine-derived fungus. Tetrahedron Letters, 40, 2489–2492.
6.
OhDC, JensenPR, FenicalW. (2006) Zygosporamide, a cytotoxic cyclic depsipeptide from the marine-derived fungus Zygosporium masonii. Tetrahedron Letters, 47, 8625–8628.
7.
BelofskyGN, JensenPR, FenicalW. (1999) Sansalvamide: A new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium. Tetrahedron Letters, 40, 2913–2916.
8.
NumataA, TakahashiC, ItoY, TakadaT, KawaiK, UsamiY, MatsumuraE, ImachiM, ItoT, HasegawaT. (1993) Communesins, cytotoxic metabolites of a fungus isolated from a marine alga. Tetrahedron Letters, 34, 2355–2358.
SteinbergPD, de NysR, KjellebergS. (2002) Chemical cues for surface colonization, Journal of Chemical Ecology, 28, 1935–1951.
12.
FuestaniN. (2004), Biofouling and antifouling. Natural Product Reports, 21, 94–104.
13.
CescuttiP, PupulinR, DelbenF, AbbateM, DentiniM, SparapanoL, RizzoR, CrescenzibV. (2002) New exopolysaccharides produced by Aureobasidium pullulans grown on glucosamine. Carbohydrate Research, 337, 1203–1209.
14.
ShigemoriH, TenmaM, ShimazakiK, KobayashiJ. (1998) Three new metabolites from the marine yeast Aureobasidium pullulans. Journal of Natural Products, 61, 696–698.
15.
HeH, FaulknerDJ. (2004) A new imidazole alkaloid from the marine sponge Leucetta microraphis. Journal of Organic Chemistry, 57, 2176–2178.
16.
RadhikaP, RaoVL, LaatschH. (2004) Chemical constituents of a marine soft coral of the genus Labophytum. Chemical & Pharmaceutical Bulletin, 52, 1345–1348.
17.
WeaverN, JohnstonNC, BenjaminR, LawJH. (1968) Novel fatty acids from the royal jelly of honeybees (Apis mellifera, L.), Lipids, 3, 535–538.
18.
LiH, MatsungaS, FusetaniN. (1995) Halicylindrosides, Antifungal and cytotoxic cerebrosides from the marine sponge Halichondria cylindrata. Tetrahedron, 51, 2273–2280.
19.
HattoriT, AdachiK, ShizuriY. (1998) New ceramides from marine sponge Haliclona koremella and related compounds as antifouling substances against macroalgae. Journal of Natural Products, 61, 823–826.
20.
ZhangW, MaX, ZhangC, SuJ, YeW, ZhangX, YaoX, ZengL. (2005) Two new ceramides from the marine sponge Ircinia fasciculate. Helvetica Chimica Acta, 88, 885–890.
21.
LourencoA, LoboA, RodriguezB, JimenoM. (1996) Ceramides from the fungus Phellinus pini. Phytochemistry, 43, 617–620.
22.
QuY, ZhangH, LiuJ. (2004) Isolation and structure of a new ceramide from the basidiomycete Hygrophorus eburneus. Zeitschrift fuer Naturforschung, 59B, 241–244.
23.
IchiharaA, HashimotoM, SakamuraS. (1985) (3R,5Z)(-)-3-Hydroxy-5-dodecenoic acid, a phytotoxic metabolite of Pythium ultimum. Agricultural and Biological Chemistry, 49, 2207–2209.
24.
SjogrenJ, MagnussonJ, BrobergA, SchnurerJ. (2003) Antifungal 3-hydroxy fatty acids from Lactobacillus plantarum MiLAB 14, Applied and Environmental Microbiology, 69, 7554–7557.
25.
OkuiS, UchiyamaM, MizugakiM. (1963) Metabolism of hydroxy fatty acids. 2. Intermediates of the oxidative breakdown of ricinoleic acid by genus Candida. Journal of Biochemistry, 54, 536–540.
26.
LeeSY, ParkSH, LeeY, LeeSH. (2003) Production of chiral and other valuable compounds from microbial polyesters, p. 375–387. In: SteinbüchelE. (Ed.), Biopolymers, vol. 4:. Wiley-Vch. Verlag GmbH, Weinheim, Germany.
27.
ZhengZ, GongO, LiuT, DengY, ChenJ, ChenG. (2004) Thioesterase II of Escherichia coli plays an important role in 3-hydroxydecanoic acid production. Applied and Environmental Microbiology, 70, 3807–3813.
28.
MoireL, RezzonicoE, GoepfertS, PoirierY. (2004) Impact of unusual fatty acid synthesis on futile cycling through β-oxidation and on gene expression in transgenic plants. Plant Physiology, 134, 432–442.
29.
WachéYL, LarocheC, BergmarkK, Møller-AndersenC, AguedoM, Le DallM, WangH, NicaudJ, BelinJ. (2000) Involvement of acyl coenzyme A oxidase isozymes in biotransformation of methyl ricinoleate into γ-decalactone. Applied and Environmental Microbiology, 66, 1233–1236.
30.
BrobergA, JacobssonK, StrömK, SchnürerJ. (2007) Metabolite profiles of lactic acid bacteria in grass silage. Applied and Environmental Microbiology, 73, 5547–5552.
31.
FéronG, DufosséL, MauvaisG, BonnarmeP, SpinnlerHE. (1997) Fatty acid accumulation in the yeast Sporidiobolus salmonicolor during batch production of gamma-decalactone. FEMS Microbiology Letters, 149, 17–24.
32.
WeaverN, LawJH, JohnstonN. (1964) Studies on the lipids of royal jelly, Biochimica et Biophysica Acta, 84, 305–315
33.
NakanoK, MurakamiK, NoharaT, TomimastuT, KawasakiT. (1981) The constituents of Paris verticillata M.V. Bieb. Chemical & Pharmaceutical Bulletin, 29, 1445–1451.
34.
ChristieWW. (1993) Preparation of ester derivatives of fatty acids for chromatographic analysis. In: Advances in Lipid Methodology - Two, Oily Press, Dundee. 69–111.
35.
HirotaH, OkinoT, YoshimuraE, FusetaniN. (1998) Five new antifouling sesquiterpenes from two marine sponges of the genus Axinyssa and the nudibranch Phyllidia pustulosa, Tetrahedron, 54, 13971–13980.
36.
TomonoY, HitoraH, FusetaniN. (1999) Isogosterones A-D, antifouling 13,17-secosteroids from an octocoral Dendronephthya sp. Journal of Organic Chemistry, 64, 2272–2275.
37.
ElkhayatE, EdradaR, EbelR, WrayV, van SoestR, WiryowidagdoS, MohamedM, MuellerW, ProkschP. (2004) New luffariellolide derivatives from the Indonesian sponge Acanthodendrilla sp. Journal of Natural Products, 67, 1809–1817.
38.
HassanW, ElkhayatE, EdradaR, EbelR, ProkschP.(2007) New bromopyrrole alkaloids from the tropical marine sponges Axinella damicornis and Stylissa flabelliformis. Natural Product Communications, 2, 1–6.