From the medicinal plant Ginkgo biloba the fungal endophyte Alternaria no.28 was isolated. Extract of the fungus grown in liquid culture media exhibited marked cytotoxic activity when tested in vitro against brine shrimp (Artemia salina). Eight compounds were isolated from the extract of cultures of this endophytic fungus and were elucidated as alterperylenol (1), altertoxin I (2), alternariol (3), alternariol monomethyl ether (4), tenuazonic acid (5) and its derivative (6), together with ergosterol and ergosta-4, 6, 8, 22-tetraen-3-one by means of spectroscopic analysis. Among them, both 5 and 6 showed significant cytotoxic effects in the brine shrimp bioassy, with mortality rates of 73.6% and 68.9%, respectively, at a concentration of 10 μg.mL−1, and they were first isolated from endophytic fungi.
StrobelGA. (2002) Rainforest endophytes and bioactive products. Critical Reviews in Biotechnology, 22, 315–333.
2.
StrobelGA. (2004) Endophytes as sources of bioactive products. Microbes and Infection, 5, 535–544.
3.
SaikkonenK, WaliP, HelanderM, FaethSH. (2004) Evolution of endophyte–plant symbioses. Trends in Plant Science, 9, 275–280.
4.
StrobelG, DaisyB, CastilloU, HarperJ. (2004) Natural products from endophytic microorganisms. Journal of Natural Products, 67, 257–268.
5.
QiaoLR, HeLY, LiYL, HeY, GaoJM. (2008) Studies on anthraquinone metabolites from an endophytic fungus lr88 isolated from Maytenus hookeri. Acta Botanica Boreali-Occidentalia Sinica, 28, 1258–1260.
6.
QiaoLR, YuanL, GaoJM, ZhaoPJ, KangQJ, and ShenYM. (2007) Tricycloalternarene derivatives produced by an endophyte Alternaria alternata isolated from Maytenus hookeri. Journal of Basic Microbiology, 47, 340–343.
7.
WeiGH, YangXY, ZhangJW, GaoJM, MaYQ, FuYY, WangP. (2007) Rhizobialide, a new stearolactone produced by rhizobial Mesorhizobium sp. CCNWGX022, an endophyte from Glycyrrhiza uralensis, Chemstry & Biodiversity, 4, 893–898.
8.
OkunoT, NatsumeI, SawaiK, SawamuraK, FurusakiA, MatsumotoT. (1983) Structure of antifungal and phytotoxic pigments produced by Alternaria sp. Tetrahedron Letters, 24, 5653–5656;
9.
StackME, MazzolaEP, PageSW, PohlandAE, HighetRJ, TempestaMS, CorleyDG. (1986). Mutagenic perylenequinone metabolites of Alternaria alternata: altertoxins I, II, and III. Journal of Natural Products, 49, 866–871;
10.
StierleAC, CardellinaJHII, StrobelGA. (1989) Phytotoxins from Alternaria alternata, a pathogen of spotted knapweed. Journal of Natural Products, 52, 42–47;
11.
NishimuraS, KohmotoK. (1983) Host-specific toxins and chemical structures from Alternaria species. Annual Review of Phytopathology, 21, 87–116.
StinsonEE, OsmanSF, PfefferPE. (1982) Structure of altertoxin I, a mycotoxin from Alternaria. Journal of Organic Chemistry, 47, 4110–4113.
14.
FreemanGG. (1966) Isolation of alternariol and alternariol monomethyl ether from Alternaria dauci (kühn) groves and skolko. Phytochemistry, 5, 719–725;
15.
HarrisTM, HayJV. (1977) Biogenetically modeled syntheses of heptaacetate metabolites. alternariol and lichexanthone. Journal of the Amercan Chemical Society, 99, 1631–1637;
16.
KanakamCC, ManiNS, SubbaRao GSR. (1990) Synthesis based on cyclohexadienes: Part 4. Novel synthesis of the 6-aryl-2,4-dimethoxybenzoates. Alternariol and methyl trimethylaltenusin. Journal of the Chemical Society, Perkin Transactions1, 2233–2237;
17.
KochK, PodlechJ, PfeifferE, MetzlerM. (2005) Total Synthesis of Alternariol. Journal of Organic Chemistry, 70, 3275–3276;
18.
AbeH, FukumotoT, TakeuchiY, HarayamaT. (2007) Synthesis of alternariol through an intramolecular biaryl coupling reaction using palladium reagent. Heterocycles, 74, 265–271.
19.
NolteMJ, SteynPS, WesselsPL. (1980) Structural investigations of 3-acylpyrrolidine-2,4-diones by nuclear magnetic resonance spectroscopy and X-ray crystallography. Journal of the Chemical Society, Perkin Transactions1, 1057–1065.
20.
RosettT, SankhalaRH, StickingsCE, TaylorMEU, ThomasR. (1957) Studies in the biochemistry of microorganisms. 103. Metabolites of Alternaria tenuis Auct.: culture filtrate products. Biochemical Journal, 67, 390–400;
21.
StickingsCE. (1959) Studies in the biochemistry of microorganisms. 106. Metabolites of Alternaria tenuis auct.: the structure of tenuazonic acid. Biochemical Journal, 72, 332–340.
22.
ZhangAL, ZhaoXN, ChenH, LiuLP, KonishiY, GaoJM. (2007) Chemical constituents from the ascomycetous fungus Tuber indicum. Chemistry of Natural Compounds, 43, 349–350;
23.
GaoJM, ShenJ, ZhangAL, ZhuW, LiuJK. (2003) Chemical constituents of the fungus Leccinum extremiorientale. Chinese Journal of Organic Chemistry, 23, 853–857.
24.
ChobotV, OpletalL, JáhodárL, PatelAV, DackeCG, BlundenG. (1997) Ergosta-4,6,8,22-tetraen-3-one from the edible fungus, Pleurotus ostreatus (oyster fungus). Phytochemistry, 45, 1669–1671.
25.
QinJC, ZhangYM, GaoJM, BaiMS, YangSX, LaatschH, ZhangAL. (2009) Bioactive metabolites produced by Chaetomium globosum, an endophytic fungus isolated from Ginkgo biloba. Bioorganic & Medicinal Chemistry Letters, 19, 1572–1574.
26.
AlyAH, Edrada-EbelR, IndrianiID, WrayV, MüllerWE, TotzkeF, ZirrgiebelU, SchächteleC, KubbutatMH, LinWH, ProkschP, EbelR. (2008). Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. Journal of Natural Products, 71, 972–980.
27.
TanN, TaoY, PanJ, WangS, XuF, SheZ, LinY, JonesEBG. (2008) Isolation, structure elucidation, and mutagenicity of four alternariol derivatives produced by the mangrove endophytic fungus No. 2240. Chemistry of Natural compounds, 44, 296–300.
28.
TogashiK, KakeyaH, MorishitaM, SongYX, OsadaH. (1998) Inhibition of human telomerase activity by alterperylenol. Oncology Research, 10, 449–453.
29.
LehmannL, WagnerJ, MetzlerM. (2006) Estrogenic and clastogenic potential of the mycotoxin alternariol in cultured mammalian cells. Food and Chemical Toxicology, 44, 398–408.
30.
MeronuckRA, SteeleJA, MirochaCJ, ChristensenCM. (1972) Tenuazonic acid, a toxin produced by Alternaria alternata. Applied Microbiology, 23, 613–617;
31.
DavisND, DienerUL, Morgan-JonesG. (1977) Tenuazonic acid production by Alternaria alternata and Alternaria tenuissima isolated from cotton. Applied and Environmental Microbiology, 34, 155–157;
32.
LaatschH. (1999). Antibase. Database of microbial metabolites. Chemical Concepts, Heidelberg;
33.
SchlegelB, SchmidtkeM, DörfeltH, KleinwächterP, GräfeU. (2001) (-)-Terpestacin and L-tenuazonic acid, inducers of pigment and aerial mycelium formation by Fusarium culmorum JP 15. Journal of Basic Microbiology, 41, 179–183.
34.
SuzukiS, SanoF, YukiH. (1967) Studies on Antiviral agents. IV. Biological activity of tenuazonic acid derivatives. Chemical & Pharmaceutical Bulletin, 15, 1120–1122;
35.
AntonyM, GuptaKP, JanardananKK, MehrotraNK. (1991) Inhibition of mouse skin tumor promotion by tenuazonic acid. Cancer Letters, 61, 21–25.
