A fungal endophyte which was identified as a hitherto undescribed member of the family Xylariaceae by sequencing of the ITS region was isolated from fresh and healthy leaves of Lansium domesticum collected on tropical peatland of West Kalimantan, Indonesia. Chromatographic separation of the ethyl acetate extract of the fungus resulted in the isolation of three new arugosin type metabolites, including arugosins O (1), P (2), and Q (3). The structures were determined by analysis of 1D and 2D NMR spectra and HRMS data, and by comparison with data from the literature. Biological activities of those compounds are also reported.
ZhaoJ, ZhouL, WangJ, ShanT, ZhongL, LiuX, GaoX. (2010) Endophytic fungi for producing bioactive compounds originally from their host plants. in: Mendez-VilasA. (Eds.), Current Research, Technology and Education Topics in Applied Microbiology and Microbial Biotechnology, Formatex Research Center, Badajoz, Spain, 567-576.
2.
NaliniMS, MaheshB, TajesviMV, PrakashHS, SubbaiahV, KiniKR, ShettyHS. (2005) Fungal endophytes from the three-leaved caper, Crataeva magna (Lour.) DC. (Capparidaceae). Mycopathologia, 159, 245-249.
3.
WongKC, WongSW, SiewSS, TieDY. (1994) Volatile constituents of the fruits of Lansium domesticum Correa (Duku and Langsat) and Baccaurea motleyana (Muell. Arg.) Muell. Arg. (Rambai). Flavour and Fragrance Journal, 9, 319-324.
4.
OmarS, MarcotteM, FieldsP, SanchezPE, PovedaL, MataR, JimenezA, DurstT, ZhangJ, MacKinnon, LeamanD, ArnasonJT, PhilogèneBJR (2007) Antifeedant activities of triterpenoids isolated from tropical Rutales. Journal of Stored Products Research, 43, 92-96.
5.
YappDTT, YapSY. (2003) Lansium domesticum: skin and leaf extracts of this fruit tree interrupt the lifecycle of Plasmodium falciparum, and are active towards a chloroquine-resistant strain of the parasite (T9) in vitro. Journal of Ethnopharmacology, 85, 145-150.
6.
NishizawaM, EmuraM, YamadaH, ShiroM, Chairul, HayashiY, TokudaH. (1989) Isolation of a new cycloartanoid triterpene from leaves of Lansium domesticum: novel skin-tumor promotion inhibitors. Tetrahedron Letters, 30, 5615-5618.
7.
NishizawaM, NademotoY, SastrapradjaS, ShiroM, HayashiY. (1985) Structure of dukunolide A: A tetranortriterpenoid with a new carbon skeleton from Lansium domesticum. Journal of the Chemical Society, Chemical Communications, 395-396.
8.
NishizawaM, NademotoY, SastrapradjaS, ShiroM, HayashiY. (1985) Structure of dukunolides, bitter principles of Lansium domesticum. Journal of Organic Chemistry, 50, 5487-5490.
9.
NishizawaM, NademotoY, SastrapradjaS, ShiroM, HayashiY. (1988) Dukunolide D, E, and F: New tetranortriterpenoids from the seeds of Lansium domesticum. Phytochemistry, 27, 237-239.
10.
FunHK, ChantraprommaS, BoonnakN, ChaiyadejK, ChantraprommaK, YuXL. (2006) Seco-dukunolide F: A new tetranorterpenoid from Lansium domesticum Corr. Acta Crystallographica Section E, E62, o3725-o3727.
11.
TanakaT, IshibashiM, FujimotoH, OkuyamaE, KoyanoT, KowithayakornT, HayashiM, KomiyamaK. (2002) New onoceranoid triterpene constituents from Lansium domesticum. Journal of Natural Products, 65, 1709-1711.
12.
DongSH, ZhangCR, DongL, WuY, YueJM. (2011) Onoceranoid-type triterpenoids from Lansium domesticum. Journal of Natural Products, 74, 1042–1048.
13.
WuZY, WuY, ChenGD, HuD, LiXX, SunX, GuoLD, LiY, YaoXS, GaoH. (2014) Xylariterpenoids A–D, four new sesquiterpenoids from the Xylariaceae fungus. RSC Advances, 4, 54144-54148.
14.
KimKH, BeemelmannsC, MurilloC, GuillénA, UmañaL, Tamayo-CastilloG, KimSN, ClardyJ, CaoS. (2014) Naphthalenones and isocoumarins from a Costa Rican fungus Xylariaceae sp. CR1546C. Journal of Chemical Research, 38, 722-725.
15.
NongXH, ZhengZH, ZhangXY, LuXH, QiSH. (2013) Polyketides from a marine-derived fungus Xylariaceae sp. Marine Drugs, 11, 1718-1927.
16.
WhalleyAJS, EdwardsRL. (1995) Secondary metabolites and systematic arrangement within the Xylariaceae. Canadian Journal of Botany, 73, 802-810.
17.
WhalleyAJS, SuwannasaiN, RuchikachornN, SangvichienE, SihanonthP. (2015) Endophytic Xylariaceae from Thai plants: A research review. Suan Sunandha Science and Technology Journal, 2, 11-17.
18.
LiF, GuoW, CheQ, ZhuT, GuQ, LiD. (2016) Versicones E–H and arugosin K produced by the mangrove-derived fungus Aspergillus versicolor HDN11-84. The Journal of Antibiotics, 1-5.
19.
RukachaisirikulV, SommartU, PhongpaichitS, Hutadilok-TowatanaN, RungjindamaiN, SakayarojJ. (2007) Metabolites from the Xylariaceous fungus PSU-A80. Chemical and Pharmaceutical Bulletin, 55, 1316-1318.
20.
SunTY, KuangRQ, ChenGD, QinSY, WangCX, HuD, WuB, LiuXZ, YaoXS, GaoH. (2016) Three pairs of new isopentenyl dibenzo[b,e]oxepinone enantiomers from Talaromyces flavus, a wetland soil-derived fungus. Molecules, 21, 1-12.
21.
BallantineJA, FrancisDJ, HassallCH, WrightJLC. (1970) The biosynthesis of phenols. Part XXI. The molecular structure of arugosin, a metabolite of wild-type strain of Aspergillus rugulosus. Journal of the Chemical Society. Perkin Transactions1, 1175-1182.
22.
CatlinER, HassallCH. (1971) Biosynthesis of phenols. Part XXII. Synthesis of 3-isopentyl-2,6-dimethoxyphenyl-(3,6-dimethoxy-2,4-dimethylphenyl) methane, a degradation product of arugosin. Journal of Chemical Society (C), 460-463.
23.
ChexalKK, HolkerJSE, SimpsonTJ. (1975) The biosynthesis of fungal metabolites. Part VI. Structures and biosynthesis of some minor metabolites from variant strains of Aspergillus variecolor. Journal of Chemical Society, Perkin Transaction1, 549-554.
24.
PockrandtD, LudwigL, FanA, KönigGM, LiSM. (2012) New insights into the biosynthesis of prenylated xanthones: Xptb from Aspergillus nidulans catalyses an O-prenylation of xanthones. ChemBioChem, 13, 2764-2771.
25.
HeinSM, GloerJB, KosterB, MallochD. (1998) Arugosin F: A new antifungal metabolite from the Coprophilous fungus Ascodesmis sphaerospora. Journal of Natural Products, 61, 1566-1567.
26.
KraljA, KehrausS, KrickA, EguerevaE, KelterG, MaurerM, WortmannA, FiebigHH, KönigGM. (2006) Arugosins G and H: Prenylated polyketides from the marine-derived fungus Emericella nidulans var. acristata. Journal of Natural Products, 69, 995-1000.
27.
KjerJ, DebbabA, AlyAH, ProkschP. (2010) Methods for isolation of marine-derived endophytic fungi and their bioactive secondary products. Nature Protocols, 5, 479-490.
