Aspergillus awamori was isolated from a diseased banana fruit, Musa acuminata cv. Ambul. The fungus was fermented in potato dextrose broth and on potato dextrose agar media and the fungal media were extracted with EtOAc. Chromatographic separation of the EtOAc extracts furnished 4-methoxybenzyl 7-phenylacetamido-3-vinyl-3-cephem-4-carboxylate (1), along with three naphtho-γ-pyrones, flavasperone (2), foncesinone A (3) and aurasperone A (4), and three alkaloids, aspernigrin A (5), pestalamide C (6) and nigragillin (7). Compound 1, a known key intermediate in the chemical synthesis of cepham antibiotics, was isolated from a natural source for the first time. Compound 1 is the first 3-vinyl cephem derivative of microbial origin.
NielsonKF, MogensenJM, JohansenM, LarsenTO, FrisvadJC. (2009) Review of secondary metabolites and mycotoxins from the Aspergillus niger group. Analytical and Bioanalytical Chemistry, 395, 1225–1242.
6.
SongYC, LiH, YeYH, ShanCY, YangYM, TanRX. (2004) Endophytic naphthopyrone metabolites are co-inhibitors of xanthine oxidase, SW1116 cell and some microbial growths. FEMS Microbiology Letters, 241, 67–72.
7.
KoyamaK, OminatoK, NatoriS, TashiroT, TsuruoT. (1988) Cytotoxic and antitumor activities of fungal bis(naphtha-y-pyrone) derivatives. Journal of Pharmacobiodynamics, 11, 630–655.
8.
GhosalS, BiswasK, ChakrabartiDK. (1979) Toxic naphtha-γ-pyrones from Aspergillus niger. Journal of Agricultural and Food Chemistry, 27, 1347–1351.
9.
PhotitaW, LumyongS, LumyongP, McKenzieEHC, HydeKD. (2004) Are some endophytes of Musa acuminata latent pathogens?Fungal Diversity, 16, 131–140
Núñez-TrujilloG, CabreraR, CosoveanuA, MartinTT, GiménezC. (2013) Survey of banana endophytic fungi isolated in artificial culture media from an applied viewpoint. Journal of Horticulture, Forestry and Biotechnology, 17, 22–25.
12.
SakuraiM, KohnoJ, YamamotoK, OkudaT, NishioM, KawanoK, OhnukiT. (2002) TMC-256A1 and CI, new inhibitors of IL-4 signal transduction produced by Aspergillus niger var. niger TC 1629. The Journal of Antibiotics, 55, 685–692.
13.
CamposFR, BarisonA, DaolioC, FerreiraAG, Rodrigues-FoE. (2005) Complete 1H and 13C NMR assignments of aurasperone A and fonsecinone A, two bis-napthopyrones produced by Aspergillus aculeatus. Magnetic Resonance in Chemistry, 43, 962–965.
14.
ShaabanM, ShaabanKA, Abdel-AzizMS. (2012) Seven naphtho-γ-pyrones from the marine-derived fungus Alternaria alternata: structure elucidation and biological properties. Organic and Medical Chemistry Letters, 2, 6–9.
15.
YeYH, ZhuHL, SongYC, LiuJY, TanRX. (2005) Structural revision of aspernigrin A, reisolated from Cladosporium herbarum IFB-E002. Journal of Natural Products, 68, 1106–1108.
16.
DingG, JiangL, GuoL, ChenX, ZhangH, CheY. (2008) Pestallazines and pestalamides, bioactive metabolites from the plant pathogenic fungus Pestalotiopsis theae. The Journal of Natural Products, 71, 1861–1865.
17.
IsogaiA, HoriiT, SuzukiA, MurakoshiS, IkedaK, SatoS, TamuraS. (1975) Isolation and identification of nigragillin as a insecticidal metabolite produced by a Aspergillus niger. Agricultural and Biological Chemistry, 39, 739–740.
18.
KumarVJ, GuptaPB, KumarKSRP, RaoKVVP, PrasannaSJ, KumarGSS, SharmaHK, MukkantiK. (2010) Identification and characterization of new impurity in cefotaxime sodium drug substance. Der Pharma Chemica, 2, 230–241
19.
GauraveK., KunduS, SrivastavaR. (2012) Synthesis and in vitro antibacterial activity of some novel cephem antibiotics. International Journal of Pharmacy and Pharmaceutical Sciences, 4, 659–657.
20.
HuangSP, KoyamaY, IkedaD, KondoS, TakeuchiT. (1992) Synthesis and activity of potent 3-(isoxazolidin-5-yl)- and S-cis oxazolidium-5-ylcephalosporins. The Journal of Antibiotics, 45, 1939–1948
21.
ChaoM, HaoA. (2009) An improved and scalable preparation of 7-amino-3-vinylcephem-4-carboxylic acid. Organic Process Research & Development, 13, 924–927.
22.
HerrA, FischerR. (2014) Improvement of Aspergillus nidulans penicillin production by targeting AcvA to peroxisomes. Metabolic Engineering, 25, 131–139.
23.
KrishnarajuAV, RaoTVN, SundararajuD, VanisreeM, TsayHS, SubbarajuGV. (2005) Assessment of bioactivity of Indian medicinal plants using brine shrimp (Artemia salina) lethality assay. International Journal of Applied Science and Engineering, 3, 125–134.
24.
TakaoT, KitataniF, WatanabeN, YagiA, SakataK. (1994) Simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Bioscience, Biotechnology, and Biochemistry, 58, 1780–1783.
25.
HomansAL, FuchsA. (1970) Direct bioautography on thin-layer chromatograms as a method for detecting fungitoxic substances. Journal of Chromatography, 51, 327–329.
26.
BaratelliTDeG, GomesACC, WessjohannLA, KusterRM, SimasNK. (2011) Phytochemical and allelopathic studies of Terminalia catappa L. (Combretaceae). Biochemical Systematics and Ecology, 41, 119–125.
27.
NickavarB, AbolhasaniL, IzadpanahH. (2008) α-Amylase inhibitory activities of six Salvia species. Iranian Journal of Pharmaceutical Research, 7, 297–303.
28.
SiriwardaneAMDA, KumarNS, JayasingheL, FujimotoY. (2015) Chemical investigation of metabolites produced by an endophytic Aspergillus sp. isolated from Limonia acidissima. Natural Product Research, 29, 1384–1387.
29.
LinS, HeJ, JiangY, WuF, WangH, WuD, SunJ, ZhangD, QuH, YangB. (2014) Production of nigragillin and dihydrophaseic acid by biotransformation of litchi pericarp with Aspergillus awamori and their antioxidant activities. Journal of Functional Food, 7, 278–286.
Supplementary Material
Please find the following supplemental material available below.
For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.
For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.
