Citation: Hidayat Hussain, Natalia Root, Farah Jabeen, Ahmed Al-Harrasi, Ahmed Al-Rawahi, Manzoor Ahmad, Zahid Hassan, Ghulam Abbas, Fazal Mabood, Afzal Shah, Amin Badshah, Amjad Khan, Riaz Ahmad, Ivan R. Green, Siegfried Draeger, Barbara Schul, Karsten Krohn. Seimatoric acid and colletonoic acid: Two new compounds from the endophytic fungi, Seimatosporium sp. and Colletotrichum sp.[J]. Chinese Chemical Letters, ;2014, 25(12): 1577-1579. doi: 10.1016/j.cclet.2014.06.006 shu

Seimatoric acid and colletonoic acid: Two new compounds from the endophytic fungi, Seimatosporium sp. and Colletotrichum sp.

a.
a. Department of Chemistry, University of Paderborn, Warburger Strasse 100, Paderborn 33098, Germany;
b.
b. UoN Chair of Oman's Medicinal Plants and Marine Natural Products, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Oman;
c.
c. Department of Chemistry, University of Malakand, Chakdara, Dir (L), Pakistan;
d.
d. Department of Chemistry, CIIT, Abbottabad Campus, Abbottabad 22060, Pakistan;
e.
e. Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan;
f.
f. Department of Biotechnology, Quaid-i-Azam University, Islamabad 45320, Pakistan;
g.
g. Department of Chemistry and Polymer Science, University of Stellenbosch, P/Bag X1, Matieland 7602, South Africa;
h.
h. Institute of Microbiology, University of Braunschweig, Spielmannstraße 7, Braunschweig 38106, Germany

Corresponding author: Hidayat Hussain, Karsten Krohn,
Received Date: 28 February 2014
Available Online: 16 April 2014
Fund Project:

A new metabolite, named seimatoric acid (1), representing a new oxobutanoic acid derivative has been isolated from Seimatosporium sp., in addition to four known compounds viz., 2-hydroxymethyl-4β,5α,6β-trihydroxycyclohex-2-enone (2), (-)-phyllostine (3), (+)-epiepoxydon (4) and (+)-epoxydon monoacetate (5). Similarly one new benzoic acid derivative, named colletonoic acid (6) was isolated from the ethyl acetate fraction of Colletotrichum sp. The structures of the new compounds were elucidated by detailed ¹HNMR, ¹³C NMR, COSY, HMQC,HMBCspectroscopic analysis, and HR-EI-MS. Seimatoric acid (1) was also isolated from another taxonomical unidentified fungal strain 4295 in our group. The structures of the known compounds were elucidated by their spectral data comparison to literature data. Preliminary studies showed that colletonoic acid (6) showed good antibacterial, antifungal, and antialgal activities.
- Seimatosporium sp.,
- Colletotrichum sp.,
- Activity,
- Natural product
1. [1]
  [1] R. Maheshwari, What is an endophytic fungus? Curr. Sci. 90 (2006) 1309.
2. [2]
  [2] H. Hussain, K. Krohn, I. Ahmed, et al., Phomopsinones A-D: four new pyrenocines from an endophytic fungus, Phomopsis sp., Eur. J. Org. Chem. (2012) 1783-1789.
3. [3]
  [3] H. Hussain, K. Krohn, U. Floerke, et al., Absolute configuration of globosuxanthone A and secondary metabolites from Microdiplodia sp., Eur. J. Org. Chem. (2007) 292-295.
4. [4]
  [4] H. Hussain, K. Krohn, U. Floerke, et al., Absolute configuration of hypothemycin and new 5'-O-methylhypothemycin from Phoma sp. -a novel solid state CD/ TDDFT approach to 14 membered conformationally flexible system, Tetrahedron Asymmetry 18 (2007) 925-930.
5. [5]
  [5] H. Hussain, K. Krohn, B. Schulz, et al., Bioactive chemical constituents of two endophytic fungi, Biochem. Syst. Ecol. 35 (2007) 898-900.
6. [6]
  [6] H. Hussain, K. Krohn, D. Siegfried, et al., Exochromone: structurally unique chromone dimer with antifungal and algicidal agent from Exophiala sp., Heterocycles 74 (2007) 331-337.
7. [7]
  [7] H. Hussain, N. Akhtar, B. Schulz, et al., New bioactive 2,3-epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. from Laurus azorica, Eur. J. Org. Chem. (2009) 749-756.
8. [8]
  [8] U. Hö ller, A.D. Wright, G.F. Matthé e, et al., Fungi from marine sponges: diversity, biological activity and secondary metabolites, Mycol. Res. 104 (2000) 1354-1365.
9. [9]
  [9] B. Schulz, J. Sucker, H.J. Aust, et al., Biologically active secondary metabolites of endophytic Pezicula species, Mycol. Res. 99 (1995) 1007-1015.
10. [10]
  [10] O.F. Smetanina, A.I. Kalinovskii, Y.V. Khudyakov, et al., Metabolites of the marine fungus Asperigillus varians KMM 4630, Chem. Nat. Comp. 41 (2005) 243-244.
11. [11]
  [11] G. Mehta, K. Islam, Enantioselective total synthesis of epoxyquinone natural products (-)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (-)-panepophenanthrin: access to versatile chiral building blocks through enzymatic kinetic resolution, Tetrahedron Lett. 45 (2004) 7683-7687.
12. [12]
  [12] C. Klemke, S. Kehraus, A.D. Wright, et al., New secondary metabolites from the marine endophytic fungus Apiospora montagnei, J. Nat. Prod. 67 (2004) 1058-1063.
13. [13]
  [13] H. Hussain, K. Krohn, M.K. Tichimeme, et al., Antimicrobial chemical constituents from the endophytic fungus from Phomopsis sp. from Notobasis syriaca, Nat. Prod. Commun. 6 (2011) 1905-1906.
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沈阳化工大学材料科学与工程学院沈阳 110142