A New Furan Derivative from Harposporium sp. YMF1.01735
- PDF / 146,030 Bytes
- 3 Pages / 594 x 792 pts Page_size
- 17 Downloads / 173 Views
A NEW FURAN DERIVATIVE FROM Harposporium sp. YMF1.01735
Qiao-Mei Zheng, Sisommay Souvanhnachit, Xin Wang, and Guo-Hong Li*
The chemical constituents of the endoparasitic fungus Harposporium sp. YMF1.01735 were studied. A new furan harposporin A (1) with a known aureonitol (2) were isolated and identified from the EtOAc extract of the strain. Their structures were elucidated by NMR and MS analysis. This is the first report on the chemical constituents of the genus Harposporium. Keywords: Harposporium sp., furan derivative, harposporin A. Endoparasitic fungus is one of the important nematophagus fungi in nematode biocontrol [1]. Harposporium is a major endoparasitic fungus and has been isolated from soil, leaf mould, rotten wood, dung, and composts [2], which shows high host specificity to nematodes and produce conidia to infect free nematodes [3–5]. Some species of Harposporium can be a candidate for the development of strategies for the biological control of nematodes [6]. H. anguillulae was the first fungus described as a parasite of nematodes dating back to the late 1800 s. Species in Harposporium produce a variety shape conidia to infect nematodes [7]. The capacity to survive gut passage is one of the characteristics for nematophagous fungi to be considered potential biological control agents of gastrointestinal nematodes of livestock. H. lilliputanum can survive in fresh feces of cattle [8], and H. leptospira is able to enter dung soon after deposition on a variety of types of ground cover [9]. Up to now, no papers on the chemical constituents of the genus Harposporium have been reported. In this study, we investigated the chemical constituents of the endoparasitic fungus Harposporium sp. YMF1.01735. Two furans, harposporin A (1) and aureonitol (2), were obtained. Here, we report the isolation and structure elucidation of the two compounds. Compound 1 was obtained as a yellowish oil. The HR-ESI-MS data indicated a molecular formula of C11H14O3, based on the quasimolecular peak at m/z 195.1018 ([M + H]+, calcd 195.1016). The NMR data (Table 1) revealed two methyls, one methylene, five methines, and three quaternary carbons. The 1 H– 1 H COSY spectrum showed three fragments, –C-4–C-5–, –C-7–C-8–C-9–, and –C-10–C-11–C-12–, based on the correlations of H-4/H-5, H-7/H-8/H-9, and H-10/H-11/H-12. From the HSQC and HMBC (Table 1), H-7 (δ 6.29) correlated with the carbons at δ 19.5 (C-9) and 209.1 (C-6); one of H-4 (δ 3.15) correlated with the carbons at δ 72.4 (C-5), 131.3 (C-2), 160.8 (C-3), and 209.1 (C-6); H-10 (δ 6.87) with the carbons at δ 35.5 (C-4) and 19.3 (C-12). The configurations of the double bonds at C-7 and C-10 in compound 1 were shown to be trans based on the observed coupling constant values of 15.7 Hz between H-7 and H-8, and 15.4 Hz between H-10 and H-11 (Table 1). Based on the above data, compound 1 was named harposporin A. Compound 2 was identified as aureonitol based on reference [10] data. 10
12
O
1
8
O 5
11
HO
3
1
14
12
10 3
O1
7
HO
4 6
9
2
State Key Laboratory for Conservat
Data Loading...
