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72.
Conclusions
In summary, three novel compounds (1–3) have been isolated from
P. hysterophorus and their molecular structures established. It is
also the first report of the isolation of triterpene saponins from
Parthenium species including that of a nor-pseudoguaianolide
skeleton having a tetrahydrofuran ring in its structure, though
a partly resembling guaianolide has been reported earlier from
a different source.27 The TNF-a inhibitory study on human
neutrophils has revealed that the isolated saponins have a great
potential of being developed into a therapeutic agent. The
comparatively higher TNF-a inhibition shown by compound
2 may be attributed to the better stabilization of the receptor
dimer involving participation of Lys98 in an additional H-bond
formation as corroborated by the docking study.
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Spectral Data
3-O-[b-D-glucopyranosyl-(1→4)-b-D-glucopyranosyl]-28-O-b-D-
glucopyranosyl-oleanolic acid (1)
◦
1
White solid, mp 192–194 C; [a]D +3.0 (c 0.25, MeOH); H and
13C NMR in Table 1. Anal calcd for C48H78O18: C, 61.13; H, 8.34.
Found: C, 61.34; H, 8.61%. ESI-MS (m/z): 965 [M + Na]+.
3-O-[b-D-glucopyranosyl-(1→4)-b-D-glucopyranosyl-(1→4)-b-D-
glucopyranosyl]-28-O-b-D-glucopyranosyl-oleanolic acid (2)
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Tsuji, Phytochemistry, 1989, 32, 1167.
◦
1
White solid, mp 257–260 C; [a]D +6.2 (c 0.1, H2O); H and 13C
NMR in Table 1. Anal calcd for C54H88O23: C, 58.68; H, 8.03.
Found: C, 58.93; H, 8.29%. ESI-MS (m/z): 1127 [M + Na]+.
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Hysterolactone (3)
Colorless solid, mp 192–195 ◦C; [a]D +6.0 (c 0.5, CHCl3); IR: nmax
1
(neat) 2923, 2853, 2361, 1763, 1716 cm-1. H NMR (500 MHz,
CDCl3): d 7.39 (d, 1H, J = 5.9 Hz, H-2), 6.12 (d, 1H, J = 5.9 Hz,
H-3), 4.52 (s, 1H, H-6), 2.43 & 2.60 (2 ¥ d, 2H, J = 18.5 Hz, H-11),
2.80 (m, 1H, H-7), 1.79–2.10 (m, 4H, H-8 & H-9), 1.51 (3H, s, H-
15), 1.09 (d, 3H, J = 7.5 Hz, H-14). 13C NMR (125 MHz, CDCl3):
d 15.2 (C-13), 18.9 (C-14), 26.2 (C-9), 29.6 (C-8), 34.8 (C-10), 38.5
(C-11), 62.6 (C-5), 90.4 (C-7), 91.3 (C-6), 95.9 (C-1), 134.0 (C-3),
157.0 (C-2), 172.9 (C-12), 205.1 (C-4). Anal calcd for C14H16O4:
C, 67.73; H, 6.50. Found: C, 67.50; H, 6.77%. ESI-MS (m/z): 271
[M + Na]+.
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Acknowledgements
We gratefully acknowledge the financial support by the Depart-
ment of Biotechnology, New Delhi. We also thank CSIR for
project CMM-0017.
25 C. Bueno, C. A. Rodriguez, M. A. Garcia, A. Pandiella, J. Almeida and
A. Orfao, J. Immunol. Methods, 2002, 264, 77.
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Notes and references
1 Dictionary of Natural Products, ed. J. Buckingham, Chapman and Hall,
London, 1994.
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