Lup-20(29)-ene-3-tetradecanoate (1). White wax; crystallized from CHCl –MeOH (50 mg); MF: C H O ;
3
44 76 2
mp 103–104ꢆC; [ꢅ] 2D 5 +34.4ꢆ (0.1 g/100 mL, CHCl ). H NMR (400 MHz, CDCl ) and C NMR (100 MHz, CDCL ) spectral
1
13
3
3
3
+
+
data see Table 1. EI-MS m/z: 636 [M] (2), 621 (10), 593 (5), 468 (2), 429 (10), 413 [M – C H O ] , 409 (10), 393 (7), 365
1
4 28 3
(
5), 298 (5), 257 (10), 204 (2), 191 (5), 189 (60), 175 (5), 147 (10), 121 (10), 81 (20), 43 (100).
Alkaline Hydrolysis of Lup-20(29)-ene-3-tetradecanoate. To a solution of compound 1 (10 mg) in CHCl (10 mL),
3
1
0 mL of 2 N NaOH was added. The reaction mixture allowed to cool to room temperature and the organic layer was separated.
The aqueous layer was extracted two more times with 10 mL portions of CHCl . The combined organic layer, which was
3
concentrated and purified by preparative TLC (CHCl ), furnished a colorless solid that was identified as lupeol (5 mg) from
3
1
13
spectral data ( H and C NMR) [15]. The aqueous layer was acidified to pH 2.0 with 1 N HCl and extracted with 10 mL
portions of diethyl ether three times to yield tetradecanoic acid (1 mg), which was identified by GC-MS analysis.
+
Tetradecanoic Acid. GC-MS, EI-MS m/z (rel. int.): 228 [M] (10), 201 (5), 171 (6), 155 (40), 127 (45), 99 (20),
5
7 (85), 43 (100).
Antibiotic Activity Testing of Compound 1. Earlier, the antibacterial assay of the hexane extract of F. obovata was
studied by us against seven freshwater fish pathogenic bacteria [8]. The hexane extract was found active against five tested
pathogens. The antibacterial screening of pure compound 1 isolated from hexane extract (100 and 50 ꢄg /10 mm disc) was
carried out by the same method as described earlier.
ACKNOWLEDGMENT
The authors thank the Director, IMMT, Bhubaneswar for facilities, and K. S. Murthy, I/C SMPUnit, Central Research
Institute (AY), Bhubaneswar for identification of the plant. The authors thank DOD/MoES for funding the project.
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