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ABUTASTERONE

Year of first report:1983
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Abuta velutina [Menispermaceae] » Images of Abuta velutina Wikipedia: <br />
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Vitex strickeri [Lamiaceae] » Images of Vitex strickeri Wikipedia: <br />
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Occurence in animals:
 
ABUTASTERONE

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)460 (M-2H2O)+(1), 442 (1), 424 (2), 363 (3), 345 (10), 327 (6), 319 (1), 301 (4), 283 (4), 177 (4), 159 (15), 141 (15), 133 (8), 123 (12), 115 (34), 103 (3),97 (28), 89 (4), 85 (17), 71 (100), 67 (13), 59 (80), 53 (10), 41 (15)
HR-MS 
FAB-MS m/z497 (M+1)+

CARBON NMR

PROTON NMR

C5D5N
0138.1
0268.2 *
0368.1 *
0432.6
0551.5
06203.5
07121.7
08166.2
0934.6
1038.8
1121.2
1231.8
1348.2
1484.2
1532.1
1621.9
1750.1
1818.0
1924.6
2076.9
2121.6
2278.3
2333.1
2480.4
2572.3
2627.0
2725.4
CD3OD
01-Ha 
01-He 
02-Ha3.85 (dt, 11, 3)
03-He3.97 (br s )
04-Ha 
04-He 
05-H 
07-H5.83 (d, 2)
09-Ha3.17 (dt, 8, 2)
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.89 (s )
19-Me0.96 (s )
21-Me1.14 (s )
22-Hb3.68 (dd, 9, 2)
23-Ha 
23-Hb 
24-Ha3.54 (dd, 9, 2)
26-Me1.18 (s )
27-Me1.22 (s )
C5D5N
01-Ha1.83-1.58
01-He2.07-2.19
02-Ha4.24
03-He4.22
04-Ha1.70-1.81
04-He1.98-2.05
05-H2.97-3.03
07-H6.23 (d, 3)
09-Ha3.58 (m, w1/2 = 24)
11-Ha1.70-1.81
11-He1.83-1.95
12-Ha2.56 (ddd, 13, 13, 5)
12-He1.83-1.95
15-Ha1.83-1.95
15-Hb2.07-2.19
16-Ha2.41-2.50
16-Hb1.98-2.05
17-H2.97-3.03
18-Me1.20 (s )
19-Me1.08 (s )
21-Me1.58 (s )
22-Hb4.07 (dd, 9, 1)
23-Ha2.07-2.19
23-Hb2.41-2.50
24-Ha4.19 (dd, 2, 12)
26-Me1.45 (s )
27-Me1.50 (s )

PHYSICAL PROPERTIES

M.P.257-259 ░C (270-272░C, needles from Vitex )
[α]D2032 ░ (c 2.0; MeOH)
IR (KBr) ν max (cm-1)3380, 1660, 1640
UV (MeOH) λ max (log ε)242 (4.14)

CHROMATOGRAPHY

TLC 
RLCCsolvent system H2O-EtOAc-n-PrOH (6:6:1)
GLC 
HPLCNP-HPLC, silica (Zorbax-SIL) solvent CH2Cl2-iPrOH-H2O (100:40:3), flow-rate 1 ml. min-1, Rt 6.7 min (20E = 4.9 min); Recycle RP-HPLC : column asahipack GS-320 (50 x 2 cm i.d.) solvent MeOH, flow-rate 3.5 ml.min-1.

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell bioassay: EC50 = 1.4 x 10-7M

REFERENCES

First isolationPINHEIRO, M.L.B. et al. (1983) Phytochemistry 22, 2320-2321 Search more
GeneralLAFONT, R. et al. (1990) In: Bioanalysis of Drugs and Metabolites (Ed. E. Reid, J. D. Robinson and I. D. Wilson), Plenum, pp. 79-94 Search more
GeneralHONDA, T. et al. (1991) Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 33, 212-219 Search more
GeneralZHANG, M. et al. (1992) Phytochemistry 31, 247-250 Search more
BioactivitiesCLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 Search more

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