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STACHYSTERONE B

Year of first isolation: 1970
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Stachyurus praecox [Stachyuraceae] » Images of Stachyurus praecox Wikipedia: <br />
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Serratula wolffii [Asteraceae] » Images of Serratula wolffii Wikipedia: <br />
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Occurence in animals:
 
STACHYSTERONE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1=CCC2C(C)(C(CCC(C)(C)O)O)O
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2(C1=CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN30655-79-9
PubChem CID15922525
InChiKey
[ ChemIDPlus: search ]
ZYXLMHXQZHELAP-SVJUWISJSA-N
InChIInChI=1S/C27H42O6/c1-24(2,32)10-9-23(31)27(5,33)22-7-6-16-15-12-19(28)18-13-20(29)21(30)14-26(18,4)17(15)8-11-25(16,22)3/h6,12,17-18,20-23,29-33H,7-11,13-14H2,1-5H3/t17-,18-,20+,21-,22-,23+,25-,26+,27+/m0/s1

MASS SPECTRUM

EI-MS m/z (relative intensity %)462 (M)+; 444 (M - 18)+, 345 (M- C22-C27)+ (5), 327 (7), 99 (C22-C27)+ (86), 81 (45), 43 (100).
HR-MS444.2861 (for C27H40O5, calc. 444.2815)
LSI-MS (negative) m/z(% RI): 553 (3) [M+glyc-H]-, 461 (8) [M-H]-, 183 (100)

CARBON NMR

PROTON NMR

D2O
0137.7
0269.8
0369.9
0433.7
0552.7
06 
07122.0
08 
0941.0
1041.5
11 
1241.8
1350.2
14152.0
15133.1
1631.8
1759.5
1821.8
1925.4
2080.0
2121.06
2280.0
2328.4
2443.0
2574.4
2630.0
2730.9
CD3OD-d4
0137.2
0268.71
0368.67
0433.0
0551.6
06205.9
07121.2
08158.9
0939.96
1040.06
1121.8
1241.2
1349.1
14150.8
15130.4
1632.1
1759.1
1820.2
1924.15
2077.3
2120.5
2278.7
2327.4
2442.4
2571.4
2629.0
2730.0
CD3OD-d4
01-Ha1.465
01-He1.81
02-Ha3.80
03-He3.94
04-Ha1.65
04-He1.72
05-H2.385
07-H6.08
09-Ha2.72
11-Ha1.86
11-He1.79
12-Ha1.64
12-Hb2.31
15-H6.08
16-Ha2.25
16-Hb2.625
17-H2.20
18-Me1.14
19-Me0.97
21-Me1.25
22-H3.335
23-Ha1.32
23-Hb1.61
24-Ha1.425
24-Hb1.81
26-Me1.185
27-Me1.21
D2O
01-Ha1.41 (t 13.4)
01-He1.88
02-Ha3.95 (dt 11.7, 3.5)
03-He4.05 (bm w1/2 =8)
04-Ha1.72
04-He1.77
05-H2.32
07-H6.23 (bs w1/2 =6.3)
09-Ha2.77 (bm w1/2 =23)
11-Ha1.80
11-He1.87
12-Ha1.62
12-He2.31
15-H6.23 (bs w1/2 =6.3)
16-Ha2.53 (dd 16, 11)
16-Hb2.30 (dd 16, 8)
17-H2.24 (dd 11, 8)
18-Me1.10 (s)
19-Me1.00 (s)
21-Me1.28 (s)
22-H3.44 (dd 10.6, 1.4)
23-Ha1.34
23-Hb1.62
24-Ha1.50 (td 13, 3.5)
24-Hb1.78
26-Me1.21 (s)
27-Me1.23 (s)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1)3400 (OH), 1640 (cyclohexenone), 1590
UV (EtOH) λ max (log ε)298 (4.107)

CHROMATOGRAPHY

HPTLC 
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 8.2 x 10-8M

REFERENCES

First isolationIMAI, S. et al. (1970) J. Am. Chem. Soc. 92, 7510-7512 Search more
BioactivitiesBOURNE, P. et al. (2002) J. Insect Sci. 2:11 (pp. 11) Search more
IdentificationSIMON, A. et al. (2007) Steroids 72, 751-755 Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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