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1β-HYDROXYMAKISTERONE C

Year of first isolation: 2008
Formula:C29H48O8
Molecular weight:524
Occurence in plants:
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Occurence in animals:
 
1β-HYDROXYMAKISTERONE C

STRUCTURE DESCRIPTORS

Canonical SMILESCCC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(C(C(C(C4)O)O)O)C)C)O)O)O)C(C)(C)O
Isomeric SMILES
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[C@@H]1([C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC(C(C)(C)O)CC)O)O)O)C)C)O  » JSMol: View in 3D
[C@@H]1([C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@H](C(C)(C)O)CC)O)O)O)C)C)O  » JSMol: View in 3D
[C@@H]1([C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@@H](C(C)(C)O)CC)O)O)O)C)C)O » JSMol: View in 3D
IUPAC Name(1S,2R,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R,5R)-5-ethyl-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101851586
InChiKey
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KWOLRPNEMKAFDT-SVPRUFJPSA-N
InChIInChI=1S/C29H48O8/c1-7-15(25(2,3)35)12-22(32)28(6,36)21-9-11-29(37)17-13-19(30)18-14-20(31)23(33)24(34)27(18,5)16(17)8-10-26(21,29)4/h13,15-16,18,20-24,31-37H,7-12,14H2,1-6H3/t15-,16+,18+,20-,21+,22-,23-,24-,26-,27-,28-,29-/m1/s1

MASS SPECTRUM

HR-ESI-MS547.3251 [M+Na]+ (calculated for C29H48O8Na : 547.3247)
ESI-MS/MS m/z525 [M+H]+, 507 [M+H-H20]+, 489 [M+H-2H20]+, 471 [M+H-3H2O]+, 453 [M+H-4H2O]+, 387, 363, 345, 319, 171, 127.

CARBON NMR

PROTON NMR

CD3OD
0176.45
0268.47
0371.00
0433.52
0546.78
06205.55
07122.16
08167.23
0935.63
1043.80
1121.91
1232.49
13~49.0**
1485.04
1531.82
1621.51
1750.45
1818.04
1920.03
2077.98
2120.95
2277.22
2333.04
2450.29
2574.12
2625.60
2729.09
2825.97
2914.35
CD3OD
01-He3.82 (b)
02-Ha3.87 (t, 3.1, 3.1)
03-He4.04 (b)
04-Ha~1.80
04-He~1.80
05-H2.61 (dd, 12.5, 4.5)
07-H5.83 (d, 2.5)
09-H3.08 (bt)
11-Ha1.70
11-He1.78
12-Ha2.10 (td, 13, 13, 5)
12-He1.87
15-Ha1.99
15-Hb1.62
16-Ha1.76
16-Hb2.03
17-H2.41 (dd, 9.5, 8.5)
18-Me0.910 (s)
19-Me1.079 (s)
21-Me1.196 (s)
22-H3.41 (dd, 10.8, 1.7)
23-Ha1.56
23-Hb1.41
24-H1.47
26-H1.105 (s)
27-Me1.215 (s)
28-Ha1.57
28-Hb1.15
29-Me1.015 (t, 7.4, 7.4)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 64.0 ° (c 0.075; EtOH)
IR (KBr) ν max (cm-1)3409 (OH), 1654 (C=O), 1056 (C-O)
UV (MeOH) λ max (log ε)

CHROMATOGRAPHY

HPLCRP-HPLC Separon SGX C-18 (250 x 4 mm), solvent methanol-water (linear grad of 10-70%), flow-rate 0,6 ml/min (Ret 55.0 min); NP-HPLC Silasorb 600 (250 x 4 mm) solvent dichloromethane-isopropanol-water (84:15:1), flow-rate 0.8 ml/min (Ret 28.0 min); and two other systems.
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationBUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 Search more

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© Université Pierre & Marie Curie, Paris 6, France
© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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