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DACRYHAINANSTERONE [= 5-DEOXYKALADASTERONE]

Year of first isolation: 1982
Formula:C27H42O6
Molecular weight:462
Occurence in plants:
Dacrydium pierrei [Podocarpaceae] » Images of Dacrydium pierrei Wikipedia: Dacrydium pierrei [Podocarpaceae]
Leuzea carthamoides [Asteraceae] » Images of Leuzea carthamoides Wikipedia: Leuzea carthamoides [Asteraceae]
Serratula coronata [Asteraceae] » Images of Serratula coronata Wikipedia: Serratula coronata [Asteraceae]
Occurence in animals:
 
DACRYHAINANSTERONE [= 5-DEOXYKALADASTERONE]

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CC=C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1C2=CC[C@]2([C@]1(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,10S,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID13829647
InChiKey
[ ChemIDPlus: search ]
HHSAPBUKXSETPT-ZTUUSGHWSA-N
InChIInChI=1S/C27H42O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h8,12,15,18,20-23,29-33H,6-7,9-11,13-14H2,1-5H3/t18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z463 (MH)+, 445, 427, 361, 343, 325
EI-MS m/z (relative intensity %) 
HR-MS 

CARBON NMR

PROTON NMR

CD3OD
0136.2
0267.4
0366.9
0435.0
0550.2
06204.0
07117.8
08162.2
09145.0
1039.4
11132.4
1237.7
1347.0
1483.1
1530.0
1620.3
1749.1
1816.7
1930.0
2076.2
2119.3
2276.6
2329.1
2436.0
2527.8
2621.3
2721.9
CD3OD
01-Ha1.7
01-Hb2.1
02-Ha3.72 (m )
03-He3.84 (m )
04-Ha1.6
04-He1.78
05-H2.40
07-H5.75 (br s, w1/2=4)
09-Ha--
11-Ha6.3 (ddd, 6.5, 2, 2)
11-He--
12-Ha2.72 (br d, 18)
12-He2.42
15-Ha 
15-Hb 
16-Ha2.05
16-Hb1.75
17-H2.45
18-Me0.89 (s )
19-Me1.10 (s )
21-Me1.18 (s )
22-H3.33 (dd, 11, 2)
23-Ha1.35
23-Hb1.55
24-Ha 
24-Hb 
25-H1.55
26-Me0.91 (d, 6.5)
27-Me0.94 (d, 6.5)

PHYSICAL PROPERTIES

M.P. 
[α]D20 
IR (KBr) ν max (cm-1) 
UV (EtOH) λ max (log ε)298 (4.152), 235 (3.806)

CHROMATOGRAPHY

HPTLC 
TLCRf 0.56 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.67 (CH2Cl2-EtOH 85:15).
GLC 
HPLCNormal phase (Zorbax-Sil) Ret. 10.4 min (CH2Cl2-iPrOH-H2O, 125:25:2)

BIOLOGICAL ACTIVITIES

Drosophila melanogaster BII cell assay: EC50 = 5.2 x 10-9M

REFERENCES

First isolationHOU, S. et al. (1982) Zhiwu Xuebao 24, 347-354 Search more
GeneralSZENDREI, K. et al. (1988) J. Nat. Prod. 51, 993-995 Search more
GeneralGIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 Search more
GeneralVOLODIN, V.V. et al. (1997) Planta Med. 26, 459-461 Search more
BioactivitiesBOURNE, P. et al. (2002) J. Insect Sci. 2:11 (pp. 11) 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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