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MAKISTERONE D

Year of first isolation: 1968
Formula:C29H48O7
Molecular weight:508
Occurence in plants:
Podocarpus macrophyllus [Podocarpaceae] » Images of Podocarpus macrophyllus Wikipedia: Podocarpus macrophyllus [Podocarpaceae]
Occurence in animals:
 
MAKISTERONE D

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)C(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(C)O
Isomeric SMILES
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C1[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](O)CC(C(C)C)C(C)O)O)O)C)C  » JSMol: View in 3D
C1[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](O)C[C@H](C(C)C)C(C)O)O)O)C)C  » JSMol: View in 3D
C1[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](O)C[C@H](C(C)C)C(C)O)O)O)C)C  » JSMol: View in 3D
C1[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](O)C[C@@H](C(C)C)C(C)O)O)O)C)C  » JSMol: View in 3D
C1[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](O)C[C@@H](C(C)C)C(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-5-(1-hydroxyethyl)-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN20137-11-5
PubChem CID12312692
InChiKey
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FGBRCLVMUKRABR-ZDOCXERWSA-N
InChIInChI=1S/C29H48O7/c1-15(2)17(16(3)30)11-25(34)28(6,35)24-8-10-29(36)19-12-21(31)20-13-22(32)23(33)14-26(20,4)18(19)7-9-27(24,29)5/h12,15-18,20,22-25,30,32-36H,7-11,13-14H2,1-6H3/t16?,17?,18-,20-,22+,23-,24-,25+,26+,27+,28+,29+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)490 (M - 18)+, 363, 345, 145 (22), 127 (100)
HR-MS 

CARBON NMR

PROTON NMR

C5D5N
01 
02 
03 
04 
05 
06 
07 
08 
09 
10 
11 
12 
13 
14 
15 
16 
17 
18 
19 
20 
21 
22 
23 
24 
25 
26 
27 
28 
29 
C5D5N
01-Ha 
01-He 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me1.20 (s )
19-Me1.06 (s )
21-Me1.57 (s )
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me0.87 (d, 6)
27-Me0.87 (d, 6)
28-H 
29-Me1.30 (d )

PHYSICAL PROPERTIES

M.P. 
[α]D20+ 42° (dioxane)
IR (KBr) ν max (cm-1)3400 (OH), 1660, 1630 (cyclohexenone)
UV (EtOH) λ max (log ε)244 (?)

CHROMATOGRAPHY

HPTLCNP-TLC on silicagel : Rf 0.53 (CHCl3-EtOH 4:1); Rf 0.34 (EtOAc-MeOH 20:1)
TLC 
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

Chilo dipping test: highly active

REFERENCES

First isolationIMAI, S. et al. (1968) Tetrahedron Lett., 3883-3886 Search more
GeneralIMAI, S. et al. (1968) Tetrahedron Lett., 3887-3890 Search more
BioactivitiesBERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 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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