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CHEILANTHONE A

Year of first isolation: 1970
Formula:C27H46O6
Molecular weight:466
Occurence in plants:
Cheilanthes tenuifolia [Pteridaceae] » Images of Cheilanthes tenuifolia Wikipedia: Cheilanthes tenuifolia [Pteridaceae]
Occurence in animals:
 
CHEILANTHONE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C1CCC2(C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)C(CCC(C)(C)O)O
Isomeric SMILES
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C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)CC1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(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[C@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(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[C@@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,8R,9S,10R,13R,14R,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN26152-93-2
PubChem CID101297731
InChiKey
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MSFNGOWODGGQNW-YZENLCTGSA-N
InChIInChI=1S/C27H46O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h15-20,22-23,28,30-33H,6-14H2,1-5H3/t15-,16+,17-,18+,19-,20+,22+,23-,25+,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z 
EI-MS m/z (relative intensity %)448 (M-18)+, 430, 412, 394, 379, 332, 302, 99, 81
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 
C5D5N
01-Ha 
01-Hb 
02-Ha 
03-He 
04-Ha 
04-He 
05-H 
07-Ha 
07-He 
08-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.83 (s )
19-Me1.01 (s )
21-Me1.24 (d, 6)
22-H 
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.36 (s )
27-Me1.36 (s )
CDCl3 (2,3,22-triOAc)
01-Ha 
01-Hb 
02-Ha5.35 (w1/2 = 8)
03-He~ 5.10 (w1/2 > 16)
04-Ha 
04-He 
05-H 
07-Ha 
07-He 
08-H 
09-Ha 
11-Ha 
11-He 
12-Ha 
12-He 
15-Ha 
15-Hb 
16-Ha 
16-Hb 
17-H 
18-Me0.80
19-Me0.96
21-Me~ 0.94 (w1/2 > 16)
22-H~ 4.9
23-Ha 
23-Hb 
24-Ha 
24-Hb 
26-Me1.24
27-Me1.24
acetates2.00, 2.05, 2.09

PHYSICAL PROPERTIES

M.P.235-238 °C
[α]D20 
IR (KBr) ν max (cm-1)1684 (carbonyl)
UV (EtOH) λ max (log ε) 

CHROMATOGRAPHY

HPTLC 
TLC on silicaRf 0.20 (CHCl3-96% EtOH 4:1) identical to that of ecdysone
GLC 
HPLC 

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationFAUX, A. et al. (1970) J. Chem. Soc., Chem. Commun., 243-244 Search more

see Important notice
© 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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