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12α,20-DIHYDROXYECDYSONE

Year of first isolation: 2021
Formula:C27H44O8
Molecular weight:496
Occurence in plants:
Paris polyphylla var. yunnanensis » Images of Paris polyphylla var. yunnanensis
Occurence in animals:
 
12α,20-DIHYDROXYECDYSONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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CC(C)(CC[C@H]([C@@](C)([C@H]3CC[C@]4(C2=CC([C@@H]1C[C@H]([C@H](C[C@]1(C)C2C[C@@H]([C@]34C)O[H])O[H])O[H])=O)O[H])O[H])O[H])O[H] » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,12S,13S,14R,17S)-2,3,12,14-tetrahydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
YBADLLABDWLXQY-ANYRPRRDSA-N
InChIInChI=1S/C27H44O8/c1-23(2,33)8-7-21(31)26(5,34)20-6-9-27(35)15-10-17(28)16-11-18(29)19(30)13-24(16,3)14(15)12-22(32)25(20,27)4/h10,14,16,18-22,29-35H,6-9,11-13H2,1-5H3/t14?,16-,18+,19-,20-,21+,22-,24+,25-,26+,27+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESIMS (negative ion mode) m/z519.2930 [M+Na]+, calculated 519.2934

CARBON NMR

PROTON NMR

CD3OD
0137.3
0268.8
0368.5
0433.0
0551.9
06206.3
07122.7
08165.8
0931.1
1039.0
1130.3
1275.3
1350.3
1487.6
1531.8
1621.2
1744.2
1819.0
1924.6
2078.0
2120.3
2278.9
2327.3
2442.4
2571.5
2629.9
2729.1
CD3OD
01-Ha1.82 (dd, 12.8, 3.8)
01-Hb1.49 (t, 12.8)
02-Ha3.88 (dt, 12.8, 3.8)
03-He3.99 (m)
04-Ha1.75 (m)
04-Hb?
05-H2.45 (dd, 12.8, 4.5)
07-H5.87 (d, 2.2)
09-H3.35 (m)
11-Ha2.05 (m)
11-Hb?
12-Ha4.31 (t, 3.0)
12-Hb-
15-Ha1.93 (m)
15-Hb1.62 (m)
16-Ha2.01 (m)
16-Hb1.84 (m)
17-H3.05 (t, 9.5)
18-Me0.85 (s)
19-Me1.00 (s)
21-Me1.30 (s)
22-H3.41 (dd, 9.1, 0.6)
23-Ha1.73 (m)
23-Hb1.40 (m)
24-Ha1.83 (m)
24-Hb1.48 (m)
26-Me1.23 (s)
27-Me1.22 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+50.9° (c 0.30 ; MeOH)
IR (KBr) ν max (cm-1)33.95, 2967, 1656, 1444, 1384, 1223, 1058
UV (MeOH) λ max (log ε)240 nm (2.92) ;

CHROMATOGRAPHY

GLC
HPLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationGUO, K. et al. (2021) Phytochemistry Letters 45, 117-120 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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