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22-OXO-POLYPODINE B

Year of first isolation: 2021
Formula:C27H42O8
Molecular weight:494
Occurence in plants:
Paris verticillata [Liliaceae] » Images of Paris verticillata
Occurence in animals:
 
22-OXO-POLYPODINE B

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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[ ChemSpider: search ]
C[C@]34CC[C@H]1C(=CC(=O)[C@]2([C@@]1(C[C@@H]([C@@H](C2)O[H])O[H])C)O[H])[C@@]3(CC[C@@H]4[C@](C)(C(CCC(C)(C)O[H])=O)O[H])O[H] » JSMol: View in 3D
IUPAC Name(2S,3R,5S,10R,13R,14S,17S)-17-((R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,3,5,14-tetrahydroxy-10,13-dimethyl-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 ]
NHSMZBFIOJSEKV-KXJWQHQMSA-N
InChIInChI=1S/C27H42O8/c1-22(2,32)9-8-20(30)25(5,33)19-7-11-26(34)16-12-21(31)27(35)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h12,15,17-19,28-29,32-35H,6-11,13-14H2,1-5H3/t15-,17-,18+,19-,23+,24+,25+,26+,27+/m0/s1

MASS SPECTRUM

HRESIMS (negative ion mode) m/z495.2946 [M+H]+ (calculated for C27H43O8 495.2952)

CARBON NMR

PROTON NMR

CD3OD
0134.2
0268.4
0370.3
0436.2
0580.3
06-
07120.7
08167.1
0939.0
1045.5
1122.5
1232.6
1348.6
1485.0
1531.8
1621.7
1751.6
1817.9
1917.0
2082.0
2125.4
22217.4
2332.8
2438.1
2570.7
2629.2
2729.2
CD3OD
01-Hb1.70-1.73 (m)
01-He1.70-1.73 (m)
02-Ha3.92-3.96 (m)
03-He3.97-3.99 (m)
04-Ha2.97 (dd, 14.8, 3.0)
04-Hb1.75 (dd, 14.8, 3.0)
05-H-
07-H5.83 (d, 2.6)
09-Ha3.18-3.22 (m)
11-Ha1.81-1.84 (m)
11-Hb1.74-1.76 (m)
12-Ha2.23 (td, 13.0, 4.9)
12-Hb1.86-1.90 (m)
15-Ha1.55-1.59 (m)
15-Hb1.92-1.96 (m)
16-Ha1.48-1.53 (m)
16-Hb1.70-1.73 (m)
17-H2.66 (t, 9.4)
18-Me0.86 (s)
19-Me0.91 (s)
20-H-
21-Me1.39 (s)
22-H-
23-Ha2.71-2.75 (m)
23-Hb2.71-2.75 (m)
24-Ha1.68-1.70 (m)
24-Hb1.68-1.70 (m)
26-Me1.19 (s)
27-Me1.19 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+20.0° (c 0.10 ; MeOH)
IR (KBr) ν max (cm-1)3393, 2922, 1735, 1663
UV (MeOH) λ max (log ε)243 nm (-) ;

CHROMATOGRAPHY

TLC
GLC
HPTLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationPENG, J. et al. (2021) Chemistry & Biodiversity 18, e2100239 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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