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SPHENOCENTROSIDE B

Year of first isolation: 2019
Formula:C33H54O12
Molecular weight:642
Occurence in plants:
Sphenocentrum jollyanum [Menispermaceae] » Images of Sphenocentrum jollyanum
Occurence in animals:
 
SPHENOCENTROSIDE B

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ]
C1[C@]2([C@@](C[C@H]([C@H]1O[H])O[H])([C@H](CC3=C2CC[C@]4(C3=CC[C@@H]4[C@]([C@@H](CCC(C)(C)O[H])O[C@@H]5C(C([C@@H](C(O5)CO[H])O[H])O[H])O[H])(O[H])C)C)O[H])O)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,6S,10R,13R,17S)-17-((2R,3R)-2,6-dihydroxy-6-methyl-3-(((2R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)heptan-2-yl)-10,13-dimethyl-1,2,3,4,6,7,10,11,12,13,16,17-dodecahydro-5H-cyclopenta[a]phenanthrene-2,3,5,6-tetraol
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
NGNMQXXFOBVLLK-DJNWGTLRSA-N
InChIInChI=1S/C33H54O12/c1-29(2,41)10-9-24(45-28-27(40)26(39)25(38)21(15-34)44-28)32(5,42)22-7-6-17-16-12-23(37)33(43)14-20(36)19(35)13-31(33,4)18(16)8-11-30(17,22)3/h6,19-28,34-43H,7-15H2,1-5H3/t19-,20+,21?,22-,23-,24+,25+,26?,27?,28+,30-,31+,32+,33+/m0/s1

MASS SPECTRUM

CI-MS (NH3) m/z  
EI-MS m/z (relative intensity %)
HRESI-MS m/z (positive ion mode) m/z665.3536 [M+Na] + , calc. for C33H54O12Na 665.3514

CARBON NMR

PROTON NMR

CD3OD
0135.29
0269.87
0369.32
0430.91
0576.73
0671.20
0734.45
08124.00
09138.41
1047.07
1123.54
1238.93
1347.36
14150.63
15119.16
1631.47
1758.16
1818.61
1924.79
2076.87
2121.59
2289.91
2327.48
2440.90
2571.35
2629.75
2728.93`
[sugar] 1'105.60
[sugar] 2'75.44
[sugar] 3'71.35
[sugar] 4'77.91
[sugar] 5'78.08
[sugar] 6'62.36
CD3OD
01-Ha1.97 (m)
01-Hb1.71 (m)
02-H3.33 (m)
03-He3.98 (m)
04-Ha2.09 (m)
04-Hb1.51 (m)
05-H 
06-H4.00 (m)
07-Ha2.48 (m)
07-Hb2.15 (m)
09-H-
11-Ha2.27 (m)
11-Hb 
12-Ha2.22 (m)
12-Hb1.45 (m)
15-H5.41 (br t, 2.5)
16-Ha2.66 (dd, 11.0, 16.0)
16-Hb2.11 (m)
17-H1.93 (dd, 3.0, 7.5)
18-Me1.07 (s)
19-Me1.08 (s)
21-Me1.28 (s)
22-H3.49 (dd, 2.0, 10.0)
23-Ha1.67 (m)
23-Hb1.54 (m)
24-Ha2.03 (m)
24-Hb1.43 (m)
25-H-
26-Me1.19 (s)
27-Me1.17 (s)
[sugar] 1'4.35 (d, 7.8)
[sugar] 2'3.27 (dd, 8.0, 8.5)
[sugar] 3' 3.38 (m)
[sugar] 4' 3.37 (m)
[sugar] 5' 3.33 (m)
[sugar] 6' 3.87 (dd, 2.0, 12.0)
[sugar] 6''3.68 (5.0, 12.0)

PHYSICAL PROPERTIES

M.P. 
[α]D20+
IR (KBr) ν max (cm-1)
UV (DAD) λ max (log ε)- () ;

CHROMATOGRAPHY

HPTLC
TLC
HPLC
GLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationAJAYI, I.O. et al. (2019) Steroids 150, 108456 Search more

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