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BRAINESTEROSIDE E

Year of first isolation: 2010
Formula:C33H54O11
Molecular weight:626
Occurence in plants:
Brainea insignis [Ferns] » Images of Brainea insignis
Occurence in animals:
 
BRAINESTEROSIDE E

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)O)O)O
Isomeric SMILES
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C1[C@]2([C@H](C[C@H]([C@H]1O)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5S,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101514326
InChiKey
[ ChemIDPlus: search ]
CNAKQRUFJWYXIC-RZRISBNSSA-N
InChIInChI=1S/C33H54O11/c1-16(2)6-7-25(37)32(5,41)24-9-11-33(42)18-12-20(35)19-13-22(43-29-28(40)27(39)26(38)23(15-34)44-29)21(36)14-30(19,3)17(18)8-10-31(24,33)4/h12,16-17,19,21-29,34,36-42H,6-11,13-15H2,1-5H3/t17-,19+,21-,22+,23+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+/m0/s1

MASS SPECTRUM

ESI-MS (positive) m/z627 [M+H]+, 649 [M+Na]+
ESI-MS (negative) m/z625 [M-H]-, 661 [M+Cl]-

CARBON NMR

PROTON NMR

DMSO-d6
0141.9
0267.2
0377.7
0420.2
0553.1
06199.2
07121.5
08164.4
0946.1
1037.8
1120.0
1230.7
1346.6
1482.7
1530.2
1620.1
1748.7
1817.0
1915.1
2075.6
2120.8
2275.5
2329.1
2436.1
2527.4
2622.2
2723.0
[sugar] 1'100.2
[sugar] 2'73.5
[sugar] 3'76.3
[sugar] 4'70.0
[sugar] 5'76.7
[sugar] 6'61.0
DMSO-d6
01-Ha1.44 (m)
01-He1.90 (m)
02-He3.92 (br, s)
03-Ha3.63 (m)
04-Ha1.92 (m)
04-He1.51 (m)
05-H2.22 (dd, 3.3, 12.0)
07-H5.69 (d, 2.4)
09-H2.62 (m)
11-Ha1.48 (m)
11-He1.62 (m)
12-Ha1.66 (m)
12-He1.98 (m)
15-Ha1.77(m)
15-Hb1.51 (m)
16-Ha1.52 (m)
16-Hb1.91 (m)
17-H2.20 (t, 9.2)
18-Me0.75 (s)
19-Me0.89 (s)
21-Me1.04 (s)
22-H3.12 (m)
23-Ha1.35 (m)
23-Hb1.06 (m)
24-Ha1.36 (m)
24-Hb1.13 (m)
25-H1.49 (m)
26-Me0.84 (d, 6.8)
27-Me0.85 (d, 6.8)
[sugar] 1'4.29 (d, 7.8)
[sugar] 2'2.97 (m)
[sugar] 3'3.13 (m)
[sugar] 4'3.04 (m)
[sugar] 5'3.09 (m)
[sugar] 6'a3.61 (m)
[sugar] 6'b3.40 (m)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 22.1 ° (c 0.26; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)245 (4.10) ;

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationWU, P. et al. (2010) Phytochemistry 71, 975-981 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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