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BRAINESTEROSIDE A

Year of first isolation: 2010
Formula:C33H52O11
Molecular weight:624
Occurence in plants:
Brainea insignis [Blechnaceae] » Images of Brainea insignis Wikipedia: Brainea insignis [Blechnaceae]
Occurence in animals:
 
BRAINESTEROSIDE A

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CC2C3(C1(CCC4C3=CC(=O)C5C4(CC(C(C5)OC6C(C(C(C(O6)CO)O)O)O)O)C)C)O2)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@]31[C@H](C[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O3)C)C » JSMol: View in 3D
IUPAC Name(2S,4S,6S,7R,10R,11R,13S,14R,16R)-6-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-13-hydroxy-7,11-dimethyl-14-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadec-1(18)-en-17-one
CAS-RN 
PubChem CID101514322
InChiKey
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DXNDVPXPNDDWTO-IEAOMMROSA-N
InChIInChI=1S/C33H52O11/c1-15(2)6-7-24(37)32(5,41)23-12-25-33(44-25)17-10-19(35)18-11-21(42-29-28(40)27(39)26(38)22(14-34)43-29)20(36)13-30(18,3)16(17)8-9-31(23,33)4/h10,15-16,18,20-29,34,36-41H,6-9,11-14H2,1-5H3/t16-,18-,20-,21+,22+,23-,24+,25-,26+,27-,28+,29+,30+,31+,32+,33-/m0/s1

MASS SPECTRUM

ESI-MS (positive) m/z647 [M+Na]+, 1271 [2M +Na]+
ESI-MS (negative) m/z623 [M-H]-, 659 [M+Cl]-

CARBON NMR

PROTON NMR

DMSO-d6
0137.3
0265.7
0374.1
0429.1
0550.1
06202.1
07122.6
08157.2
0936.9
1038.2
1120.0
1233.8
1340.3
1471.0
1558.8
1626.5
1746.3
1815.8
1923.6
2074.7
2120.4
2275.5
2329.1
2435.9
2527.4
2622.3
2722.9
[sugar] 1'101.4
[sugar] 2'72.8
[sugar] 3'76.6
[sugar] 4'70.1
[sugar] 5'77.1
[sugar] 6'61.1
DMSO-d6
01-Ha1.30 (m)
01-He1.66 (m)
02-Ha3.71 (m)
03-He3.94 (br, s)
04-Ha1.35 (m)
04-He1.68 (m)
05-H2.30 (dd, 3.3, 13.2)
07-H5.82 (d, 2.2)
09-H2.73 (m)
11-Ha1.62 (m)
11-He1.77 (m)
12-Ha1.64 (m)
12-He2.05 (m)
15-Hb3.99 (br, s)
16-Ha1.72
16-Hb1.81
17-H1.50
18-Me0.89 (s)
19-Me0.89 (s)
21-Me1.03 (s)
22-H3.10 (m)
23-Ha1.23 (m)
23-Hb1.07 (m)
24-Ha1.34 (m)
24-Hb1.14 (m)
25-H1.48 (m)
26-Me0.83 (d, 6.8)
27-Me0.84 (d, 6.8)
[sugar] 1'4.20 (d, 7.8)
[sugar] 2'3.04 (t, 8.4)
[sugar] 3'3.14 (t, 8.4)
[sugar] 4'3.04 (t, 8.4)
[sugar] 5'3.10 (m)
[sugar] 6'a3.65 (br, d, 11.6)
[sugar] 6'b3.39 (dd, 5.6, 11.6)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20+ 14.2 ° (c 0.29; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)241 (3.38) ;

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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