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BRAINESTEROSIDE B

Year of first isolation: 2010
Formula:C33H52O10
Molecular weight:608
Occurence in plants:
Brainea insignis [Ferns] » Images of Brainea insignis
Occurence in animals:
 
BRAINESTEROSIDE B

STRUCTURE DESCRIPTORS

Canonical SMILESCC(C)CCC(C(C)(C1CC=C2C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)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(C1=CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)C)C » JSMol: View in 3D
IUPAC Name(2S,3R,5R,9R,10R,13R,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID101514323
InChiKey
[ ChemIDPlus: search ]
VGJBFMQFJIFARZ-POJUCENFSA-N
InChIInChI=1S/C33H52O10/c1-16(2)6-9-26(37)33(5,41)25-8-7-18-17-12-21(35)20-13-23(42-30-29(40)28(39)27(38)24(15-34)43-30)22(36)14-32(20,4)19(17)10-11-31(18,25)3/h7,12,16,19-20,22-30,34,36-41H,6,8-11,13-15H2,1-5H3/t19-,20-,22-,23+,24+,25-,26+,27+,28-,29+,30+,31-,32+,33+/m0/s1

MASS SPECTRUM

ESI-MS (positive) m/z609 [M+H]+, 631 [M +Na]+
ESI-MS (negative) m/z607 [M-H]-, 643 [M+Cl]-

CARBON NMR

PROTON NMR

DMSO-d6
0137.3
0265.7
0374.2
0429.2
0549.8
06201.4
07119.8
08155.1
0937.5
1038.4
1120.0
1239.0
1347.1
14148.9
15128.4
1630.5
1757.1
1819.5
1923.2
2074.9
2120.0
2275.6
2329.1
2436.0
2527.4
2622.2
2722.8
[sugar] 1'101.3
[sugar] 2'72.7
[sugar] 3'76.4
[sugar] 4'70.0
[sugar] 5'76.9
[sugar] 6'61.0
DMSO-d6
01-Ha1.30 (t, 12.8)
01-He1.65 (dd, 4.0, 12.8)
02-Ha3.69 (m)
03-He3.90 (br, s)
04-Ha1.49 (m)
04-He1.70 (m)
05-H2.25 (dd, 4.0, 13.2)
07-H5.96 (d, 2.4)
09-H2.69 (m)
11-Ha1.57 (m)
11-He1.71 (m)
12-Ha1.56 (m)
12-He2.16 (m)
15-H6.05 (br, s)
16-Ha2.08 (m)
16-Hb2.52 (m)
17-H20.1 (dd, 8.4, 9.6)
18-Me1.09
19-Me0.84 (s)
21-Me1.04 (s)
22-H3.13 (m)
23-Ha1.40 (m)
23-Hb1.11 (m)
24-Ha1.40 (m)
24-Hb1.11 (m)
25-H1.49 (m)
26-Me0.84 (d, 6.8)
27-Me0.85 (d, 6.8)
[sugar] 1'4.22 (d, 7.6)
[sugar] 2'3.04 (m)
[sugar] 3'3.14 (m)
[sugar] 4'3.04 (m)
[sugar] 5'3.10 (m)
[sugar] 6'a3.63 (br, d, 11.6)
[sugar] 6'b3.40 (dd, 5.2, 11.6)

PHYSICAL PROPERTIES

M.P.°C ;
[α]D20- 80.8 ° (c 0.15; MeOH)
IR (KBr) ν max (cm-1)
UV (EtOH) λ max (log ε)249 (3.65), 296 (3.74) ;

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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