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2-O-SINAPOYL MAKISTERONE A

Year of first isolation: 2023
Formula:C39H56O11
Molecular weight:700
Occurence in plants:
Fibraurea incisa [Menispermaceae] » Images of Fibraurea incisa Wikipedia: Fibraurea incisa [Menispermaceae]
Occurence in animals:
 
2-O-SINAPOYL MAKISTERONE A

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2CC[C@@]4(C)[C@@]3(O)CC[C@@]4([C@](C)([C@H](O)C[C@@H](C)C(C)(O)C)O)[H])=O)([H])C[C@@H](O)[C@@H](OC(/C=C/C5=CC(OC)=C(O)C(OC)=C5)=O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-((2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
YZXUMPLPZGHEBG-NDVQSBSMSA-N
InChIInChI=1S/C39H56O11/c1-21(35(2,3)45)15-32(42)38(6,46)31-12-14-39(47)24-18-26(40)25-19-27(41)30(20-36(25,4)23(24)11-13-37(31,39)5)50-33(43)10-9-22-16-28(48-7)34(44)29(17-22)49-8/h9-10,16-18,21,23,25,27,30-32,41-42,44-47H,11-15,19-20H2,1-8H3/b10-9+/t21-,23?,25+,27-,30+,31+,32-,36-,37-,38-,39-/m1/s1

MASS SPECTRUM

HRESIMQTOFMS (positive ion mode) m/z723.3721 [M+Na]+, calculated for C39H56O11 Na+ 723.3715

CARBON NMR

PROTON NMR

CD3OD
0134.2
0272.5
0366.4
0432.9
0551.7
06205.8
07122.3
08168.1
0935.0
1039.6
1121.6
1232.5
1348.8
1485.2
1531.9
1621.4
1750.4
1818.1
1924.3
2078.0
2121.0
2275.4
2334.4
2441.7
2573.8
2627.5
2726.2
2814.9
O-Me [3]',[5]'56.0
[1]'126.7
[2]', [6]'106.9
[3]',[5]'139.7
[4]'139.7
[7]'147.2
[8]'116.1
[9]'168.5
CD3OD
01-Ha1.93 (m)
01-Hb1.63 (m)
02-Ha5.11 (ddd, 12.2, 4.1, 3.1)
03-Ha4.16 (br dd, 5.0, 3.1)
04-Ha1.88 (m)
04-Hb1.75 (m)
05-H2.48 (dd, 13.4, 4.1)
07-H5.85 (d, 2.4)
09-H3.29 (ddd, 11.2, 7.5, 2.4)
11-Ha1.74 (m)
11-Hb1.90 (m)
12-Ha1.90 (m)
12-Hb2.18 (td, 13.1, 4.9)
15-Ha1.98 (td, 11.5, 6.2)
15-Hb1.63 (m)
16-Ha1.75 (m)
16-Hb2.02 (m)
17-Ha2.37 (dd, 9.4, 8.8)
18-Me0.91 (s)
19-Me1.02 (s)
21-Me1.20 (s)
22-H3.47 (dd, 11.2, 1.0)
23-H1.75 (m), 1.20 (m)
24-H1.75 (m)
26-Me1.17 (m)
27-Me1.15 (m)
28-Me0.95 (d, 6.8)
OMe-[3]', [5]'3.88 (s)
[2]'-H, [6]'-H 6.92 (s)
[7]'-H7.68 (d, 15.9)
[8]'-H6.42 (d, 15.9)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+2 ° (c 0.2 ; MeOH)
IR (KBr) ν max (cm-1)3426, 2966, 1683, 1652, 1605, 1516; 1461, 1384, 1284, 1152, 1117, 978, 914, 876, 832
UV (MeOH) λ max (log ε)nm (-) ; 204 (4.20), 226 (sh)(4.29), 241 (4.38),329 54.25)

CHROMATOGRAPHY

TLC
HPTLC
HPLC
GLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationKAKUMU, Y. et al. (2023) J. Nat. Prod. in press Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
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