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3-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:
 
3-O-SINAPOYL MAKISTERONE A

STRUCTURE DESCRIPTORS

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](OC(/C=C/C5=CC(OC)=C(O)C(OC)=C5)=O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-2,14-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-3-yl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
TUPUZJZSKGDISE-ZSMXHOAUSA-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)25-19-28(27(41)20-36(25,4)23(24)11-13-37(31,39)5)50-33(43)10-9-22-16-29(48-7)34(44)30(17-22)49-8/h9-10,16-18,21,23,25,27-28,31-32,41-42,44-47H,11-15,19-20H2,1-8H3/b10-9+/t21-,23?,25+,27+,28-,31+,32-,36-,37-,38-,39-/m1/s1

MASS SPECTRUM

HRESIMQTOFMS (positive ion mode) m/z723.3726 [M+Na]+, calculated for C39H56O11 Na+ 723.3715

CARBON NMR

PROTON NMR

CD3OD
0138.5
0267.2
0371.8
0430.4
0552.7
06205.4
07122.1
08168.3
0935.3
1039.3
1121.6
1232.5
1348.7
1485.2
1531.8
1621.4
1750.4
1818.1
1924.4
2078.0
2121.0
2275.4
2334.5
2441.7
2573.8
2627.5
2726.1
2814.9
[1]'126.8
[2]', [6]'107.0
[3]', [5]'149.5
[4]'139.6
CD3OD
01-Ha1.98 (m)
01-Hb1.55 (dd, 13.3, 12.2)
02-Ha4.05 (ddd, 12.2, 4.1, 3.4)
03-Ha5.26 (br dd, 5.8, 3.4)
04-Ha1.87 (m)
04-Hb1.55 (m)
05-H2.30 (dd, 1.7, 5.8)
07-H5.84 (d, 2.4)
09-H3.21 (ddd, 11.3, 7.5, 2.4)
11-Ha1.84 (m)
11-Hb1.74 (m)
12-Ha1.90 (m)
12-Hb2.16 (td, 13.0, 4.2)
15-Ha1.98 (m)
15-Hb1.61 (m)
16-Ha1.74 (m)
16-Hb2.01 (m)
17-Ha2.37 (dd, 9.5, 8.9)
18-Me0.91 (s)
19-Me1.04 (s)
21-Me1.20 (s)
22-H3.47 (dd, 11.2, 1.1)
23-H1.58 (m), 1.19 (m)
24-H1.75 (m)
26-Me1.17 (m)
27-Me1.15 (m)
28-Me0.95 (d, 6.8)
OMe-[3]', [5]'3.90 (s)
[2]'-H, [6]'-H 6.94 (s)
[7]'-H7.66 (d, 15.9)
[8]'-H6.49 (d, 15.9)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+58 ° (c 0.2 ; MeOH)
IR (KBr) ν max (cm-1)3419, 2966, 1693, 1655, 1604, 1516; 1459, 1384, 1284, 1116, 990, 915, 856, 834
UV (MeOH) λ max (log ε)nm (-) ; 205 (4.33), 226 (sh)(4.35), 240 (4.42),329 (4.29)

CHROMATOGRAPHY

HPLC
GLC
HPTLC
TLC

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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