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AJUGASTERONE E

Year of first isolation: 2022
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
Ajuga lupulina [Lamiaceae (alt. Labiatae)] » Images of Ajuga lupulina Wikipedia: Ajuga lupulina [Lamiaceae (alt. Labiatae)]
Occurence in animals:
 
AJUGASTERONE E

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(CC5[C@](C)(O)C(O[C@@H]5C)=O)=O)(O)C)[H])=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(3S,5R)-3-hydroxy-4-((3R)-3-hydroxy-2-oxo-3-((2S,3R,5R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)butyl)-3,5-dimethyldihydrofuran-2(3H)-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
LJFDZZJQINNHIL-XAOOTUCPSA-N
InChIInChI=1S/C29H42O9/c1-14-16(27(4,35)24(34)38-14)12-23(33)28(5,36)22-7-9-29(37)17-10-19(30)18-11-20(31)21(32)13-25(18,2)15(17)6-8-26(22,29)3/h10,14-16,18,20-22,31-32,35-37H,6-9,11-13H2,1-5H3/t14-,15?,16?,18+,20-,21+,22+,25-,26-,27+,28-,29-/m1/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 557.2726 [M+Na]+ (calculated 557.2721)

CARBON NMR

PROTON NMR

CD3OD
0137.4
0268.7
0368.5
0432.9
0531.8
06206.3
07122.2
08167.5
0935.1
1039.3
1121.7
1232.5
1348.8
1485.1
1531.9
1621.5
1711.8
1817.9
1924.4
2082.2
2125.5
22215.7
2334.8
2449.5
2576.2
26180.7
2719.6
2879.6
2920.1
CD3OD
01-Ha1.47 (d, 12.9)
01-Hb1.85-1.80 (overlap)
02-Ha3.86 (dt, 12.0, 2.4)
03-He3.98 (brs)
04-Ha1.78-1.70 (overlap)
04-Hb1.78-1.70 (overlap)
05-H2.41 (dd, 12.9, 4.4)
07-H5.82 (brs)
09-H3.19 (m)
11-Ha1.65-1.59 (overlap)
11-Hb1.85-1.80 (overlap)
12-Ha2.26 (td, 13.0, 4.8)
12-Hb1.91 (m)
15-Ha1.99 (m)
15-Hb1.65-1.59 (overlap)
16-Ha1.78-1.70 (overlap)
16-Hb1.85-1.80 (overlap)
17-H2.71-2.67 (àverlap)
18-Me0.92 (s)
19-Me0.99 (s)
21-Me1.44 (s)
23-Ha2.99 (dd, 19.0, 4.6)
23-Hb2.87 (dd,19.0; 7.8)
24-H2.69-2.64 (overlap)
27-Me1.32 s)
28-H4.17 (m)
29-H1.39 (d, 6.1)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D2053° (c 0.1; MeOH)
IR (KBr) ν max (cm-1)
UV (MeOH) λ max (log ε)204.5 nm (0.91) ; 242.5 nm (1.43)

CHROMATOGRAPHY

HPTLC
TLC
GLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationWANG, K.J. et al. (2022) Nat. Prod. Res. in press Search more

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© Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Prague, Czech Republic
© Institut National de la Recherche Agronomique, Versailles, France
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