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ACAULESTERONE

Year of first isolation: 2020
Formula:C29H44O11
Molecular weight:568
Occurence in plants:
Rhaponticum acaule [Asteraceae] » Images of Rhaponticum acaule
Occurence in animals:
 
ACAULESTERONE

STRUCTURE DESCRIPTORS

Canonical SMILES 
Isomeric SMILES
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C[C@@]12[C@@](C(C=C3C2[C@H](O)C[C@@]4(C)[C@@]3(O)CC[C@@H]4[C@](C)([C@H](O)CC5(O)C(C)(C)OC(C5O)=O)O)=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name4-((2R,3R)-2,3-dihydroxy-3-((2S,3R,5R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-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)-3,4-dihydroxy-5,5-dimethyldihydrofuran-2(3H)-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
FHHPAOMWMLUKQV-IXOTWIQESA-N
InChIInChI=1S/C29H44O11/c1-24(2)29(39,22(35)23(36)40-24)12-20(34)27(5,37)19-6-7-28(38)14-9-15(30)13-8-16(31)17(32)10-25(13,3)21(14)18(33)11-26(19,28)4/h9,13,16-22,31-35,37-39H,6-8,10-12H2,1-5H3/t13-,16+,17-,18+,19-,20+,21?,22?,25-,26+,27+,28+,29?/m0/s1

MASS SPECTRUM

HRESIMS (negative ion mode) m/z567.2810 [M-H]–, (positive mode 569.2950 [M+H]+, calc. for C29H44O11 568.2884

CARBON NMR

PROTON NMR

CD30D
0139.0
0268.9
0368.5
0433.2
0552.7
06206.7
07122.9
08168.4
0942.9
1039.9
1169.4
1243.6
1348.5
1485.0
1531.9
1621.5
1750.2
1818.8
1924.6
2077.6
2120.8
2277.1
2335.2
2489.3
2580.0
2624.7
2711.3
2874.4
29176.9
CD30D
01-Ha1.38 (dd "t" 12.8)
01-Hb2.58 (ss, 12.8, 4.3))
02-Ha4.01 (ddd, 11.7, 7.2, 2.8)
03-He3.98 (ddd "br d", 2.7)
04-Ha1.70 (brd)
04-Hb1.70
05-H2.36 (dd, 13.0, 3.6)
07-H5.84 (d, 2.4)
09-H3.16 (dd, 8.9, 2.6)
11-H4.12 (ddd, 12.0, 8.9, 6.3)
12-HaZ.Z1 (dd "t", 12.0, 12.0)
12-Hb2.01 (dd;, 12/0, 6.3)
15-Ha1.82
15-Hb1.80 (m)
16-Ha1.6Z (m)
16-Hb2.01 (m)
17-H2.35 (ss "t", 8.3)
18-Me0.89 (s)
19-Me1.06 (s)
21-Me1.27 (s)
22-H3.29 (br d, 11.1)
23-Ha1.89 (ddd "brd", 15.9)
23-Hb1.71
26-Me1.41 (s)
27-Me1.46 (s)
28-H4.57 (s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D25+ 35.0° (c 0.08 ; MeOH)
IR (KBr) ν max (cm-1)3326, 2943, 2835, 1736, 1656, 1443, 1217, 1110, 1021
UV (MeOH) λ max (log ε)232 nm (-) ;

CHROMATOGRAPHY

HPLC
GLC
TLC
HPTLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationZUGHDANI, M. et al. (2020) Phytochemistry 180, 112530 Search more

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