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PUNICESTERONE A

Year of first isolation: 2022
Formula:C34H49NO8
Molecular weight:599
Occurence in plants:
Aspergillus puniceus [Fungi] » Images of Aspergillus puniceus Wikipedia: Aspergillus puniceus [Fungi]
Occurence in animals:
 
PUNICESTERONE 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](OC(C5=CC=CN=C5)=O)C[C@@H](C)C(C)(O)C)O)[H])=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2R,3R,5R)-2,6-dihydroxy-5,6-dimethyl-2-((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)heptan-3-yl nicotinate
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
KXJOBCGJVAZVBC-SSOFOOIFSA-N
InChIInChI=1S/C34H49NO8/c1-19(30(2,3)40)14-28(43-29(39)20-8-7-13-35-18-20)33(6,41)27-10-12-34(42)22-15-24(36)23-16-25(37)26(38)17-31(23,4)21(22)9-11-32(27,34)5/h7-8,13,15,18-19,21,23,25-28,37-38,40-42H,9-12,14,16-17H2,1-6H3/t19-,21?,23+,25-,26+,27+,28-,31-,32-,33-,34-/m1/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 600.3529 (M+H)+, calculated for C34H50NO8 600.3531

CARBON NMR

PROTON NMR

DMSO-d6
0136.6
0266.8
0366.6
0432.0
0550.1
06202.7
07120.6
08165.0
0933.1
1037.7
1120.1
1231.0
1347.0
1483.0
1530.3
1620.1
1749.1
1817.1
1923.8
2075.2
2121.5
2278.0
2331.6
2440.1
2570.7
2626.2
2727.2
2814.4
29106.0
[01]'164.5
[02]'126.8
[03]'149.5
[05]'152.4
[06]'124.2
[07]'138.0
DMSO-d6
01-Ha1.27 (d, 12.0)
01-Hb1.59 (m)
02-Ha3.59 (dt, 12.0, 3.0)
03-He3.77 (br, s)
04-Ha1.18 (m)
04-Hb1.49 (m)
05-H2.21 (dd, 13.0, 4.0)
07-H5.64 (d, 1.5)
09-H2.99 (t, 8.3)
11-Ha1.67 (m)
11-Hb1.67 (m)
12-Ha1.85 (m)
12-Hb2.05 (M)
15-Ha1.54 (m)
15-Hb1.83 (M)
16-Ha1.52 (m)
16-Hb2.02 (m)
17-H2.27 (t, 9.0)
18-Me0.78 (s)
19-Me0.83 (s)
21-Me1.30 (s)
22-H5.14 (d, 11.5)
23-Ha1.56 (m)
23-Hb1.87 (m)
24-H1.19 (m)
26-Me0.98 (s)
27-Me0.99 (s)
28-Me0.89 (d, 5.5)
[03]'9.14 (s)
[05]'8.84 (d, 5.0)^
[06]'7.65 (dd, 8.0, 5.0)
[07]'8.37 (d, 8.0)

PHYSICAL PROPERTIES

M.P.188-190°C ;
[α]D25+48° (c 0.1 ; MeOH)
IR (film) ν max (cm-1)3385, 2966, 1716, 1651, 1595, 1381, 1290, 1199, 1112, 1051, 1028, 949
UV (MeOH) λ max (log ε)220 nm (4.12; 242 nm (4.04)

CHROMATOGRAPHY

HPTLC
GLC
HPLC
TLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

First isolationHUANG, Z.-H. et al. (2022) Phytochemistry 205, 113511 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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