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PUNICESTERONE D

Year of first isolation: 2022
Formula:C28H46O6
Molecular weight:478
Occurence in plants:
Aspergillus puniceus [Fungi] » Images of Aspergillus puniceus Wikipedia: Aspergillus puniceus [Fungi]
Occurence in animals:
 
PUNICESTERONE D

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)C)O)[H])=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17S)-17-((2R,3R,5R)-2,3-dihydroxy-5,6-dimethylheptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
CAS-RN 
PubChem CID 
InChiKey
[ ChemIDPlus: search ]
KQBCIGPPRFLKLS-YVOHVHGBSA-N
InChIInChI=1S/C28H46O6/c1-15(2)16(3)11-24(32)27(6,33)23-8-10-28(34)18-12-20(29)19-13-21(30)22(31)14-25(19,4)17(18)7-9-26(23,28)5/h12,15-17,19,21-24,30-34H,7-11,13-14H2,1-6H3/t16-,17?,19+,21-,22+,23+,24-,25-,26-,27-,28-/m1/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 479.3367 (M+H)+, calculated for C28H47O6 479.3367

CARBON NMR

PROTON NMR

DMSO-d6
0136.6
0266.8
0366.6
0431.5
0550.1
06202.7
07120.4
08165.2
0933.1
1037.6
1120.0
1230.9
1346.8
1483.0
1530.3
1620.0
1748.6
1817.1
1923.9
2075.7
2120.8
2272.9
2335.7
2434.3
2532.8
2618.3
2719.9
2814.7
DMSO-d6
01-Ha1.26 (t, 12.6)
01-Hb1.60 (m)
02-Ha3.60 (m)
03-He3.76 (br, s)
04-Ha1.47
04-Hb1.57
05-H2.19
07-H5.62 (d, 2.1)
09-H3.00 (t, 8.2)
11-Ha1.53
11-Hb1.65 (m)
12-Ha1.71 (m)
12-Hb2.01 (td, 12.8, 4.5)
15-Ha1.51
15-Hb1.79 (m)
16-Ha1.53 (m)
16-Hb1.89 (dd, 20.1, 10.2)
17-H2.21
18-Me0.76 (s)
19-Me0.83 (s)
21-Me1.05 (s)
22-H3.25 (dd, 10.2, 5.3)
23-Ha1.03
23-Hb1.15 (t, 11.1)
24-H1.55
25-H1.49
26-Me0.79 (d, 6.7)
27-Me0.83 (d, 6.6)
28-Me0.76 (d, 6.4)
[02-OH]4.44 (d, 5.9)
[03-OH]4.36 (d, 2.8)
[14-OH]4.64 (s)
[20-OH]3.59 (s)
[22-OH]4.32 (d, 5.4)

PHYSICAL PROPERTIES

M.P.279-281 °C ;
[α]D25+73° (c 0.1 ; MeOH)
IR (film) ν max (cm-1)3317, 2943, 2833, 1665, 1448, 1414, 1113, 1022, 667
UV (MeOH) λ max (log ε)243 nm (3.98)

CHROMATOGRAPHY

GLC
HPLC
TLC
HPTLC

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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