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PUNICESTERONE G

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 G

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@@H]([C@H](O)C[C@H](CO)C(C)C)C)[H])=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,13R,14S,17R)-2,3,14-trihydroxy-17-((2S,3R,5S)-3-hydroxy-5-(hydroxymethyl)-6-methylheptan-2-yl)-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 ]
ZYMJGGGMFRKAAF-ZVRIDVFASA-N
InChIInChI=1S/C28H46O6/c1-15(2)17(14-29)10-22(30)16(3)18-7-9-28(34)20-11-23(31)21-12-24(32)25(33)13-26(21,4)19(20)6-8-27(18,28)5/h11,15-19,21-22,24-25,29-30,32-34H,6-10,12-14H2,1-5H3/t16-,17+,18+,19?,21-,22+,24+,25-,26+,27+,28+/m0/s1

MASS SPECTRUM

HRESIMS (positive ion mode) m/z 479.3364 (M+H)+, calculated for C28H47O6 479.3367

CARBON NMR

PROTON NMR

DMSO-d6
0136.6
0266.7
0366.5
0431.5
0550.1
06202.8
07120.3
08164.9
0933.3
1037.6
1120.1
1230.3
1346.4
1482.7
1530.6
1625.7
1747.1
1815.3
1923.9
2041.8
2112.7
2271.0
2328.7
2443.9
2527.9
2619.0
2719.5
2863.1
DMSO-d6
01-Ha1.27
01-Hb1.60
02-Ha3.61 (d, 9.2)
03-He3.77 (br, s)
04-Ha1.47
04-Hb1.57 (m)
05-H2.20 (dd, 13.1, 3.9)
07-H5.63 (d, 2.3)
09-H3.01 (t, 8.3)
11-Ha1.50
11-Hb1.65 (m)
12-Ha1.80 (m)
12-Hb2.01 (td, 12.8, 4.4)
15-Ha1.49
15-Hb1.60
16-Ha1.36 (dd, 21.0, 11.9)
16-Hb1.81
17-H1.90 (DT, 10.7, 8.6)
18-Me0.60 (s)
19-Me0.84 (s)
20-H1.60
21-Me0.83
22-H3.53 (d, 9.6)
23-Ha1.08 (DDD, 14.4, 10.5, 5.9)
23-Hb1.26
24-H1.44 (m)
25-H1.78 (m)
26-Me0.82 (d, 7.0)
27-Me0.85 (d, 7.0)
28-CH2OH3.31, 3.40
[02-OH]4.44 (d, 4.3)
[03-OH]4.36 (br, s)
[14-OH]4.65 (s)
[22-OH]4..48 (d, 3.1)
[28-OH]4.57 (br, s)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D25+33° (c 0.1 ; MeOH)
IR (film) ν max (cm-1)3323, 2947, 2833, 1678, 1450, 1415, 1259, 1203, 1111, 1022, 802, 660
UV (MeOH) λ max (log ε)242 nm (3.77)

CHROMATOGRAPHY

HPTLC
TLC
HPLC
GLC

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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