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RHAPOCASTERONE B

Year of first isolation: 2020
Formula:C29H44O9
Molecular weight:536
Occurence in plants:
Rhaponticum acaule [Asteraceae] » Images of Rhaponticum acaule Wikipedia: Rhaponticum acaule [Asteraceae]
Occurence in animals:
 
RHAPOCASTERONE B

STRUCTURE DESCRIPTORS

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[C@H](O)[C@@H]/5O)CC5=C(C)/C)O)=O)([H])C[C@@H](O)[C@@H](O)C1 » JSMol: View in 3D
IUPAC Name(2S,3R,5R,10R,11R,13R,14S,17S)-17-((R)-1-((2S,5R,6S)-5,6-dihydroxy-4-(propan-2-ylidene)tetrahydro-2H-pyran-2-yl)-1-hydroxyethyl)-2,3,11,14-tetrahydroxy-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 ]
OCWFUZDLPYVGLK-JOFOISKBSA-N
InChIInChI=1S/C29H44O9/c1-13(2)14-8-22(38-25(35)24(14)34)28(5,36)21-6-7-29(37)16-10-17(30)15-9-18(31)19(32)11-26(15,3)23(16)20(33)12-27(21,29)4/h10,15,18-25,31-37H,6-9,11-12H2,1-5H3/t15-,18+,19-,20+,21-,22-,23?,24+,25-,26-,27+,28+,29+/m0/s1

MASS SPECTRUM

HRESIMS (negative ion mode) m/z535.2901 [M-H]–, (positive mode 537.3053 [M+H]+, , and 559.2871 [M+Na]+, , calc. for C29H44O9 536.2985

CARBON NMR

PROTON NMR

CD3OD
0139.0
0268.9
0368.5
0433.2
0552.7
06206.7
07122.7
08168.7
0942.8
1039.9
1169.4
1243.6
1348.3
1484.9
1531.8
1621.7
1750.4
1819.2
1924.6
2077.1
2121.7
2275.0
2326.4
24127.0
25131.2
2620.10
2720.41
2868.9
2996.5
CD3OD
01-Ha1.39 (dd, 12.7, 12.7)
01-Hb2.88 (ss, 12.7, 5.0)
02-Ha4.02 (ddd, 12.0, 7.0, 3.4)
03-He3.96 (br s)
04-Ha1.78
04-Hb1.70
05-H2.34 (dd, 13.2, 2.9)
07-H5.81 (d, 2.2)
09-H3.16 (dd, 9.0, 2.5)
11-H4.11 (ddd, 15.8, 10.2, 6.6)
12-HaZ.Z2 (dd "t", 12.0, 12.0)
12-Hb2.10 (dd;, 12.0, 6.3)
15-Ha1.97 (m)
15-Hb1.60 (m)
16-Ha1.99
16-Hb1.75
17-H2.43 (ss "t", 8.3)
18-Me0.84 (s)
19-Me1.06 (s)
21-Me1.33 (s)
22-H374 (dd, 12.0, 2.0)
23-Ha2.14 (dd)
23-Hb2.48 (dd)
26-Me1.79 (d, 1.3)
27-Me1.75 (s)
28-H4.36 (d, 1.1)
29-H5.16 (d, 1.1)

PHYSICAL PROPERTIES

M.P.— °C ;
[α]D20+32.3° (c 0.124 ; MeOH)
IR (KBr) ν max (cm-1)3370, 2963, 29.34, 1648, 1443, 1377, 1032
UV (MeOH) λ max (log ε)230 nm (-) ;

CHROMATOGRAPHY

GLC
TLC
HPTLC
HPLC

BIOLOGICAL ACTIVITIES

 

REFERENCES

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