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Year of first isolation: |
1972 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Ipomoea calonyction [Convolvulaceae] »  ![Wikipedia: Ipomoea calonyction [Convolvulaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4(C3(CC(C(C4)O)O)C)O)O)C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)CCC(C)C)O)O)C)O)O)C » 
| | IUPAC Name | (2S,3R,5S,9R,10R,11R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,5,11,14-pentahydroxy-10,13-dimethyl-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | 38778-30-2 | | PubChem CID | 122217 | InChiKey
[ ChemIDPlus: search ] | LRJUYAVTHIEHAI-LHBNDURVSA-N | | InChI | InChI=1S/C27H44O8/c1-14(2)6-7-20(31)25(5,33)19-8-9-26(34)15-10-21(32)27(35)13-17(29)16(28)11-24(27,4)22(15)18(30)12-23(19,26)3/h10,14,16-20,22,28-31,33-35H,6-9,11-13H2,1-5H3/t16-,17+,18+,19-,20+,22+,23+,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | HR-MS | 496.3033 (calc. for C27H44O8 496.3034) |
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| C5D5N | | 01 | 36.2 | | 02 | 68.2 * | | 03 | 69.9 * | | 04 | 35.9 | | 05 | 80.0 | | 06 | 201.1 | | 07 | 120.3 | | 08 | 165.0 | | 09 | 46.2 | | 10 | 45.5 | | 11 | 69.6 | | 12 | 44.0 | | 13 | 48.2 | | 14 | 84.2 | | 15 | 31.7 | | 16 | 21.4 | | 17 | 49.4 | | 18 | 17.4 | | 19 | 18.8 | | 20 | 76.8 | | 21 | 21.4 | | 22 | 76.8 | | 23 | 30.1 | | 24 | 37.0 | | 25 | 28.2 | | 26 | 22.4 ** | | 27 | 23.4 ** |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.28 (d, 2.5) | | 09-Ha | | | 11-Ha | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.24 (s ) | | 19-Me | 1.38 (s ) | | 21-Me | 1.53 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.82 (d, 6) | | 27-Me | 0.82 (d, 6) |
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| M.P. | 238-244 °C | | [α]D20 | +49.6 ° (c 1; pyridine) | | IR (KBr) ν max (cm-1) | 3600-3100 (OH), 1660, 1630 | | UV (EtOH) λ max (log ε) | 236 (3.95) |
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| HPTLC | | | TLC | NP-TLC on silicagel Rf 0.27 (CHCl3-EtOH 4:1); RP-TLC on paraffin coated silica gel Rf 0.37 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.37 (MeOH-H2O 65:35) | | GLC | GLC Ret 5.1 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C | | HPLC | |
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Drosophila melanogaster BII cell assay: EC50 = 2.2 x 10-8M | Calliphora vicina imaginal disc assay: EC50 = 1.5 x 10-9M | Drosophila melanogaster Kc-H cell assay: EC50 = 2.0 x 10-9M | Drosophila melanogaster Kc-H cell assay: EC50 = 1.4 x 10-9M |
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| First isolation | CANONICA, L. et al. (1972) Chem. Commun., 1060-1061 |
 | | General | CANONICA, L. et al. (1975) Phytochemistry 14, 525-527 |
| | General | CANONICA, L. et al. (1977) Gazz. Chim. Ital. 107, 123-130 |
| | Bioactivities | CHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 |
| | Bioactivities | CHERBAS, P. et al. (1982) J. Chem. Soc., Chem. Commun., 1307-1308 |
| | General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
| | General | BIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 |
| | Bioactivities | CLEMENT, C.Y. et al. (1993) Insect Biochem. Molec. Biol. 23, 187-193 |
| | Bioactivities | TERENTIOU, P. et al. (1993) Insect Biochem. Molec. Biol. 23, 131-136 |
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Permanent link to this datasheet: MURISTERONE A
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