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Year of first isolation: |
1968 |
| Formula: | C19H26O5 |
| Molecular weight: | 334 |
| Occurence in plants: |
Achyranthes rubrofusca [Amaranthaceae] »  ![Wikipedia: Achyranthes rubrofusca [Amaranthaceae]](/images/wikipedia.png)
Lychnis flos-culculi [Caryophyllaceae] »
Silene otites [Caryophyllaceae] »
Palisota schweinfurthii [Commelinaceae] »
Leuzea carthamoides [Asteraceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2=O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CCC2=O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13S,14R)-2,3,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,9,11,12,15,16-decahydrocyclopenta[a]phenanthrene-6,17-dione | | CAS-RN | 19466-41-2 | | PubChem CID | 12315102 | InChiKey
[ ChemIDPlus: search ] | OMQCWEJQYPUGJG-DTDIXVHCSA-N | | InChI | InChI=1S/C19H26O5/c1-17-9-15(22)14(21)8-12(17)13(20)7-11-10(17)3-5-18(2)16(23)4-6-19(11,18)24/h7,10,12,14-15,21-22,24H,3-6,8-9H2,1-2H3/t10-,12-,14+,15-,17+,18+,19+/m0/s1 |
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| CI-MS (NH3) m/z | 352 (M+H+NH3)+, 335 (M+H)+, 317 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| CD3OD | | 01 | 37.3 | | 02 | 68.4 * | | 03 | 68.6 * | | 04 | 32.8 | | 05 | 52.0 | | 06 | 205.8 | | 07 | 122.4 | | 08 | 164.6 | | 09 | 35.8 | | 10 | 39.3 | | 11 | 20.6 | | 12 | 24.9 | | 13 | 54.1 | | 14 | 80.4 | | 15 | 29.1 | | 16 | 34.0 | | 17 | 214.8 | | 18 | 17.6 | | 19 | 24.6 |
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| C5D5N | | 01-Ha | 1.43 (dd, 13, 12) | | 01-Hb | 1.78 | | 02-Ha | 3.83 (ddd, 12, 4, 3) | | 03-He | 3.94 (q, 3) | | 04-Ha | 1.73 | | 04-He | 1.78 | | 05-H | 2.4 (dd, 12, 5) | | 07-H | 5.91 (d, 2.5) | | 09-Ha | 3.18 (m, w1/2=22) | | 11-Ha | 1.7 | | 11-He | 1.9 | | 12-Ha | 2.1 | | 12-He | 1.5 | | 15-Ha | 2.3 | | 15-Hb | 2.0 | | 16-Ha | 2.4 | | 16-Hb | 2.05 | | 18-Me | 0.88 (s ) | | 19-Me | 0.99 (s ) |
| CDCl3 | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.94 (ddd ) | | 03-He | 5.32 (ddd ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.94 (d ) | | 09-Ha | 3.11 (ddd ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 18-Me | 0.85 (s ) | | 19-Me | 1.04 (s ) |
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| M.P. | 230 °C (decomp.) | | [α]D20 | + 119 ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | 3410 (OH), 1741 (cyclopentanone), 1646 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 240 (?) |
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| TLC | NP-TLC on silica gel : Rf 0.26 (EtOAc-MeOH-NH4OH, 85:10:5) (20E : 0.18); Rf 0.41 (CH2Cl2-EtOH 85:15) (20E : 0.15); Rf 0.41 (CHCl3-EtOH 4:1) | | GLC | | | NP-HPLC | NP-HPLC, Ret 6.2 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); Ret 10.1 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min); | | RP-HPLC | RP-HPLC, Ret 6.0 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN-0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.4 min). |
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Drosophila melanogaster BII cell assay: EC50 = >10-4M | Drosophila melanogaster imaginal disc assay: EC50 = 7.9 x 10-3M | Sarcophaga assay: inactive |
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| First isolation | TAKEMOTO, T. et al. (1968) Tetrahedron Lett. 3053-3056 |
 | | General | HORN, D.H.S. et al. (1971) In: Naturally Occuring Insecticides (eds., Jcobson M., Crosby D.G), Marcel Dekker, New York, pp. 333-459 |
| | Bioactivities | CHIHARA, C.J. et al. (1972) J. Insect Physiol. 18, 1115-1123 |
| | General | TOM, W.-M. et al. (1975) J. Chem. Soc., Chem. Commun. 24-25 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | General | KUSAMBA, C. et al. (1995) Fitoterapia LXVI, 175-178 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
| | Identification | VOKÁČ, K. et al. (2002) Collect. Czech. Chem. Commun. 67, 124-139 |
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Permanent link to this datasheet: RUBROSTERONE
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