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Year of first isolation: |
1969 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Ajuga japonica [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Ajuga japonica [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
Ajuga remota [Lamiaceae (alt. Labiatae)] »
Leuzea carthamoides [Asteraceae] »
Vitex madiensis [Lamiaceae (alt. Labiatae)] »
Vitex strickeri [Lamiaceae (alt. Labiatae)] »
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| Occurence in animals: |
Gerardia savaglia [Zoanthidae] »
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)C)O)O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 23044-80-6 | | PubChem CID | 441826 | InChiKey
[ ChemIDPlus: search ] | LQGNCUXDDPRDJH-UKTRSHMFSA-N | | InChI | InChI=1S/C27H44O7/c1-14(2)6-7-22(32)26(5,33)21-8-9-27(34)16-11-17(28)15-10-18(29)19(30)12-24(15,3)23(16)20(31)13-25(21,27)4/h11,14-15,18-23,29-34H,6-10,12-13H2,1-5H3/t15-,18+,19-,20+,21-,22+,23+,24-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 462 (M-H2O)+, 379 (5), 361 (16), 343 (64), 335 (1), 325 (39), 317 (2), 299 (6), 281 (4), 145 (23), 127 (6), 109 (21), 101 (2), 83 (25), 43 (100) | | HR-MS | | | FAB-MS (glycerol) m/z (relative intensity %) | 480 (M)+ (12) | | DEI m/z (relative intenzity %) | 481 (M+H)+ (0.1), 480 (M)+ (O.1), 343 (100) |
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| C5D5N | | 01 | 39.6 | | 02 | 68.2 (d ) | | 03 | 68.5 (d ) | | 04 | 32.9 | | 05 | 52.5 (d ) | | 06 | 204.2 (s ) | | 07 | 122.4 (d ) | | 08 | 164.4 (s ) | | 09 | 42.8 | | 10 | 39.8 | | 11 | 68.9 (d ) | | 12 | 44.2 | | 13 | 48.3 (s ) | | 14 | 84.3 (s ) | | 15 | 31.9 | | 16 | 21.6 (t ) | | 17 | 50.0 (d ) | | 18 | 19.0 (q ) | | 19 | 24.9 (q ) | | 20 | 76.9 (s ) | | 21 | 21.6 (q ) | | 22 | 76.9 (d ) | | 23 | 30.3 | | 24 | 37.2 | | 25 | 28.2 | | 26 | 23.4 (q ) | | 27 | 22.5 (q ) |
| CD3OD | | 01 | 39.9 | | 02 | 68.9 | | 03 | 68.5 | | 04 | 33.3 | | 05 | 52.7 | | 06 | 206.7 | | 07 | 122.7 | | 08 | 165.7 | | 09 | 42.9 | | 10 | 39.0 | | 11 | 69.5 | | 12 | 43.8 | | 13 | 48.5 | | 14 | 84.9 | | 15 | 31.8 | | 16 | 21.5 | | 17 | 50.3 | | 18 | 18.8 | | 19 | 24.6 | | 20 | 77.8 | | 21 | 21.0 | | 22 | 77.9 | | 23 | 30.5 | | 24 | 37.6 | | 25 | 29.2 | | 26 | 23.4 | | 27 | 22.8 |
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| CD3OD | | 01-Ha | 1.39 | | 01-He | 2.59 (dd, 13, 4.2) | | 02-Ha | 4.01 | | 03-He | 3.96 (m, w1/2=8) | | 04-Ha | 1.72 | | 04-He | 1.89 | | 05-H | 2.35 (dd, 12, 5) | | 07-H | 5.80 (d, 2.5) | | 09-Ha | 3.15 (dd, 8.8, 2.8) | | 11-Ha | 4.07 (m, w1/2=28) | | 11-He | -- | | 12-Ha | 2.22 (ddd, 13, 13, 5) | | 12-He | 2.16 | | 14-H | -- | | 15-Ha | 1.95 | | 15-Hb | 1.58 | | 16-Ha | 1.98 | | 16-Hb | 1.74 | | 17-H | 2.41 (m) | | 18-Me | 0.88 (s) | | 19-Me | 1.06 (s) | | 21-Me | 1.20 (s) | | 22-Hb | 3.32 (dd, 11, 2) | | 23-Ha | 1.22 | | 24-Ha | | | 24-Hb | | | 25-H | 1.55 | | 26-Me | 0.92 (d, 6.4) | | 27-Me | 0.93 (d, 6.4) |
| C5D5N | | 01-Ha | | | 01-He | 3.44 | | 02-Ha | 4.56 (m) | | 03-He | 4.20 (m) | | 04-Ha | | | 04-He | | | 05-H | 3.00 (m) | | 07-H | 6.30 (d, 2) | | 09-Ha | 3.86 (dd, 8.2) | | 11-Ha | 4.60 (m) | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.27 (s) | | 19-Me | 1.32 (s) | | 21-Me | 1.57 (s) | | 22-Hb | 3.78 (d, 9) | | 23-Ha | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.81 (d, 5) | | 27-Me | 0.80 (d, 5) |
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| M.P. | | | [α]D20 | + 37 ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | 3400, 1655 | | UV (MeOH) λ max (log ε) | 243 (4.014) |
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| TLC | NP-TLC on silica Rf 0.35 (EtOAc-MeOH-NH3 85:15:5); Rf 0.21 (CH2Cl2-EtOH 85:15); Rf 0.22 (CHCl3-EtOH 80:20); RP-TLC on paraffin coated silica gel Rf 0.5 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.36 (MeOH-H2O 65:35). | | DCCC | CHCl3-MeOH-H2O (13:7:4 v/v) | | GLC | Ret 7.55 min on 1.5% OV101 (0.9 m x 4.5 mm i.d.) at 285°C after silylation at 140°C for 60 h (E: 5.85 min) | | HPLC | NP-HPLC, column Zorbax-SIL, solvent CH2Cl2-iPrOH-H2O 125:25:2, flow-rate 1 ml. min-1 Ret 33.3 min; RP-HPLC, column Spherisorb-ODS 1ml.min-1, linear gradient 20% to 50% ACN in 0.1%TFA in 40 min, flow-rate 1 ml.min-1 , Ret 15.0 min. |
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Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-8M; 8.0 x 10-8M | Drosophila melanogaster BII cell assay: EC50 = 6.2 x 10-8M | Sarcophaga assay: highly active |
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| First isolation | IMAI, S. et al. (1969) J. Chem. Soc., Chem. Commun. 546-547 |
 | | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | KUBO, I. et al. (1984) Agric. Biol. Chem. 48, 1683-1684 |
| | General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
| | General | GUERRIERO, A. et al. (1985) Comp. Biochem. Physiol. B 80, 277-278 |
| | General | KUBO, I. et al. (1985) In: Chemically mediated interactions between plants and other organisms (eds., Cooper-Driver G.A., T. Swain), Plenum Publishing Corp. pp. 171-194 |
| | General | BIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 |
| | Identification | GIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 |
| | General | ZHANG, M. et al. (1992) Phytochemistry 31, 247-250 |
| | Identification | PIS, J. et al. (1994) Phytochemistry 37, 707-711 |
| | General | MINGSHEN, L. et al. (1998) Chin. J. Magn. Resonance 15, 539-542 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
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Permanent link to this datasheet: AJUGASTERONE C
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