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Year of first isolation: |
1985 |
| Formula: | C28H46O7 |
| Molecular weight: | 494 |
| Occurence in plants: |
Diploclisia glaucescens [Menispermaceae] »  ![Wikipedia: Diploclisia glaucescens [Menispermaceae]](/images/wikipedia.png)
Vitex canescens [Lamiaceae (alt. Labiatae)] »
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| Occurence in animals: |
Acromyrmex octospinosus [Formicidae] »
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| Canonical SMILES | CC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)C(C)(C)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(CC[C@@H]2[C@](C)([C@@H](C[C@@H](C(C)(C)O)C)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 12312688 | InChiKey
[ ChemIDPlus: search ] | IJRBORPEVKCEQD-TUVIPRGISA-N | | InChI | InChI=1S/C28H46O7/c1-15(24(2,3)33)11-23(32)27(6,34)22-8-10-28(35)17-12-19(29)18-13-20(30)21(31)14-25(18,4)16(17)7-9-26(22,28)5/h12,15-16,18,20-23,30-35H,7-11,13-14H2,1-6H3/t15-,16-,18-,20+,21-,22-,23+,25+,26+,27+,28+/m0/s1 |
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| CI-MS (NH3) m/z | 495 (M+H)+, | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| C5D5N | | 01 | 38.1 (t ) | | 02 | 68.1 (d ) | | 03 | 68.1 (d ) | | 04 | 32.5 (t ) | | 05 | 51.4 (d ) | | 06 | 203.3 (s ) | | 07 | 121.6 (d ) | | 08 | 166.1 (s ) | | 09 | 34.6 (d ) | | 10 | 38.7 (s ) | | 11 | 21.2 (t ) | | 12 | 31.8 (t ) | | 13 | 48.2 (s ) | | 14 | 84.2 (s ) | | 15 | 32.1 (t ) | | 16 | 21.6 (t ) | | 17 | 50.1 (d ) | | 18 | 17.9 (q ) | | 19 | 24.5 (q ) | | 20 | 77.1 (s ) | | 21 | 21.4 (q ) | | 22 | 76.2 (d ) | | 23 | 35.3 (t ) | | 24 | 43.5 (d ) | | 25 | 72.3 (s ) | | 26 | 27.0 (q )* | | 27 | 29.0 (q )* | | 28 | 16.8 (q ) |
| CD3OD | | 01 | 37.42 | | 02 | 68.73 | | 03 | 68.54 | | 04 | 32.86 | | 05 | 51.81 | | 06 | 206.44 | | 07 | 122.17 | | 08 | 167.89 | | 09 | 35.14 | | 10 | 39.28 | | 11 | 21.55 | | 12 | 32.50 | | 13 | 49.0* | | 14 | 85.31 | | 15 | 31.76 | | 16 | 21.62 | | 17 | 50.42 | | 18 | 18.00 | | 19 | 24.39 | | 20 | 78.05 | | 21 | 20.72 | | 22 | 77.83 | | 23 | 35.18 | | 24 | 44.40 | | 25 | 74.06 | | 26 | 25.92 | | 27 | 28.20 | | 28 | 16.85 |
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| CD3OD | | 01-Ha | 1.43 (dd, 13.3; 12.2) | | 01-He | 1.80 (dd, 13.3; 4.4) | | 02-Ha | 3.84 (ddd, 12.2; 4.4; 3.2) | | 03-He | 3.95 (q, 3; 3; 3) | | 04-Ha | 1.71 | | 04-He | 1.71 | | 05-H | 2.39 (dd, 12.7; 4.4) | | 07-H | 5.81 (d, 2.6) | | 09-Ha | 3.15 (ddd, 11.5; 7.0; 2.6) | | 11-Ha | 1.71 | | 11-He | 1.81 | | 12-Ha | 2.13 | | 12-He | 1.88 | | 15-Ha | 1.96 | | 15-Hb | 1.59 | | 16-Ha | 1.77 | | 16-Hb | 2.0 | | 17-H | 2.38 (dd, 10; 8) | | 18-Me | 0.889 (s) | | 19-Me | 0.967 (s) | | 21-Me | 1.140 (s) | | 22-H | 3.48 (dd, 9.5; 2.2) | | 23-Ha | 1.86 | | 23-Hb | 1.06 | | 24-H | 1.65 | | 26-Me | 1.189 (s) | | 27-Me | 1.193 (s) | | 28-Me | 1.034 (s) |
| D2O | | 01-Ha | 1.38 | | 01-He | 1.88 | | 02-Ha | 3.99 (m, w1/2 = 22) | | 03-He | 4.06 (m, w1/2 = 8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.34 (t ) | | 07-H | 5.97 (d, 2.5) | | 09-Ha | 3.11 (m, w1/2 = 22) | | 11-Ha | 1.73 | | 11-He | 1.85 | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.34 (m ) | | 18-Me | 0.87 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1.22 (s ) | | 22-H | 3.48 (dd, 11,2) | | 23-Ha | 1.85 | | 23-Hb | 1.00 | | 24-H | 1.60 | | 26-Me | 1.16 (s )* | | 27-Me | 1.19 (s )* | | 28-Me | 1.02 (d, 6.7) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400, 1850 | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | Silica plates (EtOAc-95% EtOH 4:1) | | GLC | | | HPLC | NP-HPLC, Column Zorbax-SIL 25 x 0.46 cm, solvent CH2Cl2-iPrOH-H2O 125:25:2, flow-rate 2 ml.min-1, 13.6 min (makisterone A : 16.7 min). RP-HPLC, Column Whatman ODS-2 50 x 0.94 cm, solvent ACN-H2O 1:4, flow-rate 4 ml.min-1. |
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Drosophila melanogaster BII cell assay: EC50 = 2.2 x 10-7M |
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| First isolation | MILLER, R.W. et al. (1985) Planta Med. 51, 40-42 |
 | | General | MAURER, P. et al. (1993) Aust. J. Chem. 23, 29-35 |
| | Bioactivities | HARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 |
| | Identification | SUKSAMRARN, A. et al. (1997) Phytochemistry 45, 1149-1152 |
| | First isolation | LAOSOOKSAHIT, S. et al. (2003) The Journal of KMITNB 13(1), 1-13 |
| | Struct. analysis | BUDĚŠÍNSKÝ, M. et al. (2008) Steroids 73, 502-514 |
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Permanent link to this datasheet: 24-EPI-MAKISTERONE A
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