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Year of first isolation: |
1968 |
| Formula: | C29H48O7 |
| Molecular weight: | 508 |
| Occurence in plants: |
Lemmaphyllum microphyllum [Polypodiaceae] »  ![Wikipedia: Lemmaphyllum microphyllum [Polypodiaceae]](/images/wikipedia.png)
Podocarpus elatus [Podocarpaceae] »
Podocarpus macrophyllus [Podocarpaceae] »
Leuzea carthamoides [Asteraceae] »
Serratula coronata [Asteraceae] »
Diploclisia glaucescens [Menispermaceae] »
Microsorum scolopendria [Polypodiaceae] »
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| Occurence in animals: |
Dysdercus fasciatus [Pyrrhocoridae] »
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![MAKISTERONE C [= PODECDYSONE A, LEMMASTERONE]](images/ecdy/227.gif)
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| Canonical SMILES | CCC(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](O)CC(C(C)(C)O)CC)O)O)C)C » 
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](O)C[C@H](C(C)(C)O)CC)O)O)C)C »
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](O)C[C@@H](C(C)(C)O)CC)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-5-ethyl-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101249757 | InChiKey
[ ChemIDPlus: search ] | CIQDSODCPIIBBH-BFSOYOPGSA-N | | InChI | InChI=1S/C29H48O7/c1-7-16(25(2,3)34)12-24(33)28(6,35)23-9-11-29(36)18-13-20(30)19-14-21(31)22(32)15-26(19,4)17(18)8-10-27(23,29)5/h13,16-17,19,21-24,31-36H,7-12,14-15H2,1-6H3/t16?,17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 508 (M)+, 493, 490, 475, 472, 457, 454, 439, 363, 345, 189, 171, 145 (M-363)+, 127, 109 | | HR-MS | |
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| D2O | | 01 | 37.9 | | 02 | 69.9 | | 03 | 69.9 | | 04 | 33.8 | | 05 | 52.9 | | 06 | 211.5 | | 07 | 124.2 | | 08 | - | | 09 | 36.6 | | 10 | 40.8 | | 11 | 22.3 | | 12 | 33.4 | | 13 | 49.9 | | 14 | 87.6 | | 15 | 32.9 | | 16 | 22.4 | | 17 | 51.2 | | 18 | 19.7 | | 19 | 25.8 | | 20 | 80.6 | | 21 | 22.2 | | 22 | 77.7 | | 23 | 35.2 | | 24 | 50.1 | | 25 | 77.5 | | 26 | 28.7 | | 27 | 28.7 | | 28 | 26.0 | | 29 | 16.6 |
| CD3OD | | 01 | 37.36 | | 02 | 68.69 | | 03 | 68.50 | | 04 | 32.84 | | 05 | 51.78 | | 06 | 206.43 | | 07 | 122.10 | | 08 | 168.01 | | 09 | 35.09 | | 10 | 39.25 | | 11 | 21.53 | | 12 | 32.50 | | 13 | 49.50 | | 14 | 85.17 | | 15 | 31.79 | | 16 | 21.62 | | 17 | 50.41 | | 18 | 18.07 | | 19 | 24.43 | | 20 | 78.01 | | 21 | 2096 | | 22 | 77.20 | | 23 | 25.97 | | 24 | 50.28 | | 25 | 74.11 | | 26 | 25.60 | | 27 | 29.10 | | 28 | 33.02 | | 29 | 14.37 |
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| D2O | | 01-Ha | 1.38 | | 01-Hb | 1.88 | | 02-Ha | 3.99 (m, w1/2=22) | | 03-He | 4.07 (m, w1/2=8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.36 (t) | | 07-H | 5.97 (db, 1.6) | | 09-Ha | 3.11 (m, w1/2=22) | | 11-Ha | 1.74 | | 11-He | 1.86 | | 12-Ha | 1.99* | | 12-He | 1.96* | | 15-Ha | 1.66 | | 15-Hb | 2.06 (m) | | 16-Ha | 1.90* | | 16-Hb | 1.80* | | 17-H | 2.34 (m) | | 18-Me | 0.872 (s) | | 19-Me | 1.000 (s) | | 21-Me | 1.240 (s) | | 22-H | 3.56 (d, 10) | | 23-Ha | 1.44 | | 23-Hb | 1.44 | | 24-Hb | 1.49 | | 26-Me | 1.198 (s) | | 27-Me | 1.209 (s) | | 28-Ha | 1.61 | | 28-Hb | 1.25 | | 29-Me | 0.997 (t, 7.5) |
| CD3OD | | 01-Ha | 1.43 | | 01-Hb | 1.79 | | 02-Ha | 3.84 (m, w1/2=22) | | 03-He | 3.94 (m, w1/2=8) | | 04-Ha | 1.65 | | 04-He | 1.75 | | 05-H | 2.37 (dd, 12, 5) | | 07-H | 5.80 (d, 2.5) | | 09-Ha | 3.16 (m, w1/2=22) | | 11-Ha | 1.66 | | 11-He | 1.79 | | 12-Ha | 2.13 | | 12-He | 1.87 | | 15-Ha | 2.00 | | 15-Hb | 1.55 | | 16-Ha | 2.00 | | 16-Hb | 1.77 | | 17-H | 2.39 (m ) | | 18-Me | 0.89 (s ) | | 19-Me | 0.96 (s ) | | 21-Me | 1.20 (s ) | | 22-Hb | 3.42 | | 23-Ha | 1.43 | | 23-Hb | 1.55 | | 24-Ha | 1.45 | | 26-Me | 1.21 (s ) | | 27-Me | 1.10 (s ) | | 28-CH2- | 1.14, 1.53 | | 29-Me | 1.01 (t, 6.5) |
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| M.P. | 258-259°C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400-3470 (OH), 1643-1650 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 243-244 (4.146) |
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| HPTLC | | | TLC | NP-TLC on silica gel : Rf 0.28 (CHCl3-EtOH 4:1); Rf 0.49 (EtOAc-MeOH-NH4OH 85:10:5); Rf 0.46 (CH2Cl2-EtOH 85:15) | | GLC | | | HPLC | Normal phase (Zorbax-Sil) Ret 17.2 min (solvent : CH2Cl2-iPrOH-H2O 125:25:2) (20E: 53.2 min); Reverse phase (Spherisorb-5ODS-2) Ret 17.5 min (solvent : ACN-0.1% TFA in H2O 23:77) (20E 5.5 min) |
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Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-7M | Drosophila melanogaster Kc-H cell assay: EC50 = 1.3 x 10-7M | Calliphora assay: 100% (20-hydroxyecdysone = 100%) | Musca assay: 0% (20-hydroxyecdysone = 100%) |
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| First isolation | IMAI, S. et al. (1968) Tetrahedron Lett. 3883-3886 |
 | | General | GALBRAITH, M.N. et al. (1968) J. Chem. Soc., Chem. Commun. 971-972 |
| | General | TAKEMOTO, T. et al. (1968) Tetrahedron Lett. 4061-4064 |
| | Bioactivities | CHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 |
| | 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. (1988) Phytochemistry 27, 737-741 |
| | General | FELDLAUFER, M.F. et al. (1991) Arch. Insect Biochem. Physiol. 18, 71-80 |
| | 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 |
| | General | JAYASINGHE, L. et al. (2003) Steroids 68, 447-450 |
| | General | SNOGAN, E. et al. (2007) Phytochemical Analysis 18, 441-450 |
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Permanent link to this datasheet: MAKISTERONE C [= PODECDYSONE A, LEMMASTERONE]
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