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Year of first isolation: |
1984 |
| Formula: | C28H46O7 |
| Molecular weight: | 478 |
| Occurence in plants: |
Microsorum scolopendria [Polypodiaceae] »  ![Wikipedia: Microsorum scolopendria [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
Drosophila melanogaster [Diptera] »
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![20-DEOXYMAKISTERONE A [= 24-METHYL-ECDYSONE]](images/ecdy/66.gif)
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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)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@H](C)[C@@H](C[C@H](C(C)(C)O)C)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,10R,13R,14S,17R)-17-[(3R)-3,6-dihydroxy-5,6-dimethylheptan-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 | 129729856 | InChiKey
[ ChemIDPlus: search ] | BKQNQEPDBSCBHY-QNGCTKKYSA-N | | InChI | InChI=1S/C28H46O6/c1-15(25(3,4)33)11-21(29)16(2)17-8-10-28(34)19-12-22(30)20-13-23(31)24(32)14-26(20,5)18(19)7-9-27(17,28)6/h12,15-18,20-21,23-24,29,31-34H,7-11,13-14H2,1-6H3/t15?,16?,17-,18?,20+,21-,23-,24+,26-,27-,28-/m1/s1 |
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| CI-MS (NH3) m/z | 496 [M+H+NH3]+, 479 [M+H]+, 461 [M+H-H2O]+, 443 [M+H-2H2O]+, 425 [M+H-3H2O]+, 240, 223, 180 | | GC-MS (fully silylated derivative) | m/z 567 (SIM) | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| D2O | | 01 | 38.3 | | 02 | 70.1 | | 03 | 70.0 | | 04 | 34.1 | | 05 | 53.3 | | 06 | 211.2 | | 07 | 123.9 | | 08 | n.d. | | 09 | 36.7 | | 10 | 40.8 | | 11 | n. d. | | 12 | 33.1 | | 13 | 49.1 | | 14 | 87.9 | | 15 | 33.6 | | 16 | n.d. | | 17 | 50.0 | | 18 | 18.0 | | 19 | 25.8 | | 20 | 44.6 | | 21 | 15.5 | | 22 | 74.1 | | 23 | 33.7 | | 24 | 42.4 | | 25 | 77.0 | | 26 | 27.8 | | 27 | 28.3 | | 28 | 15.5 |
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| D2O | | 01-Ha | 1.38 (t, 13) | | 01-He | 1.88 | | 02-Ha | 3.99 (w 1/2=22) | | 03-He | 4.07 (w 1/2=8) | | 04-Ha | 1.75 | | 04-He | 1.75 | | 05-H | 2.34 (t) | | 07-H | 5.96 (d, 2.4) | | 09-Ha | 3.11 (w 1/2=22) | | 11-Ha | 1.71 | | 11-He | 1.85 | | 12-Ha | 1.88 | | 12-He | 1.88 | | 15-Ha | 1.62 | | 15-Hb | 2.03 | | 16-Ha | 1.95* | | 16-Hb | 1.85* | | 17-H | 1.84 | | 18-Me | 0.746 (s) | | 19-Me | 1.000 (s) | | 20-H | 1.84 | | 21-Me | 0.935 (d, 6.8) | | 22-H | 3.85 (d, 10) | | 23-Ha | 1.13 (m) | | 23-Hb | 1.56 | | 24-Ha | 1.66 | | 26-Me | 1.179 (s) | | 27-Me | 1.196 (s) | | 28-Me | 0.935 (d, 6.8) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | RP-HPLC | Retention time 18 min [column Ultrasphere ODS, 15 cm long, 4.6 mm i.d., eluted with a linear gradient (30 min) of MeOH-H2O from 35:65 to 80:20, flow-rate 1 ml.min-1] (20E 13 min, E : 16 min). | | IS-RP-HPLC | Retention time 64 min [column Waters Resolve C18 5?m, 15 cm long, 3.9 mm i.d. eluted with a gradient of ACN/aqueous buffer (20 mM tris/perchlorate, pH 7.5)] (E : 59 min) |
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Drosophila melanogaster BII cell assay: EC50 = 2.1 x 10-6M |
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| First isolation | REDFERN, C.F. et al. (1984) Proc. Natl. Acad. Sci. U.S.A. 5463-5467 |
 | | General | PAK, M.D. et al. (1987) J. Liq. Chromatogr. 10, 2591-2611 |
| | Bioactivities | DINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 |
| | Struct. analysis | SNOGAN, E. et al. (2007) Phytochemical Analysis 18, 441-450 |
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Permanent link to this datasheet: 20-DEOXYMAKISTERONE A [= 24-METHYL-ECDYSONE]
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