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Year of first isolation: |
1967 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Polypodium vulgare [Polypodiaceae] »  ![Wikipedia: Polypodium vulgare [Polypodiaceae]](/images/wikipedia.png)
Vitex megapotamica [Lamiaceae (alt. Labiatae)] »
Helleborus genus [Ranunculaceae] »
Pfaffia iresinoides [Amaranthaceae] »
Leuzea carthamoides [Asteraceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1C2CC[C@]2([C@]1(CC[C@@H]2[C@@]([C@@H](CCC(C)(C)O)O)(C)O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | 18069-14-2 | | PubChem CID | 441833 | InChiKey
[ ChemIDPlus: search ] | GMFLGNRCCFYOKL-ACCCYTKYSA-N | | InChI | InChI=1S/C27H44O8/c1-22(2,32)9-8-20(30)25(5,33)19-7-11-26(34)16-12-21(31)27(35)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h12,15,17-20,28-30,32-35H,6-11,13-14H2,1-5H3/t15-,17-,18+,19-,20+,23+,24+,25+,26+,27+/m0/s1 |
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| FAB-MS m/z | FAB (xenon): 587 (M+glycerol-H)-, 495 (M-H) | | CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 478, 460, 442, 424, 361, 360, 344, 343, 99, 81 | | HR-MS | |
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| C5D5N | | 01 | 34.9 | | 02 | 68.1 | | 03 | 69.9 | | 04 | 36.1 | | 05 | 79.9 | | 06 | 201.0 | | 07 | 119.9 | | 08 | 167.0 | | 09 | 38.4 | | 10 | 44.8 | | 11 | 22.1 | | 12 | 32.2 | | 13 | 48.2 | | 14 | 84.1 | | 15 | 31.8 | | 16 | 21.4 | | 17 | 50.1 | | 18 | 18.0 | | 19 | 17.3 | | 20 | 76.9 | | 21 | 21.7 | | 22 | 77.7 | | 23 | 27.6 | | 24 | 42.3 | | 25 | 69.7 | | 26 | 30.1 | | 27 | 30.2 |
| CD3OD | | 01 | 36.2 | | 02 | 70.2 | | 03 | 68.4 | | 04 | 34.2 | | 05 | 80.3 | | 06 | 202.3 | | 07 | 120.6 | | 08 | 167.5 | | 09 | 39.0 | | 10 | 45.4 | | 11 | 22.5 | | 12 | 32.6 | | 13 | 48.6 | | 14 | 85.0 | | 15 | 31.7 | | 16 | 21.4 | | 17 | 50.4 | | 18 | 18.0 | | 19 | 17.0 | | 20 | 77.9 | | 21 | 21.0 | | 22 | 78.4 | | 23 | 27.3 | | 24 | 42.4 | | 25 | 71.3 | | 26 | 29.7 | | 27 | 28.9 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.26 (br dt, 11.4, 4.0) | | 03-He | 4.15 (br s ) | | 04-Ha | | | 04-He | | | 07-H | 6.25 (d , 2.2) | | 09-Ha | 3.62 (br t, 8.6) | | 11-Ha | | | 11-He | | | 12-Ha | 2.54 (dt, 12.6, 4.6) | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.43 (q, 10.2) | | 16-Hb | | | 17-H | 2.96 (t, 9) | | 18-Me | 1.19 (s ) | | 19-Me | 1.13 (s ) | | 21-Me | 1.57 (s ) | | 22-H | 3.84 (br d, 9.2) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.35 (s ) | | 27-Me | 1.35 (s ) |
| CD3OD | | 01-Ha | 1.68 | | 01-Hb | 1.78 | | 02-Ha | 3.94 | | 03-He | 3.99 | | 04-Ha | 1.75 | | 04-He | 2.08 | | 07-H | 5.85 (d, 2.5) | | 09-Ha | 3.19 (m, w1/2=22) | | 11-Ha | 1.7 | | 11-He | 1.8 | | 12-Ha | 2.13 | | 12-He | 1.88 | | 15-Ha | 2.00 | | 15-Hb | 1.60 | | 16-Ha | 2.00 | | 16-Hb | 1.75 | | 17-H | 2.39 (m) | | 18-Me | 0.89 (s) | | 19-Me | 0.92 (s) | | 21-Me | 1.20 (s) | | 22-H | 3.33 (dd, 11, 2 ) | | 23-Ha | 1.28 | | 23-Hb | 1.66 | | 24-Ha | 1.75-1.8 | | 24-Hb | 1.45 | | 26-Me | 1.19 (s) | | 27-Me | 1.19 (s) |
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| M.P. | 254-257°C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3340 (OH), 1687 (chelated carbonyl), 1657, 1636 | | UV (EtOH) λ max (log ε) | 243 nm (4.11), 317 nm (2.07) |
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| TLC | NP-TLC silica : Rf 0.33 (Me2CO) ; Rf 0.32 (CHCl3-EtOH 4:1) ; Rf 0.22 (CHCl3-EtOH 4:1) ; Rf 0.18 (EtOAc-MeOH-NH4OH 85:10:5) ; Rf 0.19 (CH2Cl2-EtOH 85:15) . RP-TLC on paraffin coated silica gel Rf 0.50 (MeOH-H2O 50:50); RP-TLC on C18-bonded silica gel Rf 0.47 (MeOH-H2O 65:35) | | GLC | Ret 7.5 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 (heptakis-TMS ether) (E : 5.85 min) | | RP-HPLC | (Spherisorb-5ODS2) ACN-0.1% TFA in H2O (23:77), 1 ml.min-1, Ret. 5.8 min. | | NP-HPLC | (Zorbax-Sil) CH2Cl2-iPrOH-H2O (125:40:3), 1 ml.min-1, Ret. 11.3 min. |
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Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-9M | Galleria mellonella in vivo assay: ED50 = 7.8 ug/g | Sarcophaga bullata in vivo assay: ED50 = 7.8 ug/g | Dermestes vulpinus in vivo assay: ED50 = 29.0 ug/g | Calliphora assay: 400% (20-hydroxyecdysone = 100%) |
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| First isolation | JIZBA, J. et al. (1967) Tetrahedron Lett. 5139-5143 |
 | | Identification | RIMPLER, H. et al. (1969) Tetrahedron Lett. 329-333 |
| | General | HARDMAN, R. et al. (1976) Phytochemistry 15, 1515-1516 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
| | General | BIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 |
| | Identification | NISHIMOTO, N. et al. (1987) Phytochemistry 26, 2505-2507 |
| | General | WILSON, I.D. et al. (1988) In: Bioanalysis of Drugs and Metabolites (Eds. E. Reid, J. D. Robinson, I. D. Wilson), Plenum, pp. 313-320 |
| | Identification | GIRAULT, J.-P. et al. (1988) Phytochemistry 27, 737-741 |
| | Bioactivities | SLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 |
| | Identification | COLL, J. et al. (1994) Tetrahedron 50, 7247-7252 |
| | Struct. analysis | PIS, J. et al. (1994) Phytochemistry 37, 707-711 |
| | Bioactivities | HARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 |
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Permanent link to this datasheet: POLYPODINE B
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