Reaktion #1001830

ord-eb6aaf2d82c043398675d7e0bfb15881

Reaktionsgleichung

CC1=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)OC([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O)CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1
3
CC1=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)OC([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O)CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1
27-O-β-D-glucopyranosyl viscosalactone B
CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2C(O)C[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C[C@H](O)[C@]6(C)[C@H]4CC[C@]23C)C1
4
CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2C(O)C[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C[C@H](O)[C@]6(C)[C@H]4CC[C@]23C)C1
4,16-dihydroxy-5β,6β-epoxyphysagulin D
→
CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O)CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1
compounds 8
Ausbeute 28.0%
CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O)CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1
viscosalactone B
Ausbeute 28.0%

Edukte

CC1=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)OC([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O)CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1
3
CC1=C(CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)OC([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O)CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1
27-O-β-D-glucopyranosyl viscosalactone B
CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2C(O)C[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C[C@H](O)[C@]6(C)[C@H]4CC[C@]23C)C1
4
CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2C(O)C[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C[C@H](O)[C@]6(C)[C@H]4CC[C@]23C)C1
4,16-dihydroxy-5β,6β-epoxyphysagulin D

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeSimilarly, fraction III was purified by Prep
  2. 2
    SonstigeHPLC (MeOH—H2O, 6:4, v/v) and yield pure compound 12 (15 mg, 0.0097%) at 112 min
  3. 3
    SonstigeFraction 3 was further purified by HPLC (MeOH—H2O, 6:4, v/v)

Vorschrift

Isolation of withanolides. The combined crude extract from PhytoMyco Research Corporation (4 g) was stirred with n-hexane (500 mL) and filtered. The hexane insoluble portion (3.2 g) was chromatographed on MPLC using CHCl3 and MeOH (v/v) under gradient condition. The fractions collected were I (600 mg CHCl3:MeOH, 9:1), II (500 mg, CHCl3:MeOH, 8:2), III (1.2 g, CHCl3:MeOH, 7:3), and IV (200 mg, CHCl3:MeOH, 1:1). Repeated MPLC of fraction I using hexane-EtOAc (1:1, v/v) yielded pure compounds 6 (120 mg, 0.078%), 7 (50 mg, 0.032%) and a fraction 1 (4.0 mg). This fraction was further purified by PTLC (hexane-EtOAc, 6:4, v/v) to yield the pure compound 9 (2.1 mg, 0.0014%). Purification of fraction II by preparative HPLC using MeOH—H2O (1:1, v/v) afforded compound 10 (20 mg, 0.013%) at 19.5 min and fraction 2 (50 mg) at 24.2-28.1 min. It was further purified on HPLC by using MeOH—H2O (4:6, v/v) and gave compound 11 (40 mg, 0.026%) at 32.96 min. Similarly, fraction III was purified by Prep. HPLC (MeOH—H2O, 6:4, v/v) and yield pure compound 12 (15 mg, 0.0097%) at 112 min and fractions 3 (950 mg) at 20-45 min and 4 (16 mg) at 140-160 min. Fraction 3 was further purified by HPLC (MeOH—H2O, 6:4, v/v) to afford compounds 8 (200 mg, 0.13%) and 5 (10 mg, 0.0065%) at 66.8 and 78.6 min, respectively, and 700 mg of sucrose at 132 min. Fraction 4 was subjected to HPLC (MeOH—H2O, 7:3, v/v) yielded compound 2 (12 mg, 0.0078%) at 81 min. The fraction IV was purified by HPLC (MeOH—H2O, 7:3) and collected fractions 5 (13 mg) at 20-30 min and fraction 6 (30 mg) at 30.1-66 min. The fraction 6 was purified by HPLC (MeOH—H2O, 7:3, v/v) to yield compound 3 (8.5 mg, 0.0055%) at 57.9 min. Fraction 5 was further purified by HPLC using MeOH—H2O (6:4, v/v) and afforded pure compound 1 (10.5 mg, 0.0068%) at 59.3 min and a mixture of compounds 4 and 12 at 96.4 min (5.0 mg, 0.0032%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07264831B2uspto-grants-2007_09