Desacetyluvaricin from Uvaria accuminata, Configuration of Uvaricin at C-36

Jolad, Shivanand D.; Hoffmann, Joseph J.; Cole, Jack R.; Barry, Clifton E.; Bates, Robert B.; Linz, Gary S.; König, Wilfried Α.

doi:10.1021/np50040a023

Cited by 66 publications

(51 citation statements)

References 2 publications

(4 reference statements)

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“…The IR spectra were measured on a Hitachi 260 ± 30 spectrophotometer. 1 H-NMR (400 MHz) and 13 Table 1; 13 C-NMR data (100 MHz, CDCl 3 ): see Table 1 C-NMR data [8], [15].…”

Section: Methodsmentioning

confidence: 99%

New Adjacent Bis-Tetrahydrofuran Annonaceous Acetogenins fromAnnona muricata

Chang¹,

Liaw²,

Lin³

et al. 2003

Planta med

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Bioactivity-guided fractionation led to the isolation of two new Annonaceous acetogenins, annocatacin A ( 1). and annocatacin B ( 2). from the seeds and the leaves, respectively, of Annona muricata. Compounds 1 and 2 are the first examples where the adjacent bis-tetrahydrofuran ring system is located at C-15. The new structures were elucidated and characterized by spectral and chemical methods. Both Annonaceous acetogenins 1 and 2 showed significant in vitro cytotoxicity toward the human hepatoma cell lines, Hep G2 and 2,2,15, and were compared with the known adjacent bis-tetrahydrofuran acetogenins, neoannonin ( 3). desacetyluvaricin ( 4). bullatacin ( 5). asimicin ( 6). annoglaucin ( 7). squamocin ( 8). and rollimusin ( 9).

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“…The IR spectra were measured on a Hitachi 260 ± 30 spectrophotometer. 1 H-NMR (400 MHz) and 13 Table 1; 13 C-NMR data (100 MHz, CDCl 3 ): see Table 1 C-NMR data [8], [15].…”

Section: Methodsmentioning

confidence: 99%

New Adjacent Bis-Tetrahydrofuran Annonaceous Acetogenins fromAnnona muricata

Chang¹,

Liaw²,

Lin³

et al. 2003

Planta med

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“…33. ); the absolute configuration of the lactic acid was established by chiral gas chromatography (105).…”

Section: Degradation Methodsmentioning

confidence: 99%

“…IR (64,89,105) Epomuricenin-A = Epoxymurin-A Annona muricata (seeds) (108), (stem bark) (109) isolated as a mixture with epomuricenin-B (108) isolated as a mixture with epoxymurin-B (109) C3sH6203; M = 530…”

Section: Cd: Negative Cotton Effect -+ (S)-c-4 (83)mentioning

confidence: 99%

“…Epoxyrollin A * = Dieporeticanin-l (106) Epoxyrollin B* = Diepomuricanin-A (106) Uleicin A* (106,162) Uleicin B* (106,162) Uleicin C* = Sylvaticin (106,162) Uleicin D* (106,162) Uleicin E* (106,162) Uleirollin (106) Uvaria acuminata Desacetyluvaricin (105) Uvaricin (1,105) U varia grand!flora Isodesacetyluvaricin (123) U varia hookeri Isodesacetyluvaricin (137) Narumicin I, II (mixture) (137) Squamocin (137) Squamocinone (137) Uvariamicin-I, II, III (mixture) (137) Uvaria narum Isodesacetyluvaricin (124) Narumicin I, II (mixture) (124,137) Panalicin (139) Squamocin (137,139) Squamocinone (137,139) Uvariamicin I, II, III (mixture) (137,141) * Wrong structure …”

Section: Rollinia Uleimentioning

confidence: 99%

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Acetogenins from Annonaceae

Cavé

Figadère

Laurens

et al. 1997

Fortschritte Der Chemie Organischer Naturstoffe Progress in the Chemistry of Organic Natural Products

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“…On the other hand, from the fat-soluble fraction, several antitumor agents, e.g., uvaretin (4), 3) uvaricin, 4) and desacetyluvaricin 5) have been isolated.…”

mentioning

confidence: 99%

Cytotoxic C-Benzylated Dihydrochalcones from Uvaria acuminata

Ichimaru

Nakatani

Takahashi

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new C-benzylated dihydrochalcones, isochamuvaritin (1) and acumitin (2), have been isolated from the African medicinal plant Uvaria acuminata, together with the previously reported benzylbenzoate (3), uvaretin (4), isouvaretin (5), diuvaretin (6), and uvangoletin (7). The structural elucidation of compounds 1 and 2 in spectroscopic studies is described. C-Benzylated dihydrochalcones, especially 1, 2, 4, and 6, showed considerable cytotoxicity toward human promyelocytic leukemia HL-60 cells.

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Desacetyluvaricin from Uvaria accuminata, Configuration of Uvaricin at C-36

Cited by 66 publications

References 2 publications

New Adjacent Bis-Tetrahydrofuran Annonaceous Acetogenins fromAnnona muricata

New Adjacent Bis-Tetrahydrofuran Annonaceous Acetogenins fromAnnona muricata

Acetogenins from Annonaceae

Cytotoxic C-Benzylated Dihydrochalcones from Uvaria acuminata

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