Search results for "Annonaceae"
showing 10 items of 37 documents
Diepoxyrollin and Diepomuricanin B: Two New Diepoxyacetogenins from Rollinia membranacea Seeds
1997
Diepoxyrollin (1) and diepomuricanin B (2), two new Annonaceous acetogenins were isolated from the cytotoxic MeOH extract of the seeds of Colombian Rollinia membranacea. Five others known acetogenins were also isolated, dieporeticanin 1, dieporeticanin 2, diepomuricanin A, rollinone, and sylvaticin. Their structures were elucidated on the basis of spectral data. Compounds 1 and 2 belong to the rare type of diepoxyacetogenins, which are probably precursors of the mono-tetrahydrofuran acetogenins.
3-acetylaltholactone and related styryl-lactones, mitochondrial respiratory chain inhibitors.
2000
A novel furano-pyrone, 3-acetylaltholactone, and two other known styryl-lactones, altholactone and 5-acetoxyisogoniothalamin oxide, have been isolated from Goniothalamus arvensis (Annonaceae) stem bark. We report here the isolation and structural elucidation of these compounds with furane-pyrone and styryl-pyrone skeletons, postulating also for the first time their mechanism of cytotoxicity based on inhibition on mammalian mitochondrial respiratory chain.
Anti-inflammatory activity of berenjenol and related compounds.
2008
Berenjenol ( 1), isolated from OXANDRA cf. XYLOPIOIDES (Annonaceae), was tested on two different experimental models of inflammation. The compound showed anti-inflammatory activity in the test of acute mouse ear edema induced by TPA (54 % inhibition, 1 μmol/ear) as well as in the test of subchronic inflammation induced by repeated application of TPA (57 % inhibition, 7 × 1 μmol/ear). Moreover, while it reduced the expression of both COX-2 (65 % inhibition at 50 μM) and iNOS (80 % inhibition at 50 μM), it was not active against TNF- α and IL-1 β in murine macrophages (RAW 264.7) stimulated with LPS. Structural modification of 1 gave two derivatives, berenjenol acetate ( 2) and 3-oxo-berenjen…
Chromone and phenanthrene alkaloids from Dennettia tripetala.
2002
Dennettine, a new 2,6-dimethoxychromone and three known phenanthrene alkaloids (uvariopsine, stephenanthrine and argentinine) in addition to the phenolic and known compound vanillin were isolated from the roots of Dennettia tripetala. Their structures were determined by physical and spectroscopical one dimensional (1D) and 2D-NMR analysis, including heteronuclear multiple bond correlation and nuclear Overhauser enhancement spectroscopy.
Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I).
1994
Natural products from the plants of the family Annonaceae, collectively called Annonaceous acetogenins, are very potent inhibitors of the NADH-ubiquinone reductase (Complex I) activity of mammalian mitochondria. The properties of five of such acetogenins are compared with those of rotenone and piericidin, classical potent inhibitors of Complex I. Rolliniastatin-1 and rolliniastatin-2 are more powerful than piericidin in terms of both their inhibitory constant and the protein-dependence of their titre in bovine submitochondrial particles. These acetogenins could be considered therefore the most potent inhibitors of mammalian Complex I. Squamocin and otivarin also have an inhibitory constant …
Prenylated benzopyran derivatives from two Polyalthia species
1996
Two new benzopyran derivatives, (6E,10E)-isopolycerasoidol and polycerasoidin methyl ester, have been isolated from a methanolic extract of the stem bark of Polyalthia cerasoides. Their structures were established on the basis of chemical and spectral evidence. Polyalthia sclerophylla contains (6E,10E)-isopolycerasoidol, besides the known polycerasoidin and polycerasoidol. In addition, a known phenylpropene derivative, trans-asarone, has also been isolated from both species and fully characterized.
Acetogenins, Aporphinoids, and Azaanthraquinone from Annona cherimolia Seeds.
1989
We have isolated several known steroids, glycosides, isoquinoline, and azaanthraquinone alkaloids, and five acetogenins belonging to a new group of secondary metabolites, the bis-tetrahydrofuran gamma-lactones, from the seeds of ANNONA CHERIMOLIA. The azaanthraquinone alkaloid isolated was identified as cleistopholine. One new acetogenin is reported here: laherradurine; a second new one was isolated, but its structure has not been determined. The other three: cherimoline, dihydrocherimoline, and asimicine have already been reported.
Bisbenzyltetrahydroisoquinolines, a New Class of Inhibitors of the Mitochondrial Respiratory Chain Complex I
2004
Four bisbenzyltetrahydroisoquinoline alkaloids (-)-medelline, (+)-antioquine, (+)-aromoline, and (+)-obamegine were isolated from the fruits of Xylopia columbiana. These compounds, the previously isolated alkaloids (+)-thaligrisine and (+)-isotetrandrine, as well as their O-acetylated derivatives were assayed on submitochondrial particles from beef heart as inhibitors of the mammalian respiratory chain. The results revealed that these alkaloids act as selective inhibitors of mitochondrial complex I in a 0.15 - 4.71 microM range. O-Acetylation, which increases their lipophilicity, considerably increased the inhibitory potency.
Nuevos fármacos inspirados en Annonáceas
2014
Los metabolitos secundarios activos (MSA) juegan un papel importante en el descubrimiento de nuevos medicamentos. Moléculas naturales con esqueletos complejos, tales como las estatinas aisladas de Aspergillus terreus, o las acetogeninas específicas de la familia Annonaceae, no hubieran podido ser inventadas en ningún laboratorio. Los MSA aislados en Annonaceae, especialmente las acetogeninas y los alcaloides isoquinoleínicos, pueden ser considerados como fuente constante de inspiración para químicos, farmacólogos y para todos los investigadores interesados en el descubrimiento de una nueva familia de medicamentos. Active secondary metabolites (ASM) play a highly significant role in the drug…
N-Cinnamoyltetraketide Derivatives from the Leaves of Toussaintia orientalis
2015
Seven N-cinnamoyltetraketides (1−7), including the new Ztoussaintine E (2), toussaintine F (6), and toussaintine G (7), were isolated from the methanol extract of the leaves of Toussaintia orientalis using column chromatography and HPLC. The configurations of E-toussaintine E (1) and toussaintines A (3) and D (5) are revised based on single-crystal X-ray diffraction data from racemic crystals. Both the crude methanol extract and the isolated constituents exhibit antimycobacterial activities (MIC 83.3−107.7 μM) against the H37Rv strain of Mycobacterium tuberculosis. Compounds 1, 3, 4, and 5 are cytotoxic (ED50 15.3−105.7 μM) against the MDA-MB-231 triple negative aggressive breast cancer cel…