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Cytotoxic Phenanthrene, Dihydrophenanthrene, and Dihydrostilbene Derivatives and Other Aromatic Compounds from Combretum laxum
- Source :
- Molecules, Volume 25, Issue 14, Molecules, Vol 25, Iss 3154, p 3154 (2020)
- Publication Year :
- 2020
- Publisher :
- Multidisciplinary Digital Publishing Institute, 2020.
-
Abstract
- The chemical investigation of the roots and stems of Combretum laxum yielded a new dihydrostilbene derivative, 4&prime<br />hydroxy-3,3&prime<br />4-trimethoxy-5-(3,4,5-trimethoxyphenoxy)-bibenzyl (1), two phenanthrenes (2&ndash<br />3), and three dihydrophenanthrenes (4&ndash<br />6), along with one lignan, three triterpenoids, one aurone, one flavone, one naphthoquinone, and two benzoic acid derivatives. Their structures were determined by 1D and 2D nuclear magnetic resonance (NMR) spectroscopic techniques and/or mass spectrometry data. The occurrence of dihydrostilbenoid, phenanthrene and dihydrophenanthrene derivatives is unprecedented in a Combretum species native to the American continent. 2,7-Dihydroxy-4,6-dimethoxyphenanthrene, 2,6-dihydroxy-4,7-dimethoxy-9,10-dihydrophenanthrene and 5-O-methyl apigenin are novel findings in the Combretaceae, as is the isolation of compounds belonging to the chemical classes of aurones and naphthoquinones, while (+)-syringaresinol is reported for the first time in the genus Combretum. Compounds 1&ndash<br />6 were also evaluated for their in vitro cytotoxicity against five human cancer cell lines, and radical-scavenging ability against 1,1-diphenyl-2-picryl-hydrazyl (DPPH). 6-Methoxycoelonin (4) was the most cytotoxic against melanoma cells (IC50 2.59 &plusmn<br />0.11 &micro<br />M), with a high selectivity index compared with its toxicity against nontumor mammalian cells (SI 25.1). Callosin (6), despite exhibiting the strongest DPPH-scavenging activity (IC50 17.7 &plusmn<br />0.3 &micro<br />M), proved marginally inhibitory to the five cancer cell lines tested, indicating that, at least for these cells, antioxidant potential is unrelated to antiproliferative activity.
- Subjects :
- phenanthrene
Magnetic Resonance Spectroscopy
DPPH
Combretum
Pharmaceutical Science
antioxidant activity
combretaceae
01 natural sciences
Antioxidants
Analytical Chemistry
chemistry.chemical_compound
0302 clinical medicine
Chlorocebus aethiops
Drug Discovery
Apigenin
Dihydrostilbenoids
Melanoma
Lignan
biology
Naphthoquinone
Chemistry (miscellaneous)
030220 oncology & carcinogenesis
MCF-7 Cells
Molecular Medicine
Stereochemistry
Dihydrostilbenoid
Article
Cell Line
lcsh:QD241-441
03 medical and health sciences
Picrates
lcsh:Organic chemistry
Cell Line, Tumor
Aurone
Animals
Humans
Physical and Theoretical Chemistry
Vero Cells
cytotoxic activity
Combretaceae
bibenzyl
Plant Extracts
Biphenyl Compounds
Organic Chemistry
Phenanthrenes
biology.organism_classification
dihydrophenanthrene
0104 chemical sciences
010404 medicinal & biomolecular chemistry
chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....816a9eb2ecf85858c9b6abf28f778a73
- Full Text :
- https://doi.org/10.3390/molecules25143154