Pobeguinine: a monoterpene indole alkaloid and other bioactive constituents from the stem bark of Nauclea pobeguinii
-
Jean J.K. Bankeu
,
Stéphanie Madjouka
Abstract
Phytochemical investigation of dichloromethane neutral phase of stem bark of Nauclea pobeguinii led to the isolation of a new monoterpene indole alkaloid, pobeguinine 1 along with 14 known compounds including (−)-naucleofficine D (2a), (+)-naucleofficine D (2b), naucleidinal (3), quafrinoic acid (4), betulinic acid (5), ursolic acid (6), quinovic acid (7), quinovic acid 3-O-α-L-rhamnopyranoside (8a), quinovic acid 3-O-β-D-fucopyranoside (8b), β-sitosterol (9), β-sitosterol 3-O-β-D-glucopyranoside (10), benzoic acid (11), lacceroic acid (12) and n-heptacosane (13). The structure of compound 1 was unambiguously assigned on the basis of single-crystal X-ray diffraction technique. The Hirshfeld surface analysis was further carried out to quantitatively analyze the role of various types of hydrogen bonding in crystal stability. These structures were elucidated using spectroscopic methods. The isolates were evaluated for their radical scavenging properties as well as inhibitory activities against urease and tyrosinase enzymes with IC50 values ranging from 13.4 to 58.9, 46.0 to 86.7 and 39.4 to 87.1 μg/mL, respectively. Compound 6 exhibited maximum radical scavenging activity with IC50 13.4 μg/mL, while compound 4 exhibited maximum tyrosinase with IC50 39.4 μg/mL. All the isolates showed moderate urease inhibition.
Acknowledgments
The authors are very grateful to The World Academy of Sciences (TWAS) and the International Center for Chemical and Biological Sciences (ICCBS), University of Karachi, Pakistan, for their financial and technical support through the ICCBS-TWAS Postdoctoral Fellowship number 3240280476 granted to B.K.J.J.
Disclosure statement: The authors declare that there is no conflict of interest regarding the publication of this manuscript.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2017-0127).
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Artikel in diesem Heft
- Frontmatter
- Research Articles
- Diverse bioactive compounds from Sarcophtyton glaucom: structure elucidation and cytotoxic activity studies
- Pobeguinine: a monoterpene indole alkaloid and other bioactive constituents from the stem bark of Nauclea pobeguinii
- Why is the hydrolytic activity of acetylcholinesterase pH dependent? Kinetic study of acetylcholine and acetylthiocholine hydrolysis catalyzed by acetylcholinesterase from electric eel
- Evaluation of Lavandula stoechas L. subsp. stoechas L., Mentha spicata L. subsp. spicata L. essential oils and their main components against sinusitis pathogens
- Screening of the five different wild, traditional and industrial Saccharomyces cerevisiae strains to overproduce bioethanol in the batch submerged fermentation
- The effects of inulin and fructo-oligosaccharide on the probiotic properties of Lactobacillus spp. isolated from human milk
- A proteomics analysis of adventitious root formation after leaf removal in lotus (Nelumbo nucifera Gaertn.)
- Larval hemolymph of rhinoceros beetle, Allomyrina dichotoma, enhances insulin secretion through ATF3 gene expression in INS-1 pancreatic β-cells
- Antimalarial activity of the isolates from the marine sponge Hyrtios erectus against the chloroquine-resistant Dd2 strain of Plasmodium falciparum
- Rapid-communication
- Bioactive compounds from bay leaves (Laurus nobilis) extracted by microwave technology
- Erratum
- Erratum to: Transcriptome profiling reveals an IAA-regulated response to adventitious root formation in lotus seedling
- Erratum to: A comparative proteomic analysis for adventitious root formation in lotus root (Nelumbo nucifera Gaertn)
Artikel in diesem Heft
- Frontmatter
- Research Articles
- Diverse bioactive compounds from Sarcophtyton glaucom: structure elucidation and cytotoxic activity studies
- Pobeguinine: a monoterpene indole alkaloid and other bioactive constituents from the stem bark of Nauclea pobeguinii
- Why is the hydrolytic activity of acetylcholinesterase pH dependent? Kinetic study of acetylcholine and acetylthiocholine hydrolysis catalyzed by acetylcholinesterase from electric eel
- Evaluation of Lavandula stoechas L. subsp. stoechas L., Mentha spicata L. subsp. spicata L. essential oils and their main components against sinusitis pathogens
- Screening of the five different wild, traditional and industrial Saccharomyces cerevisiae strains to overproduce bioethanol in the batch submerged fermentation
- The effects of inulin and fructo-oligosaccharide on the probiotic properties of Lactobacillus spp. isolated from human milk
- A proteomics analysis of adventitious root formation after leaf removal in lotus (Nelumbo nucifera Gaertn.)
- Larval hemolymph of rhinoceros beetle, Allomyrina dichotoma, enhances insulin secretion through ATF3 gene expression in INS-1 pancreatic β-cells
- Antimalarial activity of the isolates from the marine sponge Hyrtios erectus against the chloroquine-resistant Dd2 strain of Plasmodium falciparum
- Rapid-communication
- Bioactive compounds from bay leaves (Laurus nobilis) extracted by microwave technology
- Erratum
- Erratum to: Transcriptome profiling reveals an IAA-regulated response to adventitious root formation in lotus seedling
- Erratum to: A comparative proteomic analysis for adventitious root formation in lotus root (Nelumbo nucifera Gaertn)
