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A New Benzopyranyl ...
A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii
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- Nyandoro, Stephen S., 1975 (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,Univ Dar Es Salaam, Coll Nat & Appl Sci, Chem Dept, POB 35061, Dar Es Salaam, Tanzania;Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden
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- Maeda, Gasper (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,Univ Dar Es Salaam, Coll Nat & Appl Sci, Chem Dept, POB 35061, Dar Es Salaam, Tanzania;Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden
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- Munissi, J. J. E. (author)
- Univ Dar Es Salaam, Coll Nat & Appl Sci, Chem Dept, POB 35061, Dar Es Salaam, Tanzania
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- Gruhonjic, Amra (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden
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- Fitzpatrick, Paul A. (author)
- Gothenburg University,Göteborgs universitet,Sahlgrenska Cancer Center,Univ Gothenburg, Sahlgrenska Canc Ctr, SE-40530 Gothenburg, Sweden
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- Lindblad, Sofia (author)
- Uppsala universitet,Organisk kemi
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- Duffy, S. (author)
- Griffith Univ, Griffith Inst Drug Discovery, Discovery Biol, Nathan, Qld 4111, Australia
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- Pelletier, J. (author)
- McGill Univ, Dept Biochem, Montreal, PQ H3G 1Y6, Canada
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- Pan, F. F. (author)
- Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Coll Chem, Key Lab Pesticide & Chem Biol,Minist Educ, Luoyu Rd 152, Wuhan 430079, Hubei, Peoples R China;Univ Jyvaskyla, Dept Chem, POB 35, FI-40014 Jyvaskyla, Finland
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- Puttreddy, R. (author)
- Univ Jyvaskyla, Dept Chem, POB 35, FI-40014 Jyvaskyla, Finland
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- Avery, V. M. (author)
- Griffith Univ, Griffith Inst Drug Discovery, Discovery Biol, Nathan, Qld 4111, Australia
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- Erdelyi, Mate, 1975 (author)
- Uppsala universitet,Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,Organisk kemi,Univ Gothenburg, Dept Chem & Mol Biol, SE-41296 Gothenburg, Sweden;
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(creator_code:org_t)
- 2019-07-29
- 2019
- English.
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In: Molecules. - : MDPI AG. - 1420-3049 .- 1431-5157. ; 24:15
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https://doi.org/10.3...
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Abstract
Subject headings
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- Phytochemical investigations of ethanol root bark and stem bark extracts of Cleistochlamys kirkii (Benth.) Oliv. (Annonaceae) yielded a new benzopyranyl cadinane-type sesquiterpene (cleistonol, 1) alongside 12 known compounds (2-13). The structures of the isolated compounds were established from NMR spectroscopic and mass spectrometric analyses. Structures of compounds 5 and 10 were further confirmed by single crystal X-ray crystallographic analyses, which also established their absolute stereochemical configuration. The ethanolic crude extract of C. kirkii root bark gave 72% inhibition against the chloroquine-sensitive 3D7-strain malaria parasite Plasmodium falciparum at 0.01 mu g/mL. The isolated metabolites dichamanetin, (E)-acetylmelodorinol, and cleistenolide showed IC50 = 9.3, 7.6 and 15.2 mu M, respectively, against P. falciparum 3D7. Both the crude extract and the isolated compounds exhibited cytotoxicity against the triple-negative, aggressive breast cancer cell line, MDA-MB-231, with IC50 = 42.0 mu g/mL (crude extract) and 9.6-30.7 mu M (isolated compounds). Our findings demonstrate the potential applicability of C. kirkii as a source of antimalarial and anticancer agents.
Subject headings
- NATURVETENSKAP -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- Cleistochlamys kirkii
- Annonaceae
- benzopyranyl sesquiterpene
- cleistonol
- antiplasmodial activity
- malaria
- cytotoxicity
- cadinane-type sesquiterpenes
- absolute-configuration
- circular-dichroism
- uvaria
- constituents
- flavonoids
- roots
- Biochemistry & Molecular Biology
- Chemistry
- Cleistochlamys kirkii
Publication and Content Type
- ref (subject category)
- art (subject category)
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Nyandoro, Stephe ...
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Maeda, Gasper
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Munissi, J. J. E ...
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Gruhonjic, Amra
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Fitzpatrick, Pau ...
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Lindblad, Sofia
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Duffy, S.
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Pelletier, J.
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Pan, F. F.
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Puttreddy, R.
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Avery, V. M.
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Erdelyi, Mate, 1 ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Biological Scien ...
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and Biochemistry and ...
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NATURAL SCIENCES
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Molecules
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University of Gothenburg
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Uppsala University