Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley

doi:10.1007/s13659-016-0106-6

Natural Products and Bioprospecting ›› 2016, Vol. 6 ›› Issue (5): 261-265.DOI: 10.1007/s13659-016-0106-6

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Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley

Vincent E. Rasamison¹, Peggy J. Brodie², Emilio F. Merino³, Maria B. Cassera³, Michel A. Ratsimbason¹, Stephan Rakotonandrasana¹, Andriamalala Rakotondrafara¹, Elie Rafidinarivo⁴, David G. I. Kingston², Harinantenaina L. Rakotondraibe⁵

1. Centre National d'Application de Recherches Pharmaceutiques, B. P. 702, 101 Antananarivo, Madagascar;
2. Department of Chemistry and the Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg, VA 24061, USA;
3. Department of Biochemistry and the Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, VA 24061, USA;
4. Institut Supérieur de Technologie, B. P. 8122, 101 Antananarivo, Madagascar;
5. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA

Received:2016-06-30 Revised:2016-08-30 Online:2018-02-08 Published:2016-10-24
Supported by:
The authors are thankful to the ICBG project (Grant No U01 TW000313) and the CNARP for financial support during the plant collections and the supply of chemicals critical to this study.Thanks are also due to the College of Pharmacy at The Ohio State University,USA and the Department of Chemistry and Virginia Tech Center for Drug Discovery,Virginia Tech,USA for facilitating the acquisition of the NMR spectra

Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley

1. Centre National d'Application de Recherches Pharmaceutiques, B. P. 702, 101 Antananarivo, Madagascar;
2. Department of Chemistry and the Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg, VA 24061, USA;
3. Department of Biochemistry and the Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, VA 24061, USA;
4. Institut Supérieur de Technologie, B. P. 8122, 101 Antananarivo, Madagascar;
5. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA

通讯作者: Harinantenaina L. Rakotondraibe,e-mail:rakotondraibe.1@osu.edu
基金资助:
The authors are thankful to the ICBG project (Grant No U01 TW000313) and the CNARP for financial support during the plant collections and the supply of chemicals critical to this study.Thanks are also due to the College of Pharmacy at The Ohio State University,USA and the Department of Chemistry and Virginia Tech Center for Drug Discovery,Virginia Tech,USA for facilitating the acquisition of the NMR spectra

Abstract

Abstract: Melicope madagascariensis (Rutaceae) is an endemic plant species of Madagascar that was first classified as a member of the genus Euodia J. R. & G. Forst (Rutaceae) under the scientific name Euodia madagascariensis Baker. Based on morphological characteristics, Thomas Gordon Hartley taxonomically revised E. madagascariensis Baker to be M. madagascariensis (Baker) T.G. Hartley. Chemotaxonomical studies have long been used to help the identification and confirmation of taxonomical classification of plant species and botanicals. Aiming to find more evidences to support the taxonomical revision performed on E. madagascariensis, we carried out phytochemical investigation of two samples of the plant. Fractionation of the ethanol extracts prepared from two stem bark samples of M. madagascariensis (Baker) T. G. Hartley led to the isolation of seven known furoquinoline alkaloids 1-7 and two known methoxyflavones 8 and 9. The presence of furoquinoline alkaloids and methoxyflavones in the title species is in agreement with its taxonomic transfer from Euodia to Melicope. Antiprotozoal evaluation of the isolated compounds showed that 6-methoxy-7-hydroxydictamnine (heliparvifoline, 3) showed weak antimalarial activity (IC₅₀=35 μM) against the chloroquine-resistant strain Dd2 of Plasmodium falciparum. Skimmianine (4) displayed moderate cytotoxicity with IC₅₀ value of 1.5 lM against HT- 29 colon cancer cell line whereas 3,5-dihydroxy-3',4',7-trimethoxyflavone (9) was weakly active in the same assay (IC₅₀=13.9 μM).

Key words: Chemotaxonomy, Furoquinoline alkaloids, Methoxyflavones, Antimalarial activity, Cytotoxicity, Melicope madagascariensis (Rutaceae)

摘要： Melicope madagascariensis (Rutaceae) is an endemic plant species of Madagascar that was first classified as a member of the genus Euodia J. R. & G. Forst (Rutaceae) under the scientific name Euodia madagascariensis Baker. Based on morphological characteristics, Thomas Gordon Hartley taxonomically revised E. madagascariensis Baker to be M. madagascariensis (Baker) T.G. Hartley. Chemotaxonomical studies have long been used to help the identification and confirmation of taxonomical classification of plant species and botanicals. Aiming to find more evidences to support the taxonomical revision performed on E. madagascariensis, we carried out phytochemical investigation of two samples of the plant. Fractionation of the ethanol extracts prepared from two stem bark samples of M. madagascariensis (Baker) T. G. Hartley led to the isolation of seven known furoquinoline alkaloids 1-7 and two known methoxyflavones 8 and 9. The presence of furoquinoline alkaloids and methoxyflavones in the title species is in agreement with its taxonomic transfer from Euodia to Melicope. Antiprotozoal evaluation of the isolated compounds showed that 6-methoxy-7-hydroxydictamnine (heliparvifoline, 3) showed weak antimalarial activity (IC₅₀=35 μM) against the chloroquine-resistant strain Dd2 of Plasmodium falciparum. Skimmianine (4) displayed moderate cytotoxicity with IC₅₀ value of 1.5 lM against HT- 29 colon cancer cell line whereas 3,5-dihydroxy-3',4',7-trimethoxyflavone (9) was weakly active in the same assay (IC₅₀=13.9 μM).

关键词: Chemotaxonomy, Furoquinoline alkaloids, Methoxyflavones, Antimalarial activity, Cytotoxicity, Melicope madagascariensis (Rutaceae)

Vincent E. Rasamison, Peggy J. Brodie, Emilio F. Merino, Maria B. Cassera, Michel A. Ratsimbason, Stephan Rakotonandrasana, Andriamalala Rakotondrafara, Elie Rafidinarivo, David G. I. Kingston, Harinantenaina L. Rakotondraibe. Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley[J]. Natural Products and Bioprospecting, 2016, 6(5): 261-265.

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Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley

Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley

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