Prenylated chromones and coumarins from the leaves of Billburttia capensoides Sales & Hedge (Apiaceae)

Mahefarivo  Andrianjakaniaina; Diano Lova  Rakotondramanana; Paule Annécie  Benatrehina; Carla  Slebodnick; Léa  Rasoanaivo; Rinasoambolanoro  Rakotosaona; Harinantenaina Liva  Rakotondraibe; Richard Stephan  Rakotonandrasana; Emile Vincent  Rasamison

doi:10.30574/gscbps.2021.16.2.0233

Authors

Mahefarivo Andrianjakaniaina National Center of Applied Pharmaceutical Research, B.P.Box 702, Antananarivo 101, Madagascar.
Diano Lova Rakotondramanana Laboratory of Natural Substances Chemistry and Biological Organic Chemistry, Faculty of Sciences, University of Antananarivo, B.P. Box 906, Antananarivo101, Madagascar.
Paule Annécie Benatrehina College of Pharmacy, Division of Medicinal Chemistry and Pharmacognosy, The Ohio State University, Columbus, OH 43210, USA.
Carla Slebodnick Department of Chemistry and Virginia Tech, Blacksburg, Virginia 24061-0212, USA.
Léa Rasoanaivo High Education Institute of Antsirabe-Vakinankaratra, University of Antananarivo, B.P. Box 906, Antananarivo101, Madagascar.
Rinasoambolanoro Rakotosaona National Center of Applied Pharmaceutical Research, B.P.Box 702, Antananarivo 101, Madagascar.
Harinantenaina Liva Rakotondraibe College of Pharmacy, Division of Medicinal Chemistry and Pharmacognosy, The Ohio State University, Columbus, OH 43210, USA.
Richard Stephan Rakotonandrasana National Center of Applied Pharmaceutical Research, B.P.Box 702, Antananarivo 101, Madagascar.
Emile Vincent Rasamison High Education Institute of Antsirabe-Vakinankaratra, University of Antananarivo, B.P. Box 906, Antananarivo101, Madagascar.

DOI:

https://doi.org/10.30574/gscbps.2021.16.2.0233

Keywords:

Billburttia capensoides, Apiaceae, Chemical constituents, Prenylated chromones, Coumarins

Abstract

Billburttia Sales & Hedge is a new genus endemic to Madagascar, which belongs to the Apiaceae family and comprises of two species, namely Billburttia capensoides and B. vaginoides. The present work was undertaken in a view to explore secondary metabolites from the leaves of B. capensoides, contributing to have more knowledge on the chemical profile of this species. Liquid-liquid partition followed by chromatographic separation of its ethanolic extract led to the isolation of two new prenylated chromones, 2'R-hydroxy-7-O-methylallopeucenin and the known coumarins imperatorin and xanthotoxin. Their chemical structures were established on the basis of spectroscopic methods including nuclear magnetic resonance (NMR) and high resolution mass spectrometry, and by comparison with the reported data in the literature. The structure of the compound 3 was confirmed by single-crystal X-ray diffraction. This is the first report on the nonvolatile constituents of B. capensoides. The presence of imperatorin and xanthotoxin supported that the new endemic genus Billburttia belongs to the Apiaceae family. All these data may induce further research on this species in order to find new chemical entities with biological and chemotaxonomic interests.

Metrics

Metrics Loading ...

References

Magee AR, Van Wyk BE, Tilney PM, Sales F, Hedge I, Downie SR. Billburttia. A new genus of Apiaceae (tribe Apieae) endemic to Madagascar. Plant Systematics and Evolution. 2009; 283: 237-245.

Humbert JH. Contributions à l’étude de la Flore de Madagascar et des Comores. Fascicule 5. Notuae Systematicae. 1956; 15: 118-128.

Rakotonandrasana SR, Oskolski AA, Tilney PM., Kotina EL, Van Wyk BE. The rediscovery of Billburttia vaginoides, with notes on the morphology, anatomy, traditional uses and conservation status of the genus Billburttia (Apieae, Apiaceae). Phytotaxa. 2017; 321: 265–276.

Rakotonandrasana SR, Rabehaja DJR, Paoli M, Serra DR, Andrianjara C, Bighelli A, Ramanoelina PAR, Tomi F. Chemical composition of the essential oils from the aerial parts of two Malagasy endemic species (Apiaceae): Billburttia capensoides Sales & Hedge and Billburttia vaginoides Sales & Hedge. Natural Product Research. 2018; 33(8): 1200-1203.

He F, Wang M, Gao M, Zhao M, Bai Y, Zhao C. Chemical composition and biological activities of Gerbera anandria. Molecules. 2014; 19: 4046-4057.

Koziol E, Skalicka-Wozniak K. Imperatorin-pharmacological meaning and analytical clues: profound investigation. Phytochemistry Reviews. 2016; 15(4): 627-649.

Marumoto S, Miyazawa M. Biotransformation of Bergapten and Xanthotoxin by Glomerella cingulata. Journal of Agriculture and Food Chemistry. 2010; 58(13): 7777-7781.

Sigurdsson S, Jonsdottir S, Gudbjarnason S. Geographical variation of the furanocoumarin composition of the fruits of Icelandic Angelica archangelica. Zeitschrift für Naturforschung. C, Journal of biosciences. 2012; 67(1-2): 1-7.

Griffiths PJF, Ellis GP. Benzopyrones. VI. Ultraviolet absorption spectra of chromone and 2-substituted chromones. Spectrochimica Acta, Part A. 1972; 28(4): 707-713.

Feng Y, Blunt JW, Cole ALJ, Munro MHG. The isolation of two new chromone derivatives from the New Zealand fungus Tolypocladium extinguens. Journal of Natural Products. 2002; 65(11): 1681-1682.

Leonti M, Casu L, Solinas MN, Cottiglia F, Caboni, Floris C, Gertsch J, Saba AR. A chromone from Seseli praecox (Apiaceae). Natural Product Communications. 2010; 5(4): 551-554.

Liu G, Zheng R.R, Liu ZW, Wang WJ, Li GQ, Fan CL, Zhang XQ, Ye WC, Che CT. Enantiomeric chromones from Harrisonia perforata. Phytochemistry Letters. 2014; 10: 295-299.

Lemmich J. Monoterpene, chromone and coumarin glucosides of Diplolophium buchananii. Phytochemistry. 1995; 38(2): 427-432.

Fu YH, Guo JM, Xie YT, Yu XM, Su QT, Qiang L, Kong L, Liu YP. Prenylated chromones from the fruits of Artocarpus heterophyllus and their potential anti-HIV-1 activities. Journal of Agriculture and Food Chemistry. 2020; 68(7): 2024-2030.

Liu YP, Yu XM., Zhang W, Wang T, Jiang B, Tang HX, Su QT, Fu YH. Prenylated chromones and flavonoids from Artocarpus heterophyllus with their potential antiproliferative and anti-inflammatory activities. Bioorganic Chemistry. 2020; 101: 104030.