Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596313
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

New cytotoxic prenylated flavonoids from Commiphora opobalsamum stem bark

Authors

  • AA El-Gamal

    1   Department of Pharmacognosy, King Saud University, College of Pharmacy, P.O. Box 2457, Riyadh Saudi Arabia
    2   Department of Pharmacognosy, Mansoura University, College of Pharmacy, 35516, El-Mansoura, Egypt

  • SM Al-Massarani

    1   Department of Pharmacognosy, King Saud University, College of Pharmacy, P.O. Box 2457, Riyadh Saudi Arabia

  • WM Abdel-Mageed

    1   Department of Pharmacognosy, King Saud University, College of Pharmacy, P.O. Box 2457, Riyadh Saudi Arabia

  • A El-Shaibany

    3   Department of Pharmacognosy Sana'a University, College of Pharmacy P.O. Box 33039 Sana'a, Yemen

  • HM Al-Mahbashi

    4   Department of Forensic Medicine and Clinical Toxicology, University, Sana'a, College of Medicine, Sana'a, Yemen

  • OA Basudan

    1   Department of Pharmacognosy, King Saud University, College of Pharmacy, P.O. Box 2457, Riyadh Saudi Arabia

  • FA Badria

    2   Department of Pharmacognosy, Mansoura University, College of Pharmacy, 35516, El-Mansoura, Egypt

  • MS Al-Said

    1   Department of Pharmacognosy, King Saud University, College of Pharmacy, P.O. Box 2457, Riyadh Saudi Arabia

  • MS Abdel-Kader

    5   Department of Pharmacognosy, Sattam Bin Abdulaziz University, College of Pharmacy, 11942, Al-kharj Saudi Arabia
Further Information

Publication History

Publication Date:
14 December 2016 (online)

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The genus of the myrrhs, Commiphora, (Burseraceae) is the richest genus of flowering plants in Frankincense. It comprises approximately 190 species of shrubs and trees distributed throughout the sub tropical regions of Africa, the western Indian Ocean islands, Arabian Peninsula, India and Vietnam [1 – 2]. The flora of Yemen has eight species of genus Commiphora where C. opobalsamum is one of them [3].. Previous phytochemical investigation of genus Commiphora revealed the presence of terpenoids, flavonids, lignans and steroids [4 – 5]. As part of our continuous interest in identifying potential bioactive compounds, we thoroughly investigated the chemical constituents and cytotoxic activity of C. opobalsamum growing in Yemen. Phytochemical investigation of the cytotoxic CH2Cl2 fraction of the stem bark of the titled plant (IC50= 14 and 17 µg/mL against MCF-7 and HEPG-2) was subjected to chromatographic purification to afford ten flavonoids, six of them (5 – 10) are isolated for the first time while the other four were reported before. The structures of the isolated compounds were elucidated by using different spectroscopic techniques. The known compounds were identified as naringenin (1), isosakurantin (2), mearnsetin (3) and kaempferol (4), while the new isolated compounds were identified as 6-(γ,γ-dimethylallayl)- 5,7,3',5' tetrhydroxy-5' methoxy flavanone (5), 6-(γ,γ-dimethylallayl)- 5,7,3',5' tetrhydroxy-5' methoxy dihydroflavonol (6), 6- (3"-hydroxy-3"-methyl butyl) 5,7,3'5'-tetrhydroxy-5-methoxy dihydroflavonol (7), 6-(γ,γ-dimethylallayl)-5,7,3',5' tetrhydroxy-5' methoxyflavonol (8), 6- (3"-hydroxy-3"-methyl butyl) 5,7,3'5'-tetrhydroxy-5-methoxy flavonol 7-O-β-D-glucopyranoside (9) and 2-(3,5-dihydroxy-4-methoxyphenyl)-3,5-dihydroxy-8,8-dimethyl-7,8-dihydropyrano [3,2-g] chromen-4 (6H)-one (10). Compound 9 showed the highest cytotoxic activity against MCF-7 and HEPG-2 cells line with IC50 (µg/mL) 8 and 12 µg/mL respectively and followed by compounds 5 and 3.

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Acknowledgements: The authors are thankful to the deanship of Scientific Research at King Saud University for funding the work through the Research Group Project no. RGP-VPP-326.

Keywords: Commiphora opobalsamum, cytotoxic activity, new prenylated flavonoids..

References:

[1] Daly DC, Harley MM, Martínez-Habibe M-C, Weeks A. Burseraceae. In: K. Kubitzki, ed. Families and genera of flowering plants. Springer-Verlag, New York. 2011; 10:76 – 104

[2] Weeks A. and Simpson BB. Molecular phylogenetic analysis of (Burseraceae) yields insight on the evolution and historical biogeography of an “impossible” genus. Mol Phylogenet Evol 2007; 42: 62 – 79

[3] Wood JR with color illustrations by Hugo Haig-Thomas A Hand book of the Yemen Flora 1997; P 197, 1st ed. Royal Botanic Garden's Kew.

[4] Abbas FA, AL-Massarani SM, Khan S, AL-Howiriny TA, Mossa JS, Abourashed EA. Phytochemical and biological studies on Saudi Commiphora opobalsamum L. Nat Prod Res 2007; 21: 383 – 391

[5] Suliman MHA. Prenylated flavonoids from the stem wood of Commiphora opobalsamum. J King Saud Univ Sci 2015; 27: 71 – 75


No conflict of interest has been declared by the author(s).

 
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