title: Bioactive phenylpropanoid analogues from Piper betle L. var. birkoli leaves.
abstract: Phytochemical analyses of the chloroform extract of Piper betle L. var. birkoli, Piperaceae, leaves led to the isolation of two new phenylpropanoid analogues: bis-chavicol dodecanoyl ester (2) and bis-hydroxychavicol dodecanoyl ester (3), along with one known compound: allyl-3-methoxy-4-hydroxybenzene (1) on the basis of spectroscopic data 1D (1H and13C) and 2D (1H-1H COSY and HMBC) NMR, as well as ESI-MS, FT-IR, HR-ESI-MS and LC-ESI-MS. Compound 2 and 3 exhibited excellent antioxidant DPPH radical scavenging activity with IC50values of 12.67 μg/mL and 1.08 μg/mL compared to ascorbic acid as a standard antioxidant drug with IC50value of 6.60 μg/mL. Evaluation of cytotoxic activity against two human oral cancer cell lines (AW13516 and AW8507) showed significant effect with GI50values of 19.61 and 23.01 μg/mL for compound 2 and 10.25 and 13.12 μg/mL for compound 3, compared to Doxorubicin®as a standard cytotoxic drug with GI50value of < 10 μg/mL.
authors.affiliation: a Division of Pharmacognosy and Phytochemistry, Department of Pharmaceutical Sciences and Technology , Birla Institute of Technology , Mesra, Ranchi , India.
authors.forename: Akhtar
authors.initials: A
authors.lastname: Atiya
authors.affiliation: b Division of Medicinal Chemistry, Department of Pharmaceutical Sciences and Technology , Birla Institute of Technology , Mesra, Ranchi , India.
authors.forename: Barij Nayan
authors.initials: BN
authors.lastname: Sinha
authors.affiliation: a Division of Pharmacognosy and Phytochemistry, Department of Pharmaceutical Sciences and Technology , Birla Institute of Technology , Mesra, Ranchi , India.
authors.forename: Uma Ranjan
authors.initials: UR
authors.lastname: Lal
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002853:Chromatography, Liquid; D007851:Dodecanol / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D009062:Mouth Neoplasms / Q000188:drug therapy; D010636:Phenols / Q000737:chemistry / Q000494:pharmacology; D031721:Piper betle / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: C000605268:4-allylphenol; D000498:Allyl Compounds; D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D016166:Free Radical Scavengers; D010636:Phenols; D007851:Dodecanol
keywords: Piper betle; SAR; antioxidant; cytotoxic; phenylpropanoid analogues