title: Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities.
abstract: The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, two pentane-2,4-diol glucosides, seven phenolic compounds, and three sugars, were isolated. The structures of five triterpene glycosides were elucidated on the basis of spectroscopic and chemical methods. Upon evaluation of the bioactivity of the isolated compounds, it was found that some or most of the compounds have potent or moderate inhibitory activities against the following: melanogenesis in B16 melanoma cells induced by α-melanocyte-stimulating hormone (α-MSH); generation of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-teradecanoylphorbol 13-acetate (TPA) in Raji cells; t TPA-induced inflammation in mice, and proliferation of one or more of HL-60, A549, AZ521, and SK-BR-3 human cancer cell lines, respectively. Western blot analysis established that paradoxoside E inhibits melanogenesis by regulation of expression of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1) and TRP-2. In addition, tieghemelin A was demonstrated to exhibit cytotoxic activity against A549 cells (IC50 13.5 μM) mainly due to induction of apoptosis by flow cytometry. The extract of defatted shea kernels and its constituents may be, therefore, valuable as potential antioxidant, anti-inflammatory, skin-whitening, chemopreventive, and anticancer agents.
authors.affiliation: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
authors.forename: Jie
authors.initials: J
authors.lastname: Zhang
authors.affiliation: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Kurita
authors.affiliation: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
authors.forename: Takuro
authors.initials: T
authors.lastname: Shinozaki
authors.affiliation: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
authors.forename: Motohiko
authors.initials: M
authors.lastname: Ukiya
authors.affiliation: School of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi-shi, Chiba 274-855, Japan.
authors.forename: Ken
authors.initials: K
authors.lastname: Yasukawa
authors.affiliation: Application Center, Agilent Technologies Japan Ltd., 9-1 Takakura-cho, Hachioji-shi, Tokyo 192-0033, Japan.
authors.forename: Naoto
authors.initials: N
authors.lastname: Shimizu
authors.affiliation: Graduate School of Medical Science, Kanazawa University, 13-1 Takara-maschi, Kanazawa 920-8640, Japan.
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.affiliation: World Agroforestry Centre (ICRAF), Nelson Marlborough Institute of Technology (NMIT), Nelson 7010, New Zealand.
authors.forename: Eliot T
authors.initials: ET
authors.lastname: Masters
authors.affiliation: Department of Endocrinology and Metabolism, Medical Hospital of Tokyo Medical and Dental University, 1-5-45 Yushima, Bunkyo-ku, Tokyo 113-8519, Japan.
authors.forename: Momoko
authors.initials: M
authors.lastname: Akihisa
authors.affiliation: College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan; Akihisa Medical Clinic, 1086-3 Kamo, Sanda-shi, Hyogo 669-1311, Japan. Electronic address: akihisa_toshihiro@yahoo.co.jp.
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Akihisa
mesh_terms: D000818:Animals; D000956:Antigens, Viral / Q000187:drug effects; D001713:Biphenyl Compounds / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018922:HL-60 Cells; D006801:Humans; D008543:Melanins / Q000037:antagonists & inhibitors; D051379:Mice; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000494:pharmacology; D010088:Oxidoreductases; D010851:Picrates / Q000494:pharmacology; D012503:Saponins / Q000494:pharmacology; D029632:Sapotaceae / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000521:alpha-MSH / Q000187:drug effects
chemical_list: D000956:Antigens, Viral; D001713:Biphenyl Compounds; C033305:Epstein-Barr virus early antigen; D006027:Glycosides; D008543:Melanins; D010851:Picrates; D012503:Saponins; D014315:Triterpenes; C473294:tieghemelin; D000521:alpha-MSH; D009828:Oleanolic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D010088:Oxidoreductases; C064056:tyrosinase-related protein-1; D014442:Monophenol Monooxygenase
keywords: Anti-inflammatory activity; Antioxidant activity; Cytotoxic activity; Epstein–Barr virus early antigen (EBV-EA); Melanogenesis-inhibitory activity; Oleanane-type triterpene glycoside; Sapotaceae; Shea butter; Shea kernel; Vitellaria paradoxa