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Volume 13. Issue 11. Pages 1419-1568. 2018 ISSN 1934-578X (Printed); ISSN 1555-9475 (Online) NPC Natural Product Communications

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Volume 13. Issue 11. Pages 1419-1568. 2018 ISSN 1934-578X (Printed); ISSN 1555-9475 (Online) NPC Natural Product Communications Volume 13. Issue 11. Pages 1419-1568. 2018 ISSN 1934-578X (printed); ISSN 1555-9475 (online) www.naturalproduct.us NPC Natural Product Communications EDITOR-IN-CHIEF HONORARY EDITOR DR. PAWAN K AGRAWAL PROFESSOR GERALD BLUNDEN Natural Product Inc. The School of Pharmacy & Biomedical Sciences, 7963, Anderson Park Lane, University of Portsmouth, Westerville, Ohio 43081, USA Portsmouth, PO1 2DT U.K. [email protected] [email protected] EDITORS ADVISORY BOARD PROFESSOR MAURIZIO BRUNO Department STEBICEF, Prof. Giovanni Appendino Prof. Niel A. Koorbanally University of Palermo, Viale delle Scienze, Novara, Italy Durban, South Africa Parco d’Orleans II - 90128 Palermo, Italy Prof. Chiaki Kuroda [email protected] Prof. Norbert Arnold Halle, Germany Tokyo, Japan PROFESSOR CARMEN MARTIN-CORDERO Department of Pharmacology, Faculty of Pharmacy, Prof. Yoshinori Asakawa Prof. Hartmut Laatsch Tokushima, Japan Gottingen, Germany University of Seville, Seville, Spain [email protected] Prof. Vassaya Bankova Prof. Marie Lacaille-Dubois PROFESSOR VLADIMIR I. KALININ Sofia, Bulgaria Dijon, France G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Prof. Roberto G. S. Berlinck Prof. Shoei-Sheng Lee Far Eastern Branch, Russian Academy of Sciences, São Carlos, Brazil Taipei, Taiwan Pr. 100-letya Vladivostoka 159, 690022, Vladivostok, Russian Federation Prof. Anna R. Bilia Prof. M. Soledade C. Pedras [email protected] Florence, Italy Saskatoon, Canada PROFESSOR YOSHIHIRO MIMAKI Prof. Geoffrey Cordell Prof. Luc Pieters School of Pharmacy, Chicago, IL, USA Antwerp, Belgium Tokyo University of Pharmacy and Life Sciences, Prof. Fatih Demirci Prof. Peter Proksch Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan Eskişehir, Turkey Düsseldorf, Germany [email protected] Prof. Phila Raharivelomanana PROFESSOR STEPHEN G. PYNE Prof. Francesco Epifano Chieti Scalo, Italy Tahiti, French Polynesia Department of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia Prof. Ana Cristina Figueiredo Prof. Stefano Serra [email protected] Lisbon, Portugal Milano, Italy PROFESSOR MANFRED G. REINECKE Prof. Cristina Gracia-Viguera Dr. Bikram Singh Department of Chemistry, Texas Christian University, Murcia, Spain Palampur, India Forts Worth, TX 76129, USA [email protected] Dr. Christopher Gray Prof. Marina Stefova Saint John, NB, Canada Skopj, Republic of Macodenia PROFESSOR WILLIAM N. SETZER Department of Chemistry, The University of Alabama in Huntsville, Prof. Dominique Guillaume Prof. Leandros A. Skaltsounis Huntsville, AL 35809, USA Reims, France Zografou, Greece [email protected] Prof. John L. Sorensen Prof. Duvvuru Gunasekar PROFESSOR PING-JYUN SUNG Tirupati, India Manitoba, Canada National Museum of Marine Biology and Aquarium Prof. Hisahiro Hagiwara Prof. Johannes van Staden Checheng, Pingtung 944 Niigata, Japan Scottsville, South Africa Taiwan [email protected] Prof. Judith Hohmann Prof. Valentin Stonik Szeged, Hungary Vladivostok, Russia PROFESSOR YASUHIRO TEZUKA Faculty of Pharmaceutical Sciences, Hokuriku University, Prof. Tsukasa Iwashina Prof. Winston F. Tinto Ho-3 Kanagawa-machi, Kanazawa 920-1181, Japan Tsukuba, Japan Barbados, West Indies [email protected] Prof. Leopold Jirovetz Prof. Sylvia Urban PROFESSOR DAVID E. THURSTON Vienna, Austria Melbourne, Australia Institute of Pharmaceutical Science Faculty of Life Sciences & Medicine Prof. Phan Van Kiem Prof. Karen Valant-Vetschera Hanoi, Vietnam Vienna, Austria King’s College London, Britannia House 7 Trinity Street, London SE1 1DB, UK [email protected] INFORMATION FOR AUTHORS Full details of how to submit a manuscript for publication in Natural Product Communications are given in Information for Authors on our Web site http://www.naturalproduct.us. Authors may reproduce/republish portions of their published contribution without seeking permission from NPC, provided that any such republication is accompanied by an acknowledgment (original citation)-Reproduced by permission of Natural Product Communications. 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All issues are dispatched by airmail throughout the world, excluding the USA and Canada. 2018 NPC Natural Product Communications Vol. 13 No. 11 Effect of Resveratrol Dimers and Tetramers Isolated from Vitaceous 1531 - 1534 and Dipterocarpaceous Plants on Human SIRT1 Enzyme Activity Kiyomi Hikitaa, Norikazu Setoa, Yusuke Takahashia, Ayako Nishigakia, Yuya Suzukia, Tomiyasu Murataa, * Arthorn Loisruangsinb, Nanik Siti Aminahc, Yoshiaki Takayad, Masatake Niwac and Norio Kanedaa aLaboratory of Analytical Neurobiology, Faculty of Pharmacy, Meijo University, Yagotoyama 150, Tempaku, Nagoya, Aichi 468-8503, Japan bDivision of Chemistry, Faculty of Liberal Arts and Science, Kasetsart University, 1 Moo 6, Kamphaeng San District, NakhonPathom Province 73140, Thailand cDepartment of Chemistry, Faculty of Science and Technology, Universitas Airlangga, Surabaya 60115, Indonesia dLaboratory of Medicinal Resources Chemistry, Faculty of Pharmacy, Meijo University, Yagotoyama 150, Tempaku, Nagoya, Aichi 468-8503, Japan [email protected] Received: May 15th, 2018; Accepted: August 9th, 2018 SIRT1 is a mammalian ortholog of the yeast enzyme Sir2, which is an NAD+-dependent deacetylase of histones, p53, FOXO, NF-κB, PGC-1α, and other transcription factors. The Sir2 protein is reported as a longevity protein in yeast. Resveratrol, a polyphenol isolated from various types of plant families, particularly the Vitaceae family, is a known naturally occurring SIRT1 activator. In this study, we evaluated the effects of four types of resveratrol dimers and four types of tetramers isolated from vitaceous plants, and one type of resveratrol tetramer isolated from a dipterocarpaceous plant on purified human SIRT1 enzyme activity. Of the resveratrol dimers examined, (+)-ε-viniferin and pallidol exhibited no effect on SIRT1 enzyme activity, whereas (+)-ampelopsin B and (−)-ampelopsin F showed inhibitory activity on SIRT1. However, all the resveratrol tetramers examined, i.e., (+)-vitisin A, (−)-vitisin B, (+)-hopeaphenol, (−)-hopeaphenol, and (−)-isohopeaphenol markedly inhibited the human SIRT1 enzyme activity. (+)-Hopeaphenol exhibited the most potent inhibitory activity, which was comparable with that exhibited by a known SIRT1 inhibitor suramin. Since SIRT1 inhibitors reportedly possess anticancer activity, (+)-hopeaphenol and other resveratrol oligomers can be used as a seed compound for anticancer drugs. Keywords: Sirtuin, Resveratrol oligomer, (+)-Hopeaphenol, SIRT1 inhibitor. Sirtuins are members of a family of yeast silent information Because resveratrol is an effective activator of SIRT1, it will be regulator 2 (Sir2), which are NAD+-dependent protein deacetylases interesting to examine whether the resveratrol oligomers have the that promote yeast longevity [1, 2]. DNA sequences of sirtuins are ability to regulate the SIRT1 enzyme activity. In the present study, highly conserved from bacteria to humans [3]. Seven types of we evaluated the effects of resveratrol dimers and tetramers (Figure sirtuins (SIRT1–SIRT7) are found in mammals, and SIRT1 is a 1) isolated from vitaceous plants and a tetramer isolated from mammalian ortholog of yeast Sir2 [4, 5]. SIRT1 has been most dipterocarpaceous plants on recombinant human SIRT1 (rhSIRT1) extensively studied in the contexts of aging and longevity in enzyme activity. mammals [6]. It catalyzes the deacetylation of many proteins, including histones and transcription factors such as p53, FOXO, His-tagged rhSIRT1 was expressed using the Escherichia coli (E. NF-κB, and PGC-1α [6, 7], and activates stress defense and DNA coli) expression system and purified by Ni2+-Sepharose affinity repair mechanisms, thus aiding the preservation of genomic chromatography. The enzyme showed a single band on SDS- integrity [8]. SIRT1 also functions in the regulation of metabolism polyacrylamide gel electrophoresis (SDS-PAGE) (Figure 2a). The and has thus been described as a potential tumor suppressor gene molecular weight estimated using SDS-PAGE was larger than the [9]. Reportedly, SIRT1 has a pivotal role in the pathophysiology of value estimated from the cDNA sequence of hSIRT1 (84 kDa). various
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