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NPC Natural Product Communications

EDITOR-IN-CHIEF

DR. PAWAN K AGRAWAL Natural Product Inc. 7963, Anderson Park Lane, Westerville, Ohio 43081, USA agrawal@naturalproduct.us

EDITORS

PROFESSOR ALEJANDRO F. BARRERO Department of Organic Chemistry, University of Granada, Campus de Fuente Nueva, s/n, 18071, Granada, Spain afbarre@ugr.es

PROFESSOR ALESSANDRA BRACA Dipartimento di Chimica Bioorganicae Biofarmacia, Universita di Pisa, via Bonanno 33, 56126 Pisa, Italy braca@farm.unipi.it

PROFESSOR DEAN GUO State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China gda5958@163.com

PROFESSOR YOSHIHIRO MIMAKI School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan mimakiy@ps.toyaku.ac.jp

PROFESSOR STEPHEN G. PYNE Department of Chemistry University of Wollongong Wollongong, New South Wales, 2522, Australia spyne@uow.edu.au

PROFESSOR MANFRED G. REINECKE Department of Chemistry, Texas Christian University, Forts Worth, TX 76129, USA m.reinecke@tcu.edu

PROFESSOR WILLIAM N. SETZER Department of Chemistry The University of Alabama in Huntsville Huntsville, AL 35809, USA wsetzer@chemistry.uah.edu

PROFESSOR YASUHIRO TEZUKA Faculty of Pharmaceutical Sciences Hokuriku University Ho-3 Kanagawa-machi, Kanazawa 920-1181, Japan y-tezuka@hokuriku-u.ac.jp

PROFESSOR DAVID E. THURSTON Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy, University of London, 29-39 Brunswick Square, London WC1N 1AX, UK david.thurston@pharmacy.ac.uk

ADVISORY BOARD

Prof. Viqar Uddin Ahmad Karachi, Pakistan

Prof. Giovanni Appendino Novara, Italy

Prof. Yoshinori Asakawa Tokushima, Japan

Prof. Roberto G. S. Berlinck São Carlos, Brazil

Prof. Anna R. Bilia Florence, Italy

Prof. Maurizio Bruno Palermo, Italy

Prof. César A. N. Catalán Tucumán, Argentina

Prof. Josep Coll Barcelona, Spain

Prof. Geoffrey Cordell Chicago, IL, USA

Prof. Fatih Demirci Eskişehir, Turkey

Prof. Dominique Guillaume Reims, France

Prof. Ana Cristina Figueiredo Lisbon, Portugal

Prof. Cristina Gracia-Viguera Murcia, Spain

Prof. Duvvuru Gunasekar Tirupati, India

Prof. Hisahiro Hagiwara Niigata, Japan

Prof. Kurt Hostettmann Lausanne, Switzerland

Prof. Martin A. Iglesias Arteaga Mexico, D. F, Mexico

Prof. Leopold Jirovetz Vienna, Austria

Prof. Vladimir I Kalinin Vladivostok, Russia

Prof. Niel A. Koorbanally Durban, South Africa

Prof. Chiaki Kuroda Tokyo, Japan

Prof. Hartmut Laatsch Gottingen, Germany

Prof. Marie Lacaille-Dubois Dijon, France

Prof. Shoei-Sheng Lee Taipei, Taiwan

Prof. Imre Mathe Szeged, Hungary

Prof. Ermino Murano Trieste, Italy

Prof. M. Soledade C. Pedras Saskatoon, Canada

Prof. Luc Pieters Antwerp, Belgium

Prof. Peter Proksch Düsseldorf, Germany

Prof. Phila Raharivelomanana Tahiti, French Polynesia

Prof. Luca Rastrelli Fisciano, Italy

Prof. Stefano Serra Milano, Italy

Prof. Monique Simmonds Richmond, UK

Dr. Bikram Singh Palampur, India

Prof. John L. Sorensen Manitoba, Canada

Prof. Johannes van Staden Scottsville, South Africa

Prof. Valentin Stonik Vladivostok, Russia

Prof. Winston F. Tinto Barbados, West Indies

Prof. Sylvia Urban Melbourne, Australia

Prof. Karen Valant-Vetschera Vienna, Austria

HONORARY EDITOR

PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences,

University of Portsmouth, Portsmouth, PO1 2DT U.K.

axuf64@dsl.pipex.com

Diterpenoids from Fagonia mollis Amal Sallama,b, Alfarius Eko Nugrohoa, Yusuke Hirasawaa, Wong Chin-Piowa, Toshio Kanedaa, Osamu Shirotac, Sahar R. Gedarab and Hiroshi Moritaa* aFaculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-ku, Tokyo 142-8501, Japan

bPharmacognosy Department, Faculty of Pharmacy, Mansoura University, Egypt

cFaculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki City, Kagawa 769-2193, Japan moritah@hoshi.ac.jp

Received: June 18th, 2014; Accepted: July 14th, 2014

A new acyclic diterpenoid (1) and a new erythroxan diterpenoid (2), together with 4 erythroxan diterpenoids and 3 triterpenoids, have been isolated from the aerial parts of Fagonia mollis. Their structures were elucidated on the basis of 1D and 2D NMR data. The cytotoxic activity of the isolated compounds was investigated against HL-60 cancer cells. Keywords: Fagonia mollis, Erythroxan, Diterpenoids. Fagonia mollis Del. (Zygophyllaceae) is an annual low shrub 20-40 cm high, or a perennial with a woody base [1a,b]. It grows wild in the desert east of the Nile river and in the Sinai Peninsula in Egypt [1b]. A methanolic extract of F. mollis was reported to exhibit antischistosomal activity [1c], and the saponin mixtures of F. mollis showed anti-inflammatory, analgesic and antipyretic effects [1d]. Previous phytochemical investigations of F. mollis resulted in the isolation of flavonoid glycosides, triterpenes and saponins [2a,b]. Our investigation on the aerial parts of F. mollis resulted in the isolation of two new diterpenoids (1 and 2, Figure 1), along with fagonone (3) [2c], fagonene (4) [2d], 2,7-dioxofagonene (5) [2d], 7-hydroxyfagonene (6) [2d], quinovic acid (7), quinovic acid-3-O--D-glucopyranoside (8) [2e] and 3-O-[-D-(2-O-sulfo)gluco-pyranosyl]quinovic acid (9) [2f]. The structure elucidations of 1 and 2, and their cytotoxic activities are described herein. Compound 1, a white amorphous solid, was determined to be C26H44O6 from HRESIMS data, indicating the presence of 5 double-bond equivalents. The 1H NMR data of 1 (Table 1) showed the presence of 5 methyls, and 6 olefinic protons, and the 1H and 13C NMR data of 1 indicated the presence of 4 double bonds and a hexose moiety, implying the aglycone moiety of 1 to be acyclic. Further analyses of the 1H and 13C NMR data of the aglycone moiety of 1 revealed their similarities to those of geranyllinalool [2g], except for those in the vicinity of C-3. Therefore, 1 was assumed to be geranyllinalool-3-O-glycoside. Further analyses of the 1D and 2D-NMR (HSQC, 1H-1H COSY, HMBC and NOESY, Figure 2) data of 1, supported the structure of 1 to be geranyllinalool-3-O--glycopyranoside. The sugar moiety was suggested to be glucose based on the 13C NMR chemical shifts; acid hydrolysis of 1 confirmed this identity as D-glucose. Unfortunately, we were unable to determine the configuration of C-3 since hydrolysis of 1 yielded a dehydration product of geranyllinalool. Thus, 1 was determined to be geranyllinalool-3-O--D-glucopyranoside. Compound 2, a white amorphous solid, was determined to be C20H34O3 from HRESIMS data. The 1H and 13C NMR spectra of 2 (Table 1) showed signals similar to those of other erythroxan diterpenoids isolated in this study, suggesting the structure of 2 to

Figure 1: Structures of 1 and 2.

be an erythroxan diterpenoid. Furthermore, the chemical shift differences between 2 and 6, which was isolated from the same fraction, resembled those of 2-oxofagonene [3] and 2-oxo-5-epi-fagonene [2d], suggesting the structure of 2 to be 7-hydroxy-5-epi-fagonene. The planar structure of 2 was confirmed to be the same as 6 from analyses of its HSQC, 1H-1H COSY, and HMBC correlations (Figure 2). The -orientation of C-19 was confirmed from the NOESY correlation of H3-19/H3-20. The configurations of the other chiral centers were deduced to be the same as 6 based on the 1H and 13C NMR chemical shifts, and NOESY correlations.

Figure 2: Selected 2D NMR correlations of 1 and 2.

Experimental

General: Optical rotations, JASCO DIP-1000 polarimeter; UV, Shimadzu UVmini-1240 spectrophotometer; IR, JASCO FT/IR-4100 spectrophotometer; High-resolution ESI MS, LTQ Orbitrap XL (Thermo Scientific); 1H and 2D NMR, 700 MHz spectrometer at 300K; 13C NMR spectra 175 MHz spectrometer. Materials: Fagonia mollis aerial parts, collected from Sinai Peninsula, Egypt in 2012, were identified by Prof. Dr Loutfy Boulos, Professor of Systematic Botany, Egypt. Voucher specimens (HOMA1208) are deposited in the Herbarium of Mansoura University. Extraction and isolation: Finely powdered aerial parts of F. mollis (700 g) were extracted with MeOH at room temperature. The

NPC Natural Product Communications 2014 Vol. 9 No. 9

1243 - 1244

1244 Natural Product Communications Vol. 9 (9) 2014 Sallam et al.

combined extracts were evaporated under reduced pressure to give a residue (60 g), which was dissolved in water and partitioned with solvents of increasing polarities, n-hexane, CHCl3 and EtOAc, to give n-hexane (9.0 g), CHCl3 (26 g) and EtOAc fractions (2.0 g). Repeated separation and purification of the CHCl3 fraction using silica gel (CHCl3/MeOH or n-hexane/EtOAc), ODS (H2O/MeOH), and Sephadex LH-20 (CHCl3/MeOH, 1:1) CC yielded fagonone (3, 25 mg, 0.005%), 2,7-dioxofagonene (5, 12.5 mg, 0.002%), fagonene (4, 6.7 mg, 0.001%), quinovic acid (7, 72.8 mg, 0.01%), quinovic acid-3-O--D-glucopyranoside (8, 24.5 mg, 0.004%), compound 1 (17.8 mg, 0.003%), and a mixture of 7β-hydroxy-fagonene (6) and compound 2. The mixture was then separated by RP-HPLC (Cholester 4.6 mm x 25 cm, UV detection 210 nm, mobile phase: MeCN/H2O 33:77, flow-rate: 1 mL/min) to obtain pure 6 (tR 29.4 min, 1.7 mg, 0.0003%) and compound 2 (tR 35.2 min, 1.0 mg, 0.0002%). In addition, separation of the EtOAc fraction by Sephadex LH-20 (CHCl3/MeOH, 1:1) and ODS (H2O/MeOH) CC yielded 3-O-[-D-(2-O-sulfo)glucopyranosyl] quinovic acid (9, 1.1 mg, 0.000009%). Geranyllinalool-3-O--D-glycopyranoside (1) D

27: +2 (c 1.0, CHCl3) IR (neat) 3382 cm–1. 1H and 13C NMR: Table 1. MS (ESI): m/z 475 [M + Na]+; HRMS-ESI: m/z [M + Na]+ calcd for C26H44O6Na: 475.3036; found 475.3051. 7-Hydroxy-5-epi-fagonene (2) D

27:+28 (c 1.0, CHCl3). IR (neat): 3356 cm–1. UV/Vis max (MeOH) nm (log ): 205 (3.60). 1H and 13C NMR: Table 1. MS (ESI) m/z 345 [M + Na]+; HRMS-ESI: m/z [M + Na]+ calcd for C20H34O3Na: 345.2406; found 345.2406.

Acid hydrolysis of 1: 1 (1.0 mg) was treated with 1N aqueous HCl (50 μL) at 100oC for 1 h. After neutralization with 1N aqueous NaOH, the mixture was extracted with CHCl3. The aqueous layer was submitted to HPLC analysis (GL science NH2 column φ 4.6 x 250 mm, eluent: 70% aqueous MeCN, flow rate 1.0 mL/min, JASCO OR-1590 chiral detector). Retention times of authentic L-glucose and D-glucose were 7.5 min with negative and positive intensity, respectively. The sugar in the aqueous layer of the hydrolysate of 1 had a retention time of 7.5 min with positive intensity. The CHCl3 layer yielded a dehydration product of geranyllinalool. Cytotoxic activity: HL-60, human promyelocyctic leukemia cells were maintained in RPMI-1640 medium. The growth medium was supplemented with 10% fetal calf serum and 1% Penicillin-Streptomycin. The cells (5 x 103 cells/well) were cultured in Nunc disposable 96-well plates containing 90 µL of growth medium per well and were incubated at 37oC in a humidified incubator of 5% CO2. Ten µL of serially diluted samples (50 µM, 25 µM, 12.5 µM, and 6.25 µM) were added to the cultures after 24 h of incubation. After 48 h of incubation with the samples, 15 µL of MTT (5 mg/mL) was added to each of the wells. The cultures were incubated for another 3 h before the cell supernatant was removed. Then, 50 µL of DMSO was added to each well. The formed formazan crystals were dissolved by re-suspension by pipette. The optical density was measured using a microplate reader (Bio-Rad) at 550 nm with a reference wavelength of 700 nm. In all experiment, 3 replicates were used. Cisplatin was used as positive control (IC50 = 0.87 M). Acknowledgments - This work was partly supported by the mission sector of the Ministry of High Education, Egypt and Grants-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS).

Table 1: 1H and 13C NMR data of 1 and 2 (300K).

1 (in CD3OD) 2 (in CDCl3) H (J, Hz) C H (J, Hz) C H (J, Hz) C H (J, Hz) C

1a 5.20 (1H; d, 11.0) 115.8 15 132.0 1a 1.43 (1H; m) 17.5 12a 1.10 (1H; m) 28.91b 5.23 (1H; d, 17.9) 16 1.66 (3H; s) 25.9 1b 1.67 (1H; m) 12b 1.67 (1H; m) 2 5.93 (1H; dd, 17.9, 11.0) 144.5 17 1.59 (3H; s) 17.8 2a 1.99 (1H; m) 26.8 13 36.3 3 81.4 18 1.59 (3H; s) 16.08 2b 2.08 (1H; m) 14a 1.23 (1H; m) 29.6 4 1.60 (2H; t, 7.9) 42.7 19 1.59 (3H; s) 16.10 3 5.17 (1H; br s) 120.5 14b 1.70 (1H; m) 5 2.06 (2H; m) 23.6 20 1.38 (3H; s) 23.2 4 143.3 15 3.37 (1H; dd, 9.4, 2.7) 81.3 6 5.09 (1H; t, 7.5) 125.4 1' 4.35 (1H; d, 7.8) 99.5 5 39.0 16a 3.58 (1H; dd, 10.9, 9.4) 62.6 7 135.9 2' 3.16 (1H; dd, 9.0, 7.8) 75.2 6a 1.20 (1H; dd, 12.0, 10.6) 46.9 16b 3.77 (1H; dd, 10.9, 2.7) 8 1.97 (2H; t, 7.9) 40.9 3' 3.32 (1H; t, 9.0) 78.2 6b 2.13 (1H; dd, 12.0, 4.0) 17 0.92 (3H; s) 19.2 9 2.06 (2H; m) 27.8 4' 3.28 (1H; t, 9.0) 71.7 7 3.56 (1H; td, 10.6, 4.0) 68.0 18 1.61 (3H; s) 18.0 10 5.09 (1H; t, 7.5) 125.4 5' 3.17 (1H; ddd, 9.0, 5.6, 2.3) 77.6 8 1.18 (1H; ddd, 10.6, 10.6, 2.6) 48.9 19 1.06 (3H; s) 21.8 11 135.8 6'a 3.64 (1H; dd, 11.9, 5.6) 62.8 9 37.4 20 0.78 (3H; s) 13.6 12 1.97 (2H; t, 7.9) 40.8 6'b 3.80 (1H; dd, 11.9, 2.3) 10 1.21 (1H; m) 53.4 13 2.06 (2H; m) 27.6 11a 1.10 (1H; m) 34.8 14 5.11 (1H; t, 7.5) 125.8 11b 1.63 (1H; m)

References

[1] (a) Tackholm V. (1974) Students' Flora of Egypt, Cooperative Printing Company, Beirut; (b) Boulos L. (2000) Flora of Egypt, Al Hadara Publishing, Cairo; (c) Yousif F, Wassel G, Boulos L, Labib T, Mahmoud K, El-Hallouty S, El Bardicy S, Mahmoud S, Ramzy F, Gohar L, El-Manawaty M, El Gendy MAM, Fayad W, El-Menshawi B. (2012) Contribution to in vitro screening of Egyptian plants for schistosomicidal activity. Pharmaceutical Biology, 50, 732-739; (d) El-Shabrawy OA, El-Gindi OD, Melek FR, Abdel-Khalik SM, Haggag MY. (1997) Biological properties of saponin mixtures of Fagonia cretica and Fagonia mollis. Fitoterapia, 68, 219-222.

[2] (a) Melek FR, Miyase T, El-Gindi OD, Abdel-Khalik SM and Haggag MY. (1996) Saponins from Fagonia mollis. Phytochemistry, 42, 1405-1407; (b) Attia AA, Youssef SA. (1999) Triterpenes and flavonoids from Fagonia mollis Del var. grandiflora. Bulletin of Pharmaceutical Sciences (Assiut University), 22, 67-72; (c) Abdel-Kader MS, Omar AA, Abdel-Salam NA, Stermitz FR. (1993) Erythroxan diterpenes and flavonoids from Fagonia bruguieri. Phytochemistry, 33, 718-720; (d) Abdel-Kader MS, Omar AA, Abdel-Salam NA, Stermitz FR. (1994) Erythroxan diterpenes from Fagonia species. Phytochemistry, 36, 1431-1433; (e) Ferrari F, de Cornelio IK, Monache FD, Bettolo GBM. (1981) Quinovic acid glycosides from roots of Macfadyena unguis-cati. Planta Medica, 43, 24-27 (f) Smati D, Mitaine-Offer A-C, Miyamoto T, Hammiche V, Lacaille-Dubois M-A. (2007) Ursane-type triterpene saponins from Zygophyllum geslini. Helvetica Chimica Acta, 90, 712-719; (g) Guella G, Pietra F. (2000) A new-skeleton diterpenoid, new prenylbisabolanes, and their putative biogenetic precursor, from the red seaweed Laurencia microcladia from Il Rogiolo: Assigning the absolute configuration when two chiral halves are connected by single bonds. Helvetica Chimica Acta, 83, 2946-2952.

[3] Abdel-Kader MS, Omar AA, Stermitz FR. (1997) Erythroxan diterpenes from Fagonia glutinosa. Planta Medica, 63, 374-376.

Natural Product Communications Vol. 9 (9) 2014 Published online (www.naturalproduct.us)

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Natural Product Communications 2014

Volume 9, Number 9

Contents

Original Paper Page

The Leaf, Wood and Bark Oils of three Species of Myodocarpus (Myodocarpaceae) Endemic to New Caledonia Nicolas Lebouvier, Douglas Lawes, Edouard Hnawia, Michael Page, Joseph Brophy and Mohammed Nour 1223

Iridoids and a Norsesquiterpenoid from the Leaves of Villaria odorata Mario A. Tan, Raychel Ann U. Villacorta, Grecebio Jonathan D. Alejandro and HiromitsuTakayama 1229

Induction, Cloning and Functional Expression of a Sesquiterpene Biosynthetic Enzyme, -Guaiene Synthase, of Aquilaria microcarpa Cell Cultures Jung-Bum Lee, Syun Hirohashi, Yoshimi Yamamura, Futoshi Taura and Fumiya Kurosaki 1231

Zerumbone Induces G2/M Cell Cycle Arrest and Apoptosis via Mitochondrial Pathway in Jurkat cell Line Heshu Sulaiman Rahman, Abdullah Rasedee, Max Stanley Chartrand, Hemn Hassan Othman, Swee Keong Yeap and Farideh Namvar 1237

Diterpenoids from Fagonia mollis Amal Sallam, Alfarius Eko Nugroho, Yusuke Hirasawa, Wong Chin-Piow, Toshio Kaneda, Osamu Shirota, Sahar R. Gedara and Hiroshi Morita 1243

Cytotoxicity of the Diterpene 14-O-Methyl-ryanodanol from Erythroxylum passerinum in an Astrocytic Cells Model Noélio de Jesus Menezes-Filho, Cleide dos Santos Souza, Tereza Cristina Silva Costa, Victor Diógenes Amaral da Silva, Cátia Suse de Oliveira Ribeiro, Marizeth Liborio Barreiros, Jose Fernando Oliveira Costa, Jorge Mauricio David, Juceni P.L. David and Silvia Lima Costa 1245

Absolute Configuration of Cembrane Diterpenoids from Bursera multijuga Juan D. Hernández-Hernández, Hugo A. García-Gutiérrez, Luisa U. Román-Marín, Yunuen I. Torres-Blanco, Carlos M. Cerda-García-Rojas and Pedro Joseph-Nathan 1249

Trichostemonoate, a New Anticancer Tirucallane from the Stem Bark of Walsura trichostemon Kiettipum Phontree, Jirapast Sichaem, Suttira Khumkratok, Pongpun Siripong and Santi Tip-pyang 1253

A New Cycloartane Glucoside from Rhizophora stylosa Phan Thi Thanh Huong, Chau Ngoc Diep, Nguyen Van Thanh, Vu Anh Tu, Tran Hong Hanh, Nguyen The Cuong, Nguyen Phuong Thao, Nguyen Xuan Cuong, Do Thi Thao, Tran Huy Thai, Nguyen Hoai Nam, Ninh Khac Ban, Phan Van Kiem and Chau Van Minh 1255

Kolgaosides A and B, Two New Triterpene Glycosides from the Arctic Deep Water Sea Cucumber Kolga hyalina (Elasipodida: Elpidiidae) Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjashchenko, Sergey N. Fedorov, Pavel S. Dmitrenok, Ekaterina A. Yurchenko, Vladimir I. Kalinin, Antonina V. Rogacheva and Andrey V. Gebruk 1259

Acaricidal Activity against Panonychus citri and Active Ingredient of the Mangrove Plant Cerbera manghas Yecheng Deng, Yongmei Liao, Jingjing Li, Linlin Yang, Hui Zhong, Qiuyan Zhou and Zhen Qing 1265

Three New Steroid Biglycosides, Plancisides A, B, and C, from the Starfish Acanthaster planci Alla A. Kicha, Thi H. Dinh, Natalia V. Ivanchina, Timofey V. Malyarenko, Anatoly I. Kalinovsky, Roman S. Popov, Svetlana P. Ermakova, Thi T. T. Tran and Lan P. Doan 1269

Unusual 2(1H)-Pyrazinones Isolated from a Culture of a Brazilian Marine-Derived Streptomyces sp. Sérgio S. Thomasi, Ana C. Granato, Luis H. Romano, Liene Dhooghe, Eduardo S. P. do Nascimento, Alberto C. Badino, Maria F. G. F. da Silva, Antonio G. Ferreira and Tiago Venâncio 1275

An HPLC Evaluation of Cytochalasin D Biosynthesis by Xylaria arbuscula Cultivated in Different Media Luciana da S. Amaral, Edson Rodrigues-Filho, Carolina A. A. Santos, Lucas M. de Abreu and Ludwig H. Pfenning 1279

A Simple Method for Isolation and Purification of DIBOA-Glc from Tripsacum dactyloides Cammy D. Willett, Robert N. Lerch, Keith W. Goyne, Nathan D. Leigh, Chung-Ho Lin and Craig A. Roberts 1283

Antimicrobial Metabolites from Endophytic Streptomyces sp. YIM61470 Xueqiong Yang, Yun Liu, Shuquan Li, Fangfang Yang, Lixing Zhao, Li Peng and Zhongtao Ding 1287

Genkwanin 4´-O-glucosyl-(1→2)-rhamnoside from New Chemotype of Asplenium normale in Japan Tao Fujiwara, Ayumi Uehara, Junichi Kitajima, Tsukasa Iwashina, Sadamu Matsumoto and Yasuyuki Watano 1289

Potent SIRT1 Enzyme-stimulating and Anti-glycation Activities of Polymethoxyflavonoids from Kaempferia parviflora Asami Nakata, Yuka Koike, Hirofumi Matsui, Tsutomu Shimada, Masaki Aburada and Jinwei Yang 1291 Protective Activity of C-Geranylflavonoid Analogs from Paulownia tomentosa against DNA Damage in 137Cs Irradiated AHH-1Cells Hyung-In Moon, Min Ho Jeong and Wol Soon Jo 1295

Antibacterial Activities of Oxyprenylated Chalcones and Napthtoquinone against Helicobacter pylori Charles Bodet, Christophe Burucoa, Steeve Rouillon, Nicolas Bellin, Vito Alessandro Taddeo, Serena Fiorito, Salvatore Genovese and Francesco Epifano 1299

Anti-proliferation Effect on Human Breast Cancer Cells via Inhibition of pRb Phosphorylation by Taiwanin E Isolated from Eleutherococcus trifoliatus Hui-Chun Wang, Yen-Hsueh Tseng, Hui-Rong Wu, Fang-Hua Chu, Yueh-Hsiung Kuo and Sheng-Yang Wang 1303

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