Two new c-glucosyl benzoic acids and flavonoids from Mallotus nanus and their antioxidant activity

Volume 4. Issue 3. Pages 307-456. 2009 ISSN 1934-578X (printed); ISSN 1555-9475 (online)

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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 [email protected] EDITORS

PROFESSOR ALESSANDRA BRACA Dipartimento di Chimica Bioorganicae Biofarmacia, Universita di Pisa, via Bonanno 33, 56126 Pisa, Italy [email protected]

PROFESSOR DEAN GUO State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China [email protected]

PROFESSOR J. ALBERTO MARCO Departamento de Quimica Organica, Universidade de Valencia, E-46100 Burjassot, Valencia, Spain [email protected]

PROFESSOR YOSHIHIRO MIMAKI School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan [email protected]

PROFESSOR STEPHEN G. PYNE Department of Chemistry University of Wollongong Wollongong, New South Wales, 2522, Australia [email protected]

PROFESSOR MANFRED G. REINECKE Department of Chemistry, Texas Christian University, Forts Worth, TX 76129, USA [email protected]

PROFESSOR WILLIAM N. SETZER Department of Chemistry The University of Alabama in Huntsville Huntsville, AL 35809, USA [email protected]

PROFESSOR YASUHIRO TEZUKA Institute of Natural Medicine Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan [email protected]

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 [email protected]

ADVISORY BOARD Prof. Berhanu M. Abegaz Gaborone, Botswana

Prof. Viqar Uddin Ahmad Karachi, Pakistan

Prof. Øyvind M. Andersen Bergen, Norway

Prof. Giovanni Appendino Novara, Italy

Prof. Yoshinori Asakawa Tokushima, Japan

Prof. Lee Banting Portsmouth, U.K.

Prof. Anna R. Bilia Florence, Italy

Prof. Maurizio Bruno Palermo, Italy

Prof. Josep Coll Barcelona, Spain

Prof. Geoffrey Cordell Chicago, IL, USA

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Prof. Duvvuru Gunasekar Tirupati, India

Prof. A.A. Leslie Gunatilaka Tucson, AZ, USA

Prof. Stephen Hanessian Montreal, Canada

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

Prof. Jerzy Jaroszewski Copenhagen, Denmark

Prof. Leopold Jirovetz Vienna, Austria

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Prof. Norbert De Kimpe Gent, Belgium

Prof. Hartmut Laatsch Gottingen, Germany

Prof. Marie Lacaille-Dubois Dijon, France

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Prof. Peter Proksch Düsseldorf, Germany

Prof. Satyajit Sarker Wolverhampton, UK

Prof. Raffaele Riccio Salerno, Italy

Prof. Monique Simmonds Richmond, UK

Prof. Valentin Stonik Vladivostok, Russia

Prof. Hiromitsu Takayama Chiba, Japan

Prof. Karen Valant-Vetschera Vienna, Austria

Prof. Peter G. Waterman Lismore, Australia

Prof. Paul Wender Stanford, USA

HONORARY EDITOR

PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences,

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

[email protected]

A New Rearranged Abietane Diterpene and other Constituents from Clerodendrum philipinum Ha Van Oanha, Pham Xuan Sinha, Nguyen Thai Ana, Ta Manh Hungb, Tran Thi Lan Huongb, Do Thi Nguyet Quea, Nguyen Phuong Thaoc, Nguyen Xuan Cuongc, Nguyen Tien Datc, Chau Van Minhc and Phan Van Kiemc,* aHanoi University of Pharmacy, 17 Le Thanh Tong, Hanoi, Vietnam bNational Institute of Drug Qualification Control, 48 Hai Ba Trung, Hanoi, Vietnam cInstitute of Natural Product Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi, Vietnam [email protected] Received: October 4th, 2008; Accepted: December 4th, 2008

From the methanolic extract of the roots of Clerodendrum philipinum, a new rearranged abietane diterpene (1) and eight known compounds were isolated by various chromatography methods. Their structures were identified by means of spectroscopic methods, including 1D- and 2D-NMR, as 17(15→16),18(4→3)-bisabeo-11,12,14,16-tetrahydroxy-3,5,8,11,13,15-abietahexaen-7-one (1), binankadsurin A, clerodenoside A, martynoside, acteoside, isoacteoside, astragalin, β-sitosterol, and daucosterol. Binankadsurin A was found for the first time from a Clerodendrum species. Keywords: Clerodendrum philipinum, Verbenaceae, abietane, crolerodendrum A. Clerodendrum species (Verbenaceae) have been widely used in Vietnamese traditional medicine for treatment of cough, fever, inflammation, hepatitis and pulmonary tuberculosis, and as a phlogistic [1,2]. Although a number of studies have been reported on chemical constituents of Clerodendrum species possessing various biological activities, such as hypolipidemic effects, and NF-kappaB inhibition [3-8], there is no report to date on the chemical constituents and biological activity of C. philipinum. Herein, we describe the isolation and structural elucidation of nine compounds from the methanol extract of the roots of this species. Compound 1 was obtained as an orange powder. Its ESI mass spectrum revealed quasi molecular ion peaks at m/z 342.9 [M + H]+ and 364.9 [M + Na]+, corresponding to the molecular formula C20H22O5. The 1H NMR spectrum of 1 (measured in CDCl3 + CD3OD) showed singlet signals for four methyl groups at δ 2.41, 1.89, 1.86, and 1.52, and for two olefinic protons at δ 6.52 and 6.21. The downfield-shifted resonances at δ 2.41, 1.89, and 1.86 indicated that these methyl groups were attached to double-bonds.

OH

H3C

CH3

CH3

HO

CH3

O

O

HO

HH3C

CH3

HO

O

OH

HOOH

12

34

56

7

89

10

1112 13

14

15

16

17

18

19

20

Figure 1: Structure of 1 and its important H-C long range correlations in the HMBC spectrum in DMSO-d6.

The 13C NMR and DEPT spectra of 1 showed the presence of 20 carbon atoms, including 4 methyl, 2 methylene, 2 olefinic methine, and one carbonyl groups. Four methyl groups were also recognized at δC 13.43, 16.40, 20.04, and 20.34. The signals of a double bond conjugated to a carbonyl group (δC 191.47) appeared at δC 167.01 (C-5) and 117.86 (C-6). These observations suggested that the structure of 1 was similar to mandarone E, reported from C. mandarinorum [9]. Therefore, the structure and NMR data of 1 were first deduced by comparing with the corresponding data of mandarone E [9] and further confirmed by the HSQC and HMBC spectra. The NMR data of rings A and B of 1 were similar to those of mandarone E. However, the resonances

NPC Natural Product Communications 2009 Vol. 4 No. 3

323 - 325

324 Natural Product Communications Vol. 4 (3) 2008 Oanh et al.

Table 1: NMR spectral data of 1.

C δCa,c δH

a,d HMBCa (H to C)

δCb,c δH

b,d

1 29.32 1.18 /3.37 m 2, 3, 5, 20 29.12 1.48/3.85 m 2 30.17 2.17/2.52 m 3, 4 29.82 2.22/2.50 m 3 141.25 - 141.68 - 4 125.70 - 124.60 - 5 167.01 - 166.44 - 6 117.86 6.21 s 4, 5, 7, 8, 10 117.54 6.17 s 7 191.47 - 190.67 - 8 109.46 - 108.85 - 9 130.27 - 130.49 - 10 39.58 - 39.49 - 11 132.20 - 132.19 - 12 149.44 - 149.66 - 13 116.97 - 116.77 - 14 150.13 - 149.97 14.03 s, OH 15 100.66 6.52 s 12, 13, 16 100.75 6.65 s 16 154.57 - 154.92 - 17 13.43 2.41 s 15, 16 13.65 2.46 s 18 16.40 1.89 s 3, 4, 5 14.72 1.88 s 19 20.34 1.86 s 3, 4 20.46 1.87 s 20 20.04 1.52 s 1, 5, 9, 10 22.25 1.21 s

a measured in CDCl3+ CD3OD, b measured in DMSO-d6, c125 MHz, d500 MHz. of C-11, C-13, C-14, C-16, and C-17 differed [9]. In the case of benzofuran rearranged abietane diterpenoid compounds, such as mandarones and teuvincenones [9-11], the C-16 signal appears in the range δ 148-149, while this value for 1 was highly deshielded to δ 154.57, suggesting the opening of the benzoforan ring and the addition of hydroxyl groups at C-12 and C-16. The opening was consistent with the ESIMS result, which revealed that the molecular weight of 1 (342) was 18 Da higher than that of mandarone E (324), which was further confirmed by the HREIMS (found m/z 342.1454, calcd 342.1467 for C20H22O5). Furthermore, cross peaks from H-6 (δH 6.21) to C-5 (δC 167.01) and C-7 (δC 191.47), from H-17 (δH 2.41) to C-15 (δC 100.66) and C-16 (δC 154.57), and from H-15 (δH 6.52) to C-12 (δC 149.44), C-13 (δC 116.97), C-14 (δC 150.13), C-16 (δC 154.57) and C-17 (δC 13.43) were observed in the HMBC spectrum (measured in CDCl3 + CD3OD). In addition, HMBC cross peaks (measured in DMSO-d6) between 14-OH (δH 14.03) and C-13 (δC 116.77)/C-14 (δC 149.97)/ C-8 (δC 108.85) were also observed. The detailed HMBC correlations are shown in Table 1 (measured in CDCl3 + CD3OD) and Figure 1 (measured in DMSO-d6). Thus the structure of 1 was determined to be 17(15→16),18(4→3)-bisabeo-11,12,14,16-tetrahydroxy-3,5,8,11,13,15-abietahexaen-7-one; this was named crolerodendrum A.

The structures of known compounds were determined, by comparing their physicochemical and spectral data with literature values, as binankadsurin A [12], clerodenoside A [13], martynoside [14], acteoside [15,16], isoacteoside [16], astragalin [17], β-sitosterol [18], and daucosterol [19]. Binankadsurin A was found as a constituent of a Clerodendrum species for the first time. Experimental

General: The ESI mass spectra were obtained from an Agilent 1200 LC-MSD Trap spectrometer and the HREIMS was obtained on a Jeol JMSHX-100 mass spectrometer. The NMR experiments were recorded on a Bruker AM500 FT-NMR spectrometer. Plant materials: The roots of Clerodendrum philipinum Schauer. were collected in Thanh Oai, Hanoi, Vietnam in March 2008 and identified by Dr Tran Van On, Hanoi University of Pharmacy, Vietnam. A voucher specimen (HNIP/15610/08) was deposited at the herbarium of Hanoi University of Pharmacy, Vietnam. Extraction and isolation: The air dried and powdered roots (1 kg) of C. philipinum were extracted with methanol (each 3 × 10 L) by sonication for 30 min. The MeOH extract was concentrated under reduced pressure. The obtained residue (30 g) was suspended in water (3 L) and successively partitioned with n-hexane, chloroform, and ethyl acetate (each 3 × 2 L) to give n-hexane (8.0 g), chloroform (10.6 g), ethyl acetate (4.2 g), and water (8.3 g) residues, after removal of the solvents. The chloroform part was subjected to a silica gel column, eluting with a gradient of n-hexane/ethyl acetate to give three fractions, A1–A3. Compounds 1 (20.0 mg) and binankadsurin A (21.0 mg) were obtained from fractions A1 and A2, respectively, by a silica gel column using n-hexane/acetone (10:1, v/v) as an eluent. β-Sitosterol (200.0 mg) was recrystallized from fraction A3 in a mixture of n-hexane/ethyl acetate (4:1, v/v). The ethyl acetate and water residues were combined and chromatographed on a silica gel column eluting with a gradient of chloroform/methanol (from 20:1 to 1:1, v/v) to afford four fractions, B1–B4. Daucosterol (150.0 mg) was obtained from fraction B1 by recrystallization from a mixture of chloroform/methanol (5:1, v/v). Fraction B2 was chromatographed on an YMC RP-18 column eluting with methanol/water (1:3, v/v) to afford clerodenoside A (18.0 mg) and astragalin (8.0 mg).

Chemical constituents from Clerodendrum philipinum Natural Product Communications Vol. 4 (3) 2008 325

Similar conditions were applied for fraction B3 to obtain martynoside (17.0 mg). Fraction B4 was chromatographed on a silica gel column using chloroform/methanol (5:1, v/v) as eluent to afford acteoside (30.0 mg) and isoacteoside (11.0 mg). 17(15→16),18(4→3)-Bisabeo-11,12,14,16-tetrahydroxy-3,5,8,11,13,15-abietahexaen-7-one [crolerodendrum A (1)]

Orange powder. MP: 215-217oC [ ]20

Dα : +70 (c 0.5, MeOH). Rf: 0.55 (chloroform-acetone-H2O, 1:2:0.1).

1H NMR (500 MHz): Table 1. 13C NMR (125 MHz): Table 1. ESIMS: m/z 343 [M + H]+; 365 [M + Na]+. HREIMS: m/z 342.1454, calcd 342.1467 for C20H22O5 20.0 mg (2×10-5 % of dried weight). Acknowledgments - The authors would like to thank Dr Tran Van On, Hanoi University of Pharmacy, Vietnam for the plant identification and Mr Dang Vu Luong, Institute of Chemistry, VAST for recording the NMR spectra.

References

[1] Loi DT. (2001) Glossary of Vietnamese Medical Plants. Medicine Publishing House, Hanoi, Vietnam, 37-40. [2] Bich DH, Trung DQ, Chuong BX, Dong NT, Dam DT, Hien PV, Lo VN, Mai PD, Man PK, Nhu DT, Tap N, Toan T. (2004) The

medicinal plants and animals of Vietnam. Hanoi Science and Technology Publisher, 1st edition, Hanoi, Vietnam, 278. [3] Liu S, Zhu H, Zhang S, Zhang X, Yu Q, Xuan L. (2008) Abietane diterpenoids from Clerodendrum bungei. Journal of Natural

Products, 71, 755-779. [4] Park MA, Kim HJ. (2007) Anti-inflammatory constituents isolated from Clerodendron trichotomum Tunberg leaves (CTL) inhibits

pro-inflammatory gene expression in LPS-stimulated RAW 264.7 macrophages by suppressing NF-kappaB activation. Archives of Pharmacal Research, 30, 755-760.

[5] Chae S, Kang KA, Kim JS, Hyun JW, Kang SS. (2006) Trichotomoside: a new antioxidative phenylpropanoid glycoside from Clerodendron trichotomum. Chemistry & Biodiversity, 3, 41-48.

[6] Miller RE, McConville MJ, Woodrow IE. (2006) Cyanogenic glycosides from the rare Australian endemic rainforest tree Clerodendrum grayi (Lamiaceae). Phytochemistry, 67, 43-51.

[7] Adeneye AA, Adeleke TI, Adeneye AK. (2008) Hypoglycemic and hypolipidemic effects of the aqueous fresh leaves extract of Clerodendrum capitatum in Wistar rats. Journal of Ethnopharmacology, 116, 7-10.

[8] Pandey R, Verma RK, Gupta MM. (2006) Neo-clerodane diterpenoids from Clerodendrum inerme. Phytochemistry, 66, 643-648. [9] Fan TP, Min JD, Iinuma M, Tanaka T. (2000) Rearranged abietane diterpenoids from Clerodendrum mandarinorum. Journal of

Asian Natural Product Research, 2, 237-243. [10] Bruno M, Torre MC, Savona G, Piozzi F, Rodriguer B. (1990) A rearranged abietane diterpenoid from the root of Teucrium

fruticans. Phytochemistry, 29, 2710-2712. [11] Cuadrado MJS, Bruno M, Torre MC, Piozzi F, Savona G, Rodriguer B. (1992) Rearranged abietane diterpenoids from the root of

two Teucrium species. Phytochemistry, 31, 1697-1701. [12] Ookawa N, Ikeya Y, Sugama K, Taguchi H, Maruno M. (1995) Dibenzocyclooctadiene lignans from Kadsura japonica.

Phytochemistry, 39, 1187-1191. [13] Abe F, Nagao T, Okabe H. (2002) Antiproliferative constituents in plants 9. Aerial parts of Lippia dulcis and Lippia canescens.

Biological & Pharmaceutical Bulletin, 25, 920-922. [14] Leitao GL, Kaplan MAC. (1994) Phenylpropanoid glucosides from Aegiphila obducta. Journal of Natural Products, 57,

1703-1707. [15] Sasaki H, Nishimura H, Chin M, Mitsuhashi H. (1989) Hydroxycinnamic acid esters of phenethylalcohol glycosides from

Rehmannia glutinosa var. purprea. Phytochemistry, 28, 876-879. [16] Miyase T, Koizumi A, Ueno A, Noro T, Kuroyanagi M, Fukushima S, Akiyama Y, Takemoto T. (1982) Studies on the acyl

glycosides from Leucoseptrum japonicum (Miq.) Kitamura et Murata. Chemical & Pharmaceutical Bulletin, 30, 2732-2737. [17] Kazuma K, Noda N, Suzuki M. (2003) Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry, 62,

229-237. [18] Goad JL, Akihisa T. (1997) Analysis of Sterols, Blackie Academic and Professional Pub., First edition, 378. [19] Voutquenne L, Lavaud C, Massiot G, Sevenet T, Hadi HA. (1999) Cytotoxic isoprenes and glycosides of long-chain fatty alcohols

from Dimocarpus fumatus. Phytochemistry, 50, 63-69.

Novel Macrolide from Wild Strains of the Phytopathogen Fungus Colletotrichum acutatum Gabriela Mancilla, Daniel Jiménez-Teja, Marienca Femenía-Ríos, Antonio J. Macías-Sánchez, Isidro G. Collado and Rosario Hernández-Galán 395

Fatty Acid Profile and in vitro Antioxidant and Antibacterial Activities of Red Grape (Vitis vinifera L. cvs. Öküzgözü and Boğazkere) Marc Extracts Bilge Çıbık, Zuhal Özaydın, Nazlı Böke, Ülkü Karabay, Murat Pekmez, Nazlı Arda and Süheyla Kırmızıgül 399

Fatty Acid Derived Compounds – The Dominant Volatile Class of the Essential Oil Poor Sonchus arvensis subsp. uliginosus (Bieb.) Nyman Niko Radulović, Polina Blagojević and Radosav Palić 405

Analysis of Essential Oil from Teucrium maghrebinum Greuter et Burdet Growing Wild in Algeria Carmen Formisano, Daniela Rigano, Felice Senatore, Malik R. Y. Al-Hillo, Franco Piozzi and Sergio Rosselli 411

The Essential Oil of Thymus aureopunctatus (Beck) K. Malý Sanja Ćavar, Milka Maksimović and Danijela Vidic 415

Essential Oil Constituents of Eclipta prostrata (L.) L. and Vernonia amygdalina Delile Akinola O. Ogunbinu, Guido Flamini, Pier L. Cioni, Isiaka A. Ogunwande and Sunday O. Okeniyi 421

Chemical Composition of the Leaf Essential Oil of Casimiroa edulis La Llave & Lex. (Rutaceae) from Monteverde, Costa Rica Sarah L. Miller, William A. Haber and William N. Setzer 425

Essential Oil Composition of Three Peperomia Species from the Amazon, Brazil Patrícia Natália B. de Lira, Joyce Kelly R. da Silva, Eloisa Helena A. Andrade, Pergentino José C. Sousa, Nayla N. S. Silva and José Guilherme S. Maia 427

Composition and Antimicrobial Activity of Marrubium incanum Desr. (Lamiaceae) Essential Oil Silvana Petrović, Milica Pavlović, Zoran Maksimović, Marina Milenković, Maria Couladis, Olga Tzakou

and Marjan Niketić 431

Review/Account The Flavonoids and Phenolic Acids of the Genus Silphium and Their Chemosystematic Value Jeffrey D. Williams, Małgorzata Wojcińska, Lalita M. Calabria, Klaus Linse, Jennifer A. Clevinger and Tom J. Mabry 435

Solvent Derived Artifacts in Natural Products Chemistry Federica Maltese, Frank van der Kooy and Robert Verpoorte 447

Natural Product Communications 2009

Volume 4, Number 3

Contents

Original Paper Page

Sesquiterpene and Acyclic Diterpenes from Hyptis verticillata Jacq. Duanne A. C. Biggs, Roy B. R. Porter and William F. Reynolds 307

Minor Chemical Constituents of Caesalpinia bonduc Athar Ata, Chibuike C. Udenigwe, Elikana M. Gale and Radhika Samarasekera 311

Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp. Harald Gross, Anthony D. Wright, Uwe Reinscheid and Gabriele M. König 315

A New Rearranged Abietane Diterpene and other Constituents from Clerodendrum philipinum Ha Van Oanh, Pham Xuan Sinh, Nguyen Thai An, Ta Manh Hung, Tran Thi Lan Huong, Do Thi Nguyet Que, Nguyen Phuong Thao, Nguyen Xuan Cuong, Nguyen Tien Dat, Chau Van Minh and Phan Van Kiem 323

Antimicrobial Evaluation of Clerodane Diterpenes from Polyalthia longifolia var. pendula Koneni V. Sashidhara, Suriya P. Singh and P.K. Shukla 327

Antifouling Sesterterpenes from the New Zealand Marine Sponge Semitaspongia bactriana Michael Stewart, Craig Depree and Karen J Thompson 331

Genetic and Withaferin A Analysis of Iranian Natural Populations of Withania somnifera and W. coagulans by RAPD and HPTLC Mohammad Hossein Mirjalili, Seyyed Mohammad Fakhr-Tabatabaei, Houshang Alizadeh, Alireza Ghassempour and Fateme Mirzajani 337

Cytotoxic and HLE-inhibitory Tetramic Acid Derivatives from Marine-derived Fungi Kerstin Neumann, Stefan Kehraus, Michael Gütschow, and Gabriele M. König 347

Murrayakoeninol- A New Carbazole Alkaloid from Murraya koenigii (Linn) Spreng Mumu Chakraborty, Sudipta Saha and Sibabrata Mukhapadhyay 355

Alkaloid Synthesis and Accumulation in Leucojum aestivum in vitro Cultures Strahil Berkov, Atanas Pavlov, Vasil Georgiev, Jaume Bastida, Monique Burrus, Mladenka Ilieva and Carles Codina 359

Exudate Flavonoids of Primula spp: Structural and Biogenetic Chemodiversity Karin M. Valant-Vetschera, Tshering Doma Bhutia and Eckhard Wollenweber 365

Antioxidant and Antimicrobial Effects of the Mangrove Tree Heritiera fomes Helle Wangensteen, Huong Cam Thi Dang, Shaikh Jamal Uddin, Mahiuddin Alamgir and Karl Egil Malterud 371

Possibility for Selective Accumulation of Polyphenolics in Tissue Cultures of Senno (Lychnis senno Siebold et Zucc.) Shinjiro Ogita, Junko Miyazaki, Toshinari Godo and Yasuo Kato 377

Phenolic Glucosides from Flacourtia indica Swati Madan, Steve T. Pannakal, Seru Ganapaty, Gyanendra N. Singh and Yatendra Kumar 381

Antimicrobial Phenolic Compounds from Anabasis aphylla L. Hua Du, Ye Wang, Xiaojiang Hao, Chun Li, Youliang Peng, Jihua Wang, Hao Liu and Ligang Zhou 385

Aureobasidin, New Antifouling Metabolite from Marine-Derived Fungus Aureobasidium sp. Ahmed Abdel-Lateff, Ehab S. Elkhayat, Mostafa A. Fouad and Tatsufumi Okino 389

Continued inside back cover