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