Subscribe to RSS
DOI: 10.1055/s-2008-1034318
© Georg Thieme Verlag KG Stuttgart · New York
New Abietane Diterpenoids from the Mangrove Avicennia marina
Publication History
Received: September 12, 2007
Revised: December 12, 2007
Accepted: January 24, 2008
Publication Date:
07 March 2008 (online)
Abstract
Phytochemical investigations of the twigs of Avicennia marina yielded three new abietane diterpenoids 11-hydroxy-8,11,13-abietatriene 12-O-β-xylopyranoside (1), and a pair of inseparable epimers 6Hα-11,12,16-trihydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial 11,6-hemiacetal (2) and 6Hβ-11,12,16-trihydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial 11,6-hemiacetal (3), as well as the new lignan (7′S ∗,8′R ∗)-4,4′,9′-trihydroxy-3,3′,5,5′-tetramethoxy-7,8-dehydro-9-al-2,7′-cyclolignan (5), together with 6,11,12,16-tetrahydroxy-5,8,11,13-abitetetraen-7-one (4), lyoniresinol (6), lyoniresinol 9′-O-β-D-glucopyranoside (7), and diacetylmartynoside (8). Structure elucidation of the new compounds was accomplished by analysis of their spectroscopic data. Compounds 2 - 4 showed moderate cytotoxic and antimicrobial activities.
Key words
Avicennia marina - Acanthaceae - abietane diterpenoids - lignans
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Duke N C. A systematic revision of the mangrove genus Avicennia (Avicenniaceae) in Australasia. Aust Syst Bot. 1991; 4 229-334
- 2 Lin P, Fu Q. Environmental ecology and economic utilization of mangroves in China. Beijing: Higher Education Press and Springer Verlag Berlin. Heidelberg; 1994 18-50
- 3 Ito C, Katsuno S, Kondo Y C, Tan H T-W, Furukawa H. Chemical constituents of Avicennia alba. Isolation and structural elucidation of new naphthoquinones and their analogues. Chem Pharm Bull. 2000; 48 339-43
- 4 Koenig G, Rimpler H. Iridoid glucosides in Avicennia marina. . Phytochemistry. 1985; 24 1245-8
- 5 Fauvel M T, Bousquet M A, Moulis C, Gleye J, Jensen S R. Iridoid glucosides from Avicennia germinans. . Phytochemistry. 1995; 38 893-4
- 6 Feng Y, Li X M, Duan X J, Wang B G. Iridoid glucosides and flavones from the aerial parts of Avicennia marina. . Chem Biodivers. 2006; 3 799-806
- 7 Matsumoto T, Imai S, Takeda S, Mitsuki M. Revision of structures of nellionol and dehydronellionol. Bull Chem Soc Jpn. 1983; 56 2013-7
- 8 Matsumoto T, Imai S, Takeda Y. The syntheses and absolute configurations of nellionol and 5-dehydronellionol. Bull Chem Soc Jpn. 1985; 58 1165-70
- 9 Vecchiett V, Ferrari G, Orsini F, Pelizzoni F. Alkaloid and lignan constituents of Cinnamosma madagascariensis. . Phytochemistry. 1979; 18 1847-9
- 10 Miyamura M, Nohara T, Tomimatsu T, Nishiokat I. Seven aromatic compounds from bark of Cinnamomum cassia. . Phytochemistry. 1983; 22 215-8
- 11 Abe F, Nagao T, Okabe H. Antiproliferative constituents in plants 9. Aerial parts of Lippia dulcis and Lippia canescens. . Biol Pharm Bull. 2002; 25 920-2
- 12 Jia Z, Koike K, Nikaido T, Ohmoto T. Two novel triterpenoid pentasaccharides with an unusual glycosyl glycerol side chain from Ardisia crenata. . Tetrahedron. 1994; 50 11 853-64
- 13 Dahse H M, Schlegel B, Gräfe U. Differentiation between inducers of apoptosis and nonspecific cytotoxic drugs by means of cell analyzer and immunoassay. Pharmazie. 2001; 56 489-91
- 14 European Pharmacopoeia, 3th Edition. Stuttgart; Deutscher Apothekerverlag 1997: 13
- 15 Afonin S, Glaser R W, Berditchevskaja M, Wadhwani P, Gührs K , Möllmann U. et al . 4-Fluoro-phenylglycine as a label for 19F-NMR structure analysis of membrane associated peptides. ChemBioChem. 2003; 4 1151-63
- 16 Fraga B M, Díaz C E, Guadaño A, González-Coloma A. Diterpenes from Slavia broussonetii transformed roots and their insecticidal activity. J Agric Food Chem. 2005; 53 5200-6
- 17 Gonzalez A G, Castro Z EA, Luis J G, Ravelo A G. New secoditerpenes from Salvia texana. Transformations of 6, 7-secoabietanes in basic medium and their possible formation via oxygen singlet participation. J Chem Res Synop. 1989; 5 132-3
- 18 Kelecom A, Dos Santos T C, Medeiros W LS. Secoabietane diterpenes from Coleus barbatus. . Phytochemistry. 1987; 26 2337-40
- 19 Rao C B, Rao T N, Vijayakumar E KS. Chemical examination of Premna latifolia Roxb.: isolation and characterization of some new diterpenes. Indian J Chem Section B. 1979; 18B 513-24
- 20 Wang B G, Ebel R, Wang C Y, Wray V, Proksch P. New methoxylated aryltetrahydronaphthalenelignans and a norlignan from Aglaia cordata. . Tetrahedron Lett. 2002; 43 5783-7
- 21 Cullmann F, Becker H. Lignans from the liverwort Lepicolea ochroleuca. . Phytochemistry. 1999; 52 1651-6
- 22 Scher J M, Zapp J, Becker H. Lignan derivatives from the liverwort Bazzania trilobata. . Phytochemistry. 2003; 62 769-77
- 23 Chawla A S, Sharma A K, Handa S S, Dhar K L. A lignan from Vitex negundo seeds. Phytochemistry. 1992; 31 4378-9
- 24 Martini U, Zapp J, Becker H. Lignans from the liverwort Bazzania trilobata. . Phytochemistry. 1998; 49 139-46
- 25 Dictionary of Natural Products. Chapman & Hall /CRC: Hampden Data Services Ltd 2005 Version 13: 1
Prof. Wenhan Lin
State Key Laboratory of Natural and Biomimetic Drugs
Peking University
Beijing 100083
Peoples Republic of China
Phone: Phone: +86-10-8280-6188
Fax: Fax: +86-10-8280-2724
Email: E-mail: whlin@bjmu.edu.cn
Dr. Isabel Sattler
Leibniz Institute for Natural Product Research and Infection Biology
Hans-Knöll-Institute
Beutenbergstr. 11a
07745 Jena
Germany
Phone: +49-3641-656-920
Fax: +49-3641-656-679
Email: isabel.sattler@hki-jena.de
- www.thieme-connect.de/ejournals/toc/plantamedica