Planta Med 2008; 74(4): 432-437
DOI: 10.1055/s-2008-1034318
Natural Products Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

New Abietane Diterpenoids from the Mangrove Avicennia marina

Li Han1 , 2 , Xueshi Huang1 , Hans-Martin Dahse1 , Ute Moellmann1 , Susanne Grabley1 , Wenhan Lin2 , Isabel Sattler1
  • 1Leibniz Institute for Natural Product Research and Infection Biology, Hans-Knöll-Institute, Jena, Germany
  • 2State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing, Peoples Republic of China
Further Information

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.

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

>