New Pyrrolizidine Alkaloids and Glycosides from Anchusa strigosa

Abstract

Six new pyrrolizidine alkaloids, a new carboxylic acid, a new phenolic and a new oleanane glycoside, together with the known compounds 7,7′-bis-(4-hydroxy-3,5-dimethoxyphenyl)-8,8′-dihydroxymethyltetrahydrofuran 4′-O-β-D-glucopyranoside, rosmarinic acid, caffeic acid, tormentic acid 28-O-β-D-glucopyranoside, euscaphic acid 28-O-β-D-glucopyranoside, euscaphic acid, and allantoin were isolated from Anchusa strigosa roots. Their structures were established by high resolution NMR, MS, elemental analysis, and chemical reactions.

Anchusa strigosa - Boraginaceae - pyrrolizidine alkaloids - phenolic glycoside - oleanane glycoside

References

• 1 Feinbrun-Dothan N. Flora Palaestina Part III. The Israel Academy of Sciences and Humanities Jerusalem; 1978: pp. 84
• 2 Said O, Khalil K, Fulder S, Azaizeh H. Ethnopharmacological survey of medicinal herbs in Israel, the Golan Heights and the West Bank region.  J Ethnopharmacol. 2002;  83 251-65
• 3 Al-Khalil S. A survey of plants used in Jordanian traditional medicine.  Int J Pharmacogn. 1995;  33 317-23
• 4 Al-douri N A. A survey of medicinal plants and their traditional uses in Iraq.  Pharm Biol. 2000;  38 74-9
• 5 Ali-Shtayeh M S, Yaghmour R M, Faidi Y R, Salem K, Al-Nuri M A. Antimicrobial activity of 20 plants used in folkloric medicine in the Palestinian area.  J Ethnopharmacol. 1998;  60 265-71
• 6 Abuereish G M. Pepsin inhibitor from roots of Anchusa strigosa .  Phytochemistry. 1998;  48 217-21
• 7 Braca A, Bader A, Morelli I, Scarpato R, Turchi G, Pizza C, De Tommasi N. New pregnane glycosides from Caralluma negevensis .  Tetrahedron. 2002;  58 5837-48
• 8 Gongora L, Mañez S, Giner R M, Recio M C, Gray A I, Rios J L. Phenolic glycosides from Phagnalon rupestre .  Phytochemistry. 2002;  59 857-60
• 9 Tezuka Y, Kasimu R, Li J X, Basnet P, Tanaka K, Namba T, Kadota S. Constituents of roots of Salvia deserta Schang. (Xinjiang-Danshen).  Chem Pharm Bull. 1998;  46 107-12
• 10 Ulubelen A. Constituents of the leaves and the stems of Clematis vitalba .  Phytochemistry. 1970;  9 233-4
• 11 Fang J M, Wang K C, Cheng Y S. Steroids and triterpenoids from Rosa laevigata .  Phytochemistry. 1991;  30 3383-7
• 12 Connolly J D, Hill R A. Dictionary of terpenoids. Chapman & Hall London; 1991 Vol. 2: pp. 1369
• 13 El-Shazly A, Sarg T, Ateya A, Abdel Aziz A, El-Dahmy S, Witte L, Wink M. Pyrrolizidine alkaloids from Echium setosum and Echium vulgare .  J Nat Prod. 1996;  59 310-3
• 14 Wiedenfeld H, Röder E. Pyrrolizidine alkaloids from Ageratum conyzoides .  Planta Med. 1991;  57 578-9
• 15 Gu Z M, Fang X P, Zeng L, Kozlowski J F, McLaughlin J L. Novel cytotoxic annonaceous acetogenins: (2,4-cis and trans)-bulladecinones from Annona bullata (Annonaceae).  Bioorg Med Chem Lett. 1994;  4 473-8
• 16 Kelley R B, Seiber J N. Pyrrolizidine alkaloid chemosystematics in Amsinckia .  Phytochemistry. 1992;  31 2369-87
• 17 David J M, Chavez J P, Chai H B, Pezzuto J M, Cordell G A. Two new cytotoxic compounds from Tapiria guianensis .  J Nat Prod. 1998;  61 287-9
• 18 Dou H, Zhou Y, Chen C, Peng S, Liao X, Ding L. Chemical constituents of the aerial parts of Schnabelia tetradonta .  J Nat Prod. 2002;  65 1777-81
• 19 Mattocks A R. Chemistry and toxicology of pyrrolizidine alkaloids. Academic Press: New York; 1986