Introduction Anchusa strigosa Banks et Sol Boraginaceae), commonly known in Jordan as ªHemhemº, is a herbaceous perennial plant widely distributed in the Mediterranean and Irano-Turanian regions [1]. In Jordan and Palestine all parts of the plant are largely used in folk medicine for the treatment of several diseases. The roots decoction is used as a diuretic, for abdominal pain, and for the treatment of stomach ulcers, while the leaves cataplasm is ap- plied to bone fractures and as a counter-irritant, and the leaves juice is applied externally for skin diseases, arthritis, and wounds [2], [3]; the flower decoction is taken as a herbal tea as an analge- sic, sedative, sudorific, and diuretic remedy [4]. Previous phar- macological work on aqueous extracts of A. strigosa roots report- ed gastric protection and healing of ethanol-induced stomach ul- cer, inhibition of pepsin activity, and a mild antimicrobial activ- ity [5], [6], while no chemical studies on the plant roots are avail- able. As a part of our ongoing study of bioactive compounds from Jordanian medicinal plants [7], we have studied A. strigosa roots. Herein, we describe the isolation and characterization of six new pyrrolizidine alkaloids 1 ± 6), one carboxylic acid 7), one phe- nolic glycoside 8), and one oleanane glycoside 9) Fig. 1), to- gether with seven known compounds from the title plant. Materials and Methods General experimental procedures Optical rotations were measured on a Perkin-Elmer 241 polari- meter equipped with a sodium lamp 589 nm) and a 1 dm micro- cell. Elemental analysis was obtained from a Carlo Erba 1106 ele- mental analyzer. UV spectra were recorded on a Perkin-Elmer- Lambda 12 spectrophotometer. A Bruker DRX-600 NMR spectro- meter with the UXNMR software package was used for NMR ex- periments [7]. ESIMS positive mode) were obtained from a Fin- ningan LC-Q Deca Termoquest spectrometer, equipped with Xca- libur software. TLC was performed on precoated Kieselgel 60 F 254 plates Merck, Darmstadt, Germany); compounds were detected by CeSO 4 ) 2 /H 2 SO 4 Sigma-Aldrich, Milano, Italy) solution and/or with Dragendorff's reagent. Column chromatography was per- formed over Sephadex LH-20 Pharmacia); droplet countercur- rent chromatography DCCC) was carried out on an apparatus New Pyrrolizidine Alkaloids and Glycosides from Anchusa strigosa Alessandra Braca 1 Ammar Bader 2 Tiziana Siciliano 1 Ivano Morelli 1 Nunziatina De Tommasi 3 Affiliation 1 Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Pisa, Italy 2 Faculty of Pharmacy, Al-Zaytoonah University of Jordan, Amman, Jordan 3 Dipartimento di Scienze Farmaceutiche, Università di Salerno, Fisciano SA), Italy Correspondence Dr. Alessandra Braca ´ Dipartimento di Chimica Bioorganica e Biofarmacia ´ Università di Pisa ´ Via Bonanno, 33 ´ 56126 Pisa ´ Italy ´ Fax: +39-050-43321 ´ E-mail: braca@farm.unipi.it Received January 31, 2003 ´ Accepted May 10, 2003 Bibliography Planta Med 2003; 69: 835±841 ´  Georg Thieme Verlag Stuttgart ´ New York ´ ISSN 0032-0943 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¢-di- hydroxymethyltetrahydrofuran 4¢-O-b-D-glucopyranoside, ros- marinic acid, caffeic acid, tormentic acid 28-O-b-D-glucopyrano- side, euscaphic acid 28-O-b-D-glucopyranoside, euscaphic acid, and allantoin were isolated from Anchusa strigosa roots. Their structures were established by high resolution NMR, MS, ele- mental analysis, and chemical reactions. Key words Anchusa strigosa ´ Boraginaceae ´ pyrrolizidine alkaloids ´ pheno- lic glycoside ´ oleanane glycoside Original Paper 835