LAMIALES NEWSLETTER LAMIALES Issue number 2 November 1993 will be available to all readers. If you would like to be added to it CONTENTS SPANISH LABIATAE: please send details of your inter- A SOURCE FOR ests to the editors. NATURAL ANTIOXIDANT Editorial 1 At the moment we need more COMPOUNDS articles for inclusion. We would Spanish Labiatae: 1 like to receive summaries of Francisco A. Tomás-Barberán current research, comments on A source for natural Laboratorio de Fitoquímica, published articles, or general CEBAS (CSIC), P. O. BOX antioxidant compounds thoughts on the current directions 4195, Murcia 30080, Spain. of Lamiales research. For exam- Recent research 2 ple the trend towards greater The members of the Labiatae are on the genera Junellia emphasis on cladistic studies, well known from the phytochem- and Glandularia especially of molecular data ical view point, by their essential should be helping to clarify prob- oils. For this reason, many The flavonoid aglycones 3 lem areas in the classification of species (mainly from the subfam- of Scutellaria the Lamiales while there is a vast ily Nepetoideae Erdtman) are scope for research into a whole industrially exploited. In addi- range of biologically (?or taxo- Directory of Lamiales 5 tion, many species are used as nomically) active compounds. spices for seasoning of different research Much taxonomic work is needed foods. Important spices in Spain on the Teucrioideae and Viti- are Rosmarinus officinalis, Salvia Lamiales Newsletter 11 coideae. We need your support officinalis, Thymus vulgaris, Thy- mailing list with articles on such issues. mus piperella, Mentha sp., Orig- In the next issue we hope to anum vulgare, Satureja montana Bibliography of recent 17 include articles on economic uses and Origanum marjorana. How- taxonomic publications of Lamiales, nutlet anatomy, a ever, Labiatae species also con- on the Lamiales systematic arrangement of genera tain substantial amounts of in the Lamiales, and Brazilian flavonoid aglycones and glyco- Labiatae. How about some con- sides, which have interesting bio- tributions on the position of the logical activities (Barberán, EDITORIAL Pogostemoideae or Lavandula, or 1986). These flavonoids are gen- further thoughts on the origins of erally responsible, at least partly, R. M. Harley & A. Paton the hexacolpate pollen grain and for the antioxidant properties of Herbarium, Royal Botanic the Nepetoideae (see Pozhidaev, these spices which extend the Gardens, Kew, Richmond, A. Grana 31: 361- 379 (1992)). keeping time of various foods. In Surrey, TW9 3AE, UK many cases, the flavonoids pre- The proceedings of the first sent in the Labiatae are responsi- Welcome to the Lamiales Advances in Labiate Science con- ble for the pharmacological Newsletter. This edition contains ference have now been published activity of those species used in a directory of researchers and (available from the Royal Botanic traditional medicine. For these their interests. This directory is Gardens, Kew at the extremely rea- reasons, the study of Labiatae by no means complete. Indeed sonable price of £26.70 including flavonoids is of interest. there are people on our mailing postage). We should now perhaps list who are not included in it sim- look ahead to the next Lamiales During the last ten years we ply because we do not know their Conference, the date and venue of have been looking at the particular interest. The directory which still have to be decided. flavonoid composition of Span- will be constantly updated and Anyone got any thoughts? ish Labiatae, and generally clear ➣ 1 correlations between the chemi- the active flavonoids, since the port the separation of Junellia cal features of the flavonoids and extracts, which are non-toxic, RECENT RESEARCH from Verbena and the affinity of THE FLAVONOID AGLYCONES OF the systematics of the different could be added to foods as spice ON THE GENERA Glandularia. SCUTELLARIA L. SPECIES genera have been found. Thus, extracts, which are not consid- JUNELLIA AND In a taxonomic study of the the presence of flavone p- ered as food additives. It is inter- GLANDULARIA IN genus Glandularia J.F.Gmel. I. I. Chemesova coumaroyl-glucosides and 8- esting that the plant wastes of SOUTH AMERICA Komarov Botanical Institute, St. Petersburg, 197376, Russia hydroxylated flavones 7-allosyl- the industrial extraction of essen- (Botta, in press) eight taxa are glucosides (in non-acetylated, tial oils, are a valuable source for recognized in the subgenera Silvia Botta monoacetylated and diacetylated such flavonoid extracts. After Paraglandularia (G. crithmifolia The genus Scutellaria L. compris- cule: Group 1 flavonoid agly- Instituto de Botánica Darwinion, forms) are characteristic com- the removal of the essential oils (Gillies et Hook.) Schnack et es 360 species distributed cones are represented by 16 com- Labarden 200, Casilla Correo 22, pounds of many members of the by steam distillation, the remain- Covas , G. hookeriana Covas et throughout the world. Until now, pounds; Group 2 by significantly 1642 San Isidro, Argentina subfamily Lamioideae (Tomás- ing plant material still contains Schnack) and Glandularia (G. the flavonoid algycone composi- more, 56 compounds (41 of which Barberán and Gil, 1992), includ- the unaltered flavonoids, and araucana (Philippi) Botta, G. tion of only 27 species of this are one- and two-substituted B ing Sideritis, Stachys, Galeopsis, these could be later extracted by aurantiaca (Speg.) Botta, G. genus have been studied. Analy- ring flavonoids). In some species Ballota, Marrubium, Phlomis and other procedures to get the flava (Gillies et Hook.) Covas et sis of literature up to 1992 shows Group 2 flavonoids are dominant, Leonurus species. The presence antioxidant flavonoids. Junellia Mold. is a genus with Schnack, G. platensis (Sprengel) that Scutellaria species produce for example, in S. amoena of flavonoid p-coumaroyl-gluco- about 47 species inhabiting the Schnack et Covas, G. macrosper- unusual flavonoid aglycones. To Wright. - 13 compounds, S. It is important to show that such sides in the genus Anisomeles has Andino-Patagonian region of ma (Sprengel) Troncoso and G. provide a means of classifying baicalensis Georgi. - 32, S. discol- chemotaxonomical studies pro- also been fully documented, and- South America. This genus parodii (Covas et Schnack). New them, the flavonoid and dihy- or Colebr. - 13, S. viscidula vide very interesting data for for this reason the occurrence of which displays its maximum synonomy is established and two droflavonoid aglycones found in Bunge. - 7. industries which are concerned in this type of flavonoids in species diversity in the Patagonian new combinations made. The species of Scutellaria are divided the recovery of such active sub- of the related genus Pogostemon region of Argentina, is a member Patagonian species are described into two groups according to sub- Among the Group 2 flavonoids, stances. should be tested. On the other of tribe Verbeneae together with and illustrated; the data on kary- stitutions in the B ring: Group 1 compounds completely lacking B Verbena, Glandularia, Hierobot- ology, distribution maps, a list of hand, the occurrence of lipophilic References with substitutions (OCH3 or OH) ring substitutes and compounds externally located flavonoid agly- ana, Urbania and Tamonea. In a the examined herbarium materi- at the 4’ (for example: apigenin, with 2’-substitution tend to show BARBERA´ N, F. A. T. (1986). The cones with an A-ring substitution previous paper (Botta, 1989) the al and vernacular names are scutellarein, luteolin, cartamidin biological activity. Studies have Flavonoids of the Labiatae. delimitation of Junellia from given for each taxon. In many etc.); and Group 2 without substi- been made on the antithrombic, pattern 5,6-dihydroxy-7,8- Fitoterapia, 57: 67-95. dimethoxyflavone, including the these genera was discussed and cases nomenclatural problems tution at the 4’ position (for cytotoxic actions of 5, 2’- dihy- flavones thymonin, thymusin and MIURA, K. & NAKATANI, N. (1989). an infrageneric classification pro- and affinities between the species example: chrysin, baicalein, 3, 5, droxy - 6, 7, 8, 6’ - tetram- pebrellin among others, is Antioxidative activity of the posed. are also analysed. Observations 7-trimethoxyflavanon, 5, 7, 2’-tri- ethoxyflavone. The accumulation flavonoids from thyme (Thymus restricted to some related genera on leaves, stems and pollen with hydroxy-6’-methoxyflavone etc.). of these unusual flavonoids by vulgaris L.). Agric. Biol. Chem., of the subfamily Nepetoideae In continuation of this study, a SEM were made. A list of 53: 3043-3045. such as Thymus, Mentha, Sature- recent paper (Botta, unpub- doubtful species is provided. GROUP 1GROUP 2 ja, Micromeria, Acinos, Orig- R´IOS, J. L., MAÑEZ, S., PAYA, M. & lished) presents descriptions of R2 R1 RR1 anum, etc. (Tomás-Barberán et ALCARAZ, M. J. (1992). Antioxi- species, illustrations and maps dant activity of flavonoids from showing their geographical distri- O 2' 3' O 2' 3' al., 1988; Tomás-Barberán and 4' R 4' Sideritis javalambrensis. Phyto- bution, together with a dichoto- 6' 5' 6' 5' Wollenweber, 1990). References chemistry, 31: 1947-1950. mous key based on gross mor- R2 The 8-hydroxylated flavone gly- TOMA´ S-BARBERA´ N, F. A., HUSAIN, phological characters. Phyloge- Botta, S. M. (1989). Estudios en el O O cosides of the Lamioideae have S. Z. & GIL, M. I. (1988). The Dis- netical relations between the R2 R1 RR1 shown antioxidant activities tribution of methylated flavones in species are also discussed. SEM género sudamericano Junellia (Verbenaceae-Verbenoideae) I. O O (Ríos et al. 1992), as did the 5,6- the Lamiaceae. Biochem. Systemat. observations were made on B R B Delimitación y tratamiento infra- A A dihydroxy-7,8-dimethoxy Ecol., 16: 43-46. leaves, stems, mericarps and genérico. Darwiniana 29(1-4): 371- R flavonoid aglycones from TOMA´ S-BARBERA´ N, F. A. & WOL- pollen of several species. 2 396 (1989). O O the Nepetoideae (Miura and LENWEBER, E. (1990). Flavonoid Nakatani, 1989). This is probably aglycones from the leaf surfaces of In collaboration with Peter Botta, S.