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C- Glycosylflavonoids in the Leaves of Gymnosperms

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C- Glycosylflavonoids in the Leaves of Gymnosperms Biochemical Systematics and Ecology, 1975, Vol. 2, pp. 169 to 170. Pergamon Press. Printed in England. C- Glycosylflavonoids in the Leaves of Gymnosperms GERARD J. NIEMANN and HOWARD J. MILLER Botanical Laboratory, University of Utrecht, The Netherlands Key Word Index--Gymnospermae; vitexin; chemosystematics. The finding of vitexin derivatives as major may be exceptional in this respect within the flavonoids in needles of Larix /aricina,' L. Pinaceae, or even among the Gymnospermae. sibirica, "L./eptolepis, 3 L. decidua, "L. gme/infi " Therefore, leaves of a 46 species of gymno- and, to a lesser extent, in those of L. occiden- sperms were subjected to a screening for tails" instigated a literature survey on C- C-glycoflavonoids occurring as major con- glycosides within the gymnosperms. Sur- stituents. prisingly, no reports had been made at the time Fresh material was collected from the of Alston's review in 1968, s although many Pinetum Blijdenstein, Hilversum and from the species had been investigated for flavonoids.' Cantonspark, Baarn, both in the Netherlands, Apart from the Larix compounds, C-glycosides in Sept. 1973. Extracts were compared had been reported in only two other species; directly and as acid hydrolysates; where C- a vitexin-like compound from Ephedra ameri- glycosides were suspected they were iso- cana" and vitexin and orientin as minor lated chromatographically and their nature constituents in Dioon spinu/osum leaves. ° The was determined by R f, UV and spectral shifts. question, therefore, arose whether the larch C-Glycosides (vitexin and a related com- TABLE 1. C-GLYCOSYL-FLAVONOIDS IN GYMNOSPERMS Family Species C-glycosyl Flavonoid* Cycadaceae Ceratozamia mexicana Brongn. -- Cycas taiwaniana Carruth. V + G Dioon edule Lindl. D. spec. Encephalartos lehmannfi Lehm. Zamia media Jacq. Ginkgoaceae Ginkgo biloba L. -- Araucariaceae Araucaria araucana (Molina) C. Koch. -- A. bidwillii Hook. Cephalotaxaceae Cephalotaxus fortunei Hook. -- C. harringtoniana (Forbes) C. Koch Cupressaceae Juniperus communis L. -- J. chinensis L. Chamaecyparis formonensis Mats. Thuja occidentalis L. Callitris robusta R. Br. ex Mirb. Tetraclinis articulata (Vahl) Mast. Cupressus sempervirens L. Heyderia decurrens C. Koch 'Niemann, G. J. and Bekooy, R. (1971) PhytochemistrylO, 893. 'Medvedeva, S. A., Tjukavkina, N. A. and Ivanova, S. Z. (1973) Khim. Prir. Soedin. 119. 'Niemann, G. J. (1973) Phytochemistry 12, 2056, 'Niemann, G. J., unpublished data. •Alston, R. E. (1968) Recent Advances in Phytochemistry (Mabry, T. J., Alston. R. E. and Runeckles, V. C., Eds.). VoI. 1, p. 305. North Holland, Amsterdam. 'Harborne, J. B. (1967) Comparative Biochemistry of the Flavonoids. Academic Press, New York. 'Harborne, J. B. (1966) Comparative Phytochemistry (Swain, T., Ed.), p. 271. 'Carson, J. L. and Wallace, J. W. (1972) Phytochemistry11, 842. (Received 17 June 1974. Accepted 29 July 1974) 169 170 GERARD J. NIEMANN AND HOWARD J. MILLER TABLE 1. Continued 1axodiaceae Crypzomenajaponica (L.f.) D. Don. Metesequoia gJyptostroboides Hu Et Cheng Sequoia sempervirens (D. Don in Lamb,) Endl. V Sequoiadendron giganteum (Lindl.) Buchh. Taxodium ascendens Brongn. Taxaceae Taxus baccata L T. cupidata Sieb. ~ Zucc 1~ canadensis Marsh. Torreya californica Torr. T. grandis Fort, T. nucifera (L.) Sieb. ~ Zu(x. Pinaceae Abies belsamea (L) Mill. A. grandis (DougJ.) Lindl. Cedrus libeni A. Rich, in Bory Kete/eerJa fortunei (A. Murr.) Carr. Larix sibirica Ledeb. V L./aricina (Du Roi) K. Kocht V L. /eptolepls (Sieb. ~ Zucc.) Gord.t V L. decidua Mill.t V L. gmelinfi (Rupr.) Kuzenevat V L. occidenteh's Nutt.t V Picea breweriana S. Watson Pinusjeffreyi Grey. ~ Bale P. sylvestris L. Pseudolarix amabihs (J, Nels) Rehd. Pseudotsuga menziesii (Mirbel) Franco Tsuga chinensis (French.) Britzel Podocarpaceae Podocarpus elatus R. Br. V P. falcatus (Thunb.) R. Br. ex Mirb. Saxegothea conspicua Lindl. V Ephedraceae Ephedra altissima Desf. G E, distachya L. G 3700 ° V--vitexin or vitexin glycoside; G--glycoflavone related to vitexin. t Results from previous work on Larix. pound) were found in 7 species (including gymnosperms. The results suggest that there one Larix spec.) distributed in 5 families may be some genus-specific distribution but (Table 1). It appears that C-glycoflavonoids this can only be proved by investigation of are widely, but infrequently distributed in the many more species. .
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