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Luteolin glycosides as taxonomic markers in Ferula and related genera
Biochemical Systematics and Ecology, Vol. 17, No. 4, pp. 309-310, 1989. Printed in Great Britain.
0305-1978/89 $3.00+0.00 © 1989 Maxwell Pergamon Macmillan plc.
Luteolin Glycosides as Taxonomic Markers in Ferula and Related Genera X. Y. CHEN and Q. X. LIU* Department of Biology, University of Nanjing, Nanjing, China; *Jiangsu Botanical Institute, Nanjing, China
Key Word Index--Soranthus; Schumannia; Talassia; Ferula; Umbelliferae; flavonoids; luteolin; chemotaxonomy. Abstract--Soranthus, Schumannia and Talassia differ from Ferula by containing luteolin 7-glycosides in their leaves, tn Ferula, only the distinct species Ferula conocaula contains luteolin. Quercetin 3-glycosides, which are rather common in Ferula, were also detected in leaves of Talassia transiliensis and Ferula conocaula. Soranthus and Schumannia contain luteolin 7-diglucoside and this suggests the possibility of combining the two monotypic genera. The systematic relationship between Talassia and Ferula is also discussed.
Introduction Each tribe in the Umbelliferae characteristically contains a small number of large genera, comprising the bulk of the species, and a large number of small 'satellite' genera [1]. In the tribe Peucedaneae, Ferula L. is one of the largest genera, with about 80 species mainly distributed in the Mediterranean region and central Asia. Among the related genera are Soranthus Ledeb. and Schumannia Kuntz., both monotypic and Chinese, and Talassia Korov., of which one of the three species grows in China. Pimenov et al. [2, 3] suggested that these three genera should be included in Ferula on the basis of carpological characters. In the Flora of China [4], the generic status of the three groups was accepted. Chemical studies of Ferula species have concentrated on essential oils and coumarins. Components such as terpenoid coumarins, esters of aromatic acids, terpene alcohols, sesquiterpene lactones [5, 6] and secondary propenyl bisulphides [7] have been reported from roots and gum resins. Leaves of Ferula sadlerana contain quercetin glycosides [8]. In a recent survey of Chinese Ferula species (Chen and Liu, unpublished results), 13 of the 16 species contained glycosides of quercetin, kaempferol and apigenin, with quercetin being the most common. Flavonoids have been of systematic value in
the tribe Peucedaneae. Flavonoid data supported both the separation of Ostericum Hoffm. from Angelica L. [9] and the recognition of the monotypic genus Czernaevia Turcz. [10]. It therefore appeared potentially interesting to examine the flavonoids of Ferula and related groups. Results and Discussion Luteolin 7-glycosides were detected in leaves of Soranthus meyerii, Schumannia kaerlinii, Talassia transiliensis and Ferula conocaula. Quercetin 3-glycosides also occurred in the latter two species (see Table 1). Talassia transiliensis is particularly rich in flavonoids, containing at least TABLE 1. LEAF FLAVONOIDS OF SORANTHUS, SCHUMANNIA, TALASSIA AND FERULA
Plant species Soranthus meyeriiLedeb. Schumannia karelinii (Bge.) Korov. Talassia transiliensis (Herd.) Korov.
Ferula conocaula Korov. Other ferula species~
Flavonoids present Flavonol glycosides Flavone glycosides Lu 7 diglucoside --
Lu 7-diglucoside
Qu 3-glucoside Qu 3-rhamnoside
Lu 7 glucoside Lu 7-diglucoside Lu 7 rutinoside Lu 7-glucoside Ap 7-glycosides (in three species)
Qu 3-glucoside Qu 3-glycosides (in eight species) Km 3-glycosides (in three species)
*Chen and Liu, unpublished results. (To be submitted to Acta Phytotax. Sin.).
(Received 12 October 1988) 309
310 three luteolin and t w o quercetin glycosides. A l t h o u g h the c o m p o u n d s reported here are not u n c o m m o n in the Umbelliferae [8, 11], the distribution of luteolin glycosides is of value as a t a x o n o m i c marker in these plants. According to the investigations so far, luteolin glycosides are absent from most species of Ferula, with the exception of F. conocaula. The Ferula species with a garlic-like odour, caused by a high concentration of disulphides, are often used medicinally and the g u m secreted by these plants can be used as asafetida [12]. In the authors' earlier survey, it was the three o d o r o u s species (F. krylovii, F. sinkiangensis and F. fukangensis) that did not s h o w detectable levels of leaf flavonoids. The situation is m o r e c o m p l e x than this in F. conocaula, which exhibited high concentrations of both flavonoids and disulphides. This species is also distinct in both leaf shape and inflorescence structure and has an isolated position within the genus. Nevertheless, it w o u l d be premature to make any t a x o n o m i c changes before e x a m i n i n g further species, especially those occurring in the Asiatic part of the U.S.S.R. and neighbouring areas. The aglycone pattern of S o r a n t h u s and Schum a n n i a differs f r o m that of Ferula, the latter lacking luteolin. Plants of both m o n o t y p i c genera are readily distinguished from those of Ferula by gross m o r p h o l o g y and inflorescence structure. Chemical data supports the separation of these genera from Ferula, As S o r a n t h u s and S c h u m a n n i a s h o w the same leaf flavonoid compound, as well as similarities in m o r p h o l o g i c a l and ecological characters, it seems reasonable to c o m b i n e the t w o genera into one, Soranthus. In contrast, there are no significant differences in m o r p h o l o g y between Talassia and Ferula and the spectrum of leaf flavonoids of T. transiliensis is to a great extent similar to that of F. conocaula. Sampling of other species of Talassia and Ferula is necessary before any t a x o n o m i c changes, e.g. sinking the f o r m e r into the latter, can be suggested. Finally, it should be m e n t i o n e d here that species of Talassia w e r e originally transferred from P e u c e d a n u m L. [13]. Luteolin glycosides have been reported from P e u c e d a n u m and
x.Y. CHENANDQ. X. LIU m a n y of the genera of the Peucedaneae s h o w similar aglycone patterns. Thus the presence of luteolin c o m p o u n d s is of interest in systematic revisions of the Ferula c o m p l e x as well as other taxa in the tribe Peucedaneae.
Experimental Plant material. Plants of Ferula conocaula were kindly provided by Professor K. M. Shen and Ms X. M. Qin of the Institute of Biology and Soil Sciences of Xinjiang, Academica Sinica. Other species were collected by the authors in Xinjiang in June and July of 1988and dried as for herbarium specimens. Vouchers are deposited in the herbarium of the University of Nanjing (N). Flavonoid identifications. Standard procedures of flavonoid identification were used [14], with slight modifications as follows. UV spectra were measured in methanol using a UVIKON KONTRON860. Five shifts were recorded (NaOMe, NaOAc, NaOAc-H3BO3,5% AICI3, 5% AICI3-18% HCI). Glycosides were cochromatographedin BAW, TBA, 15% HOAc and H20; alygconesin Forestat,CAW and BAW.
Acknowledgement--This work was supported by the National Foundationfor Natural Sciencesof China.
References 1. Heywood, V. H, (1971) The Biology and Chemtstry of the Umbelliferae (Heywood,V. H., ed.), p. 31. Academic Press, London. 2. Pimenov, M. G. and Kirillina, N. A. (1980) Botany Z (Leningrad) 65, 1756. 3. Pimenov,M. G. (1983) Biol. Nauk. 12, 74. 4. Shan, R. H. and Sheh, M. L. (ed) (1979) Flora Reipublicae Popularis Sinicae, Tomus 55, 1. Academic Press, Beijing. 5. Pimenov, M. G., Sklyar,Y. E., Savina,A. A. and Baranova, Y. V. (1982) Biochem. Syst. Ecol. 10, 133. 6. Borisov, V. N., Pimenov, M. G. and Banovskii, A. I. (1977) Rastit. Resur. 13, 276. 7. Ashraf, M., Ahmad, R., Mahmood, S. and Bhatty, M. K. (t980) Pakistan J. Sci. Industr. Res. 23, 68. 8. Crowden, K. K., Harborne,J. B. and Heywood, V. H (1969) Phytochemistry 8, 1963. 9. Harborne,J. B., Heywood,V. H. and Chen,X. Y. (1986)Biochem. Syst. Ecol. 14, 81. 10. Chen, X. Y. and Heywood, V. H. (1988) Acta Phytotax. Sin. 26, 29. 11. Harborne,J. B. and Williams, C. A. (1972) Phytochemistry 11, 1741. 12. Shen, K. M. (1986)Awei. Xinjiang Renmin Press, Urumchi. 13. Korovin, E. P. (1963) Flora Kazachstana 6, 384. 14. Harborne, J. B. (1984) Phytochemical Methods, 2nd edn. Chapman and Hall, London.
0305-1978/89 $3.00+0.00 © 1989 Maxwell Pergamon Macmillan plc.
Luteolin Glycosides as Taxonomic Markers in Ferula and Related Genera X. Y. CHEN and Q. X. LIU* Department of Biology, University of Nanjing, Nanjing, China; *Jiangsu Botanical Institute, Nanjing, China
Key Word Index--Soranthus; Schumannia; Talassia; Ferula; Umbelliferae; flavonoids; luteolin; chemotaxonomy. Abstract--Soranthus, Schumannia and Talassia differ from Ferula by containing luteolin 7-glycosides in their leaves, tn Ferula, only the distinct species Ferula conocaula contains luteolin. Quercetin 3-glycosides, which are rather common in Ferula, were also detected in leaves of Talassia transiliensis and Ferula conocaula. Soranthus and Schumannia contain luteolin 7-diglucoside and this suggests the possibility of combining the two monotypic genera. The systematic relationship between Talassia and Ferula is also discussed.
Introduction Each tribe in the Umbelliferae characteristically contains a small number of large genera, comprising the bulk of the species, and a large number of small 'satellite' genera [1]. In the tribe Peucedaneae, Ferula L. is one of the largest genera, with about 80 species mainly distributed in the Mediterranean region and central Asia. Among the related genera are Soranthus Ledeb. and Schumannia Kuntz., both monotypic and Chinese, and Talassia Korov., of which one of the three species grows in China. Pimenov et al. [2, 3] suggested that these three genera should be included in Ferula on the basis of carpological characters. In the Flora of China [4], the generic status of the three groups was accepted. Chemical studies of Ferula species have concentrated on essential oils and coumarins. Components such as terpenoid coumarins, esters of aromatic acids, terpene alcohols, sesquiterpene lactones [5, 6] and secondary propenyl bisulphides [7] have been reported from roots and gum resins. Leaves of Ferula sadlerana contain quercetin glycosides [8]. In a recent survey of Chinese Ferula species (Chen and Liu, unpublished results), 13 of the 16 species contained glycosides of quercetin, kaempferol and apigenin, with quercetin being the most common. Flavonoids have been of systematic value in
the tribe Peucedaneae. Flavonoid data supported both the separation of Ostericum Hoffm. from Angelica L. [9] and the recognition of the monotypic genus Czernaevia Turcz. [10]. It therefore appeared potentially interesting to examine the flavonoids of Ferula and related groups. Results and Discussion Luteolin 7-glycosides were detected in leaves of Soranthus meyerii, Schumannia kaerlinii, Talassia transiliensis and Ferula conocaula. Quercetin 3-glycosides also occurred in the latter two species (see Table 1). Talassia transiliensis is particularly rich in flavonoids, containing at least TABLE 1. LEAF FLAVONOIDS OF SORANTHUS, SCHUMANNIA, TALASSIA AND FERULA
Plant species Soranthus meyeriiLedeb. Schumannia karelinii (Bge.) Korov. Talassia transiliensis (Herd.) Korov.
Ferula conocaula Korov. Other ferula species~
Flavonoids present Flavonol glycosides Flavone glycosides Lu 7 diglucoside --
Lu 7-diglucoside
Qu 3-glucoside Qu 3-rhamnoside
Lu 7 glucoside Lu 7-diglucoside Lu 7 rutinoside Lu 7-glucoside Ap 7-glycosides (in three species)
Qu 3-glucoside Qu 3-glycosides (in eight species) Km 3-glycosides (in three species)
*Chen and Liu, unpublished results. (To be submitted to Acta Phytotax. Sin.).
(Received 12 October 1988) 309
310 three luteolin and t w o quercetin glycosides. A l t h o u g h the c o m p o u n d s reported here are not u n c o m m o n in the Umbelliferae [8, 11], the distribution of luteolin glycosides is of value as a t a x o n o m i c marker in these plants. According to the investigations so far, luteolin glycosides are absent from most species of Ferula, with the exception of F. conocaula. The Ferula species with a garlic-like odour, caused by a high concentration of disulphides, are often used medicinally and the g u m secreted by these plants can be used as asafetida [12]. In the authors' earlier survey, it was the three o d o r o u s species (F. krylovii, F. sinkiangensis and F. fukangensis) that did not s h o w detectable levels of leaf flavonoids. The situation is m o r e c o m p l e x than this in F. conocaula, which exhibited high concentrations of both flavonoids and disulphides. This species is also distinct in both leaf shape and inflorescence structure and has an isolated position within the genus. Nevertheless, it w o u l d be premature to make any t a x o n o m i c changes before e x a m i n i n g further species, especially those occurring in the Asiatic part of the U.S.S.R. and neighbouring areas. The aglycone pattern of S o r a n t h u s and Schum a n n i a differs f r o m that of Ferula, the latter lacking luteolin. Plants of both m o n o t y p i c genera are readily distinguished from those of Ferula by gross m o r p h o l o g y and inflorescence structure. Chemical data supports the separation of these genera from Ferula, As S o r a n t h u s and S c h u m a n n i a s h o w the same leaf flavonoid compound, as well as similarities in m o r p h o l o g i c a l and ecological characters, it seems reasonable to c o m b i n e the t w o genera into one, Soranthus. In contrast, there are no significant differences in m o r p h o l o g y between Talassia and Ferula and the spectrum of leaf flavonoids of T. transiliensis is to a great extent similar to that of F. conocaula. Sampling of other species of Talassia and Ferula is necessary before any t a x o n o m i c changes, e.g. sinking the f o r m e r into the latter, can be suggested. Finally, it should be m e n t i o n e d here that species of Talassia w e r e originally transferred from P e u c e d a n u m L. [13]. Luteolin glycosides have been reported from P e u c e d a n u m and
x.Y. CHENANDQ. X. LIU m a n y of the genera of the Peucedaneae s h o w similar aglycone patterns. Thus the presence of luteolin c o m p o u n d s is of interest in systematic revisions of the Ferula c o m p l e x as well as other taxa in the tribe Peucedaneae.
Experimental Plant material. Plants of Ferula conocaula were kindly provided by Professor K. M. Shen and Ms X. M. Qin of the Institute of Biology and Soil Sciences of Xinjiang, Academica Sinica. Other species were collected by the authors in Xinjiang in June and July of 1988and dried as for herbarium specimens. Vouchers are deposited in the herbarium of the University of Nanjing (N). Flavonoid identifications. Standard procedures of flavonoid identification were used [14], with slight modifications as follows. UV spectra were measured in methanol using a UVIKON KONTRON860. Five shifts were recorded (NaOMe, NaOAc, NaOAc-H3BO3,5% AICI3, 5% AICI3-18% HCI). Glycosides were cochromatographedin BAW, TBA, 15% HOAc and H20; alygconesin Forestat,CAW and BAW.
Acknowledgement--This work was supported by the National Foundationfor Natural Sciencesof China.
References 1. Heywood, V. H, (1971) The Biology and Chemtstry of the Umbelliferae (Heywood,V. H., ed.), p. 31. Academic Press, London. 2. Pimenov, M. G. and Kirillina, N. A. (1980) Botany Z (Leningrad) 65, 1756. 3. Pimenov,M. G. (1983) Biol. Nauk. 12, 74. 4. Shan, R. H. and Sheh, M. L. (ed) (1979) Flora Reipublicae Popularis Sinicae, Tomus 55, 1. Academic Press, Beijing. 5. Pimenov, M. G., Sklyar,Y. E., Savina,A. A. and Baranova, Y. V. (1982) Biochem. Syst. Ecol. 10, 133. 6. Borisov, V. N., Pimenov, M. G. and Banovskii, A. I. (1977) Rastit. Resur. 13, 276. 7. Ashraf, M., Ahmad, R., Mahmood, S. and Bhatty, M. K. (t980) Pakistan J. Sci. Industr. Res. 23, 68. 8. Crowden, K. K., Harborne,J. B. and Heywood, V. H (1969) Phytochemistry 8, 1963. 9. Harborne,J. B., Heywood,V. H. and Chen,X. Y. (1986)Biochem. Syst. Ecol. 14, 81. 10. Chen, X. Y. and Heywood, V. H. (1988) Acta Phytotax. Sin. 26, 29. 11. Harborne,J. B. and Williams, C. A. (1972) Phytochemistry 11, 1741. 12. Shen, K. M. (1986)Awei. Xinjiang Renmin Press, Urumchi. 13. Korovin, E. P. (1963) Flora Kazachstana 6, 384. 14. Harborne, J. B. (1984) Phytochemical Methods, 2nd edn. Chapman and Hall, London.