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Syringa vulgaris L. (Common Lilac): In Vitro Culture and the Occurrence and Biosynthesis of Phenylpropanoid Glycosides

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Medicinal and Aromatic Plants III

Part of the book series: Biotechnology in Agriculture and Forestry ((AGRICULTURE,volume 15))

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Abstract

Syringa vulgaris L., or common lilac is a horticulturally important member of the Oleaceae, a family in which other economically significant genera (Olea, Fraxinus, Jasminum, Forsythia) also occur. Thirty species of Syringa are found distributed across the temperate and south temperate zones of Europe and Asia, while the common lilac has been introduced even more widely as an ornamental. A woody shrub (or small tree) in habit (Fig. 1), lilac is typical of the 01eaceae in having opposite leaves, a calyx of four fused sepals and a corolla of four united petals. The highly scented flowers occur in thyrses, each branch bearing a terminal flower.

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References

  • Amiot M-J, Fleuriet A, Macheix J-J (1986) Importance and evolution of phenolic compounds in Olive during growth and maturation. J Agric Food Chem 34:823–826.

    Article  CAS  Google Scholar 

  • Amrhein N, Godeke KH (1977) α-Aminooxy-ß-phenylpropionic acid — a potent inhibitor of L-phenylalanine ammonia-lyase in vitro and in vivo. Plant Sci Lett 8:313–317.

    Article  CAS  Google Scholar 

  • Andary C, Ibrahim RK (1986) Biosynthetic capacity of Stachys seedlings for verbascoside and related caffeoyl derivatives. Z Naturforsch 41c:18–21.

    Google Scholar 

  • Andary C, Wylde R, Laffite C, Privat G, Winternitz F (1982) Structures of verbascoside and oroban-choside, caffeic acid sugar esters from Orobanche rapum-genistae. Phytochemistry 21:1123–1127.

    Article  CAS  Google Scholar 

  • Andary C, Privat G, Wylde R, Heitz A (1985a) Pheliposide et arenarioside, deux nouveaux esters heterosidiques de l’acide cafeique isoles de Orobanche arenaria. J Nat Prod 48:778–783.

    Article  CAS  Google Scholar 

  • Andary C, Wylde R, Heitz A, Rascol JP, Roussel JL, Laffite C (1985b) Poliumoside, a caffeic acid glycoside ester from Teucrium belion. Phytochemistry 24:362–364.

    Article  CAS  Google Scholar 

  • Becker H, Hsieh WC, Wylde R, Laffite C, Andary C (1982) Structure of echinacoside. Z Naturforsch 37c:351–353.

    CAS  Google Scholar 

  • Birkofer L, Kaiser C, Thomas U (1968) Acteosid und Neoacteosid; Zuckerester aus Syringa vulgaris L. Z Naturforsch 23b:1051–1058.

    Google Scholar 

  • Bolwell G, Cramer C, Lamb C, Schuch W, Dixon R (1986) L-Phenylalanine ammonia-lyase from Phaseolus vulgaris: modulation of the levels of active enzyme by trans-cinnamic acid. Planta 169:97–107.

    Article  CAS  Google Scholar 

  • Bowsher RR, Henry DP (1983) Decarboxylation of p-tyrosine: a potential source of p-tyramine in mammalian tissues. J Neurochem 40:992–1002.

    Article  PubMed  CAS  Google Scholar 

  • Burger JFW, Brandt EV, Ferreira D (1987) Iridoid and phenolic glycosides from Harpagophytum procumbens. Phytochemistry 26:1453–1457.

    Article  CAS  Google Scholar 

  • Caldwell MM, Robberecht R, Flint SD (1983) Internal filters: prospects for UV-acclimation in higher plants. Physiol Plant 58:445–450.

    Article  CAS  Google Scholar 

  • Calis I, Lahloub MF, Rogenmoser E, Sticher O (1984) Isomartynoside, a phenylpropanoid glycoside from Galeopsis pubescens. Phytochemistry 23:2313–2315.

    Article  CAS  Google Scholar 

  • Calis I, Gross GA, Sticher O (1987) Phenylpropanoid glycosides isolated from Scrophularia scopolii. Phytochemistry 26:2057–2061.

    Article  CAS  Google Scholar 

  • Calis I, Gross GA, Sticher O (1988) Two phenylpropanoid glycosides from Scrophularia scopolii. Phytochemistry 27:1465–1468.

    Article  CAS  Google Scholar 

  • Camm EL, Towers GHN (1973) Phenylalanine ammonia lyase. Phytochemistry 12:961–975.

    Article  CAS  Google Scholar 

  • Chappie CCS, Ellis BE (1984) Preparative and analytical liquid chromatography of complex caffeoyl esters. J Chromatogr 285:171–177.

    Article  Google Scholar 

  • Chappie CCS, Walker MA, Ellis BE (1986) Plant tyrosine decarboxylase can be strongly inhibited by L-α-aminooxy-β-phenylpropionate. Planta 167:101–105.

    Article  Google Scholar 

  • Christenson JG, Dairman W, Udenfriend S (1970) Preparation and properties of a homogeneous aromatic L-aromatic amino acid decarboxylase from hog kidney. Arch Biochem Biophys 141:356–367.

    Article  PubMed  CAS  Google Scholar 

  • Cooper R, Solomon PH, Kubo I, Nakanishi K, Shoolery JN, Occolowitz JL (1980) Myricoside, an african armyworm antifeedant: separation by droplet countercurrent chromatography. J Am Chem Soc 102:7953–9755.

    Article  CAS  Google Scholar 

  • Dixon RA, Bolwell GP (1986) Modulation of the phenylpropanoid pathway in bean (Phaseolus vulgaris) cell suspension cultures. In: Morris P, Scragg A, Stafford A, Fowler M (eds) Secondary metabolism in plant cell cultures. Cambridge Univ Press, Cambridge.

    Google Scholar 

  • Einset JW, Alexander JH (1984) Multiplication of Syringa vulgaris species and cultivars in tissue culture. Comb Proc Plant Prop Soc 34:628–636.

    Google Scholar 

  • Ellis BE (1983) Production of hydroxyphenylethanol glycosides in suspension cultures of Syringa vulgaris. Phytochemistry 22:1941–1943.

    Article  CAS  Google Scholar 

  • Endo K, Hikino H (1982) Structure of forsythoside C and D, antibacterial principles of Forsythia suspensa fruits. Heterocycles 19:2033–2036.

    Article  CAS  Google Scholar 

  • Endo K, Takahashi K, Abe T, Hikino H (1981) Structure of forsythoside A, an antibacterial principle of Forsythia suspenso leaves. Heterocycles 16:1311–1314.

    Article  CAS  Google Scholar 

  • Endo K, Takahashi K, Abe T, Hikino H (1982) Structure of forsythoside B, an antibacterial principle of Forsythia koreana stems. Heterocycles 19:261–264.

    Article  CAS  Google Scholar 

  • Epps HMR (1944) Studies on bacterial amino-acid decarboxylases 2.1(-)-tyrosine decarboxylase from Streptococcus faecalis. Biochem J 38:242–249.

    PubMed  CAS  Google Scholar 

  • Fleuriet A, Machiex JJ, Andary C, Villemur P (1984) Identification and quantitative determination of verbascoside by high performance liquid chromatography in the fruit of six cultivars of Olea europaea L. Physiol Vég 299:253–256.

    CAS  Google Scholar 

  • Floris G, Giartosio A, Rinaldi A (1983) Diamine oxidase from Lens esculenta seedlings: purification and properties. Phytochemistry 22:1871–1874.

    Article  CAS  Google Scholar 

  • Gamborg OL, Eveleigh DE (1968) Culture methods and detection of glucanases in suspension cultures of wheat and barley. Can J Biochem 46:417–421.

    Article  PubMed  CAS  Google Scholar 

  • Glatz Z, Kovar J, Macholan L, Pec P (1987) Pea (Pisum sativum) diamine oxidase contains pyr-roloquinoline quinone as a cofactor. Biochem J 242:603–606.

    PubMed  CAS  Google Scholar 

  • Gross G-A, Lahloub MF, Anklin C, Schulten H-R, Sticher O (1988) Teucrioside, a phenylpropanoid glycoside from Teucrium chamaedrys. Phytochemistry 27:1459–1463.

    Article  CAS  Google Scholar 

  • Grunberger D, Banerjee R, Eisinger K, Oltz EM, Efros L, Caldwell M, Estevez V, Nakanishi K (1988) Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester from propolis. Experientia 44:230–232.

    Article  PubMed  CAS  Google Scholar 

  • Gugler K, Funk C, Brodelius P (1988) Elicitor-induced tyrosine decarboxylase in berberine-synthesizing suspension cultures of Thalictrum rugosum. Eur J Biochem 170:661–666.

    Article  PubMed  CAS  Google Scholar 

  • Hahlbrock K, Boudet AM, Chappell J, Kreuzaler F, Kuhn DN, Ragg H (1982) Differential induction of mRNAs by light and elicitor in cultured plant cells. In: Cifferi O, Dure L (eds) Structure and function of plant genomes. Plenum, New York.

    Google Scholar 

  • Henry M, Roussel JL, Andary C (1987) Verbascoside production in callus and suspension cultures of Hygrophila erecta. Phytochemistry 26:1961–2963.

    Article  CAS  Google Scholar 

  • Hildebrandt V, Harney PM (1983) In vitro propagation of Syringa vulgaris ‘Vesper’. HortScience 18:432–434.

    CAS  Google Scholar 

  • Hosel W (1981) Glycosylation and glycosidases. In: Conn EE (ed) The biochemistry of plants. A Comprehensive Treatise. Vol 7. Academic Press, New York.

    Google Scholar 

  • Hosoi K (1974) Purification and some properties of L-tyrosine carboxylyase from barley roots. Plant Cell Physiol 15:429–440.

    CAS  Google Scholar 

  • Imakura Y, Kobayashi S, Mima A (1985) Bitter phenyl propanoid glycosides from Campsis chinensis. Phytochemistry 24:139–146.

    Article  CAS  Google Scholar 

  • Jiminez C, Villaverde MC, Riguera R, Castedo L, Stermitz FR (1987) Three phenylpropanoid glycosides from Mussatia. Phytochemistry 26:1805–1810.

    Article  Google Scholar 

  • Jiminez C, Villaverde MC, Riguera R, Castedo L, Stermitz FR (1988) Five phenylpropanoid glycosides from Mussatia. Phytochemistry 27:2947–2951.

    Article  Google Scholar 

  • Kitigawa S, Tsukamoto H, Hisada S, Nishibe S (1984) Studies on the Chinese crude drug “Forsythiae Fructus”. VII. A new caffeoyl glycoside from Forsythia viridissima. Chem Pharm Bull 32:1209–1213.

    Article  Google Scholar 

  • Kobayashi H, Karasawa H, Miyase T, Fukushima S (1984a) Studies on the constituents of Cistanchis Herba. III. Isolation and structures of new phenylpropanoid glycosides, cistanosides A and B. Chem Pharm Bull 32:3009–3014.

    Article  CAS  Google Scholar 

  • Kobayashi H, Karasawa H, Miyase T, Fukushima S (1984b) Studies on the constituents of Cistanchis Herba. IV. Isolation and structures of two new phenylpropanoid glycosides, cistanosides C and D. Chem Pharm Bull 32:3880–3885.

    Article  CAS  Google Scholar 

  • Kobayashi H, Oguchi H, Takizawa N, Miyase T, Ueno A, Usmanghani K, Ahmad M (1987) New phenylethanoid glycosides from Cistanche tubulosa (Schrenk) Hook. f. I. Chem Pharm Bull 35:3309–3314.

    Article  CAS  Google Scholar 

  • Konishi T, Narumi Y, Watanabe K, Kiyosawa S, Shoji J (1987) Comparative studies on the constituents of a parasitic plant and its host. III. On the constituents of Boschniakia rossica Fedtsch. et Flerov. (2). Chem Pharm Bull 35:4155–4161.

    Article  CAS  Google Scholar 

  • Kvist LP, Pedersen JA (1986) Distribution and taxonomic implications of some phenolics in the family Gesneriaceae determined by EPR spectroscopy. Biochem Syst Ecol 14:385–405.

    Article  CAS  Google Scholar 

  • Lahloub MF, Gross G-A, Sticher O, Winkler T, Schulten H-R (1986) Ehrenoside, a new phenylpropanoid glycoside from Veronica bellidioides. Planta Med 52:352–355.

    Article  Google Scholar 

  • Matsumoto M, Koga S, Shoyama Y, Nishioka I (1987) Phenolic glycoside compositon of leaves and callus cultures of Digitalis purpurea. Phytochemistry 26:3225–3227.

    Article  CAS  Google Scholar 

  • Maycock AL, Aster SD, Patchett AA (1980) Inactivation of 3-(3,4-dihydroxyphenyl)alanine decarboxylase by 2-fluoromethyl)-3-(3,4-dihydroxyphenyl)alanine. Biochemistry 19:709–718.

    Article  PubMed  CAS  Google Scholar 

  • Miyase T, Koizumi A, Ueno A, Noro T, Kuroyanagi M, Fukushima S, Akiyama Y, Takemoto T (1982) Studies on the acyl glycosides from Leucoseptrumjaponicum (Miq) Kitamura et Murata. Chem Pharm Bull 30:2732–2737.

    Article  CAS  Google Scholar 

  • Molgaard P, Ravn H (1988) Evolutionary aspects of caffeoyl ester distribution in dicotyledons. Phytochemistry 27:2411–2421.

    Article  CAS  Google Scholar 

  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15:473–497.

    Article  CAS  Google Scholar 

  • Nicoletti M, Galeffi C, Messana I, Marini-Bettolo GB, Garbarino JA, Gambaro V (1988) Phenylpropanoid glycosides from Calceolaria hypericina. Phytochemistry 27:639–641.

    Article  CAS  Google Scholar 

  • Nishibe S, Okabe K, Tsukamoto H, Sakushima A, Hisada S (1982a) The structure of forsythiaside isolated from Forsythia suspensa. Chem Pharm Bull 30:1048–1050.

    Article  CAS  Google Scholar 

  • Nishibe S, Okabe K, Tsukamoto H, Sakushima A, Hisada S, Baba H, Akisada T (1982b) Studies on the Chinese crude drug “Forsythiae fructus.” VI. The structure and antibacterial activity of suspensaside isolated from Forsythia suspensa. Chem Pharm Bull 30:4548–4553.

    Article  PubMed  CAS  Google Scholar 

  • Nonaka G, Nishioka I (1977) Bitter phenylpropanoid glycosides from Conandron ramoidioides. Phytochemistry 16:1265–1267.

    Article  CAS  Google Scholar 

  • Pierik RLM, Steegmans HHM, Elias AA, Stiekema OTJ, van der Velde AJ (1988) Vegetative propagation of Syringa vulgaris L. in vitro. Acta Hortic 226:25–40.

    Google Scholar 

  • Potterat O, Msonthi JD, Hostettmann K (1988) Four iridoid glucosides and a phenylpropanoid glycoside from Sesamum angolense. Phytochemistry 27:2677–2679.

    Article  CAS  Google Scholar 

  • Ramsey B (1984) MSc Thesis, Univ of Guelph, Canada.

    Google Scholar 

  • Rao KV, Juneau RJ (1975) Glycosides of Magnolia. II. Structural elucidation of Magnolidin. Lloydia 38:339–342.

    PubMed  CAS  Google Scholar 

  • Razzaque A, Ellis BE (1977) Rosmarinic acid production in Coleus cell cultures. Planta 137:287–291.

    Article  CAS  Google Scholar 

  • Rueffer M, Zenk M (1987) Distant precursors of benzylisoquinoline alkaloids and their enzymatic formation. Z Naturforsch 42c:319–332.

    Google Scholar 

  • Sakurai A, Kato T (1983) A new glycoside, kusaginin isolated from Clerodendron trichotomum. Bull Chem Soc Jpn 56:1573–1574.

    Article  CAS  Google Scholar 

  • Sasaki H, Taguchi T, Endo T, Yosioka I, Higashiyama K, Otomasu H (1978) The glycosides of Martynia louisiana Mill. A new phenylpropanoid glycoside, martynoside. Chem Pharm Bull 26:2111–2121.

    Article  CAS  Google Scholar 

  • Scarpati ML, Delle Monache F (1963) Isolamento dal Verbascum sinuatum di due nuovi glucosidi: il verbascoside e l’isoverbascoside. Ann Chim 53:356–367.

    CAS  Google Scholar 

  • Schilling G, Hugel M, Mayer W (1982) Verbascoside and isoverbascoside from Paulownia tomentosa Steud. Z Naturforsch 37b: 1633–1635.

    CAS  Google Scholar 

  • Shields S, Wingate V, Lamb C (1982) Dual control of Phenylalanine ammonia-lyase production and removal by its product cinnamic acid. Eur J Biochem 123:389–395.

    Article  PubMed  CAS  Google Scholar 

  • Shimomura H, Sashida Y, Adachi T (1987a) Phenolic glucosides from Prunus grayana. Phytochemistry 26:249–251.

    Article  Google Scholar 

  • Shimomura H, Sashida Y, Adachi T (1987b) Cyanogenic and phenylpropanoid glucosides from Prunus grayana. Phytochemistry 26:2363–2366.

    Article  CAS  Google Scholar 

  • Shimomura H, Sashida Y, Ogawa K (1987c) Iridoid glucosides and phenylpropanoid glycosides in Ajuga species of Japan. Phytochemistry 26:1981–1983.

    Article  CAS  Google Scholar 

  • Shoyama Y, Matsumoto M, Nishioka I (1986) Four caffeoyl glycosides from callus tissue of Rehmannia glutinosa. Phytochemistry 25:1633–1636.

    Article  CAS  Google Scholar 

  • Shoyama Y, Matsumoto M, Nishioka I (1987) Phenolic glycosides from diseased roots of Rehmannia glutinosa var. purpurea. Phytochemistry 26:983–986.

    Article  CAS  Google Scholar 

  • Sticher O, Lahloub MF (1982) Phenolic glycosides of Paulownia tomentosa bark. Planta Med 46:145–148.

    Article  PubMed  CAS  Google Scholar 

  • Sticher O, Salama O, Chaudhuri RK, Winkler T (1982) Structural analysis of eukovoside, a new phenylpropanoid glycoside from Euphrasia rostkoviana Hayne. Helv Chim Acta 65:1538–1542.

    Article  CAS  Google Scholar 

  • Stoll A, Renz J, Brack A (1950) Isolierung und Konstitution des Echinacosids eines Glykosids aus den Wurzeln von Echinacea angustifolia D.C. Helv Chim Acta 33:1877–1893.

    Article  CAS  Google Scholar 

  • Thieme H (1969) Über die Identität der Glucoside Rhodiolosid und Salidrosid. Sonderdruck aus Die Pharmazie 24:118–119.

    CAS  Google Scholar 

  • Uhring J (1980) Organ and tissue culture of lilac. HortScience 15:418 (abstract).

    Google Scholar 

  • Welander NT (1987) Propagation of Syringa chinensiscv. Saugeana by in vitro culture of nodal expiants. J Hortic Sci 62:89–96.

    CAS  Google Scholar 

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Authors and Affiliations

  1. MSU-DOE Plant Research Laboratory, Michigan State University, East Lansing, MI, 48824-1312, USA

    C. C. S. Chapple

  2. Department of Plant Science, The University of British Columbia, Suite 248, 2357 Main Mall, Vancouver, B.C., Canada, V6T 2A2

    B. E. Ellis

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  1. C. C. S. Chapple
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  1. A-137, New Friends Colony, New Delhi, 110065, India

    Y. P. S. Bajaj

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Chapple, C.C.S., Ellis, B.E. (1991). Syringa vulgaris L. (Common Lilac): In Vitro Culture and the Occurrence and Biosynthesis of Phenylpropanoid Glycosides. In: Bajaj, Y.P.S. (eds) Medicinal and Aromatic Plants III. Biotechnology in Agriculture and Forestry, vol 15. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-84071-5_29

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  • DOI: https://doi.org/10.1007/978-3-642-84071-5_29

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