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Many medic inal plants contain oleanane saponins in roots, however, only scarce data on their biosynthesis in this organ are available so far, including our previous results concerning Calendula officinalis plant. Thus, the purpose of the present work was to confirm the presumable biosynthetic pathway of oleanolic acid glycosides in roots of young C. officinalis plants. First of all, the effective method of isolation of protoplasts from C. officinalis roots was established. Then, isolated root protoplasts were supplied with radioactive precursors, [2-¹⁴C] mevalonate (MV A) and [3-³H] oleanolic acid (OL) and their transformations were studied with comparison to results obtained with excised roots. The penetration of both precursors into protoplasts was more rapid and effective than in the case of excised roots. The labeling of sterols and OL during the incubation with MVA showed that the isoprenoid pathway leading to triterpenoids was operative in excised roots as well as isolated root protoplasts. Moreover, the transformations of OL into two seties of its glycosides, i.e. glucosides and glucuronides were investigated. It has been shown that both series of OL glycosides are synthesized in isolated root protoplasts in the same way as in excised roots of young marigold plants.
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p.217-223,fig.,ref.
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- Warsaw University, Miecznikowa 1, 02-089 Warsaw, Poland
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Bibliografia
- Auguścińska E., Kasprzyk Z. 1982. Studies on the labeli ng of terpenoids in shoots and cells or protoplasts from Calendula officinalis leaves. Acta Biochim. Polon., 29: 7-15.
- Auguścińska E., Kasprzyk Z. 1983. Synthesis of oleanolic acid glycosides in the shoots and in cells and protoplasts obtained from leaves of Calendula officinalis. Wissen. Zeit. EMA-Univers. Greifswald, 32: 107-109.
- Farina C., Pinza M., Pifferi G. 1998. Synthesis and anti-ulcer activity of new derivatives of glycyrrhetic, oleanolic and ursolic acids. Il Farmaco, 53: 22-32.
- Hu M., Ogawa K., Sashida Y., Xiao P. 1995. Triterpenoid glucuronide saponins from root bark of Aralia armata. Phytochemistry, 39: 179-184.
- Ida Y., Satoh Y., Katsumata M., Nagasao M., Hirai Y., Kajimoto T., Katada N., Yasuda M., Yamamoto T. 1998. Two novel oleanolic acid saponins having a sialyl Lewis X mimetic struclure from Achyranthes fauriei root. Bioorg. Med. Chem. Lett., 8: 2555-2558.
- Janiszowska W., Jurzysta M., Kasprzyk Z. 1989. Biological activities of oleanolic acid glycosides from Calendula officinalis. XIII Conference on Isoprenoids, Poznań. Abstracts of papers, p. 110-110.
- Janiszowska W., Wiłkomirski B., Kasprzyk Z. 1988. Synthesis of oleanolic acid glycosides. Pol. J. Chem., 62: 403-407.
- Kasprzyk Z., Janiszowska W., Sobczyk E. 1973. Metabolism of the new series of oleanolic acid glycosides in Calendula officinalis. Acta Biochim. Polon., 20: 231-235.
- Kasprzyk Z., Wojciechowski Z. 1967. The structure of triterpenic glycosides from the flowers of Ca len dula officinalis L. Phytochemistry, 6: 69-75.
- Kasprzyk Z., Wojciechowski Z., Janiszowska W. 1970. Incorporation of 1-14C-acetate into glycosides of Calendula officinalis. Phytochemistry, 9: 561-564.
- Marquina S., Maldonado N., Garduno-Ramirez M.L., Aranda E., Villareal M.L., Navarro V., Bye R., Delgado G., Alvarez L. 2001. Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens. Phytochemistry, 56: 93-97.
- Nagao T., Tanaka R., Okabe H. 1991. Studies on the constituents of Aster scaber Thunb. I. Strucfures of scaberosides, oleanolic acid glycosides isolated from the root. Chem. Pharm. Bull., 39: 1699-1703.
- Ruszkowski D., Szakiel A., Janiszowska W. 2003. Metabolism of [3-3H]oleanolic acid in Calendula officinalis L. roots. Acta Physiol. Plant., 25: 311-317.
- Ruszkowski D., Uniewicz K., Auguścińska E., Janiszowska W. 2004. The allelopathic properties of oleanolic acid 3-O-monoglucoside secreted by roots of Ca- len dula officinalis to the soil. Second European Allelopathy Symposium, Puławy. Abstracts, p. 101.
- Song S., Nakamura N., Ma C., Hattori M., Xu S. 2001. Five saponins from the root bark of Aralia elata. Phytochemistry, 56: 491-497.
- Takebe I., Otsuki Y., Aoki S. 1968. Isolafion of to f bacco mesophyll cells in intact and aclive state. Plant Cell Physiol., 9: 115-124.
- Wojciechowski Z., Jelonkiewicz-Konador A., Tomaszewski M., Jankowski J., Kasprzyk Z. 1971. The struclure of glycosides of oleanolic acid isolated from the roots of Calendula officinalis. Phytochemistry, 10: 1121-1124.
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