Abstract
Species of the genus Oenothera L. (Onagra Miller) from the family Onagraceae are characteristic of America, the homeland of species acclimated in Europe (Szafer and Pawłowski 1959; Raven 1968). The American flora has the most numerous representatives; plants of these species can be found in natural localities (Rickett 1970, 1971), or they are grown as decorative plants with white, pink to reddish purple, or mostly bright yellow flowers (Bailey 1950; Encke 1960). A few species are also found in Russia (Shishkin and Bobrow 1949; Grossgejm 1962). At present, the genus Oenothera is believed to be distributed throughout the world with the exception of Antarctica (Rostański 1992).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Asanaka M, Kurimura T, Koshiura R, Okuda T, Mori M, Yokoi H (1988) Abstr, 4th Int Conf on Immunopharmacology, Osaka p 47
Averett JE, Huang S, Wagner WL (1987) Flavonoid analysis of Oenothera speciosa (Onagraceae). Southwest Nat 32:117–120
Averett JE, Huang S, Wagner WL (1988) Flavonoid survey of Oenothera (Onagraceae): Sects. Gauropsis, Hartmannia, Kneiffia, Paradoxus and Xylopleurum. Am J Bot 75:476–483
Averett JE, Wagner WL, Huang S (1991) The flavonoids of Oenothera Sect. Megapterium (Onagraceae). Biochem Syst Ecol 19:87–89
Bailey LH (1950) The standard cyclopedia of horticulture. Macmillan, New York, pp 2328–2332
Bajaj YPS, Furmanowa M, Olszowska O (1988) Biotechnology of the micropropagation of medicinal and aromatic plants. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 4. Medicinal and aromatic plants I. Springer, Berlin Heidelberg New York, pp 60–103
Bartl S (1975) Die Gerbstoffe in der Gattung Oenothera. Dissertation, Universität Saarbrücken, Saarbrücken
Biagi PL, Bordoni A, Hrelia S, Celadon M, Ricci GP, Cannella V, Patrizia A, Specchia F, Masi M (1994) The effect of gamma-linolenic acid on clinical status, red cell fatty acid composition and membrane microviscosity in infants with atopic dermatitis. Drugs Expt Clin Res 20:77–84
Chenoy R, Hussain S, Tayob Y, O’Brien PMS, Moss MY, Morse PF (1994) Effect of oral gamolenic acid from evening primrose oil on menopausal flushing. Br Med J 308:501–503
Cohen Z, Vonshak A, Richmond A (1987) Fatty acid composition of Spirulina strains grown under various environmental conditions. Phytochemistry 26:2255–2258
Cohen Z, Norman HA, Heimer YM (1993) Potential use of substituted pyridazinones for selecting polyunsaturated fatty acid over-producing cell lines of algae. Phytochemistry 32:259–264
Corthout J, Pieters LA, Claeys M, Vanden Berghe DA, Vlietinck AJ (1991) Antiviral ellagitannins from Spondias mombin. Phytochemistry 30:1129–1130
Dickmann FA (1948) Oenothera biennis L. ais Ölpflanze. Pharmazie 3:275–276
Duczmal KW, Ratajczak K, Ratajczak KW (1993) Zawartość kwasu γ-linolenowego w oleju z nasion trzech gatunków rodzaju Oenothera L. Herba Pol 39:179–186
Encke F (1960) Pareys Blumengärtnerei Bd 2. Parey, Berlin, pp 197–199
Fukuchi K, Sakagami H, Okuda T, Hatano T, Tanuma S, Kitajima K, Inoue Y, Inoue S, Ichikawa S, Nonoyama M, Konno K (1989) Inhibition of Herpes simplex virus infection by tannins and related compounds. Antiviral Res 1,1:285–298
Grossgejm AA (1962) Flora Kawkaza vol 6. Akademy of Sciences USSR Moskow pp 247–248
Harborne JB (1991) Phytochemical methods. Chapman and Hall, London
Harborne JB, Baxter H (1993) (eds) Phytochemical dictionary. A handbook of bioactive compounds from plants. Taylor and Francis, London
Harte C (1994) Oenothera: contributions of a plant to biology. Monographs on theoretical and applied genetics, vol 20. Springer, Berlin Heidelberg New York
Hatano T, Yasuhara T, Matsuda M, Yazaki K, Yoshida T, Okuda T (1989) Oenothein B, a dimeric hydrolyzable tannin of cyclic structure. Chem Pharm Bull 37:2269–2271
Hatano T, Yasuhara T, Matsuda M et al. (1990) Oenothein B, a dimeric, hydrolysable tannin with macrocyclic stucture, and accompanying tannins from Oenothera erythrosepala. J Chem Soc Perkin Trans 1, 1990:2735–2743
Heeger EF (1948) Oenothera biennis L., die Gemeine Nachtkerze, als Nutzpflanze. Pharmazie 3:273–275
Hegi G (1927) Illustrierte Flora von Mittel-Europa, Bd V (2). Lehmanns, München, pp 857–873
Hegnauer R (1969) Chemotaxonomie der Pflanzen, Bd 5. Birkhäuser, Basel, pp 222–226
Hegnauer R (1986) Chemotaxonomie der Pflanzen, Bd 7. Birkhäuser, Basel, pp 298–313
Hojden B, Lamer-Zarawska E (1990) Badania uprawowe niektórych gatunków z rodzaju Oenothera L. Herba Pol 36:139–143
Hopkins BJ, Scheinmann F (1971) Triterpenes in the seed oil of evening primrose, Oenothera lamarckiana. Phytochemistry 10:1956–1961
Horrobin DF (1990) Gamma linolenic acid: An intermediate in essential fatty acid metabolism with potential as an ethical pharmaceutical and as a food. In: Johnson S, Johnson FN (eds) Gamma linolenic acid. Rev Contemp Pharmacother 1:1–45
Howard GZ, Mabry TJ (1970) Myricetin 3–0-methyl ether 3′-0-beta-D-glucoside, the major flavonoid of Oenothera speciosa (Onagraceae). Phytochemistry 9:2413–2414
Howard GZ, Mabry TJ, Raven PH (1972) Distribution of flavonoids in twenty-one species of Oenothera. Phytochemistry 11:289–291
Hudson BJF (1984) Evening primrose (Oenothera spp.) oil and seed. JAOCS 61:540–543
Ihrig M, Blume H (1994) Nachtkerzenöl Präparate: ein Qualitätsvergleich. Pharm Ztg 139:34–42
Jankowski WJ, Stołyhwo A (1995) Unusual fatty acid composition of cuticular lipids from leaves of Oenothera. J Plant Physiol 145:215–220
Jean R, Linder R, Hoffmann F, Thomas E, Wenzel G (1976) Comportement in vitro de microspores d’Oenothera coranifera Renne. C R Acad Sci Paris 283:781–784
Kadota S, Takamori Y, Kikuchi T, Motegi A, Ekimoto H (1990) Woodfruticosin, an inhibitor of DNA topoisomerase II from Woodfordia fruticosa Kurz. Tetrahedron Lett 31:393–396
Kagan J (1967) Myricetin 3-β-galactoside, the main flavonoid from Oenothera lavandulaefolia T. and G. Phytochemistry 6:317–318
Kakiuchi N, Hattori M, Namba T (1985) Inhibitory effect of tannins on reverse transcriptase from RNA tumor virus. J Nat Prod 48:614–621
Kleijnen J (1994) Evening primrose oil. Br Med J 309:824–825
Kowalewski Z, Kowalska M, Skrzypczakowa L (1968) Flavonols of Oenothera biennis L. Dissert Pharm Pharmacol 20:573–575
Krzaczek T, Bogucka-Kocka A (1994) Chromatographical analysis of phenolic acids in some species of the genus Oenothera. Eur J Pharm Sci 2(1–2):124
Krzaczek T, Bogucka-Kocka A, Śnieżko R (1995) The phenolic acids of some species of the Oenothera L. genus. Acta Soc Bot Pol 64:41–44
Krzyżaniak M, Segiet-Kujawa E (1991) Determination of γ-linolenic acid in Oenothera biennis L.. Herba Pol 37:57–62
Lamer-Zarawska E, Hojden B (1989a) Polish Oenothera a source of essential unsaturated fatty acids (EFA). Int Symp Medicines of plant origin in modern therapy with special reference to Kampo Medicine, Prague
Lamer-Zarawska E, Hojden B (1989b) Rośliny rodzaju Oenothera L. zródłem niezbęnych nienasyconych kwasów tłuszczowych. Herba Pol 35:151–156
Lamer-Zarawska E, Hojden B, Szymczak J (1989) Badanie olejów z nasion niektórych gatunków Oenothera L. Herba Pol 35:165–170
Lamer-Zarawska E, Hojden B, Nowak W (1990) Sposób agrotechniki prowadzacy do skrócenia okresu wegetacji 3 nowych roślin oleistych z rodzaju Oenothera L. — inventive project, AM Wrocław
Lamer-Zarawska E, Hojden B, Milan A (1993) Wpływ zanieczyszczeń środowiska na stopień skażenia wiesiołka (Oenothera L.) przez metale ciężkie. Herba Pol 39:217–222
Levy A, Palevitch D, Ranen C (1993) Increasing gamma linolenic acid in evening primrose grown under hot temperatures by breeding early cultivars. Acta Hortic 330:219–223
Madaus G (1938) Lehrbuch der Biologischen Heilmittel, Bd 3, Thieme, Leipzig, pp 2002–2005
Madaus G (1938) Lehrbuch der Biologischen Heilmittel, Bd 3, Thieme, Leipzig, pp 2696
Magnus V, Nigović B, Hangarter RP, Good NE (1992) N-(indol-3-ylacetyl) amino acids as sources of auxin in plant tissue culture. J Plant Growth Regul 11:19–28
Martinez LD, Noher de Halac I (1995) Organogenesis of anther-derived calluses in long-term cultures of Oenothera hookeri de Vries. Plant Cell Tissue Organ Cult 42:91–96
Masquelier J, Delaunay D (1965) Bactericidal action of the phenolic acids of wine. Bull Soc Pharm Bord 104:152–160
Middleton EJR, Kandaswami (1994) The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In: Harborne JB (ed) The flavonoids: advances in research since 1986. Chapman and Hall, London, pp 619–652
Miyamoto K, Kishi N, Koshiura R, Yoshida T, Hatano T, Okuda T (1987) Relationship between the structures and the antitumor activities of tannins. Chem Pharm Bull 35:814–822
Miyamoto K, Nomura M, Sasakura M, Matsui E, Koshiura R, Murayama T, Furukawa T, Hatano T, Yoshida T, Okuda T (1993a) Antitumor activity of oenothein B, a unique macrocyclic ellagitannin. Jpn J Cancer Res 84:99–103
Miyamoto K, Murayama T, Nomura M, Hatano T, Yoshida T, Furukawa T, Koshiura R, Okuda T (1993b) Antitumor activity and interleukin 1 induction by tannins. Anticancer Res 13:37–42
Motoyama M, Isono Y, Mori I, Matsui E, Yokoi H, Miyamoto K, Koshiura R (1988) Antitumor activities of tannins (ellagitannin) in mice. Res Home Med 7:55–58 (in Japanese)
Murashige T, Skoog F (1962) A revised medium for rapid growth and bio-assays with tobacco tissue cultures. Physiol Plant 15:473–497
Nagata T, Takebe (1971) Plating of isolated tobacco mesophyll protoplasts on agar medium. Planta 99:12–20
Nakashima H, Murakami T, Yamamoto N, Sakagami H, Tanuma S, Hatano T, Yoshida T, Okuda T (1992) Inhibition of human immunodeficiency viral replication by tannins and related compounds. Antiviral Res 18:91–103
Neumann G, Schwemmle B (1993) Flavonoids from Oenothera seedlings: identification and extranuclear control of their biosynthesis. J Plant Physiol 142:135–143
Neumann G, Schwemmle B (1994) Organ- and tissue-specific biosynthesis of flavonoids in seedlings of Oenothera odorata (Onagraceae). Bot Acta 107:95–102
Nichols BW, Wood BJB (1968) The occurrence and biosynthesis of gamma-linolenic acid in a blue-green alga, Spirulina platensis. Lipids 3:46–50
Nishizawa M, Yamagishi T, Dutschman GE, Parker WB, Bodner AJ, Kilkuskie RE, Cheng Y-C, Lee K-H (1989) Anti-AIDS agents, 1. Isolation and characterization of four new tetragalloylquinic acids as a new class of HIV reverse transcriptase inhibitors from tannic acid. J Nat Prod 52:762–768
Nonaka G-I, Nishioka I, Nishizawa M, Yamagishi T, Kashiwada Y, Dutschman GE, Bodner AJ, Kilkuskie RE, Cheng Y-C, Lee K-H (1990) Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells. J Nat Prod 53:587–595
Okuda T, Hatano T, Ogawa N, Kira R, Matsuda M (1984) Cornusin A, a dimeric ellagitannin forming four tautomers, and accompanying new tannins in Cornus officinalis. Chem Pharm Bull 32:4662–4665
Okuda T, Yoshida T, Hatano T (1989) Ellagitannins as active constituents of medicinal plants. Planta Med 55:117–122
Okuda T, Yoshida T, Hatano T (1993) Classification of oligomeric hydrolysable tannins and specificity of their occurrence in plants. Phytochemistry 32:507–521
Osamu Y, Tadashi F (1987) γ-Linolenic acid manufacture by Oenothera tissue culture. Jpn Kokai Tokkyo Koho JP: 62, 210, 995 (87, 210, 995); CA 1988, 108:73837
Penso G (1983) Index plantarum medicinalium totius mundi corumque synonymorum. OEMF, Milano, pp 677–678
Ratledge C (1991) Microorganisms for lipids. Acta Biotechnol 11:429–438
Raven PH In: Tutin TG et al. (eds) Flora Europaea, vol 2. University Press, Cambridge, pp 306–308
Raven PH, Dietrich W, Stubbe W (1979) An outline of the systematics of Oenothera subsect Euoenothera (Onagraceae). Syst Bot 4:242–252
Renner O (1956) Europäische Wildarten von Oenothera. Planta 47:219–254
Rickett HW (1970) In: Steere WC (ed) Wild flowers of the United States. McGraw-Hill, New York pp 318–329
Rickett HW (1971) In: Steere WC (ed) The evening-primrose family (Onagraceae). McGraw-Hill, New York, pp 294–298
Rostański K (1965) Kilka nowych taksonów rodzaju Oenothera L.z podrodzaju Oenothera. Fragm Flor Geobot 11:499–523
Rostanski K (1985) Zur Gliederung der Subsektion Oenothera (Sektion Oenothera, Oenothera L. Onagraceae). Feddes Reperì 96:3–14
Rostański K, Wika S (1988) Materiały do rozmieszczenia gatunków rodzaju Oenothera L. wśrodkowej części Wyżyny Krakowsko-Wieluńskiej. Frag Flor Geobot 33:33–40
Rostański K (1992) Some taxonomic problems within the genus Oenothera L. and the species differentiation of the Oenthera in Poland. In: Oil from Oenothera in prophylaxis and therapy. SympŁódź, Book of Abstracts, pp 2–8 (in Polish)
Sewón P, Tyystjärvi E (1993) Stearidonic and γ-linolenic acid contents of common borage leaves. Phytochemistry 33:1029–1032
Shimizu S, Shinmen Y, Kawashima H, Akimoto K, Yamada H (1988) Fungal mycelia as a novel source of eicosapentaenoic acid. Activation of enzymes involved in eicosapentaenoic acid. Biochem Biophys Res Commun 150:335–341
Shishkin BK, Bobrow EG (1949) Flora USSR, vol 15, Academy of Sciences USSR. Moscow, pp 628–630
Skrzypczak L, Wesołowska M, Thiem B (1988) Callus culture and micropropagation of Eustoma grandiflorum Shinn. Acta Soc Bot Pol 57:423–430
Skrzypczak L, Skrzypczak-Pietraszek E, Lamer-Zarawska E, Hojden B (1994) Micropropagation of Oenothera biennis L. and an assay of fatty acids. Acta Soc Bot Pol 63:173–177
Stubbe W, Herrmann RG (1982) Selection and maintenance of plastome mutants and interspecific genome/plastome hybrids from Oenothera. In: Edelman M, Hallick RB, Chua N-H (eds) Methods in chloroplast molecular biology, Elsevier Biomedical Press, Amsterdam, pp 149–165
Su J-D, Osawa T, Kawakishi S, Namiki M (1988) Tannin antioxidants from Osbeckia chinensis. Phytochemistry 27:1315–1319
Suzuki S, Fujino H, Yamazaki N, Tatsuo Y, Yoshizaki M (1990) Propagation of Oenothera erythrosepala Borbas by shoot apex culture. Jpn J Breed 40:367–370
Szafer W, Pawłowski B (eds) (1959) Flora Polska, vol 8 PWN, Warszawa, pp 211–219
Szepczyńska K, Wolbiś M (1962) Fenolokwasy i flawonoidy Oenothera biennis L. 15th Naukowy Zjazd Polskiego Towarzystwa Farmaceutycznego, Postępy Nauk Farmaceutycznych, Warszawa p 220 (in Polish)
Symposium (1992, 1995) Oil from Oenothera in prophylaxis and therapy. Łódż October 9–10; September 5–7, Books of Abstracts (in Polish)
Takeo M, Michiko K, Yoshinori M (1987) γ-Linolenic acid ester containing oil and lipid manufacture by Oenothera tissue culture. Jjn Kokai Tokkyo Koho. JP: 62,195, 091 (87,195, 229); CA 1988,108:110878
Thiem B, Skrzypczak-Pietraszek E, Skrzypczak L (1994) In vitro culture of some Oenothera species. 8th Int Congr Plant tissue and cell culture, Firenze, Abstracts, 176pp
Thiem B, Skrzypczak L, Lamer-Zarawska E (1995) Mikrorozmn<inline>anie gatunków rodzaju Oenothera L. II Symp Oil from Oenothera in prophylaxis and therapy, Łódż, Book of Abstracts, pp 71–74 (in Polish)
Thiem B, Skrzypczak L, Lamer-Zarawska E (1998) Fatty acids and phenolic compounds in Oenothera species from in vitro culture. Acta Soc Bot Pol (in press)
Traitler H, Winter H, Richli U, Ingenbleek Y (1984) Characterization of γ-linolenic acid in Ribes seed. Lipids 19:923–928
Wagner H (1985) New plant phenolics of pharmaceutical interest. Annu Proc Phytochem Soc Eur 24:409–425
Wagner WL, Stockhouse RE, Klein WM (1985) The systematics and evolution of the Oenothera caespitosa species complex (Onagraceae). Monogr Syst Bot vol 12, Missouri Botanical Garden, pp 1–103
Wolf RB, Kleiman R, England RE (1983) New sources of γ-linolenic acid. JAOCS 60:1858–1860
Wolfson R, Sears BB (1989) A reduction in the abundance of calcium oxalate crystals in Oenothera improves the yield of intact chloroplasts. Plant Cell Environ 12:109–112
Yaniv Z, Ranen C, Levy A, Palevitch D (1989) Effect of temperature on the fatty acid composition and yield of evening primrose (Oenothera lamarckiana) seeds. J Exp Bot 40:609–613
Yoshida T, Chou T, Matsuda M, Yasuhara T, Yazaki K, Hatano T, Nitta A, Okuda T (1991) Woodfordin D and Oenothein A, trimeric hydrolyzable tannins of macro-ring structure with antitumor activity. Chem Pharm Bull 39:1157–1162
Yoshida T, Chou T, Shingu T, Okuda T (1995) Oenotheins D, F and G, hydrolysable tannin dimers from Oenothera laciniata. Phytochemistry 40:555–561
Zinsmeister HD, Bartl S (1971) The phenolic compounds of Oenothera. Phytochemistry 10:3129–3132
Zinsmeister HD, Biering W (1973) Onagraceae, flavonol-glycosides in Oenothera hookeri. Phytochemistry 12:234
Zinsmeister HD, Schels H (1975) Onagraceae, flavonol-glycosides in Oenothera berteriana. Tabulated Phytochemical Reports. Phytochemistry 14:1468
Zinsmeister HD, Kauer H, Rossmann G (1965) Über die Gerbstoffe von Oenothera hookeri. Planta 66:301–309
Zinsmeister HD, Hopf H, Kauer H, Bartl S (1970) Gerbstoff — Untersuchungen bei der Gattung Oenothera L. Planta Med 18:160–167
Zinsmeister HD, Plitzko I, Schels H (1977) Flavonol glycosides in South American species of Oenothera Sect Oenothera. Phytochemistry 16:497
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Skrzypczak, L., Thiem, B., Wesołowska, M. (1998). Oenothera Species (Evening Primrose): In Vitro Regeneration, Production of Flavonoids, Fatty Acids, and Other Secondary Metabolites. In: Bajaj, Y.P.S. (eds) Medicinal and Aromatic Plants X. Biotechnology in Agriculture and Forestry, vol 41. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-58833-4_14
Download citation
DOI: https://doi.org/10.1007/978-3-642-58833-4_14
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-63748-3
Online ISBN: 978-3-642-58833-4
eBook Packages: Springer Book Archive