Lipophilic flavones of Primula veris L. from field cultivation and in vitro cultures

Budzianowski, Jaromir; Morozowska, Maria; Wesołowska, Maria

doi:10.1016/j.phytochem.2005.03.024

Cited by 63 publications

(44 citation statements)

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“…The leaves of Primula veris L. (cowslip) were collected from the field (A) and maintained by Dr. Maria Morozowska at the Department of Botany, Poznań University of Life Sciences, Poznań, Poland; in vitro cultures (B) were obtained by Dr. Maria Wesołowska at the Department of Pharmaceutical Botany and Plant Biotechnology, as described by Budzianowski et al (2005). The dried leaves of each collection (A and B, each 80.0 g) were separately extracted with chloroform under reflux (7 × 600 ml/h).…”

Section: Methodsmentioning

confidence: 99%

“…Flavones, a group of flavonoids, are neuroprotective, cardioprotective and chemopreventive agents acting as antioxidants and modulators of protein kinases and lipid-dependent signaling pathways (Duraj et al, 2005). The flavone zapotin (5,6,2′,6′-tetramethoxyflavone) was first identified in the tropical fruit zapote blanco ( Casimiroa edulis ) (Murillo et al, 2007), later isolated from Sargentia gregii (Meyer et al, 1985) and extracted from the leaves of Primula veris (Budzianowski et al, 2005). In a previous study it was demonstrated that zapotin prevented colon carcinogenesis (Murillo et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

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The tetramethoxyflavone zapotin selectively activates protein kinase C epsilon, leading to its down-modulation accompanied by Bcl-2, c-Jun and c-Fos decrease

Totoń¹,

Lisiak²,

Rubiś³

et al. 2012

European Journal of Pharmacology

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Zapotin, a tetramethoxyflavone, is a natural compound with a wide spectrum of activities in neoplastic cells. Protein kinase C epsilon (PKCε) has been shown to be oncogenic, with the ability to increase cell migration, invasion and survival of tumor cells. Here we report that zapotin inhibits cell proliferation. In wild-type HeLa cells with basal endogenous expression of PKCε, the IC50 was found to be 17.9 ± 1.6 μM. In HeLa cells overexpressing doxycycline-inducible constitutively active PKCε (HeLaPKCεA/E), the IC50 was 7.6 ± 1.3 μM, suggesting that PKCε enhances the anti-proliferative effect of zapotin. Moreover, we found that zapotin selectively activated PKCε in comparison with other PKC family members, but attenuated doxycycline-induced PKCε expression. As a result of zapotin treatment for 6, 12 and 24 h, the doxycycline-induced levels of the two differently phosphorylated PKCε forms (87 kDa and 95 kDa) were decreased. Migration assays revealed that increasing concentrations of zapotin (from 3.5 to 15 μM) decreased migration of HeLaPKCεA/E cells. Furthermore, zapotin significantly increased the fraction of apoptotic cells in doxycycline-induced (HeLaPKCεA/E) cells after 24 h and decreased the levels of Bcl-2, c-Jun, c-Fos. This was accompanied by a degradation of PARP-1. In summary, activation of PKCε and down-modulation of the induced PKCε level by zapotin were associated with decreased migration and increased apoptosis. These observations are consistent with the previously reported chemopreventive and chemotherapeutic action of zapotin.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The tetramethoxyflavone zapotin selectively activates protein kinase C epsilon, leading to its down-modulation accompanied by Bcl-2, c-Jun and c-Fos decrease

Totoń¹,

Lisiak²,

Rubiś³

et al. 2012

European Journal of Pharmacology

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“…Extracts from cowslip are used due to their antiviral and anti-inflammatory activities (Huckl et al, 1999). Several saponins are isolated from roots as well as a number of uncommon and common flavonoids were found in flowers, the main flavonoids are quercetin and isorhamnetin (Huckl et al, 1999;Raal, 2010), the lipophilic flavonoids were also found in leaves (Budzianowski et al, 2005). In Estonian traditional medicine tea from leaves and flowers of cowslip has been popular against common cold and flu it was also consumed as a sedative home remedy (Raal, 2010).…”

Section: Introductionmentioning

confidence: 99%

Content of Ascorbic Acid in Common Cowslip (Primula veris L.) Compared to Common Food Plants and Orange Juices

Meos¹,

Zaharova²,

Kask³

et al. 2017

Acta Biologica Cracoviensia S. Botanica

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Ascorbic acid is a well-known antioxidant found in plants. The content of ascorbic acid was assayed using a normal phase European Pharmacopoeia HPLC method for ascorbic acid in medicinal products. The content of ascorbic acid in herbs was calculated in % for absolutely dry drug. Ascorbic acid was not detected in the roots of Primula veris, in aerial parts it was detected in flowers (0.43 ± 0.034%), in blades (1.43 ± 0.11%) and petioles (1.56 ± 0.12%). In fresh leaves collected at weekly intervals the content of ascorbic acid varied from 1.19 to 2.39%, being highest from mid-May to mid-June. The fresh leaves contained 2.35 ± 0.18% of ascorbic acid and when frozen its content was quite stable for one year. The content of ascorbic acid in dried leaves decreased more than ten times in three months, in twelve months it was less than 1/20 th of the initial level. Compared to the analyzed common fresh fruits and salads (n = 10) the fresh leaves of common cowslip contained considerably more ascorbic acid. Commercial orange juices could be recommended as the most convenient source of ascorbic acid (8.6-50.4 mg/100 ml); 1-5 glasses of orange juice could fulfill the recommended daily intake of vitamin C (60 mg). Gale et al. (1995), the intake of ascorbic acid in winter was less than in summer and this was reflected in the serum levels; probably the lower plasma levels in winter increased people's susceptibility to infections. The influence of vitamin C intake on cardiovascular disease is not clear (Tomas-Barberan and Robins, 1997). Deficiency of ascorbic acid leads to scurvy, accompanied by osteoporosis and severe anemia. As a supportive medication ascorbic acid could be used in case of the following illnesses or disease states: alcoholism, arthritis, influenza, back pain, diseases of teeth and gums, dermatitis, psoriasis, bronchitis, nephritis, rheumatism, hemorrhoids, stenocardia, diabetes, atherosclerosis, jaundice, osteoporosis, prostatitis, etc. (Meos, 2003;Zilmer et al., 2006). It is also used for general strengthening of the organism and for maintaining physical and mental ability to work as well as for enhancing the capacity of the organism's resistance in the case of exhaustion or recovery period from a severe illness (Margna, 2011). As vitamin C is not synthesized in human liver, human beings must constantly supplement their diets with ascorbic acid (Ege, 1999;Dewick, 2006). It is found in many fruits and vegetables (TomasBarberan and Robins, 1997), for example in different sweet pepper cultivars, potato, green bean, tomato, quince, cucumber, marrow, peach, etc. (Dürüst et al., 1997). In addition to vegetarian diet, the organism can absorb ascorbic acid also from medicinal herbs such as common cowslip, Rosa species, blackcurrant, common sea-buckthorn, etc. (Tammeorg et al., 1975;Bunney, 1993;Raal, 2010). Keywords: ascorbic acid, vitamin C,Common cowslip (Cowslip primrose, Primula veris L. syn. Primula offcinalis Hill, Primulaceae) is a perennial herb with an ovate to oblong stalked leaves, which are arranged i...

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“…It has been found that flavones found in leaves of P. veris are synthesized in in vitro cultivated tissues of this plant [8].…”

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confidence: 98%

Flavones from Callus Tissue of Iris ensata

Boltenkov

Rybin²,

Зарембо

2005

Chem Nat Compd

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Flavonoids uncharacteristic of intact plants were isolated from callus tissue of Iris ensata and were identified as 5-hydroxy-4′-methoxyflavone, 5-hydroxy-3′-methoxyflavone, and 5-hydroxy-2′-methoxyflavone using PMR and mass spectrometry. It was proposed that the lack of growth of callus tissue after changing cultivation conditions was related to the inhibiting effect of these flavones on cell proliferation.Key words: Iris ensata, Iridaceae, callus tissue, 5-hydroxy-4′-methoxyflavone, 5-hydroxy-3′-methoxyflavone, 5-hydroxy-2′-methoxyflavone.Flavonoids are the most studied group of secondary plant metabolites from the Iridaceae family [1]. Information on the contents of these compounds is used in chemotaxonomic studies of representatives of this family. The flavonoid composition is known for almost 60% of Iris species [2]. However, little attention has been paid to the secondary metabolites of in vitro tissue from cultivated species of this genus. It has been demonstrated that Iris cell cultures contain terpenoids [3,4]. Earlier we studied the qualitative pigment composition of I. ensata Thunb. heterotrophic callus culture [5]. A determination of the nature of pigments from callus tissue of this plant indicated an acculumation of flavonoids. The goal of the present work was to isolate and identify red pigments from callus tissue of I. ensata.Extract of I. ensata callus tissue contained three isomers of 5-hydroxy-monomethoxyflavone. The isolated compounds were identified as 5-hydroxy-2-(4-methoxyphenyl)-chromen-4-one (5-hydroxy-4′-methoxyflavone) (1), 5-hydroxy-2-(3-methoxyphenyl)-chromen-4-one (5-hydroxy-3′-methoxyflavone) (2), and 5-hydroxy-2-(2-methoxyphenyl)-chromen-4-one (5-hydroxy-2′-methoxyflavone) (3).Compound 3 and other lipophilic flavones unsubstituted at the 7-position were observed in secretory emissions of aerial organs of plants from the genus Primula [6,7]. It has been found that flavones found in leaves of P. veris are synthesized in in vitro cultivated tissues of this plant [8].The results suggest that the spectrum of synthesized secondary-exchange compounds changed in callus culture of I. ensata when compared with the intact plants. According to the literature, intact plants of this species contain flavonoid pigments of the anthocyan [9, 10], flavone, and xanthone [11] types. However, the dominant pigments in callus tissue were lipophilic flavones 1-3 uncharacteristic of this plant.Our results for the pigment composition of I. ensata callus tissue showed that flavone formation in tissue was suppressed in the subcultivation medium [5]. However, the change of cultivation conditions (reduced content of phytohormones, increased concentration of saccharose, change of pH) favored flavonoid accumulation and inhibited callus growth.It was noted that the synthesis of secondary compounds in isolated instances was related to a slowing or cessation of cell proliferation [12,13]. Apparently the flavonoids identified by us and compounds similar to them in biogenetic origin were responsible for the suppression ...

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Lipophilic flavones of Primula veris L. from field cultivation and in vitro cultures

Cited by 63 publications

References 29 publications

The tetramethoxyflavone zapotin selectively activates protein kinase C epsilon, leading to its down-modulation accompanied by Bcl-2, c-Jun and c-Fos decrease

The tetramethoxyflavone zapotin selectively activates protein kinase C epsilon, leading to its down-modulation accompanied by Bcl-2, c-Jun and c-Fos decrease

Content of Ascorbic Acid in Common Cowslip (Primula veris L.) Compared to Common Food Plants and Orange Juices

Flavones from Callus Tissue of Iris ensata

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