8,2′-Dihydroxyflavone from Primula pulverulenta

Wollenweber, Eckhard; Mann, Karin; Inuma, Munekazu; Tanaka, Toŝhiyuki; Mizuno, Mizuo

doi:10.1016/0031-9422(88)80220-6

Cited by 21 publications

(12 citation statements)

References 3 publications

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“…The 1 H NMR spectrum of 2 (Table 1), interpreted with the aid of an HH-COSY spectrum, showed a set of four coupled aromatic proton signals at d H 8. 23, 7.43, 7.71 and 7.57 corresponding to the A ring H-5, H-6, H-7 and H-8, respectively (Freeman et al, 1981;Wollenweber et al, 1988). Moreover, the two meta-coupled protons present at d H 7.24 and 7.01 (each J = 2.4 Hz) were assigned to the B ring H-2 0 and H-6 0 on the basis of their 3 J coupling to the C-2 signal at d C 163.1 in the HMBC spectrum.…”

Section: Resultsmentioning

confidence: 99%

“…The remaining compounds were identified by interpretation of their 1 H NMR, 13 C NMR, EIMS and UV spectral data and by comparisons to those available in the literature, as the known flavones -5,6,2 0 ,6 0 -tetramethoxyflavone (zapotin) (1) (Dreyer and Bertelli, 1967;Ito et al, 1998), 2 0 -hydroxyflavone (3) (Blaskó et al, 1988;Wollenweber et al, 1988), 3 0 ,4 0 -dimethoxyflavone (4) (Mabry et al, 1970;Miyake et al, 2003;Ahmed et al, 2003), 3 0 ,4 0 ,5 0 -trimethoxyflavone (5) (Gaydou and Bianchini, 1978;Obrecht, 1989;Iinuma et al, 1992), 2 0 ,5 0 -dimethoxyflavone (7) (Gallagher et al, 1953;Iinuma et al, 1980;Tanaka et al, 1986), 2 0 -methoxyflavone (8) (Freeman et al, 1981;Blaskó et al, 1988), 3 0 -methoxyflavone (9) (Iinuma et al, 1980;Freeman et al, 1981), and flavone (10) (Mabry et al, 1970;Blaskó et al, 1988).…”

Section: Resultsmentioning

confidence: 99%

“…It is a well-known medicinal plant, which provides rhizome and roots (Primulae radix) with an expectorant activity associated mainly with the triterpene saponins (Schö pke, 1994). The flowers of P. veris, of similar medicinal use (Primulae flos) (Schö pke, 1994), were found to contain a number of flavonol glycosides (Karl et al, 1981;Hegnauer, 1990) and several methoxyflavones (Huck et al, 1999(Huck et al, , 2000Stecher et al, 2003), the latter representing a group of lipophilic flavonoids found earlier in the leaf exudates of some Primula species (Hegnauer, 1969(Hegnauer, , 1990Wollenweber et al, 1988Wollenweber et al, , 1990Wollenweber and Mann, 1986). A few flavonoids were also detected in the leaves of P. veris (Harborne, 1968;Hegnauer, 1990).…”

Section: Introductionmentioning

confidence: 94%

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

2005

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

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

2005

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“…Flavonoid content of some Primula species have been investigated in previous studies: Primula vulgaris (Harborne, 1968); P. pulverulenta (Wollenweber et al, 1988a(Wollenweber et al, , 1989; P. polyantha (Saito et al, 1990); P. macrophylla (Ahmad et al, 1991); P. officinalis (Karl et al, 1981); P. elatior (Petitjean-Freytet, 1993); P. faberi (Zhang et al, 1993); P. denticulata (Tokalov et al, 2004;Wollenweber et al, 1990); P. veris (Budzianowski et al, 2005;Huck et al, 1999Huck et al, , 2000; P. hirsuta, P. auricula and P. daonensis (Fico et al, 2007); P. maximowiczii (Qu et al, 2008); P. spectabilis (Vitalini et al, 2011); exudate flavonoids of Primula spp. (Bhutia et al, 2011(Bhutia et al, , 2013Valant-Vetschera et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Farinose alpine Primula species: Phytochemical and morphological investigations

et al. 2014

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This work investigated the epicuticular and tissue flavonoids, the volatiles and the glandular trichome structure of the leaves of four species of Primula L. that grow in the Italian Eastern Alps. Primula albenensis Banfi and Ferlinghetti, P. auricula L., P. farinosa L., P. halleri Gmelin produce farinose exudates that are deposited on the leaf surface as filamentous crystalloids. In addition to compounds already known, a new flavone, the 3,5-dihydroxyflavone, was isolated from the acetone extract of leaf farinas and three new flavonol glycosides, 3'-O-(β-galactopyranosyl)-2'-hydroxyflavone, isorhamnetin 3-O-α-rhamnopyranosyl-(1→3)-O-[α-rhamnopyranosyl-(1→6)]-O-β-galactopyranoside, quercetin 3-O-α-rhamnopyranosyl-(1→3)-O-[α-rhamnopyranosyl-(1→6)]-O-β-galactopyranoside, were isolated from the MeOH extract of the leaves. All the structures were elucidated on the basis of their (1)H and (13)C NMR data and 2D NMR techniques, as well as on HPLC-MS. The leaf-volatiles emitted by these Primula species were mainly sesquiterpene hydrocarbons, with the exception of P. albenensis, which produced almost exclusively a non-terpene derivative; P. halleri flowers were also examined and the volatiles emitted by the flower parts (corolla and calyx) were compared with the corresponding leaves.

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“…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].…”

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confidence: 96%

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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8,2′-Dihydroxyflavone from Primula pulverulenta

Cited by 21 publications

References 3 publications

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

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

Farinose alpine Primula species: Phytochemical and morphological investigations

Flavones from Callus Tissue of Iris ensata

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