Metabolism of iridals in plant cell cultures of Iris pallida

Marner, Franz‐Josef; Ritzdorf, Ingrid; Johnen, Georg

doi:10.1016/0031-9422(93)85451-v

Cited by 13 publications

(7 citation statements)

References 10 publications

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“…1). Subsequently, Marner's group [15,16] isolated and described several mono-cyclic [17][18][19] and bicyclic iridal structures [20], for a total of more than 40 triterpenic compounds, and also clarified their biosynthetic pathway [21][22][23][24]. In 1993, Bicchi and Rubiolo [25] showed that iridals were also present as esters of myristic acid.…”

Section: Introductionmentioning

confidence: 97%

“…Several studies on species belonging to the Iris genus have dealt with their biological activity [10][11][12][13], with the formation of irones and identification of their precursors [14][15][16][17][18][19][20][21][22][23][24][25], and have led to the isolation of different classes of secondary metabolites, namely triterpenoids, flavonoids and phenols [25][26][27]. In 1983, Krick [14] showed that iripallidal and iriflorental are the irone precursors ( Fig.…”

Section: Introductionmentioning

confidence: 99%

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A metabolomic approach to quality determination and authentication of raw plant material in the fragrance field. Iris rhizomes: A case study

Masson

Liberto

Brevard³

et al. 2014

Journal of Chromatography A

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Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

A metabolomic approach to quality determination and authentication of raw plant material in the fragrance field. Iris rhizomes: A case study

Masson

Liberto

Brevard³

et al. 2014

Journal of Chromatography A

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“…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).…”

mentioning

confidence: 99%

“…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.…”

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confidence: 99%

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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“…Among them are the bicyclic cycloiridals 6 and 7, which are found in extracts of I. pallida, I. germanica, and I. florentina [2]. These compounds serve as precursors of cis-g- (8) and cis-a-irone (9), respectively, which are constituents of the precious natural orris oil and responsible for its pleasant violet-like scent [1 ± 3]. The origin of birone (10), present in varying amounts in commercial Iris oils, is not known.…”

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confidence: 99%

Hoogianal, aβ-Irone Precursor fromIris hoogianaDykes (Iridaceae)

Marner

Hanisch

2001

HCA

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Fractionation of the lipid extract from rhizomes of Iris hoogiana Dykes resulted in the isolation of one new and several known iridals. The latter were identified by comparison with authentic standards as 1 ± 5. The structure of the new natural product, hoogianal (11), was elucidated by spectroscopic analysis. Oxidative degradation yielded b-irone (10), identified by GC-and LC-MS. The (À)-(2S)-configuration of this oxidation product was determined by enantioselective GC on a chiral cyclodextrin phase and by comparison with the corresponding ketones in laevo-and dextrorotatory commercial Iris oils.Helvetica Chimica Acta ± Vol. 84 (2001) 933 1 ) Abbreviations: HPLC high performance liquid chromatography, MPLC medium pressure liquid chromatography; ESI electrospray ionization; APCI atmospheric-pressure chemical ionization; DAD diode-array detector.2 ) The C-skeleton of the iridals is numbered in analogy to squalene. For the systematic name of 11, see Exper.Part.

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Metabolism of iridals in plant cell cultures of Iris pallida

Cited by 13 publications

References 10 publications

A metabolomic approach to quality determination and authentication of raw plant material in the fragrance field. Iris rhizomes: A case study

A metabolomic approach to quality determination and authentication of raw plant material in the fragrance field. Iris rhizomes: A case study

Flavones from Callus Tissue of Iris ensata

Hoogianal, aβ-Irone Precursor fromIris hoogianaDykes (Iridaceae)

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