Co-occurrence of prenylated xanthones and their cyclization products in cell suspension cultures of Hypericum patulum

Ishiguro, Kyoko; Nakajima, Mariko; Fukumoto, Hisae; Isoi, Koichiro

doi:10.1016/0031-9422(94)00664-f

Cited by 35 publications

(26 citation statements)

References 5 publications

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“…Data from 1 Hand/or 13 C-NMR confirmed the oxygenation pattern and allowed the localization of the prenyl, pyran and methoxyl groups. Compounds 1, 3, 5 and 6 were isolated previously from H. androsaemum roots [18], while compounds 7 (g-mangostin), 10 (garcinone B), and 11 (paxanthone) were isolated from H. patulum cell cultures [19,20]. The data obtained by us were in good agreement with those reported in the literature.…”

Section: Identified Xanthonessupporting

confidence: 88%

“…] at m/z 342) and 1 H-NMR, with two metacoupled protons on A ring (always lower l shift than those for B ring [19,20]), a singlet for one proton on B ring, a singlet for a methoxyl and signals for a prenyl group. The high l value of protons in position C-11 (l 4.12) indicates that the prenyl group is located at C8, in the neighborhood of the carbonyl group [18,20].…”

Section: Identified Xanthonesmentioning

confidence: 99%

“…1). Compounds 1 and 2 showed the UV spectral characteristics of the 1,3,5,6 oxygenated xanthones, with band IV reduced to shoulder [17], while all the other identified xanthones had an UV similar to mangiferin, typical of the 1,3,6,7 oxygenation pattern with a very well-defined band IV [18][19][20]. Data from 1 Hand/or 13 C-NMR confirmed the oxygenation pattern and allowed the localization of the prenyl, pyran and methoxyl groups.…”

Section: Identified Xanthonesmentioning

confidence: 99%

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Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

et al. 2000

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Calli and suspended cells of Hypericum androsaemum accumulated high levels of 1,3,5,6 and 1,3,6,7 oxygenated xanthones. The major compounds include simple oxygenated xanthones or derivatives with prenyl, pyran or methoxyl groups, four of them being new natural compounds. A hypothetical biosynthetic scheme is proposed based on the isolated compounds and statistical analysis. Xanthone accumulation was influenced greatly by medium factors, namely hormone supplementation. Calli grown with 4.5 mM a-naphtaleneacetic acid (NAA) +2.3 mM kinetin (KIN) had the highest specific xanthone production (1.3% biomass dry weight (DW)), whereas suspended cells grown in similar medium accumulated a lower amount (0.87% DW). Calli displayed a negative linear relationship between total xanthone accumulation and NAA concentration, in the range of 4.5 -22.5 mM. However, in this range the xanthone 1,3,6,7/1,3,5,6 ratio and the biomass production showed a positive linear relationship with NAA concentration. Substitution of 4.5 mM of NAA by the same molar amount of 2,4-dichlorophenoxyacetic acid (2,4-D), in the presence of 2.3 mM of KIN, caused a decrease in xanthone accumulation in calli. The use of N 6 -benzyladenine (BA) instead of KIN reduced xanthone production, independently of the auxin used. This effect was attenuated when both hormones were present.

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Section: Identified Xanthonessupporting

confidence: 88%

Section: Identified Xanthonesmentioning

confidence: 99%

Section: Identified Xanthonesmentioning

confidence: 99%

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Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

et al. 2000

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“…Five groups of phenolic compounds such as phenolic acids, flavonol glycosides, flavan-3-ols, flavonoid aglycones and xanthones were recorded in HR cultures (Table 1). Their identification was based on the typical UV/Vis spectral data and LC/MS in the negative ionization mode [M-H] -with the subsequent MS 2 , MS 3 and MS 4 analysis for further identification with reference to similar data previously reported [24][25][26][27][28][29][30][31][32][33]. The HPLC analysis of secondary metabolites revealed marked differences between control roots ( Figure 3A) and HR cultures ( Figure 3B).…”

Section: Hplc/dad/esi-ms N Analysismentioning

confidence: 75%

“…Xanthones in HR cultures could be distinguished in five groups: (i) compounds whose quantity increased (xanthones X6, X7, X10, X12, X13, X14, X15, X17, X19, X24, X28), (ii) compounds whose quantity decreased (xanthone X11), (iii) compounds whose quantity was not significantly modified (xanthones X1, X9, X18, X22), (iv) , thus proving that this compound loses the characteristics of C-hexosyl compounds [26]. Compounds X4, X6, and X11 showed UV spectral characteristics of the 1,3,5,6 oxygenated xanthones, with band IV reduced to shoulder while most of the other identified xanthones had UV spectra similar to mangiferin typical of the 1,3,6,7 oxygenation pattern with a very well-defined band IV [30]. Compounds X6 and X7 were identified as 1,3,5,6-tetrahydroxyxanthone and 1,3,6,7-tetrahydroxyxanthone aglycones, respectively (single intense molecular ion [M-H] -at m/z 259).…”

Section: Hplc/dad/esi-ms N Analysismentioning

confidence: 91%

Hairy roots of Hypericum perforatum L.: a promising system for xanthone production

et al. 2013

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Hypericum perforatum L. is a common perennial plant with a reputed medicinal value. Investigations have been made to develop an efficient protocol for the identification and quantification of secondary metabolites in hairy roots (HR) of Hypericum perforatum L. HR were induced from root segments of in vitro grown seedlings from H. perforatum, after co-cultivation with Agrobacterium rhizogenes A4. Transgenic status of HR was confirmed by PCR analysis using rolB specific primers. HR had an altered phenolic profile with respect to phenolic acids, flavonol glycosides, flavan-3-ols, flavonoid aglycones and xanthones comparing to control roots. Phenolics in control and HR cultures were observed to be qualitatively and quantitatively distinct. Quinic acid was the only detectable phenolic acid in HR. Transgenic roots are capable of producing flavonol glycosides such as quercetin 6-C-glucoside, quercetin 3-O-rutinoside (rutin) and isorhamnetin O-hexoside. The HPLC analysis of flavonoid aglycones in HR resulted in the identification of kaempferol. Transformed roots yielded higher levels of catechin and epicatechin than untransformed roots. Among the twenty-eight detected xanthones, four of them were identified as 1,3,5,6-tetrahydroxyxanthone, 1,3,6,7-tetrahydroxyxanthone, γ-mangostin and garcinone C were de novo synthesized in HR. Altogether, these results indicated that H. perforatum HR represent a promising experimental system for enhanced production of xanthones.

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Six New Constituents from the Fruit of Hypericum patulum and Their Anti‐Inflammatory Activity

Jiang

et al. 2022

Chemistry & Biodiversity

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Four new xanthone glucosides, 3-hydroxy-2-methoxyxanthone-4-O-β-D-glucopyranoside (1), 4,8-dihydroxy-2methoxyxanthone-3-O-β-D-glucopyranoside (2), 2-methoxyxanthone-5-O-β-D-glucopyranoside (3), 4-hydroxy-2methoxyxanthone-3-O-β-D-glucopyranoside (4), a new phenolic acid, 4,4'-dihydroxy-3,3'-imino-di-benzoic acid monomethyl ester (5), and a new isoquinoline, methyl 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline-4carboxylate (6) were isolated from the fruit of Hypericum patulum. The structural elucidation of the isolated compounds was primarily based on HR-ESI-MS, UV, IR, 1D and 2D NMR. All compounds were evaluated for their inhibitory effect against LPS-induced NO production in RAW 264.7 cells. Compound 2, 3 exhibited moderate inhibitory activity against NO production.

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Co-occurrence of prenylated xanthones and their cyclization products in cell suspension cultures of Hypericum patulum

Cited by 35 publications

References 5 publications

Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

Hairy roots of Hypericum perforatum L.: a promising system for xanthone production

Six New Constituents from the Fruit of Hypericum patulum and Their Anti‐Inflammatory Activity

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