Prenylated xanthones from cell suspension cultures of Hypericum patulum

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

doi:10.1016/0031-9422(95)00882-9

Cited by 19 publications

(10 citation statements)

References 7 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: 89%

“…] 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: 89%

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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“…Several compounds have been isolated and identified from this genus, among them napthadianthrones, a broad range of flavonoids, phloroglucinols, xanthones and the essential oils (Bombardelli et al, 1995;Couladis et al, 2001a;Ishiguro et al, 1996;). Plants of this genus are widely used in folk medicine and important pharmacological properties have been attributed to extracts of Hypericum spp.…”

Section: Introductionmentioning

confidence: 99%

Composition and antimicrobial activity of the essential oil of Hypericum rumeliacum subsp. apollinis (Boiss. & Heldr.)

Couladis

Chinou

Τζακου

et al. 2003

Phytotherapy Research

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The composition and the antimicrobial activity of the aerial parts of Hypericum rumeliacum are reported. Analysis was carried out by GC/MS. The major constituents were alpha-pinene (43.80%), beta-pinene (9.82%), dehydro-aromadendrene (6.81%) and alpha-copaene (5.41%). The essential oil showed a moderate in vitro activity against the six Gram negative and positive bacteria and a stronger one against the three-tested pathogenic activity.

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“…Its UV absorption bands and bathochromic shifts on the addition of AlCl 3 and NaOAc indicated that compound 3: a xanthone with 1-and 8-; and 3-and/or 6-hydroxyl groups. 24,25) HR-EI-MS established the molecular formula to be C 19 tons and C-6, between H-2 and C-1, C-3, C-4, and C-9a, and between H-4 and C-2, C-3, C-4a, and C-9a. Based on the above evidence, the structure of 3 was confirmed to be 1,3,5,8-tetrahydroxy-6-methoxy-7-isoprenylxanthone, and designated hyperxanthone.…”

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confidence: 99%

New Phenolic Principles from Hypericum sampsonii

Don

Huang

et al. 2004

Chem. Pharm. Bull.

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The phytochemistry and antidepressant activity of Hypericum perforatum (St. John's wort) have attracted much attention to the Hypericum genus and several biologically active components have been isolated. [1][2][3][4][5][6][7][8] Hypericum sampsonii (Guttiferae) is a herbal medicine used in the treatment of blood stasis, to relieve swelling, and as an antitumor herb in Taiwan. 9) Xanthones 10) and series of polyprenylated benzophenone derivatives [11][12][13][14][15] were previously isolated from this plant. In a continuation of our search for active components similar to H. perforatum in H. sampsonii, 15) We report here the isolation and structural determination of five new phenolic compounds together with 16 known compounds from the whole herbs of H. sampsonii. Results and DiscussionThe ethanolic extract of the whole herbs was successively partitioned with ethyl acetate and n-butanol. The ethyl acetate and BuOH-soluble fractions were chromatographed on silica gel and Sephadex LH-20 to give two new benzophenones, 2,6-dihydroxy-4-[(E)-5-hydroxy-3,7-dimethylocta-2,7-dienyloxy]benzophenone (1) and 2,6-dihydroxy-4-[(E)-7-hydroxy-3,7-dimethylocta-2-enyloxy]benzophenone (2), a new xanthone, hyperxanthone (3), a new bisanthraquinone glycoside, R-(Ϫ) -skyrin-6-O-b-D-xylopyranoside (4), and 2-caffeoyloxy-3-hydroxy-3-(3,4-dihydroxyphenyl)propyl alcohol (5) Using the anti-hepatitis B virus (HBV)-producing cell line MS-G2 in vitro cultural system-guided screening was performed, and two new benzophenones, 2,6-dihydroxy-4-[(E)-5-hydroxy-3,7-dimethylocta-2,7-dienyloxy]benzophenone (1) and 2,6-dihydroxy-4-[(E)-7-hydroxy-3,7-dimethylocta-2-enyloxy]benzophenone (2), a new xanthone, hyperxanthone (3), a new bisanthraquinone glycoside, R-(؊)-skyrin-6-O-b b-D-xylopyranoside (4), and 2-caffeoyloxy-3-hydroxy-3-(3,4-dihydroxyphenyl)propyl alcohol (5), and 16 known compounds were isolated from the anti-HBV active fraction of the whole herbs of Hypericum sampsonii. Their structures were elucidated using spectroscopic methods, mainly 2D NMR and MS spectrometry. Circular dichroism was used to determine the stereochemistry of bisanthraquinone glycosides.

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Prenylated xanthones from cell suspension cultures of Hypericum patulum

Cited by 19 publications

References 7 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

Composition and antimicrobial activity of the essential oil of Hypericum rumeliacum subsp. apollinis (Boiss. & Heldr.)

New Phenolic Principles from Hypericum sampsonii

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