Prenylated Benzophenones and Xanthones from Hypericum scabrum

Tanaka, Naonobu; Takaishi, Yoshihisa; Shikishima, Yasuhiro; Nakanishi, Yuka; Bastow, Kenneth F.; Lee, Kuo‐Hsiung; Honda, Gisho; Ito, Michiho; Takeda, Yoshio; Khojimatov, Olim K.; Ashurmetov, Ozodbek

doi:10.1021/np040024+

Cited by 102 publications

(70 citation statements)

References 30 publications

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“…The spectra obtained matched those published for hyperxanthone E (Supplemental Fig. S1; Tanaka et al, 2004). The isolated compound was used to quantify changes in the xanthone level in H. calycinum cell cultures after the addition of the elicitor (Fig.…”

Section: Elicitor-induced Xanthone Accumulationmentioning

confidence: 59%

Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures

Gaid

Sircar²,

Müller³

et al. 2012

Plant Physiology

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Although a number of plant natural products are derived from benzoic acid, the biosynthesis of this structurally simple precursor is poorly understood. Hypericum calycinum cell cultures accumulate a benzoic acid-derived xanthone phytoalexin, hyperxanthone E, in response to elicitor treatment. Using a subtracted complementary DNA (cDNA) library and sequence information about conserved coenzyme A (CoA) ligase motifs, a cDNA encoding cinnamate:CoA ligase (CNL) was isolated. This enzyme channels metabolic flux from the general phenylpropanoid pathway into benzenoid metabolism. HcCNL preferred cinnamic acid as a substrate but failed to activate benzoic acid. Enzyme activity was strictly dependent on the presence of Mg2+ and K+ at optimum concentrations of 2.5 and 100 mm, respectively. Coordinated increases in the Phe ammonia-lyase and HcCNL transcript levels preceded the accumulation of hyperxanthone E in cell cultures of H. calycinum after the addition of the elicitor. HcCNL contained a carboxyl-terminal type 1 peroxisomal targeting signal made up by the tripeptide Ser-Arg-Leu, which directed an amino-terminal reporter fusion to the peroxisomes. Masking the targeting signal by carboxyl-terminal reporter fusion led to cytoplasmic localization. A phylogenetic tree consisted of two evolutionarily distinct clusters. One cluster was formed by CoA ligases related to benzenoid metabolism, including HcCNL. The other cluster comprised 4-coumarate:CoA ligases from spermatophytes, ferns, and mosses, indicating divergence of the two clades prior to the divergence of the higher plant lineages.

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Section: Elicitor-induced Xanthone Accumulationmentioning

confidence: 59%

Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures

Gaid

Sircar²,

Müller³

et al. 2012

Plant Physiology

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“…Compound 1 should be synthesized from phloroglucinol substituted with a benzoyl and some prenyl groups followed by a transannular cyclization reaction. Compound 1 was named otogirinin A. Hyperibone K 19) isolated from H. scabrum and pulkenetione A 20) isolated from Clusia plukenetii have a similar carbon skeleton (adamantane) with that of 1, but a different substitution pattern and size of side chain moieties with those of 1.…”

Section: Resultsmentioning

confidence: 99%

Polyprenylated Benzoylphloroglucinol-Type Derivatives Including Novel Cage Compounds from Hypericum erectum

et al. 2010

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“…We have so far reported anti-HIV agent, biyouyanagin A 5) and xanthones 6,7) from H. chinense, and prenylated benzophenones and xanthones from H. scabrum. 8,9) In continuing this program, we have examined the aerial parts of H. perforatum var. angustifolium.…”

Section: 4)mentioning

confidence: 99%

Prenylated Phloroglucinol Derivatives from Hypericum perforatum var. angustifolium

et al. 2008

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Hypericum perforatum (St. John's Wort, Clusiaceae) has been used for centuries in the treatment of burns, bruises, swelling, inflammation, and anxiety, as well as bacterial and viral infections. In addition, H. perforatum has become popular herbal medicine quickly in the world for the treatment of mood disorders, since its effectiveness in the therapy for mild to moderate depression with a smaller side effects profile than that of traditional antidepressant medications has been claimed in the United States. Numerous studies have proven the clinical efficacy of H. perforatum in both human and animal behavioral models of depression.1) This medicinal herb produces various types of secondary metabolites, including flavonoids, xanthones, naphthodianthrones, and prenylated phloroglucinols.2) Among others, hyperforin, a main component of H. perforatum being classified as phloroglucinol derivatives, is regarded as a potential leads for new medicinal agents because of its various biological activities (e.g. antibacterial, apoptotic properties, anti-tumor, anti-inflammatory, and anti-depressant). 3,4) We have been studying the chemical constituents of various Hypericum plants for the purpose of the search for biologically active secondary metabolites. We have so far reported anti-HIV agent, biyouyanagin A 5) and xanthones 6,7) from H. chinense, and prenylated benzophenones and xanthones from H. scabrum. 8,9) In continuing this program, we have examined the aerial parts of H. perforatum var. angustifolium. Varieties of H. perforatum with "broad" (var. perforatum) and "narrow" (var. angustifolium) sized leaves have been recognized. 10) H. perforatum var. angustifolium was reported to contain a larger quantity of hypericin, and to have a stronger antimicrobial effect than typical variety, H. perforatum var. perforatum.11) This paper deals with the isolation and characterization of ten prenylated phloroglucinol derivatives, including two new prenylated phloroglucinols named furoadhyperforin isomers A (1) and B (2), together with five xanthones and two flavonoids from this plant material.The methanolic extracts of the air-dried aerial parts of Hypericum perforatum var. angustifolium were successively partitioned between n-hexane, EtOAc, BuOH, and H 2 O. The nhexane, the EtOAc, and the BuOH-soluble fractions were repeatedly subjected to column chromatography, respectively, to afford two new (1, 2) and 15 known (3-17) compounds.Compounds 1 and 2 showed a hydroxyl and a carbonyl absorption bands in their IR spectrum. Their molecular formulae were decided as the same of C 36 H 54 O 5 on the basis of the HR-MS data. The 1 H-and 13 C-NMR spectra of 1 and 2 resembled each other, which indicated the presence of a 2-methylbutanoyl group, three isoprenyl groups, two carbonyl groups, one enol moiety, one oxygenated quaternary carbon, one oxygenated methine, three quaternary carbons, one methine, four methylenes, and three tertiary methyls (Table 1). From these data, 1 and 2 were assumed to be prenylated phloroglucinol derivatives having ...

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Prenylated Benzophenones and Xanthones from Hypericum scabrum

Cited by 102 publications

References 30 publications

Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures

Cinnamate:CoA Ligase Initiates the Biosynthesis of a Benzoate-Derived Xanthone Phytoalexin in Hypericum calycinum Cell Cultures

Polyprenylated Benzoylphloroglucinol-Type Derivatives Including Novel Cage Compounds from <i>Hypericum erectum</i>

Prenylated Phloroglucinol Derivatives from <i>Hypericum perforatum</i> var. <i>angustifolium</i>

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