Hyperforin Accumulates in the Translucent Glands of Hypericum perforatum

Soelberg, Jens; Jørgensen, Lise Bolt; Jäger, Anna K.

doi:10.1093/aob/mcm057

Cited by 63 publications

(45 citation statements)

References 15 publications

(21 reference statements)

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“…Although we could also detect minute amounts of adhyperforin in the dark glands, the deviation was higher. Our observation corroborates earlier studies which found that hyperforin is present in minute amounts in the dark glands, with a large proportion accumulating in the Btranslucent glands^, and almost no accumulation in the non-secretory tissues of the leaves [39]. Since these translucent glands are embedded sub-epidermally within the leaves and surrounded by thick layers of parenchyma cells [35], it was not possible for us to determine the distribution of hyperforin and adhyperforin in these glands using our noninvasive IMS techniques.…”

Section: Resultssupporting

confidence: 90%

“…2), with the objective of determining the tissue-specific site of accumulation of hypericin and structural analogues. Several intramarginal, mostly punctiform, black or blackishred dark glands could be observed on the leaves [35][36][37][38] in addition to numerous scattered, pale translucent glands [39]. Some of the dark glands had dark reddish coloring, particularly visible if observed under higher magnifications.…”

Section: Resultsmentioning

confidence: 99%

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Spatial chemo-profiling of hypericin and related phytochemicals in Hypericum species using MALDI-HRMS imaging

et al. 2015

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Advanced analytical imaging techniques, including matrix-assisted laser desorption/ionization high-resolution mass spectrometry (MALDI-HRMS) imaging, can be used to visualize the distribution, localization, and dynamics of target compounds and their precursors with limited sample preparation. Herein we report an application of MALDI-HRMS imaging to map, in high spatial resolution, the accumulation of the medicinally important naphthodianthrone hypericin, its structural analogues and proposed precursors, and other crucial phytochemical constituents in the leaves of two hypericin-containing species, Hypericum perforatum and Hypericum olympicum. We also investigated Hypericum patulum, which does not contain hypericin or its protoforms. We focused on both the secretory (dark glands, translucent glands, secretory canals, laminar glands, and ventral glands) and the surrounding non-secretory tissues to clarify the site of biosynthesis and localization of hypericin, its possible precursors, and patterns of localization of other related compounds concomitant to the presence or absence of hypericin. Hypericin, pseudohypericin, and protohypericin accumulate in the dark glands. However, the precursor emodin not only accumulates in the dark glands but is also present outside the glands in both hypericin-containing species. In hypericin-lacking H. patulum, however, emodin typically accumulates only in the glands, thereby providing evidence that hypericin is possibly biosynthesized outside the dark glands and thereafter stored in them. The distribution and localization of related compounds were also evaluated and are discussed concomitant to the occurrence of hypericin. Our study provides the basis for further detailed investigation of hypericin biosynthesis by gene discovery and expression studies.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Spatial chemo-profiling of hypericin and related phytochemicals in Hypericum species using MALDI-HRMS imaging

et al. 2015

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“…These two distinct types of glands are present in the plant parts like stem, flowers and leaves, although their distribution is different between species. EO and phloroglucinol derivatives, such as hyperforin are usually found in schizogenous translucent glands that appear as light points streaks when the leaves are held to the sun (Ciccarelli et al 2001;Soelberg et al 2007). Giuliani et al (2010) have shown that Hypericum androsaemum presents typical translucent, EO producing glands, which are distributed on the leaf along both margins (margin glands) and on the lamina (lamina glands).…”

Section: Introductionmentioning

confidence: 99%

Hypericum sp.: essential oil composition and biological activities

2012

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Phytochemical composition of Hypericum genus has been investigated for many years. In the recent past, studies on the essential oils (EO) of this genus have been progressing and many of them have reported interesting biological activities. Variations in the EO composition of Hypericum species influenced by seasonal variation, geographic distribution, phenological cycle and type of the organ in which EO are produced and/or accumulated have also been reported. Although many reviews attributed to the characterization as well as biological activities of H. perforatum crude extracts have been published, no review has been published on the EO composition and biological activities of Hypericum species until recently (Crockett in Nat Prod Commun 5(9): 1493-1506, 2010 Bertoli et al. in Global Sci Books 5:29-47, 2011). In this article, we summarize and update information regarding the composition and biological activities of Hypericum species EO. Based on experimental work carried out in our laboratory we also mention possible biotechnology approaches envisaging EO improvement of some species of the genus.

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“…Many of these species produce a broad spectrum of valuable compounds, mainly naphthodianthrones (hypericin and pseudohypericin), phloroglucinols (hyperforin and adhyperforin), flavonoids (hyperoside, rutin or quercitrin), xanthones and essential oils that are associated with antiviral, antitumor, neuroprotective, antioxidant and antidepressant properties (Kirakosyan et al 2008). It has generally been accepted that these biologically active substances are synthesized, or accumulate in, different types of secretory structures including the dark glands, translucent glands, and secretory canals located in different organs of the plants (leaf, stem and flower tissues) (Soelberg et al 2007;Zobayed et al 2006;Kirakosyan et al 2008). A recent review by Bruni and Sacchetti (2009) shed light on the morphological and chemical variations among different Hypericum species and varieties.…”

Section: Introductionmentioning

confidence: 99%

Effects of plant growth regulators and elicitors on production of secondary metabolites in shoot cultures of Hypericum hirsutum and Hypericum maculatum

Coste

Vlase

Halmágyi

et al. 2011

Plant Cell Tiss Organ Cult

197

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We investigated the effects of plant growth regulators [6-benzyladenine (BA), kinetin (Kin), 6-c, c-dimethylallylaminopurine (2iP), thidiazuron (TDZ) and a-naphthaleneacetic acid (NAA)], modified Murashige and Skoog (MS) medium containing 10 mM NH 4 ? and 5 mM NO 3 -and supplemented with 2iP, BA, Kin and NAA (MSM medium), and two elicitors [jasmonic acid (JA), and salicylic acid (SA)], on plant growth and accumulation of hypericins (hypericin and pseudohypericin) and hyperforin in shoot cultures of Hypericum hirsutum and H. maculatum. Our data suggested that culture of shoots on MS medium supplemented with BA (0.4 mg l -1 ) or Kin (0.4 mg l -1 ) enhanced production of hypericins in H. maculatum and hyperforin in H. hirsutum. Hypericins and hyperforin concentrations decreased in both species when TDZ (0.4 mg l -1 ) was added to the MS medium. Also, TDZ induced hyperhydric malformations and necrosis of regenerated shoots. Cultivation of H. maculatum on MSM medium resulted in approximately twofold increased production of hypericins compared to controls, and the growth of H. hirsutum shoots on the same medium led to a 6.16-fold increase in hyperforin production. Of the two elicitors, SA was more effective in stimulating the accumulation of hypericins. At 50 lM, SA enhanced the production of hypericin (7.98-fold) and pseudohypericin (13.58-fold) in H. hirsutum, and, at 200 lM, enhanced the production of hypericin (2.2-fold) and pseudohypericin (3.94-fold) in H. maculatum.

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Hyperforin Accumulates in the Translucent Glands of Hypericum perforatum

Abstract: The accumulation of hyperforin detected in the translucent glands supports the proposed hypothesis that hyperforin is synthesized by the same biosynthetic machinery as monoterpenes in the chloroplasts of cells delimiting the gland.

Cited by 63 publications

References 15 publications

Spatial chemo-profiling of hypericin and related phytochemicals in Hypericum species using MALDI-HRMS imaging

Spatial chemo-profiling of hypericin and related phytochemicals in Hypericum species using MALDI-HRMS imaging

Hypericum sp.: essential oil composition and biological activities

Effects of plant growth regulators and elicitors on production of secondary metabolites in shoot cultures of Hypericum hirsutum and Hypericum maculatum

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