Uliginosin B, a phloroglucinol derivative from Hypericum polyanthemum: A promising new molecular pattern for the development of antidepressant drugs

Stein, Ana Cristina; Viana, Alice Fialho; Müller, Liz Girardi; Nunes, Jéssica de Matos; Stolz, Eveline Dischkaln; Rego, Jean–Claude do; Costentin, Jean; Poser, Gilsane Lino von; Rates, Stela Maris Kuze

doi:10.1016/j.bbr.2011.11.031

Cited by 45 publications

(37 citation statements)

References 48 publications

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“…display a wealth of structural variety (Avato et al 2004, Gibbons et al 2005, Manning et al 2011). A number of these compounds have been shown to induce diverse bioactivities when applied to other organisms (Schempp et al 2002, Avato et al 2004, Mennini et al 2004, Beerhues 2006, Hillwig et al 2008, Henry et al 2009, Saddiqe et al 2010, Wang et al 2011, Stein et al 2012, Zaher et al 2012). St. John’s Wort contains a single monoacylphloroglucinol that has been the subjects of hundreds of medicinal studies (hyperforin), but no known diacylphloroglucinols.…”

Section: Discussionmentioning

confidence: 99%

“… * Relative abundance based on an apigenin internal standard. 1 Taylor and Brooker, 1969; 2 Ishiguro et al, 1987; 3 Rocha et al, 1996; 4 Adam et al, 2002; 5 Huang et al, 2011; 6 Stein et al, 2012. Abbreviation: phloroisobutyrophenone=PIB; methyl=me; pren=prenyl; oxo=oxo; ib=isobutyryl; C=chromene …”

Section: Figurementioning

confidence: 99%

“…Hyperforin is also toxic to gram-positive bacteria (Reichling et al 2001, Avato et al 2004, Joray et al 2011), has been shown to be a potential anticarcinogen (Schempp et al 2002) and is an angiogenesis inhibitor (Schempp et al 2005). Four less studied, acylphloroglucinols, saroaspidin A, saroaspidin B, uliginosin A, and uliginosin B have also been shown to have a variety of biological activities (Ishiguro et al 1987, Rocha et al 1995, Stein et al 2012)…”

Section: Introductionmentioning

confidence: 99%

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Identification and biosynthesis of acylphloroglucinols in Hypericum gentianoides

Crispin

Hur

Park

et al. 2013

Physiologia Plantarum

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Species of the genus Hypericum contain a rich array of unusual polyketides, however, only a small proportion of the over 450 Hypericum species, other than the popular medicinal supplement St. John’s Wort (H. perforatum), have even been chemically characterized. H. gentianoides, a small annual used medicinally by Cherokee Americans, contains bioactive acylphloroglucinols. Here, we identify acylphloroglucinol constituents of H. gentianoides and determine a potential pathway to their synthesis. Liquid chromatography/electrospray ionization-mass spectrometry (LC/ESI-MS) and HPLC-UV indicate that the level of accumulation and profile of acylphloroglucinols in H. gentianoides vary little seasonally when grown in a greenhouse, but do vary with development and are highly dependent on the accession, highlighting the importance of the selection of plant material for study. We identify the chemical structures of the nine prevalent polyketides, based on LC/ESI-MS and hybrid quadrupole orthogonal time-of-flight mass (Q-TOF) spectrometry; these metabolites include one monomeric phlorisobutyrophenone (PIB) derivative and eight dimeric acylphloroglucinols. Q-TOF spectrometry was used to identify eight additional PIB derivatives that were not detected by LC/ESI-MS. These data lead us to propose that diacylphloroglucinols are synthesized via modification of PIB to yield diverse phloroglucinol and filicinic acids moieties, followed by dimerization of a phloroglucinol and a filicinic acid monomer to yield the observed complement of diacylphloroglucinols. The metabolomics data from H. gentianoides are accessible in PMR (http://www.metnetdb.org/pmr), a public metabolomics database with analysis software for plants and microbial organisms.

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Section: Discussionmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Identification and biosynthesis of acylphloroglucinols in Hypericum gentianoides

Crispin

Hur

Park

et al. 2013

Physiologia Plantarum

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“…Among the compounds present in this fraction are the dimeric phloroglucinols japonicin A and uliginosin B [5,6] (Fig. Cytotoxic activity and tumor suppression [8,[11][12][13] was observed as well. The phloroglucinols isolated from several P-values < 0.05 were considered statistically significant and the significance level is represented as follows: *P < 0.05, **P < 0.01, and ***P < 0.001 compared with controls.…”

Section: Resultsmentioning

confidence: 91%

Antiproliferative activity of the dimeric phloroglucinol and benzophenone derivatives of Hypericum spp. native to southern Brazil

Pinhatti¹,

Barros²,

Farias³

et al. 2013

Anti-Cancer Drugs

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A large number of plants are known to possess strong antitumor properties. Previous studies have verified the antiproliferative activity of the extracts and fractions from six species of Hypericum spp. growing in southern Brazil. In the present study, the in-vitro antiproliferative effects of two dimeric phloroglucinols (japonicin A and uliginosin B, isolated from Hypericum myrianthum) and two benzophenones (cariphenone A and cariphenone B, isolated from H. carinatum) were investigated against three tumor cell lines (HT-29 - human colon carcinoma cells; U-251 - human glioma cell line, and OVCAR-3 - human ovarian carcinoma cells). In addition, different doses of these compounds were associated with cytotoxic drugs commonly used as chemotherapy in the clinic. Cariphenone A and cariphenone B showed moderate antiproliferative activity against all tumor cell lines at a dose of 100 μg/ml. Unlike benzophenones, japonicin A and uliginosin B exerted antiproliferative effects only in the OVCAR-3 cell line. Moreover, a very strong synergistic effect was demonstrated by the association of subeffective doses of japonicin A with the chemotherapeutic drug paclitaxel, decreasing cellular proliferation of the OVCAR-3 cell line. These preliminary results provide a scientific basis to further pursue these compounds as potential combined therapy for certain tumor types.

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“…1) from Hypericum polyanthemum was studied in rats also receiving imipramine, bupropion, and fluoxetine, all (including the herbal compound) at subeffective doses. 22 combinations were as effective for relieving depression as full doses of the drugs or the herbal compound in isolation. Low-dose crude extracts of H. polyanthemum were also effective when combined with subtherapeutic doses of antidepressants.…”

Section: Hypericummentioning

confidence: 99%

Herbal Adjuncts to Antidepressants

Yarnell

2015

Alternative and Complementary Therapies

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The intentional use of herbal medicines to increase efficacy or decrease adverse effects of antidepressant drugs is reviewed, with notes about situations (mostly isolated case studies) in which such combinations might have been harmful. Hypericum perforatum (St. John's wort), a common antidepressant herb, is reviewed first, given that there are a number of concerns about possible harms that might arise from its use with various antidepressants. Although a handful of case studies suggest that there are problems, there is little definitive information, and preclinical research suggests the possibility of benefits.The safety of combining various herbs with monoamine oxidase-inhibiting drugs is reviewed next. Studies supporting the use of Crocus sativus (saffron) and Ginkgo biloba (ginkgo) to offset sexual adverse effects of selective serotonin reuptake inhibitors (SSRIs) are reviewed. Pausinystalia yohimbe (yohimbe) and its alkaloid yohimbine's ability to augment antidepressant therapy is discussed. The use of the herbal formula Rikkunshi-tō (Liù Jūn Zǐ Wán) to offset gastrointestinal adverse effects of SSRIs is reviewed. Finally, research on combining Rauvolfia serpentina (Indian snakeroot) and its alkaloid reserpine with antidepressants is mentioned. Much more research is needed in this area, given how frequently antidepressant drugs and herbs are used by patients.

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Uliginosin B, a phloroglucinol derivative from Hypericum polyanthemum: A promising new molecular pattern for the development of antidepressant drugs

Cited by 45 publications

References 48 publications

Identification and biosynthesis of acylphloroglucinols in Hypericum gentianoides

Identification and biosynthesis of acylphloroglucinols in Hypericum gentianoides

Antiproliferative activity of the dimeric phloroglucinol and benzophenone derivatives of Hypericum spp. native to southern Brazil

Herbal Adjuncts to Antidepressants

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