Identification of dehydroabietc acid from Boswellia thurifera resin as a positive GABAA receptor modulator

Rueda, Diana C.; Raith, Melanie; Mieri, Maria De; Schöffmann, Angela; Hering, Steffen; Hamburger, Matthias

doi:10.1016/j.fitote.2014.09.002

Cited by 21 publications

(22 citation statements)

References 32 publications

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“…In another experiment based on the oocyte assay, compounds 4-6 were tested for their effects on GABA A receptors (α 1 β 2 γ 2s ) by means of the two-microelectrode voltage clamp technique in Xenopus laevis oocytes [4]. All compounds were screened at concentrations of 10 and 100 µM and compared with DHA (2a) as a positive control [4]. The results are summarized in ▶ table 2.…”

Section: Resultsmentioning

confidence: 99%

“…The experiments were carried out following procedures formerly described with a few modifications [4,16]. Briefly, follicle membranes covering oocytes were enzymatically digested with 2 mg • mL − 1 collagenase (type 1A).…”

Section: Expression Of Gabaa Receptors In Xenopus Laevis Oocytesmentioning

confidence: 99%

“…For example, DHA displays not only antiulcer and antimicrobial properties, but also antitumor effects [2,3]. Recently, DHA was reported as a positive GABA A receptor modulator inducing significant receptor modulation in the oocyte assay, with a maximal potentiation of I GABA of 682.3 ± 44.7 % at 100 μM [4].…”

Section: Introductionmentioning

confidence: 99%

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Antiproliferative Activity and Effect on GABAA Receptors of Callitrisic Acid Derivatives

Stadler

Padrón

González-Cardenete

2017

PMIO

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The semisynthesis and biological activity of the naturally occurring abietane diterpenoids callitrisic acid (4a; 4-epidehydroabietic acid) and callitrisinol (6) are reported. These compounds and jiadifenoic acid C (5) were obtained from methyl callitrisate (4b) isolated from Sandarac resin for biological evaluation and comparison with the biological activities of C4 epimers such as dehydroabietic acid (2a). In particular, the antiproliferative activity against a panel of six representative human solid tumor cell lines (A549, HBL-100, HeLa, SW1573, T-47D, WiDr) and the effect on GABAA receptors (α 1 β 2 γ 2s) were evaluated. The GI50 values were in the range of 3.4–61 µM and the potentiation of IGABA was 269–311% at 100 µM. Callitrisinol (6) was found to be 6.7-fold more potent than the reference etoposide in the WiDr (colon) cancer cell line. The role of the stereogenic center at C4 for antiproliferative and GABAA receptor modulating activities in the dehydroabietane scaffold has thus been revealed.

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Section: Resultsmentioning

confidence: 99%

Section: Expression Of Gabaa Receptors In Xenopus Laevis Oocytesmentioning

confidence: 99%

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Antiproliferative Activity and Effect on GABAA Receptors of Callitrisic Acid Derivatives

Stadler

Padrón

González-Cardenete

2017

PMIO

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“…Dehydroabietic acid ( 202 ) was isolated from Boswellia thurifera , now classified as Boswellia serrata , and analysed in Xenopus laevis oocytes [ 148 ]. The compound potentiated GABA-induced chloride currents by 397.5% at 100 µM and showed an EC 50 value of 8.7 µM.…”

Section: Natural Gaba(a) Receptor Modulatorsmentioning

confidence: 99%

Structure-Dependent Activity of Natural GABA(A) Receptor Modulators

Çiçek

2018

Molecules

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GABA(A) receptors are ligand-gated ion channels consisting of five subunits from eight subfamilies, each assembled in four hydrophobic transmembrane domains. This pentameric structure not only allows different receptor binding sites, but also various types of ligands, such as orthosteric agonists and antagonists, positive and negative allosteric modulators, as well as second-order modulators and non-competitive channel blockers. A fact, that is also displayed by the variety of chemical structures found for both, synthetic as well as nature-derived GABA(A)-receptor modulators. This review covers the literature for natural GABA(A)-receptor modulators until the end of 2017 and discusses their structure-activity relationship.

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“…Ferruginol (1) has also shown promising antileishmanial activity against L. donovani promastigotes [15]. In addition, dehydroabietic acid (3) from Boswellia thurifera resin has been reported as a positive gamma-aminobutyric acid type A (GABAA) receptor modulator [16]. Recently, we reported on the synthesis and biological activity of (+)-liquiditerpenoic acid A or abietopinoic acid [17].…”

Section: Introductionmentioning

confidence: 99%

Biological Profiling of Semisynthetic C19-Functionalized Ferruginol and Sugiol Analogues

et al. 2021

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The abietane-type diterpenoids are significant bioactive compounds exhibiting a varied range of pharmacological properties. In this study, the first synthesis and biological investigation of the new abietane-diterpenoid (+)-4-epi-liquiditerpenoid acid (8a) together with several of its analogs are reported. The compounds were generated from the readily available methyl callitrisate (7), which was obtained from callitrisic acid present in Moroccan Sandarac resin. A biological evaluation was conducted to determine the effects of the different functional groups present in these molecules, providing basic structure–activity relationship (SAR) elements. In particular, the ferruginol and sugiol analogs compounds 10–16 were characterized by the presence of a phenol moiety, higher oxidization states at C-7 (ketone), and the hydroxyl, methyl ester or free carboxylic acid at C19. The biological profiling of these compounds was investigated against a panel of six human solid tumor cell lines (HBL-100, A549, HeLa, T-47D, SW1573 and WiDr), four parasitic Leishmania species (L. donovani, L. infantum, L. guyanensis and L. amazonensis) and two malaria strains (3D7 and K1). Furthermore, the capacity of the compounds to modulate gamma-aminobutyric acid type A (GABAA) receptors (α1β2γ2s) is also described. A comparison of the biological results with those previously reported of the corresponding C18-functionalized analogs was conducted.

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Identification of dehydroabietc acid from Boswellia thurifera resin as a positive GABAA receptor modulator

Cited by 21 publications

References 32 publications

Antiproliferative Activity and Effect on GABAA Receptors of Callitrisic Acid Derivatives

Antiproliferative Activity and Effect on GABAA Receptors of Callitrisic Acid Derivatives

Structure-Dependent Activity of Natural GABA(A) Receptor Modulators

Biological Profiling of Semisynthetic C19-Functionalized Ferruginol and Sugiol Analogues

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