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Labdanum resin or "gum" can be obtained from Cistus ladanifer L. by two different extraction methods: the Zamorean and the Andalusian processes. Although its main use is in the fragrance and perfumery sectors, ethnobotanical reports describe its use for medicinal purposes in managing hyperglycemia and mental illnesses. However, data concerning the bioactivities and pharmacological applications are scarce. In this work, it was found that the yield of labdanum resin extracted by the Andalusian process was 25-fold higher than the Zamorean one. Both resins were purified as absolutes, and the Andalusian absolute was purified into diterpenoid and flavonoid fractions. GC-EI-MS analysis confirmed the presence of phenylpropanoids, labdane-type diterpenoids, and methylated flavonoids, which are already described in the literature, but revealed other compounds, and showed that the different extracts presented distinct chemical profile. The potential antidiabetic activity, by inhibition of α-amylase and α-glucosidase, and the potential neuroprotective activity, by inhibition of acetylcholinesterase, were investigated. Diterpenoid fraction produced the higher α-amylase inhibitory effect (~30% and ~40% at 0.5 and 1 mg/mL, respectively). Zamorean absolute showed the highest α-glucosidase inhibitory effect (~14% and ~24%, at 0.5 and 1 mg/mL, respectively). Andalusian absolute showed the highest acetylcholinesterase inhibitory effect (~70% and ~75%, at 0.5 and 1 mg/mL, respectively). Using Caco-2 and HepG2 cell lines, Andalusian absolute and its purified fractions showed moderate cytotoxic/anti-proliferative activity at 24 h exposure (IC50 = 45-70 µg/mL, for Caco-2; IC50 = 60-80 µg/mL, for HepG2), whereas Zamorean absolute did not produce cytotoxicity (IC50 ≥ 200.00 µg/mL). Here we show, for the first time, that labdanum resin obtained by the Andalusian process, and its fractions, are composed of phytochemicals with anti-diabetic, neuroprotective and anti-proliferative potential, which are worth investigating for the pharmaceutical industry. However, toxic side-effects must also be addressed when using these products by ingestion, as done traditionally.
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Cistus , Hipoglucemiantes , Fármacos Neuroprotectores , Hipoglucemiantes/farmacología , Hipoglucemiantes/química , Fármacos Neuroprotectores/farmacología , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/aislamiento & purificación , Humanos , Cistus/química , Resinas de Plantas/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Proliferación Celular/efectos de los fármacos , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Células Hep G2 , Flavonoides/farmacología , Flavonoides/química , Flavonoides/aislamiento & purificaciónRESUMEN
This study intended to evaluate the potential industrial applications of various Acacia species (Acacia melanoxylon, Acacia longifolia, Acacia cyclops, Acacia retinodes, Acacia pycnantha, Acacia mearnsii, and Acacia dealbata) by examining their chemical composition, antioxidant, and antimicrobial properties. Using high-resolution mass spectrometry, a comprehensive analysis successfully identified targeted compounds, including flavonoids (flavonols/flavones) and phenolic acids, such as 4-hydroxybenzoic acid, p-coumaric acid, and ellagic acid. Additionally, p-coumaric acid was specifically identified and quantified within the hydroxycinnamic aldehydes. This comprehensive characterization provides valuable insights into the chemical profiles of the studied species. Among the studied species, A. pycnantha exhibited a higher concentration of total phenolic compounds, including catechin, myricetin, quercetin, and coniferaldehyde. Furthermore, A. pycnantha displayed notable antibacterial activity against K. pneumoniae, E. coli, S. Typhimurium, and B. cereus. The identified compounds in Acacia pods and their shown antibacterial activities exhibit promising potential for future applications. Moreover, vibrational spectroscopy was a reliable method for distinguishing between species. These significant findings enhance our understanding of Acacia species and their potential for various industrial applications.
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Labdanum resin from Cistus ladanifer L. (Cistaceae) is an abundant natural resource in the Iberian Peninsula worth being explored in a sustainable manner. It is already used in the cosmetic industry; mainly by the fragrances/perfumery sector. However, given the highest market share and traditional uses, labdanum resin also has the potential to be used and valued as a cosmetic ingredient for skincare. Aiming to evaluate this potential, labdanum methanolic absolute and fractions purified by column chromatography were characterized by UPLC-DAD-ESI-MS and then evaluated for UV-protection, antioxidant, anti-elastase, anti-inflammatory, and antimicrobial activities. Labdanum absolute represented ~70% of the resin; diterpenoid and flavonoid fractions represented ~75% and 15% of the absolute, respectively. Labdane-type diterpenoids and methylated flavonoids were the main compounds in labdanum absolute and in diterpenoid and flavonoid fractions, respectively. Labdanum absolute showed a spectrophotometric sun protection factor (SPF) near 5, which is mainly due to flavonoids, as the flavonoids' SPF was 13. Low antioxidant activity was observed, with ABTS radical scavenging being the most significant (0.142 ± 0.017, 0.379 ± 0.039 and 0.010 ± 0.003 mgTE/mgExt, for the absolute and flavonoid and terpene fractions, respectively). Anti-aging and anti-inflammatory activity are reported here for the first time, by the inhibition of elastase activity (22% and 13%, by absolute and flavonoid extract at 1 mg/mL), and by the inhibition of nitric oxide production in LPS-induced RAW 264.7 cells (84% to 98%, at 15 µg/mL extracts, flavonoid fraction the most active), respectively. Antimicrobial activity, against relevant skin and cosmetic product microorganisms, Staphylococcus aureus, Pseudomonas aeruginosa, Candida albicans, and Escherichia coli, revealed that only S. aureus was susceptible to labdanum absolute (MIC: 1.2 mg/mL) and its fractions (MIC: <0.3 mg/mL). In conclusion, labdanum resin showed potential to be used in sunscreen cosmetics, anti-inflammatory skincare cosmeceuticals or medicines but has low potential as a cosmetic product preservative given the low antioxidant and low-spectrum antimicrobial activities.
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MAIN CONCLUSION: Cistus ladanifer has a well-defined taxonomic identity. 2,2,6-trimethylcyclohexanone may be an authenticity and taxonomic marker. Its traits and applications make it a possible economic resource fitted for Mediterranean areas. Cistus ladanifer is a dominant shrub species endemic to the western Mediterranean region. Due to its dominant nature and its potential ecological, aromatic or pharmacological applications, C. ladanifer has been the object of numerous studies. In this review current knowledge on different aspects of this species is summarized, from its taxonomy to its chemical characterisation or its competitive traits. There are no doubts about the taxonomic entity of C. ladanifer, although the recognition of infraspecific taxa deserves more attention. Given that the fragrant exudate of C. ladanifer holds a very specific composition, one species specific carotenoid, 2,2,6-trimethylcyclohexanone, derivative is proposed as an authenticity marker for uses of C. ladanifer in pharmacological or aromatic industries. Evidence is also gathered on the extreme adaptation of C. ladanifer to stressful conditions in the Mediterranean region, such as the ability to survive in low hydric and high solar exposition conditions, presistence in poor and contaminated soils, and growth inhibition of several other plants through the release of allelochemicals. Thus, the finding of potential applications for this plant may contribute to enhance the economic dimension of derelict lands, such as mine tailings or poor agricultural Mediterranean areas.
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Cistus/química , Cistus/clasificación , Cistus/genética , Ecología , Ecosistema , Región Mediterránea , Recursos Naturales , FilogeniaRESUMEN
INTRODUCTION: Although cartilaginous tumors have low microvascular density, vessels are important for the provision of nutrition so that the tumor can grow and generate metastasis. The aim of this study was to assess the value of the vascular pattern classification as a prognostic tool in chondrosarcomas (CSs) and its relation with vascular endothelial growth factor (VEGF) expression. MATERIALS AND METHODS: This was a retrospective study of 21 enchondromas and 57 conventional CSs. Clinical data and outcome were retrieved from medical files. CSs histologic grades (on a scale of 1 to 3) were determined according to the World Health Organization classification. The vascular pattern (on a scale of A to C) was assessed through CD34, according to Kalinski. CD105 and VEGF were also evaluated. RESULTS: Poor outcome was significantly associated with vascular pattern groups B and C. Higher vascular pattern were 6.5 times more frequent in moderate-grade and high-grade CSs than in grade 1 CS. On multivariate analysis, a clear correlation was found between VEGF overexpression and B/C vascular patterns. Only 18 (benign and malignant) tumors stained for CD105. DISCUSSION: The results point to the use of the vascular pattern classification as a prognostic tool in CSs and to differentiate low-grade from moderate-grade/high-grade CSs. Vascular pattern might be also used to complement histologic grade, VEGF immunostaining, and microvascular density, for indicating a patient's prognosis. Low-grade CSs develop under low neoangiogenesis, which conforms to the slow growth rate of these tumors.