Variation of the alkaloid content of Peumus boldus (boldo)

Fuentes-Barros, Gonzalo; Castro-Saavedra, Sebastián; Liberona, Leonel; Acevedo-Fuentes, Williams; Tirapegui, Cristián; Mattar, César; Cassels, Bruce K.

doi:10.1016/j.fitote.2018.02.020

Cited by 28 publications

(35 citation statements)

References 33 publications

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“…The differences observed between NADESs and MeOH can be due to the lack of extractability of partially ionized compounds by MeOH, where electrostatic interactions could significantly contribute to their extraction [38]. Then, when this result is compared with other extraction methods [7,10,[45][46][47][48][49], it is observed that the extraction performance for boldine is still more efficient than the other extraction procedures based on conventional solvents (Table 4). This difference can be explained by the variations in the substrate, the extraction procedure or method of analysis.…”

Section: Extractability Of Boldine From Peumus Boldus Leaves With DIVmentioning

confidence: 92%

“…For example, Rogalisnki and coworkers [44], evaluated the performance of boldine extraction using hot pressurized water and supercritical CO 2 compared with methanol extraction. Also in the work of Fuentes-Barros [7], the extraction of P. boldus alkaloids for HPLC analysis was performed with methanol. As in shown in Figure 3b, in the chromatogram obtained with NADES6, boldine appeared at around t R = 18 min.…”

Section: Extractability Of Boldine From Peumus Boldus Leaves With DIVmentioning

confidence: 99%

“…For example, the concentration of boldine is higher in the bark than in the leaves. Moreover, certain classes of alkaloids are concentrated in other parts such as wood, fruits or roots and it is not possible to detect them in the leaves [7]. So, the analysis of botanical parts of Boldo tree allowed the identification of alkaloids such as boldine, isoboldine, coclaurine, N-methylcoclaurine, (−)-pronuciferine, (+)-reticuline, laurotetanin, N-methyl-laurotetanin, sinoacutin, isocorydine, isocorydine N-oxide, nor-isocorydine and laurolitsin (norboldine) ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Green Extraction of Alkaloids and Polyphenols from Peumus boldus Leaves with Natural Deep Eutectic Solvents and Profiling by HPLC-PDA-IT-MS/MS and HPLC-QTOF-MS/MS

Torres-Vega

Gómez‐Alonso

Pérez‐Navarro

et al. 2020

Plants

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Peumus boldus Mol., is a Chilean medicinal tree used for gastrointestinal and liver diseases. Such medicinal properties are associated with the presence of bioactive flavonoids and aporphine alkaloids. In this study, a new green and efficient extraction method used seven natural deep eutectic solvents (NADES) as extraction media. The extraction efficiency of these NADES was assessed, determining the contents of boldine and total phenolic compounds (TPC). Chemical profiling of P. boldus was done by high-performance liquid chromatography coupled to photo diode array detector and electrospray ion-trap mass spectrometry (HPLC-PDA-ESI-IT/MS) and electrospray ionization quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF-MS). Among the NADES tested, NADES4 (choline chloride-lactic acid) and NADES6 (proline-oxalic acid) enable better extraction of boldine with 0.427 ± 0.018 and 2.362 ± 0.055 mg of boldine g−1 of plant, respectively. Extraction of boldine with NADES4 and NADES6 was more efficient than extractions performed with methanol and water. On the other hand, the highest TPC were obtained using NADES6, 179.442 ± 3.79 mg of gallic acid equivalents (GAE g−1). Moreover, TPC in extracts obtained with methanol does not show significant differences with NADES6. The HPLC-PAD-MS/MS analysis enable the tentative identification of 9 alkaloids and 22 phenolic compounds. The results of this study demonstrate that NADES are a promising green extraction media to extract P. boldus bioactive compounds and could be a valuable alternative to classic organic solvents.

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Section: Extractability Of Boldine From Peumus Boldus Leaves With DIVmentioning

confidence: 92%

Section: Extractability Of Boldine From Peumus Boldus Leaves With DIVmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Green Extraction of Alkaloids and Polyphenols from Peumus boldus Leaves with Natural Deep Eutectic Solvents and Profiling by HPLC-PDA-IT-MS/MS and HPLC-QTOF-MS/MS

Torres-Vega

Gómez‐Alonso

Pérez‐Navarro

et al. 2020

Plants

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“…Fuentes et al reported the isolation of alkaloids from bark, wood, roots, and leaves collected near Maria Pinto, Santiago Metropolitan Region, Chile. Using an extractive methodology following the guidelines of the European Pharmacopoeia, they obtained 0.7%, 0.04%, 0.088%, and 0.025% bulk extract and 0.025%, 0.04%, 1.0%, and 0.09% of crude alkaloids in these plant parts, respectively [94]. Of these fractions, the most abundant alkaloid detected was N-methyllaurotetanine but not boldine in the total The antioxidant properties of boldine and its derivatives have been evidenced through in vivo and in vitro assays, and attributed to the presence of two phenolic groups attached to a highly conjugated system that also has a benzylamine functionality [90].…”

Section: Extractive Methodology Synthesis and Purificationmentioning

confidence: 99%

Oxoisoaporphines and Aporphines: Versatile Molecules with Anticancer Effects

et al. 2019

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Cancer is a disease that involves impaired genome stability with a high mortality index globally. Since its discovery, many have searched for effective treatment, assessing different molecules for their anticancer activity. One of the most studied sources for anticancer therapy is natural compounds and their derivates, like alkaloids, which are organic molecules containing nitrogen atoms in their structure. Among them, oxoisoaporphine and sampangine compounds are receiving increased attention due to their potential anticancer effects. Boldine has also been tested as an anticancer molecule. Boldine is the primary alkaloid extract from boldo, an endemic tree in Chile. These compounds and their derivatives have unique structural properties that potentially have an anticancer mechanism. Different studies showed that this molecule can target cancer cells through several mechanisms, including reactive oxygen species generation, DNA binding, and telomerase enzyme inhibition. In this review, we summarize the state-of-art research related to oxoisoaporphine, sampangine, and boldine, with emphasis on their structural characteristics and the relationship between structure, activity, methods of extraction or synthesis, and anticancer mechanism. With an effective cancer therapy still lacking, these three compounds are good candidates for new anticancer research.

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“…Quercetin is an abundant dietary flavonoid that is claimed to provide multiple health benefits. 19 Geographic latitude seems to affect the content of metabolites such as leaf EOs and alkaloids of P. boldus, 20,21 and the terpenes of Drimys winteri, 22 and may be the case in other Chilean species. 23 We have now examined the leaf, bark, and wood, assaying total polyphenols, total flavonoids, antioxidant potential, and separate alkaloids and polyphenols, and analyzed the leaf EO of individual C. alba trees from 3 natural populations and from a tree farm.…”

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confidence: 99%

Variation of Secondary Metabolites in the Aerial Biomass ofCryptocarya alba

Giordano

Fuentes-Barros

Castro-Saavedra

et al. 2019

Natural Product Communications

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Cryptocarya alba is an important tree species in the Chilean sclerophyllous forest. Its leaves and bark are used in traditional medicine to treat liver diseases and rheumatism. Analyses of the essential oil (EO) show serious discrepancies, and information on other constituents is limited. The aerial biomass of individual trees from 3 wild populations, some old trees, and farmed saplings were analyzed ( n = 132). The EO profiles were studied by gas chromatography/mass spectrometry (GC/MS). The alkaloidal and polyphenol compositions were determined by ultra-high-performance liquid chromatography (UHPLC)/MS-MS. The total polyphenol content, the total flavonoid content, and the antioxidant capacity (diphenylpicrylhydrazyl, azinobisethylbenzothiazolinesulfonic acid, and ferric reducing antioxidant power: DPPH, ABTS, and FRAP respectively) were determined by standard methods. Significant differences were found at the individual and population levels in the contents of polyphenols, total flavonoids, antioxidant capacity, and specific alkaloids for leaves, bark, and wood. Farmed saplings grown under less light showed higher concentrations of higenamine, N-methylcoclaurine, N-methyllaurotetanine, and isocorydine, while those receiving more light were richer in laurolitsine, boldine, coclaurine, catechin, quercetin, epicatechin, quercitrin, and procyanidins. Important variations were found according to the season, age of the tree and of the leaves. The EO composition also varied considerably. These results support the idea that the natural variability of medicinal species is an important subject for study.

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Variation of the alkaloid content of Peumus boldus (boldo)

Cited by 28 publications

References 33 publications

Green Extraction of Alkaloids and Polyphenols from Peumus boldus Leaves with Natural Deep Eutectic Solvents and Profiling by HPLC-PDA-IT-MS/MS and HPLC-QTOF-MS/MS

Green Extraction of Alkaloids and Polyphenols from Peumus boldus Leaves with Natural Deep Eutectic Solvents and Profiling by HPLC-PDA-IT-MS/MS and HPLC-QTOF-MS/MS

Oxoisoaporphines and Aporphines: Versatile Molecules with Anticancer Effects

Variation of Secondary Metabolites in the Aerial Biomass ofCryptocarya alba

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