Lepidotrichilins A and B, New Protolimonoids with Cytotoxic Activity from Trichilia Lepidota (Meliaceae)

Terra, Wagner da Silva; Vieira, Ivo José Curcino; Braz-Filho, Raimundo; Freitas, William Rodrigues de; Kanashiro, Milton; Torres, Maria Conceição M.

doi:10.3390/molecules181012180

Cited by 19 publications

(13 citation statements)

References 18 publications

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“…48,50 Dereplication analysis of a number of semipurified fractions obtained from the VLC purification of the medium polarity fraction S6). 51,52 Similarly, and even though the dereplication analysis of fraction 2J (Figure S23) S8). 45,53 Similarly, the monohydroxylated xanthone 4 could be detected in fraction 2K (Figures S30 and S31, Table S9).…”

Section: Resultsmentioning

confidence: 81%

Using ¹³C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Silva-Castro

Derbré

Ray

et al. 2021

Phytochemical Analysis

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Introduction: Xanthones are metabolites with a variety of biological properties. The Clusiaceae family, which until recently included the genus Calophyllum, is recognised for its production of monohydroxylated and polyhydroxylated xanthones. Presently, C. brasiliense is the only Calophyllum spp. known to occur in the Yucatan peninsula. Objective: To use a combination of traditional phytochemical methods and carbon-13 nuclear magnetic resonance ( 13 C-NMR) dereplication analysis to identify xanthones in the stem bark of C. brasiliense. Material and methods: Initial fractionation and purification of the stem bark extract of C. brasiliense produced macluraxanthone (1). Additional xanthones, together with chromanones and terpenoids, were identified using 13 C-NMR dereplication analysis in different semipurified fractions obtained from the low and medium polarity fractions of the stem bark extract of C. brasiliense.Results: Initial identification of macluraxanthone (1) was confirmed by 13 C-NMR dereplication analysis; additionally, 13 C-NMR dereplication analysis allowed the identification of a number of monohydroxylated and polyhydroxylated xanthones, together with chromanones and terpenoids. Conclusion:This study confirms C. brasiliense as a rich source of xanthones and the 13 C-NMR dereplication analysis as a suitable method to quickly identify the presence of different families of secondary metabolites in semipurified fractions.

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Section: Resultsmentioning

confidence: 81%

Using ¹³C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Silva-Castro

Derbré

Ray

et al. 2021

Phytochemical Analysis

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“…In recent studies, the anticancer properties have been found in some plant extracts and their isolated compounds developed by the researchers. Amongst them is X. granatum , a well-known mangrove plant, a rich source of bioactive compounds, such as protolimonoids (apotirucallanes) [ 57 , 58 ], gedunin [ 16 ], xylogranatumines A–G [ 53 ], protoxylocarpins F–H [ 25 ], and so on, which showed anticancer activity. Besides, protolimonoids exhibited a wide range of bioactivities, including insecticidal [ 59 ], and CDC25B (M-phase inducer phosphatase 2) inhibitory properties [ 60 ].…”

Section: Resultsmentioning

confidence: 99%

Ethnomedicinal Use, Phytochemistry, and Pharmacology of Xylocarpus granatum J. Koenig

Dey

Quispe

Hossain

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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The mangrove plants are the potential sources of foods and remedies for people living in the forests and nearby communities. Xylocarpus granatum J. Koenig is traditionally used to treat various diseases including diarrhea, cholera, dysentery, fever, malaria, and viral infections, among others. To summarize critically the taxonomy, ethnomedicinal, phytochemistry, and pharmacological activities of X. granatum, information was collected from different databases. An up-to-date search (till June 2020) was carried out with the help of various scientific web resources from databases such as PubMed, Science Direct, Google Scholar, and various patent offices (e.g., WIPO, CIPO, and USPTO) using the keywords “Xylocarpus granatum” and then paired with ethnomedicinal use and phytochemical, phytochemistry, and pharmacological activity (in vitro, ex vivo, and in vivo studies). Findings revealed that seeds, fruits, stem bark, leaf, and twigs of X. granatum exhibited a wide range of key phytochemicals including limonoids, phragmalin, limonoid-based alkaloids, mexicanolides, protolimonoids, flavonols, and lactones. The plant possessed potent antioxidant, anticancer, antidiabetic, antimicrobial, antimalarial, antifeedant, and neuroprotective activities. No clinical studies have been reported in the databases. Ethnomedicinal assessment indicated the application of X. granatum in various fields of medical science specially to treat various human ailments, and this was attributed to the presence of enormous alkaloids as confirmed by pharmacological studies. However, to understand the mechanism of action in-depth studies are required. In view of these findings, more research is necessary to explore and characterize the chemical compounds and toxicological aspects of this medicinal mangrove plant. Overall, it can be stated that X. granatum may be one of the hopeful medicinal herbs for the treatment of various diseases in human beings.

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“…The protolimonids 6 isolated from this plant were more toxic (IC50 9.3 mg/mL) compared to both strains tested. As for the extracts, the hexanic (IC50 62.5mg/mL) exhibited the most significant cytotoxic activity against both strains (Terra et al, 2013). It is important to note that protolimonids are proven to be toxic to tumor cells.…”

Section: Trichilia Lepidota Martmentioning

confidence: 99%

Review on the therapeutic activities of the genus Trichilia

Silva

Almeida

Silva

et al. 2021

RSD

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The genus Trichilia (Meliaceae family) has been attracting interest among Brazilian Flora, due to the biological activities of its secondary metabolites. This genus has species distributed throughout tropical America, recognized for its significant economic importance and high commercial value. Its composition consists mainly of terpenoids (triterpenes, sesquiterpenes, limonoids and steroids) and polyphenols (flavonoids and tannins). In folk medicine this genus is used in preparations such as antimicrobial, antimalarial, antiviral and antioxidant. Studies carried out with several species of the genus Trichilia show that these plants have antioxidant, anticholinesterase, antimicrobial activities against pathogens of great clinical importance, neuroprotective, anti-anaphylactic and anti-inflammatory. In addition, analgesic, antineoplasic, hepatoprotective and immunomodulatory activities have also been investigated and proven in the literature. Based on the great biotechnological potential of the genus Trichilia, from the few studies on its applications in human health and in view of the importance of searching for natural substances that have effective therapeutic activities, this review highlights the main therapeutic applications of species of this genus found in the literature, and stimulate further studies on the use of these plants in the treatment of various diseases. For this, a survey on the topic was carried out in the main sources of scientific research in the period from 2005 to 2020, leading us to conclude that this genus can be a potent ally in the search for new phytotherapic drugs.

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Lepidotrichilins A and B, New Protolimonoids with Cytotoxic Activity from Trichilia Lepidota (Meliaceae)

Cited by 19 publications

References 18 publications

Using ¹³C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Using ¹³C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Ethnomedicinal Use, Phytochemistry, and Pharmacology of Xylocarpus granatum J. Koenig

Review on the therapeutic activities of the genus Trichilia

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Lepidotrichilins A and B, New Protolimonoids with Cytotoxic Activity from Trichilia Lepidota (Meliaceae)

Cited by 19 publications

References 18 publications

Using 13C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Using 13C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Ethnomedicinal Use, Phytochemistry, and Pharmacology of Xylocarpus granatum J. Koenig

Review on the therapeutic activities of the genus Trichilia

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Using ¹³C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense

Using ¹³C‐NMR dereplication to aid in the identification of xanthones present in the stem bark extract of Calophyllum brasiliense