Pentacyclic Triterpenoids Isolated from Celastraceae: A Focus in the 13C-NMR Data

Camargo, Karen Caroline; Aguilar, Mariana Guerra de; Moraes, Acácio Raphael Aguiar; Castro, Raquel Goes de; Szczerbowski, Daiane; Miguel, Elizabeth Luciana Marinho; Oliveira, L.R.S.; Sousa, Grasiely Faria de; Vidal, Diogo M.; Duarte, Lucienir Pains

doi:10.3390/molecules27030959

Cited by 4 publications

(1 citation statement)

References 300 publications

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“…The chemical structures of the known isolated compounds were determined by comparing their 1 H and 13 C-NMR data with those available in the literature (2, [12] 3, [13] 4, [12] 5, [12] 6, [14] 7, [15] 8, [16] and 9 [17] ). nated with one or more fatty acids.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots

Marinho Miguel,

de Sousa,

Duarte

et al. 2023

Chemistry & Biodiversity

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Plants from Salacia genus are used in traditional medicine for a wide range of diseases. Previous studies reported bioactive pentacyclic triterpenoids from S. elliptica leaves and branches. In this study, the novel pentacyclic triterpenoid 7α,15α‐dihydroxyfriedelan‐3‐one (1) was obtained from the roots of Salacia elliptica, along with seven known compounds: friedelan‐3‐one (2), friedelan‐3β‐ol (3), friedelan‐1,3‐dione (4), friedelan‐3,15‐dione (5), 15α‐hydroxyfriedelan‐3‐one (6), 15α,26‐dihydroxyfriedelan‐3‐one (7), and 26‐hydroxyfriedelan‐3,15‐dione (8). Additionally, one steroid, spinasterol (9), was also identified. The chemical structures of all compounds were established through 1H and 13C‐NMR. Compound 1 was analysed by additional 2D experiments (HMBC, HSQC, COSY, and NOESY) for complete elucidation. Furthermore, the cytotoxicity of compounds 2, 3, 6, 7 and 8 against the A549 lung cancer cells model was evaluated. The flow cytometry analysis revealed a significant cytotoxic activity similar to that exhibited by the triterpenoid lupeol. Additionally, compounds 2, 3, 6, and 7 were tested for in vitro antifungal activity against Candida, Cryptococcus and Sporothrix strains. However, all compounds showed no activity at the tested concentrations.

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Section: Introductionmentioning

confidence: 99%

Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots

Marinho Miguel,

de Sousa,

Duarte

et al. 2023

Chemistry & Biodiversity

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Antimalarial compounds from the climbing stems of salacia debilis

Laryea,

Boadu Ampomah,

Ekuadzi

et al. 2023

Natural Product Research

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Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway

Fernández-Calleja,

García-Domínguez,

Redondo

et al. 2023

Front. Plant Sci.

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Phytophthora cinnamomi is an important plant pathogen responsible for dieback diseases in plant genera including Quercus, Fagus, Castanea, Eucalyptus, and Pinus, among others, all over the world. P. cinnamomi infection exerts tremendous ecological and economic losses. Several strategies have been developed to combat this pathogenic oomycete, including the search for novel anti-oomycete compounds. In this work, a Mediterranean vascular plant, Phlomis purpurea, has been screened for secondary bioactivity against this pathogen. The genus Phlomis includes a group of herbaceous plants and shrubs described as producers of many different bioactive compounds, including several triterpenoids. Triterpenoids are well-known molecules synthesized by plants and microorganisms with potent antioxidant, antitumoral, and antimicrobial activities. We have isolated by HPLC-DAD and characterized by HPLC-MS and NMR two nortriterpenoid compounds (phlomispentaol A and phlomispurtetraolone) from the root extracts of P. purpurea. One of them (phlomispentaol A) is active against the plant pathogenic oomycete P. cinnamomi (based on in vitro inhibition bioassays). Based on their chemical structure and their relationship to other plant triterpenoids, oleanolic acid is proposed to be the common precursor for these molecules. The anti-oomycete activity shown by phlomispentaol A represents a promising alternative to counteract the worldwide-scale damage caused to forest ecosystems by this pathogen.

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Pentacyclic Triterpenoids Isolated from Celastraceae: A Focus in the 13C-NMR Data

Cited by 4 publications

References 300 publications

Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots

Evaluation of Cytotoxicity and Antifungal Activity of Friedelanes from Salacia elliptica Roots

Antimalarial compounds from the climbing stems of salacia debilis

Isolation of two triterpenoids from Phlomis purpurea, one of them with anti-oomycete activity against Phytophthora cinnamomi, and insights into its biosynthetic pathway

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