Chemical constituents isolated from Clusia criuva subsp. Criuva and their chemophenetics significance

Marques, Edson de Jesus; Ferraz, Caline G.; Santos, Iago B.F. dos; Santos, Ismirna I.P. dos; El-Bachá, Ramon dos Santos; Ribeiro, Paulo R.; Cruz, Frederico G.

doi:10.1016/j.bse.2021.104293

Cited by 7 publications

(7 citation statements)

References 70 publications

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“…Herein we propose that a physical-chemical analysis of the adaxial and abaxial surfaces of the A. donax leaf, focused on its potential distribution, environmental behavior, morpho-anatomy and histology, microstructure, chemical organic and inorganic composition, wettability properties, and optical features, is a valuable strategy to get rich additional insight into the reasons behind the presence of this species in the Mediterranean flora. Our main motivation to carry out the present work was the fact that the leaf waxes were found to reveal important information regarding the ecological strategies of plants from a chemophenetics standpoint ( Janaćković et al., 2019 ; Rajčević et al., 2020 ; Marques et al., 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Leaf surfaces and neolithization - the case of Arundo donax L

et al. 2022

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Arundo donax L. (Arundinoideae subfamily, Poaceae family) is a sub-tropical and temperate climate reed that grows in arid and semi-arid environmental conditions, from eastern China to the Mediterranean basin, suggesting potential adaptations at the epicuticular level. A thorough physical-chemical examination of the adaxial and abaxial surfaces of A. donax leaf was performed herein in an attempt to track such chemophenetic adaptations. This sort of approach is of the utmost importance for the current debate about the hypothetical invasiveness of this species in the Mediterranean basin versus its natural colonization along the Plio-Pleistocene period. We concluded that the leaf surfaces contain, apart from stomata, prickles, and long, thin trichomes, and silicon-rich tetralobate phytolits. Chemically, the dominating elements in the leaf ashes are oxygen and potassium; minor amounts of calcium, silicon, magnesium, phosphorous, sulphur, and chlorine were also detected. In both surfaces the epicuticular waxes (whose density is higher in the adaxial surface than in the abaxial surface) form randomly orientated platelets, with irregular shape and variable size, and aggregated rodlets with variable diameter around the stomata. In the case of green mature leaves, the dominating organic compounds of the epicuticular waxes of both surfaces are triterpenoids. Both surfaces feature identical hydrophobic behaviour, and exhibit the same total transmittance, total reflectance, and absorption of incident light. The above findings suggest easy growth of the plant, remarkable epidermic robustness of the leaf, and control of water loss. These chemophenetic characteristics and human influence support a neolithization process of this species along the Mediterranean basin.

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Section: Introductionmentioning

confidence: 99%

Leaf surfaces and neolithization - the case of Arundo donax L

et al. 2022

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“…In addition, the new tocotrienol derivative ( 4 ) has been isolated for the first time from the genus Symphonia . However, the literature indicates that tocotrienol derivatives have already been isolated from other genera of the Clusiaceae family, such as Garcinia [ 45 , 46 ] and Clusia [ 47 ]. To the best of our knowledge, guttiferone K ( 5 ), xanthone V2 ( 7 ), pyranojacareubin ( 8 ), and kaempferol ( 14 ) were isolated for the first time from the genus Symphonia .…”

Section: Resultsmentioning

confidence: 99%

Constituents of the Stem Bark of Symphonia globulifera Linn. f. with Antileishmanial and Antibacterial Activities

et al. 2023

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The chemical investigation of the n-hexane fraction from the methanol extract of the stem bark of Symphonia globulifera Linn f., which displayed good in vitro activity against Leishmania donovani NR-48822 promastigotes (IC50 43.11 µg/mL), led to the isolation of three previously unreported polyprenylated benzophenones, guttiferone U (1), V (2)/W (3), and a new tocotrienol derivative named globuliferanol (4), along with 11 known compounds (5–15). Their structures were elucidated based on their NMR and MS data. Some isolated compounds were assessed for both their antileishmanial and cytotoxic activities against L. donovani and Vero cells, respectively. Guttiferone K (5) exhibited the best potency (IC50 3.30 μg/mL), but with low selectivity to Vero cells. The n-hexane fraction and some compounds were also assessed in vitro for their antibacterial activity against seven bacterial strains. All the samples exhibited moderate to potent antibacterial activity (MICs ≤ 15.6 µg/mL) against at least one of the tested strains.

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“…Clusia obdeltifolia, 48 Clusia burle-marxii, 49 C. pernambucensis, 16 and Clusia criuva. 5 Garcinoic acid shows many bioactive properties including antioxidant, antiproliferative, anti-inflammatory, 50,51 and hypoglycemic activities. 52 A derivative of garcinoic acid was identified to cause peak L29 with [M-H] À at m/z 441.2643 (C 27 H 38 O 5 ) with one oxygen atom more than garcinoic acid.…”

Section: Resultsmentioning

confidence: 99%

“…Clusia species are known to produce a hydrophobic resin from their flowers, a characteristic feature for the attraction of bees that collect it for building nests to prevent against nest insect attack. 4,5 Phytochemical studies of several Clusia species revealed its richness in secondary metabolites, especially prenylated benzophenones and xanthones, proanthocyanidins, terpenes, and tocotrienols, groups associated with many potential biological activities. 6 Benzophenones in Clusia show an extraordinary rich prenylation pattern with low oxidation indices.…”

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confidence: 99%

A multiplex approach of MS, 1D‐, and 2D‐NMR metabolomics in plant ontogeny: A case study on Clusia minor L. organs (leaf, flower, fruit, and seed)

Noleto‐Dias,

Farag,

Porzel

et al. 2023

Phytochemical Analysis

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IntroductionThe genus Clusia L. is mostly recognised for the production of prenylated benzophenones and tocotrienol derivatives.ObjectivesThe objective of this study was to map metabolome variation within Clusia minor organs at different developmental stages.Material and MethodsIn total 15 organs/stages (leaf, flower, fruit, and seed) were analysed by UPLC‐MS and 1H‐ and heteronuclear multiple‐bond correlation (HMBC)‐NMR‐based metabolomics.ResultsThis work led to the assignment of 46 metabolites, belonging to organic acids(1), sugars(2) phenolic acids(1), flavonoids(3) prenylated xanthones(1) benzophenones(4) and tocotrienols(2). Multivariate data analyses explained the variability and classification of samples, highlighting chemical markers that discriminate each organ/stage. Leaves were found to be rich in 5‐hydroxy‐8‐methyltocotrienol (8.5 μg/mg f.w.), while flowers were abundant in the polyprenylated benzophenone nemorosone with maximum level detected in the fully mature flower bud (43 μg/mg f.w.). Nemorosone and 5‐hydroxy tocotrienoloic acid were isolated from FL6 for full structural characterisation. This is the first report of the NMR assignments of 5‐hydroxy tocotrienoloic acid, and its maximum level was detected in the mature fruit at 50 μg/mg f.w. Seeds as typical storage organ were rich in sugars and omega‐6 fatty acids.ConclusionTo the best of our knowledge, this is the first report on a comparative 1D‐/2D‐NMR approach to assess compositional differences in ontogeny studies compared with LC‐MS exemplified by Clusia organs. Results derived from this study provide better understanding of the stages at which maximal production of natural compounds occur and elucidate in which developmental stages the enzymes responsible for the production of such metabolites are preferentially expressed.

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Chemical constituents isolated from Clusia criuva subsp. Criuva and their chemophenetics significance

Cited by 7 publications

References 70 publications

Leaf surfaces and neolithization - the case of Arundo donax L

Leaf surfaces and neolithization - the case of Arundo donax L

Constituents of the Stem Bark of Symphonia globulifera Linn. f. with Antileishmanial and Antibacterial Activities

A multiplex approach of MS, 1D‐, and 2D‐NMR metabolomics in plant ontogeny: A case study on Clusia minor L. organs (leaf, flower, fruit, and seed)

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