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

doi:10.1016/j.bse.2021.104293

Biochemical Systematics and Ecology

Volume 97, August 2021, 104293

https://doi.org/10.1016/j.bse.2021.104293 Get rights and content

Highlights

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We described the phytochemical study of Clusia criuva non-polar extracts.
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We reported the isolation of twenty-four compounds from Clusia criuva trunks.
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Chemophenetics significance of the isolated compounds is discussed.
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The cytotoxic activity against GL-15 glioblastoma-derived human cell line was tested.

Abstract

Clusia criuva belongs to the Clusiaceae family and it is endemic to the rupestrian fields in Chapada Diamantina National Park (Brazil). Phytochemical investigation of C. criuva trunks led to the isolation of five triterpenoids [winchic acid (1), betulinic acid (2), lupeol (3), friedelin (4), and friedelinol (5)], four steroids [lanosterol (6), stigmasterol (7), β-sitosterol (8), and sitostenone (9)], seven polyprenylated benzophenone derivatives [propolone A (10), propolone B (11), propolone C (12), propolone D (13), sampsonione B (14), hyperisampsin E (15), and hyperisampsin F (16)], four xanthones [neriifolone C (17), 6-deoxyisojacareubin (18), osajaxanthone F (19), and brasilixanthone B (20)], two biphenyls [aucuparina (21) and 2,2-dimethyl-5-hydroxy-7-phenylchromene (22)], and two tocotrienol derivatives [2Z- and 2E-δ-tocotrienoloic acids (23 and 24)]. Compounds 1, 11, 12, 15, and 16 were isolated for the first time in the Clusiaceae family, compounds 17, 19 and 21 were isolated for the first time in the genus Clusia, whereas 2–10, 13, 14, 18, 20, 22–24 were isolated for the first time in Clusia criuva. Compounds 1, 2, 11, 12, 13 and 15 showed potent in vitro cytotoxic activity against GL-15 glioblastoma-derived human cell line. Chemophenetics significance of these compounds is described herein.

Section snippets

Subject and source

Clusiaceae (Malpighiales) is a pantropical family consisting of about 15 genera and 800 species. The neotropical genus Clusia is one of the most representative genera of the Clusiaceae family and it encompasses up to 400 species (Alencar et al., 2020; Stevens, 2001). Species of this genus are highly diversified in Central and South America, where they can be found as trees and shrubs, hemi-epiphytes, epiphytes and lianes. Clusia species are recognized by their ability to produce a latex that

Previous work

Metabolite profiling by gas chromatography coupled with mass spectrometry (GC-MS) of the non-polar fractions of the latex of the C. criuva subsp. criuva and C. criuva subsp. parviflora allowed the identification of some simple benzenoid compounds such as acetophenone, ethyl benzoate, benzaldehyde and p-anisaldehyde, several fatty acid derivatives, and several mono and sesquiterpenoids, such as camphene, β-pinene, α-ylangene, α-copaeno, (e)-α-bergamontene, α-muurolene, δ-cadinene, α-cadinene,

Present study

In the present work, we report the isolation and identification of 24 known compounds from Clusia criuva trunks, including five triterpenoids (1–5), four steroids (6–9), seven polyprenylated benzophenone derivatives (10–16), four xanthones (17–20), two biphenyls (21–22), and two tocotrienol derivatives (23–24) (Fig. 1, Fig. 2, Fig. 3). Their structures were proposed after careful analysis of ¹H and ¹³C NMR, DEPT 135, HMBC, HMQC, COSY, NOESY and IR spectra as well as comparison with the

Chemophenetics importance

Clusia criuva Cambess went through a recent taxonomic reorganization based on the stamen/staminode morphology and geographical occurrence, causing it to be divided into two subspecies currently recognized as C. criuva subsp. criuva and C. criuva subsp. parviflora (Cortez et al., 2019). In C. criuva subsp. criuva, the anthers are three to five times larger than the apical connective extension, whereas in C. criuva subsp. parviflora the anthers are two to six times smaller than the apical

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgements

Financial support was provided by FINEP, CAPES, CNPq, and FAPESB.

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