Phytochemical profiling of several Hypericum species identified using genetic markers

Bruňáková, Katarína; Bálintová, Miroslava; Henzelyová, Jana; Kolarčik, Vladislav; Kimáková, Andrea; Petijová, Linda; Čellárová, Eva

doi:10.1016/j.phytochem.2021.112742

Cited by 11 publications

(4 citation statements)

References 90 publications

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“…The genus Hypericum L ., with about 500 known species, is the largest of the nine genera belonging to the family Hypericaceae (order Malpighiales) [ 1 , 2 ], commonly known as the St. John’s wort family. These taxa are distributed worldwide, with native and introduced species, mainly in temperate regions and tropical mountains [ 3 ].…”

Section: Introductionmentioning

confidence: 99%

Constituents, Enantiomeric Content, and ChE Inhibitory Activity of the Essential Oil from Hypericum laricifolium Juss. Aerial Parts Collected in Ecuador

Salinas

Bec

Calva

et al. 2022

Plants

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The physical properties, chemical composition, enantiomer distribution, and cholinesterase (ChE) inhibitory activity were determined for a steam-distilled essential oil (EO), with a yield of 0.15 ± 0.05 % (w/w), from H. laricifolium aerial parts, collected in southern Ecuador. The oil qualitative and quantitative analyses were performed by GC-EIMS and GC-FID techniques, using two capillary columns containing a non-polar 5%-phenyl-methylpolysiloxane and a polar polyethylene glycol stationary phase, respectively. The main constituents (>10%) detected on the two columns were, respectively, limonene (24.29, 23.16%), (E)-β-ocimene (21.89, 27.15%), and (Z)-β-ocimene (12.88, 16.03%). The EO enantioselective analysis was carried out using a column based on 2,3-diethyl-6-tert-butyldimethylsilyl-β-cyclodextrin. Two mixtures of chiral monoterpenes were detected containing (1R,5R)-(+)-α-pinene (ee = 83.68%), and (S)-(-)-limonene (ee = 88.30%) as the major enantiomers. This finding led to some hypotheses about the existence in the plant of two enantioselective biosynthetic pathways. Finally, the EO exhibited selective inhibitory effects in vitro against butyrylcholinesterase (BuChE) (IC50 = 36.80 ± 2.40 µg/mL), which were about three times greater than against acetylcholinesterase (IC50 = 106.10 ± 20.20). Thus, the EO from Ecuadorian H. laricifolium is an interesting candidate for investigating the mechanism of the selective inhibition of BuChE and for discovering novel drugs to manage the progression of Alzheimer’s disease.

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Section: Introductionmentioning

confidence: 99%

Constituents, Enantiomeric Content, and ChE Inhibitory Activity of the Essential Oil from Hypericum laricifolium Juss. Aerial Parts Collected in Ecuador

Salinas

Bec

Calva

et al. 2022

Plants

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“…For instance, shikimic acid is the precursor of aromatic amino acids and phenolic compounds, being more abundant in the early stages. The main sites of chlorogenic acid accumulation were found to be the leaves, and the amount was found to decrease linearly with the progression of phenological stages, with the top level being attained at the vegetative stage [17,18] . H. androsaemum is devoid of the black nodules that are the typical secretory structures where naphtodiantrones such as hypericin and pseudohypericin are produced in other Hypericum species [1,19] .…”

Section: Resultsmentioning

confidence: 96%

Active compounds and biological activities of Hypericum androsaemum L.: A review

Aguiar,

Costa

2023

J Pharmacogn Phytochem

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Hypericum androsaemum L. is a plant renowned in the Mediterranean basin for diuretic, hepatoprotective, anti-hypertensive, anti-hemorrhoidal, anti-depressant and skin-protective effects. This review makes a critical summary of published pharmacognostical data. H. androasemum contains significant amounts of phenolic compounds, namely chlorogenic acids, flavonoids, triterpenoids, polycyclic polyprenylated acylphloroglucinols (PPAPs) and xanthones. Extracts of the plant have shown radical scavenging activity. The fruits' extracts have shown cytotoxic activity against some cancer cell lines. The plant has some immunomodulatory, DNA-protective, anti-glycation, antidepressant and antiinflammatory effects. Given its effect on fibroblasts proliferation and migration, collagenase and tyrosinase inhibitory action, immunomodulatory effect, UV-protective and lack of phototoxicity, it has potential in skin formulas. It has shown biocidal activity against some bacteria, fungi, nematodes, mollusks and insects. At low concentrations, the extracts were nontoxic on normal cells. However, safety issues may arise with oral administration of high hyperforin H. androasemum preparations.

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“…Plants of the genus Hypericum L. (Hypericaceae) are distributed worldwide, and many Hypericum species, including Hypericum perforatum (St. John’s Wort), Hypericum monogynum , Hypericum attenuatum , Hypericum japonicum , Hypericum scabrum , and Hypericum sampsonii , have long been used in various parts of the world as ethnomedicines or folk medicines with antidepressant, antiphlogistic, febrifuge, analgesic, diuretic, and astringent properties. − In recent years, several Hypericum spp. have drawn great interest in the research community due to their structurally diverse metabolites and potential pharmaceutical applications. , Pharmacological investigations have shown that the secondary metabolites from Hypericum species present anti-inflammatory, , antidepressant, , neuroprotective, , cytotoxic, , antimicrobial, , hepatoprotective, antioxidant, immunosuppressive, anti-HIV, cognition-enhancing, and memory-facilitating activities.…”

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confidence: 99%

“…have drawn great interest in the research community due to their structurally diverse metabolites and potential pharmaceutical applications. 6,7 Pharmacological investigations have shown that the secondary metabolites from Hypericum species present anti-inflammatory, 8,9 antidepressant, 7,10 neuroprotective, 2,11 cytotoxic, 3,12 antimicrobial, 2,3 hepatoprotective, 13 antioxidant, 14 immunosuppressive, 15 anti-HIV, 16 cognition-enhancing, 17 and memory-facilitating 18 activities.…”

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confidence: 99%

Hyperelatolides A–D, Antineuroinflammatory Constituents with Unusual Carbon Skeletons from Hypericum elatoides

Xie,

Wang,

Liu

et al. 2023

J. Nat. Prod.

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Four new δand γ-lactone derivatives, hyperelatolides A−D (1−4, respectively), were discovered from the aerial portions of Hypericum elatoides R. Keller. Their structures were elucidated by analysis of NMR spectra, HRESIMS, quantum chemical calculations of NMR and ECD spectra, and X-ray crystallographic data. Hyperelatolides A (1) and B (2) represent the first examples of δ-lactone derivatives characterized by a (Z)-(5,5-dimethyl-2-(2-oxopropyl)cyclohexylidene)methyl moiety and a benzoyloxy group attached to the βand γ-positions of the δlactone core, respectively, while hyperelatolides C (3) and D (4) are unprecedented γ-lactone derivatives featuring substituents similar to those of 1 and 2. All compounds were tested for their inhibitory effects on NO production in LPS-activated BV-2 cells. Lactones 1 and 2 exhibited considerable antineuroinflammatory activity, with IC 50 values of 5.74 ± 0.27 and 7.35 ± 0.26 μM, respectively. Moreover, the mechanistic study revealed that lactone 1 significantly suppressed nuclear factor kappa B signaling and downregulated the expression of inducible nitric oxide synthase and cyclooxygenase-2 in LPS-induced cells, which may contribute to its antineuroinflammatory activity.

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Phytochemical profiling of several Hypericum species identified using genetic markers

Cited by 11 publications

References 90 publications

Constituents, Enantiomeric Content, and ChE Inhibitory Activity of the Essential Oil from Hypericum laricifolium Juss. Aerial Parts Collected in Ecuador

Constituents, Enantiomeric Content, and ChE Inhibitory Activity of the Essential Oil from Hypericum laricifolium Juss. Aerial Parts Collected in Ecuador

Active compounds and biological activities of Hypericum androsaemum L.: A review

Hyperelatolides A–D, Antineuroinflammatory Constituents with Unusual Carbon Skeletons from Hypericum elatoides

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