Phytochemical study of Pittosporum undulatum: Searching for new guaiane-type sesquiterpenes with anti-inflammatory activity

Mendes, Sofia Alexandra Carreiro; Madruga, João; Lima, Edeltrudes de Oliveira; Ferreira, Mju

doi:10.1055/s-0034-1394711

Cited by 6 publications

(3 citation statements)

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“…Several species of Pittosporum have been explored for phytochemical and pharmacological properties. Crude extracts and metabolites of plants belonging to this genus possess diverse biological activities, including antidiarrheal, antimicrobial, antimalarial, and anti-inflammatory functions. − The natural products isolated from Pittosporum include sesquiterpenoids, − triterpenoids, − neolignans and their glycosides, and carotenoids. − …”

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confidence: 99%

Structurally Diverse Sesquiterpenoid Glycoside Esters from Pittosporum qinlingense with Anti-neuroinflammatory Activity

et al. 2022

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Thirteen new sesquiterpenoid glycoside esters, including 11 aromadendrane-type compounds, pitqinlingosides A–K (1–11), one cadinane-type compound, pitqinlingoside L (12), and one eudesmane-type compound, pitqinlingoside M (13), together with seven known analogues (14–20) were isolated from the twigs, fruits, and leaves of Pittosporum qinlingense. Structures were elucidated by analysis of spectroscopic data, gas chromatography mass spectrometry (GC-MS), and chemical methods. The absolute configuration was confirmed by single-crystal X-ray crystallography analysis or electronic circular dichroism spectra. Unusual glycoside esters are characterized by the presence of polyacylated β-d-fucopyranosyl, β-d-glucopyranosyl, and β-d-xylopyranosyl units. Pitqinlingosides A (1), B (2), D (4), and F (6), pittosporanoside A1 acetate (14), and pittosporanoside A1 (16) showed significant nitric oxide production inhibition in lipopolysaccharide (LPS)-induced BV-2 microglial cells with IC50 values ranging from 0.95 to 24.12 μM. Structure–activity relationships of the isolated compounds are discussed.

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confidence: 99%

Structurally Diverse Sesquiterpenoid Glycoside Esters from Pittosporum qinlingense with Anti-neuroinflammatory Activity

et al. 2022

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“…5 Extracts and chemical components from Pittosporum plants have been recorded to show diverse biological activities, such as antimicrobial, [6][7][8][9] larvicidal, 10 antimalarial, anti-inflammatory, 11 antispasmodic, among others. [12][13][14][15] Sesquiterpenoids, [16][17][18][19][20] triterpenoids, 5,21-24 lignans 13 and their glycosides, carotenoids [25][26][27][28][29][30] and phthalides 31,32 have been found in Pittosporum plants. Eudesmane, 18,33,34 aromadendrane [34][35][36][37] 37 and guaiane 19 sesquiterpenoids and their glycosides are considered characteristic chemical constituents of Pittosporum.…”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14][15] Sesquiterpenoids, [16][17][18][19][20] triterpenoids, 5,21-24 lignans 13 and their glycosides, carotenoids [25][26][27][28][29][30] and phthalides 31,32 have been found in Pittosporum plants. Eudesmane, 18,33,34 aromadendrane [34][35][36][37] 37 and guaiane 19 sesquiterpenoids and their glycosides are considered characteristic chemical constituents of Pittosporum. Although eudesmane sesquiterpenoids have been discovered in many medicinal plants with cytotoxic, 38,39 antioxidative, 38 progesterone receptor inhibitory, 40 and other biological activities, their highly esterified glycosides representing a class of structurally distinctive metabolites have been reported mainly from the genus Pittosporum.…”

Section: Introductionmentioning

confidence: 99%

Pitsubcosides A–L, highly esterified eudesmane sesquiterpenoid glycosides with antibacterial activity from Pittosporum subulisepalum and their mechanism

Guan

Xia

Huang

et al. 2023

Pest Management Science

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BACKGROUNDPlants from the genus Pittosporum are traditionally used as antibacterial, antifungal and antiviral agents. A bioassay evaluation of the extract of Pittosporum subulisepalum revealed antibacterial activity. This study focused on the discovery of the antibacterial metabolism in P. subulisepalum, as well as the modes of action of its active components.RESULTSA chemical investigation of an ethyl acetate (EtOAc) extract of the aerial parts of P. subulisepalum led to the isolation of 12 previously undescribed eudesmane sesquiterpenoid glycoside esters (ESGEs), pitsubcosides A–L (1–12). Their structures were elucidated by extensive spectroscopic analysis, including one‐ and two‐dimensional NMR, high‐resolution electrospray ionization mass spectrometry, electronic circular dichroism spectra and single‐crystal X‐ray crystallography analysis or by comparing with authentic samples. The new ESGEs were characterized by their highly esterified glycoside moieties. Among them, compounds 1–3, 5 and 8 showed a moderate inhibitory effect against Staphylococcus aureus, methicillin‐resistant S. aureus (MRSA), Bacillus cereus, Bacillus subtilis, Pseudomonas syringae pv. actinidiae (Psa) and Erwinia carotovora with minimum inhibitory concentrations (MICs) ranging from 3.13 to 100 μm. Among them, compounds 3 and 5 showed remarkable antibacterial activity against S. aureus and Psa with MIC values of 6.25 and 3.13 μm, respectively. Live bacterial mass and the biofilms of S. aureus and Psa were quantified using methyl tetrazolium and crystal violet assays. Fluorescence microscopy and scanning electron microscopy experiments revealed an antibacterial mechanism of cell membrane architectural disruption.CONCLUSIONThe results suggest that ESGEs possess great potential for the development of antibacterial agents to control plant pathogens. © 2023 Society of Chemical Industry.

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Biplot analysis of monthly variations in essential oil concentration and chemical composition of Pittosporum tobira leaves in Mediterranean conditions

Akçura

2023

Biochemical Systematics and Ecology

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Phytochemical study of Pittosporum undulatum: Searching for new guaiane-type sesquiterpenes with anti-inflammatory activity

Cited by 6 publications

References 0 publications

Structurally Diverse Sesquiterpenoid Glycoside Esters from Pittosporum qinlingense with Anti-neuroinflammatory Activity

Structurally Diverse Sesquiterpenoid Glycoside Esters from Pittosporum qinlingense with Anti-neuroinflammatory Activity

Pitsubcosides A–L, highly esterified eudesmane sesquiterpenoid glycosides with antibacterial activity from Pittosporum subulisepalum and their mechanism

Biplot analysis of monthly variations in essential oil concentration and chemical composition of Pittosporum tobira leaves in Mediterranean conditions

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