Two New Eudesmane Sesquiterpenoids from the Flowers of Chrysanthemum indicum

Yang, Jun‐Li; Liu, Leilei; Shi, Yan‐Ping

doi:10.1007/s13659-019-0199-9

Cited by 13 publications

(4 citation statements)

References 20 publications

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“…Referring to previous research, 34,53‐57 the chemical shift of C‐7 ( δ C about 48–50 ppm) with a β ‐oriented oxygenated isopropyl group in the eudesmane‐type sesquiterpenoid glycoside is apparently downfield compared with ( δ C about 41–43 ppm) an α ‐oriented one, which may be conducive to assigning the configuration of the oxygenated isopropyl at C‐7 ( δ C 41.9) as an α ‐orientation, opposite to that in compound 1 . With respect to the NOESY spectrum, the cross peak of H‐1/H‐5 indicated they were α ‐oriented, whereas H‐7 and CH 3 ‐14 were β ‐oriented, consistent with 7‐ epi ‐1 β ‐hydroxy‐ β ‐eudesmol 54 .…”

Section: Resultssupporting

confidence: 55%

“…One noteworthy difference, the chemical shifts of C-5 (⊐ C 41.7) and C-7 (⊐ C 41.9) in 2 were dramatically upfield compared with the corresponding ones (⊐ C 47.6 and ⊐ C 48.1) in 1, as displayed in Table 2, and implied they were stereoisomers of each other. Referring to previous research, 34,[53][54][55][56][57] the chemical shift of C-7 (⊐ C about 48-50 ppm) with a ⊎-oriented oxygenated isopropyl group in the eudesmane-type sesquiterpenoid glycoside is apparently downfield compared with (⊐ C about 41-43 ppm) an ⊍-oriented one, which may be conducive to assigning the configuration of the oxygenated isopropyl at C-7 (⊐ C 41.9) as an ⊍-orientation, opposite to that in compound 1. With respect to the NOESY spectrum, the cross peak of H-1/H-5 indicated they were ⊍-oriented, whereas H-7 and CH 3 -14 were ⊎-oriented, consistent with 7-epi-1⊎-hydroxy-⊎-eudesmol.…”

Section: Structure Elucidation Of Compoundsmentioning

confidence: 99%

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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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Section: Resultssupporting

confidence: 55%

Section: Structure Elucidation Of Compoundsmentioning

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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“…Compound (7) has shown outstanding anti-inflammatory effects and is considered a potential pro-inflammatory factors inhibitor agent [9]. The compound β-eudesmol acetate (3) belongs to the group of eudesmans; it has been reported in species of the Asteraceae family and the main biological activities studied are cytotoxic, antioxidant, and antimicrobial [44][45][46].…”

Section: Chemical Profile Of Ethyl Acetate Extract Of Callus Culturesmentioning

confidence: 99%

Cytotoxic Activity of Wild Plant and Callus Extracts of Ageratina pichinchensis and 2,3-Dihydrobenzofuran Isolated from a Callus Culture

Sánchez-Ramos,

Encarnación-García,

Marquina-Bahena

et al. 2023

Pharmaceuticals

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Ageratina pichinchensis (Kunth) R.M. King & H. Rob. belongs to the Asteraceae family and is a plant native to Mexico to which several biological properties are attributed. In this study, the cytotoxic effect of four extracts from the wild plants and two extracts from A. pichinchensis callus culture were evaluated against carcinogenic cell lines including prostate carcinoma, cervical cancer, hepatocellular carcinoma, hepatoma human, lung cancer, and cellular keratinocytes. The extracts were obtained with ethyl acetate and methanol using both leaves and stems or the callus. Only the ethyl acetate extract of the callus culture influenced the cervical cancer cell line (HeLa) with an IC50 of 94.79 ± 2.0 µg/mL. From the ethyl acetate callus extract, 2,3-dihydrobenzofuran was isolated and purified and also evaluated against cancer cells. The cytotoxic evaluation of this compound showed a significant effect against the HeLa cell line with an IC50 of 23.86 ± 2.5 µg/mL. Our results contribute to the development of biotechnological alternatives and extraction processes to produce compounds with possible potential against certain types of human cancer.

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“…(Juhua) is the dried flower head of Chrysanthemum morifolium (Ramat.) Hemsl., and has the effects of dispersing wind and clearing heat, calming the liver and clearing the eyes, and clearing heat and detoxifying the body (Tu et al, 2021;Yang et al, 2019). The Compendium of Materia Medica records that CM can benefit the five veins, regulate the extremities, and cure the head wind heat tonic.…”

Section: Introductionmentioning

confidence: 99%

Chemical Antioxidant Quality Markers of Chrysanthemum morifolium Using a Spectrum-Effect Approach

Zhang

et al. 2022

Front. Pharmacol.

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Traditionally, the quality evaluation of Chrysanthemum morifolium (CM) cv. (Juhua) attributes its habitats and processing methods, however, this strategy of neglecting bioactive ingredients usually results in deviation of quality evaluation. This study aims to explore the quality marker (Q-marker) based on spectrum-effect relationship and quality control strategy of CMs. The chromatographic fingerprint of 30 flower head samples of CMs from five different habitats including Hang-baiju, Gongju, Huaiju, Taiju and Boju were constructed by high performance liquid chromatography and analyzed through chemometrics methods such as similarity analysis (SA), cluster analysis (CA) and principal component analysis (PCA). The common peaks were quantified by external standard method and relative correction factor method. The in-vitro radical scavenging capacity assays of DPPH·, ·OH and ABTS were carried out. The Q-marker was explored by the correlation analysis between the contents of common peaks and in-vitro radical scavenging capacity, and then used to evaluate the quality of 30 flower head samples of CMs. A total of eight common peaks were appointed in 30 flower head samples of CMs, and their similarities ranged from 0.640 to 0.956. CA results showed that 30 flower head samples of CMs could be divided into five categories with reference to the Euclidean distance of 5. PCA results showed that common peaks played a major role in differential contribution of CMs. The quantification of common peaks hinted that their contents possessed significant variation whether for different accessions or the same accessions of CMs. The correlation analysis showed that chlorogenic acid, 3,5-O-dicaffeoylquinic acid, unknown peak 1, 4,5-O-dicaffeoylquinic acid and kaempferol-3-O-rutinoside could be used as the Q-markers for the quality evaluation of 30 flower head samples of commercially available CMs. The analysis strategy that combines chromatographic fingerprint analysis, multiple ingredients quantification, in-vitro chemical anti-oxidant activity evaluation and spectrum-effect relationship analysis clarified the therapeutic material basis and discovered the Q-markers, which possibly offers a more comprehensive quality assessment of CMs.

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Two New Eudesmane Sesquiterpenoids from the Flowers of Chrysanthemum indicum

Cited by 13 publications

References 20 publications

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

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

Cytotoxic Activity of Wild Plant and Callus Extracts of Ageratina pichinchensis and 2,3-Dihydrobenzofuran Isolated from a Callus Culture

Chemical Antioxidant Quality Markers of Chrysanthemum morifolium Using a Spectrum-Effect Approach

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