Sesquiterpene Lactones from<i>Chrysanthemum indicum</i>

Mladenova, Kirilka; Tsankova, Elena; Stoianova-Ivanova, B.

doi:10.1055/s-2007-969486

Cited by 17 publications

(5 citation statements)

References 3 publications

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“…Its molecular formula of C 20 H 26 O 5 was determined from the HRESIMS data (m/z 369.1672 [M + Na] + ; calcd 369.1672) and NMR data (Tables 1 and 2), indicating eight indices of hydrogen deficiency. A detailed analysis of 1 H and 13 C NMR spectra indicated that the structure of compound 3 was close to that of angeloylajadin (4), previously isolated from C. indicum, 16 4). The relative configuration of the trans-fused α-methylene-γ-unsaturated lactone moiety was assigned by the NOESY correlation between H-6 (δ H 3.71) and H-8 (δ H 4.81) and the absence of correlation between H-6 and H-7, along with the large coupling constants of H-5/H-6 (J = 11.1 Hz), H-6/H-7 (J = 10.4 Hz), and H-7/H-8 (J = 10.5 Hz) (Figure 4).…”

Section: ■ Results and Discussionsupporting

confidence: 52%

“…Its molecular formula of C 20 H 26 O 5 was determined from the HRESIMS data ( m / z 369.1672 [M + Na] + ; calcd 369.1672) and NMR data (Tables and ), indicating eight indices of hydrogen deficiency. A detailed analysis of 1 H and 13 C NMR spectra indicated that the structure of compound 3 was close to that of angeloylajadin ( 4 ), previously isolated from C. indicum , only differing by the presence of a 2-methylbutanoyloxy group [δ H 2.40 (H-2′), 1.72 (H-3′), 1.50 (H-3′), 1.20 (H-5′), 0.94 (H-4′); δ C 175.7 (C-1′), 41.2 (C-2′), 26.3 (C-3′), 16.8 (C-5′), 11.8 (C-4′)] instead of an angeloyloxy group. The position of the 2-methylbutanoyloxy group was determined by the HMBC correlation between H-8 (δ H 4.81) and C-1′ (δ C 175.7) (Figure ).…”

Section: Resultsmentioning

confidence: 76%

“…The 20 known compounds were identified as angeloylajadin ( 4 ), 5-hydroxy-9-oxonerolidol ( 9 ), 8-hydroxycarvotanacetone ( 10 ), loliolidie ( 11 ), 3,5,6,-trihydroxy-7-megastimen-9-one ( 12 ), indicumenone ( 13 ), chrysetunone ( 14 ), 8-angeloyloxycostunolide ( 15 ), (2 S )-hesperetin ( 16 ), acacetin ( 17 ), apigenin ( 18 ), diosmetin ( 19 ), luteolin-7- O -glucoside ( 20 ), luteolin-7- O -glucuronide ( 21 ), luteolin-7- O -rutinoside ( 22 ), apigenin-7- O -glucoside ( 23 ), apigenin-7- O -glucuronide ( 24 ), linarin ( 25 ), acacetin-7- O -glucoside ( 26 ), and acacetin-7- O -glucuronide ( 27 ), respectively, by comparing their physicochemical and spectroscopic data with those of published values.…”

Section: Resultsmentioning

confidence: 99%

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Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production

Kim

Lee

et al. 2021

J. Nat. Prod.

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Three new guaianolide lactones (1−3) and four new 9-oxonerolidol glucosides (5−8) together with 20 known compounds were isolated from the MeOH extract of the flowers of Chrysanthemum indicum. Their structures were elucidated based on the interpretation of NMR, HRESIMS, and electronic circular dichroism (ECD) data along with acid hydrolysis. Of the isolates, sesquiterpenoids 1−4 and 15 and flavones 17 and 18 exhibited inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 cells with IC 50 values in the range 0.2−27.0 μM.

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Section: ■ Results and Discussionsupporting

confidence: 52%

Section: Resultsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 99%

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Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production

Kim

Lee

et al. 2021

J. Nat. Prod.

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“…The essential oil of Chrysanthemum leucanthemum exhibited strong activity against Salmonella typhi and Proteus mirabilis. The activity was investigated by agar dilution method [17] . Also, the essential oil of Chrysanthemum leucanthemum exhibited the activity against six Gram +ve bacteria and 8 Gram -ve bacteria.…”

Section: Pharmacological Activity Anti Bacterial Activitymentioning

confidence: 99%

Chrysanthemum leucanthemum: A review

E¹,

Adi²,

Dabolkar³

et al. 2019

Int. J. Homoeopathic Sci.

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Chrysanthemum leucanthemum also called as oxeye daisy. Introduced from Europe in the early 1800's primarily as a grass seed contaminant, and subsequently spread as an ornamental, Oxeye daisy has become a serious invader of pastures and natural areas throughout North America. It is a perennial herb that reproduces both by seed and shallow rhizomes. Single plants quickly become patches that continually increase in size. Plants flower June August and its seed germinates throughout the growing season.

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“…Sesquiterpene lactones, which exhibit various physiological activities, are abundant in Dendranthema spp. (Mladenova et al, 1985). Chloroform fractions from D. zawadskii (DZ) have strong antibacterial activity against Bacillus subtilis, Staphylococcus aureus, and Vibrio parahaemolyticus, and contain sesquiterpene lactones, angeloylcumambrin B, and cumambrin A (Jang et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Beneficial effects of the extracts and fractions of Dendranthema zawadskii and quantitative analysis of phenolic compounds by HPLC/UV

So,

Lee,

Lee

et al. 2024

Chem. Pap.

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Dendranthema spp. are good sources of phenolic compounds with pharmacological effects. To improve industrial material e ciency and economic feasibility, Dendranthema zawadskii (DZ) was fractionated, and its functional substances and biological activities were evaluated. The linarin contents in the butanol (Bu) and ethyl acetate (EtOAc) fractions were 77.360 mg/g and 70.603 mg/g, respectively, which were approximately 3.4 times higher than those in the methanol extract. In the EtOAc fraction, the luteolin content was 52.135 mg/g (6.4 times higher than that in the methanol extract) and the 3,5-DCQA content was 184.704 mg/g (9.7 times higher than that in the methanol extract). Excluding the hexane (He) and chloroform (Ch) fractions, cell viability was 80% or higher at concentrations of ≤200 μg/mL for HaCaT cells and 25 μg/mL for B16F10 cells, indicating a lack of toxicity. The total polyphenol content of the EtOAc fraction was 370.50 mg/g and the total avonoid content was 947.47 mg/g, which were signi cantly higher than those of the other fractions. As a result, the antioxidant activity of the EtOAc fraction at a low concentration of 25 μg/mL was 92.47%, similar to that of the control, and at 100 μg/mL, the He and Bu fractions exhibited high antioxidant activity (>90%). The EtOAc fraction had the highest tyrosinase inhibitory activity (33.33%) and inhibited melanin formation by 37.12% compared with that in the α-MSH treatment group. The antibacterial activities of 100 mg/mL He, Ch, and EtOAc fractions against Staphylococcus aureus were higher than that of the positive control, and the antibacterial activity against Pseudomonas aeruginosawas higher than that of the positive control for all fractions (100 mg/mL). The Ch fraction had the strongest activity against Candida albicans. Overall, the EtOAc fraction of DZ has a high potential as an industrial material, as it can be safely used with high functionality and polyphenol and avonoid contents, with extensive potential applications in cosmetics, functional foods, and pharmaceuticals.

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Sesquiterpene Lactones fromChrysanthemum indicum

Cited by 17 publications

References 3 publications

Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production

Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production

Chrysanthemum leucanthemum: A review

Beneficial effects of the extracts and fractions of Dendranthema zawadskii and quantitative analysis of phenolic compounds by HPLC/UV

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