Constituents of Coreopsis lanceolata Flower and Their Dipeptidyl Peptidase IV Inhibitory Effects

Published on Sep 23, 2020in Molecules4.412
· DOI :10.3390/MOLECULES25194370
Bo-Ram Kim9
Estimated H-index: 9
Sunil Babu Paudel2
Estimated H-index: 2
(Yeungnam University)
+ 3 AuthorsAh-Reum Han7
Estimated H-index: 7
A new polyacetylene glycoside, (5R)-6E-tetradecene-8,10,12-triyne-1-ol-5-O-β-glucoside (1), was isolated from the flower of Coreopsis lanceolata (Compositae), together with two known compounds, bidenoside C (10) and (3S,4S)-5E-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-β-glucopyranoside (11), which were found in Coreopsis species for the first time. The other known compounds, lanceoletin (2), 3,2'-dihydroxy-4-3'-dimethoxychalcone-4'-glucoside (3), 4-methoxylanceoletin (4), lanceolin (5), leptosidin (6), (2R)-8-methoxybutin (7), luteolin (8) and quercetin (9), were isolated in this study and reported previously from this plant. The structure of 1 was elucidated by analyzing one-dimensional and two-dimensional nuclear magnetic resonance and high resolution-electrospray ionization-mass spectrometry data. All compounds were tested for their dipeptidyl peptidase IV (DPP-IV) inhibitory activity and compounds 2-4, 6 and 7 inhibited DPP-IV activity in a concentration-dependent manner, with IC50 values from 9.6 to 64.9 μM. These results suggest that C. lanceolata flower and its active constituents show potential as therapeutic agents for diseases associated with type 2 diabetes mellitus.
#1Hyoung-Geun Kim (Kyung Hee University)H-Index: 7
#2Young Sung Jung (Kyung Hee University)H-Index: 7
Last. and Nam-In Baek (Kyung Hee University)H-Index: 2
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(1) Background: Many flavonoids derived from natural sources have been reported to exhibit antioxidant and anti-inflammatory effects. Our preliminary study suggested that Coreopsis lanceolata flowers (CLFs) include high flavonoid content; (2) Methods: CLFs were extracted in 80% (v/v) aqueous methanol and fractionated into ethyl acetate, n-butanol, and water fractions. Repeated column chromatographies for the organic fractions led to the isolation of seven flavanones. Quantitative analysis of the...
#1Bo-Ram KimH-Index: 9
#2Punam Thapa (Yeungnam University)H-Index: 2
Last. Joo-Won Nam (Yeungnam University)H-Index: 9
view all 9 authors...
The scaly bulbs of Lilium longiflorum (Liliaceae) are used as a food ingredient and a traditional medicine in East Asia. A preliminary study revealed that treatment with 100 μg/mL of the ethyl acetate fraction of this plant material inhibited dipeptidyl peptidase IV (DPP-IV) to 58.99%. Phytochemical studies were conducted to identify the active ingredient, and five compounds, namely, 1 (2.9 mg, 75.8% purity at 320 nm), 2 (12.2 mg, 97.9% purity at 320 nm), 3 (3.1 mg, 66.5% purity at 320 nm), 4 (6...
#1Hyoung-Geun Kim (Kyung Hee University)H-Index: 7
#2Hyun-Ji Oh (Kyung Hee University)H-Index: 3
Last. Nam-In Baek (Kyung Hee University)H-Index: 41
view all 8 authors...
Abstract Seven new chalcones, lanceolein A–G (compounds 5 and 7–12), as well as five known chalcones (1–4 and 6), were isolated from the methanolic extract of Coreopsis lanceolata flowers. The chemical structures of 5 and 7–12 were determined on the basis of spectroscopic data interpretation. All compounds inhibited the production of nitrite oxide (NO) induced by LPS in RAW264.7 macrophage cells. Also, compounds 1–6 showed moderated cytotoxicity against human colon cancer cell lines, while compo...
#1Bo-Ram KimH-Index: 9
#2Hyo Young Kim (KAERI)H-Index: 6
Last. Ah-Reum Han (KAERI)H-Index: 7
view all 6 authors...
Dipeptidyl peptidase IV (DPP-IV), a new target for the treatment of type 2 diabetes mellitus, degrades incretins such as glucagon-like peptide 1 (GLP-1) and glucose-dependent insulinotropic polypeptide. DPP-IV inhibitors shorten the inactivation of GLP-1, permitting the incretin to stimulate insulin release, thereby combating hyperglycemia. In our ongoing search for new DPP-IV inhibitors from medicinal plants and foods, three flavonol glycosides (1–3) were isolated from the seeds of Lens culinar...
#1Quantao Ma (Beijing University of Chinese Medicine)H-Index: 6
#2Yaqi Li (Beijing University of Chinese Medicine)H-Index: 6
Last. Baosheng Zhao (Beijing University of Chinese Medicine)H-Index: 6
view all 8 authors...
With the improvement of living standards and a change in lifestyle, the incidence of type 2 diabetes mellitus (T2DM) is increasing. Its etiology is too complex to be completely understand yet. Metabonomics techniques are used to study the changes of metabolites and metabolic pathways before and after the onset of diabetes and make it more possible to further understand the pathogenesis of T2DM and improve its prediction, early diagnosis, and treatment. In this review, we summarized the metabonom...
#1Daisuke Nakabo (Kindai University)H-Index: 1
#2Yuka Okano (Kindai University)H-Index: 2
Last. Yoshiharu Okada (Kindai University)H-Index: 8
view all 7 authors...
Chalcones, flavanones, and flavonols, including 8-methoxybutin isolated from Coreopsis lanceolata L. petals, were successfully synthesized with total yields of 2–59% from O-methylpyrogallols using the Horner–Wadsworth–Emmons reaction as a key reaction. Aurones, including leptosidin, were also successfully synthesized with 5–36% total yields using the Aldol condensation reaction as a key reaction. Each chalcone, flavanone, flavonol, and aurone with the 3,4-dihydroxy groups in the B-ring showed hi...
#1Nagaraju Kerru (UKZN: University of KwaZulu-Natal)H-Index: 12
#2Ashona Singh-Pillay (UKZN: University of KwaZulu-Natal)H-Index: 9
Last. Parvesh Singh (UKZN: University of KwaZulu-Natal)H-Index: 18
view all 4 authors...
Abstract Diabetes mellitus is a medical condition characterized by the body's loss of control over blood sugar. The frequency of diagnosed cases and consequential increases in medical costs makes it a rapidly growing chronic disease that threatens human health worldwide. In addition, its unnerving statistical projections are perilous to both the economy of the nation and man's life expectancy. Type-I and type-II diabetes are the two clinical forms of diabetes mellitus. Type-II diabetes mellitus ...
#1Juliana Mikaelly Dias Soares (UNIVASF: Universidade Federal do Vale do São Francisco)H-Index: 4
#2Ana Ediléia Barbosa Pereira Leal (UNIVASF: Universidade Federal do Vale do São Francisco)H-Index: 3
Last. Helinando P. de Oliveira (UNIVASF: Universidade Federal do Vale do São Francisco)H-Index: 17
view all 5 authors...
Background: The development of alternatives for insulin secretion control in vivo or in vitro represents an important aspect to be investigated. In this direction, natural products have been progressively explored with this aim. In particular, flavonoids are potential candidates to act as insulin secretagogue. Objective: To study the influence of flavonoid on overall modulation mechanisms of insulin secretion. Methods: The research was conducted in the following databases and platforms: PubMed, ...
#1Jia Guo (NAU: Nanjing Agricultural University)H-Index: 7
#2Ao Wang (NAU: Nanjing Agricultural University)H-Index: 1
Last. Zhihong Xin (NAU: Nanjing Agricultural University)H-Index: 18
view all 11 authors...
Abstract Polyacetylene glycosides, (6Z, 12E)-tetradecadiene-8,10-diyne-1-ol-3( R )-O- β -D-glucopyranoside (trivially named coreoside E) and (6Z, 12E)-tetradecadiene-8,10-diyne-1-ol-3( R )-O- β -L-arabinopyranosyl-(1 → 2)- β -D-glucopyranoside (trivially named coreoside F), were isolated from buds of Coreopsis tinctoria Nutt., together with one known compound, coreoside B. Their chemical structures were elucidated by extensive spectroscopic analysis and on the basis of their chemical reactivitie...
#1Kuo Xu (Peking Union Medical College)H-Index: 5
#2Peng-Fei Yang (Peking Union Medical College)H-Index: 3
Last. Pei-Cheng Zhang (Peking Union Medical College)H-Index: 22
view all 6 authors...
An approach for discriminating the threo and erythro configurations of polyacetylene glycosides by 1H NMR spectroscopy was developed. Using acetic acid-d4/D2O as the solvent, a relatively larger 3JHH value (7.0 Hz) for the acyclic vicinal diol group was unambiguously assigned to the threo configuration, whereas the smaller value (3.5 Hz) was assigned to the erythro configuration. This convenient method requires no hydrolysis or derivatization and is suitable for micromolar concentrations of poly...
Cited By5
#1Jonh A. M. Santos (Federal Institute of Pernambuco)
#2Cláudia Laís Araújo Almeida Santos (UFPE: Federal University of Pernambuco)
Last. Juliano Carlo Rufino Freitas (UFCG: Federal University of Campina Grande)H-Index: 3
view all 5 authors...
Polyacetylene glycosides (PAGs) constitute a relatively small class of secondary metabolites characterized by the presence of a sugar unit anomerically connected to a polyacetylene. These compounds are found in fungi, seaweed, and more often in plants. PAGs exhibit a wide range of biological and pharmacological activities and, as a result, the literature of these compounds has grown exponentially in recent years.
#1Yijia Jia (NEAU: Northeast Agricultural University)
#2Shengbao Cai (Kunming University of Science and Technology)
Last. Yang Li (NEAU: Northeast Agricultural University)H-Index: 1
view all 5 authors...
Dietary polyphenols with great antidiabetic effects are the most abundant components in edible products. Dietary polyphenols have attracted attention as dipeptidyl peptidase-IV (DPP-IV) inhibitors ...
#1Bo-Ram KimH-Index: 9
#2Sunil Babu Paudel (Yeungnam University)H-Index: 2
Last. Chang Hyun JinH-Index: 10
view all 12 authors...
Coreopsis species have been developed to produce cultivars of various floral colors and sizes and are also used in traditional medicine. To identify and evaluate mutant cultivars of C. rosea and C. verticillata, their phytochemical profiles were systematically characterized using ultra-performance liquid chromatography time-of-flight mass spectrometry, and their anti-diabetic effects were evaluated using the dipeptidyl peptidase (DPP)-IV inhibitor screening assay. Forty compounds were tentativel...
#1Sibhghatulla Shaikh (Yeungnam University)H-Index: 15
#2Eun-Ju Lee (Yeungnam University)H-Index: 2
Last. Inho Choi (Yeungnam University)H-Index: 41
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Type 2 diabetes mellitus (T2DM) is an increasing global public health problem, and its prevalence is expected to rise in coming decades. Dipeptidyl peptidase-4 (DPP-4) is a therapeutic target for the management of T2DM, and its inhibitors prevent the degradation of glucose-dependent insulinotropic peptide and glucagon-like peptide 1, and thus, maintain their endogenous levels and lower blood glucose levels. Various medicinal plant extracts and isolated bioactive compounds exhibit DPP-4 inhibitor...
#3Jeong-Yong Park (Andong National University)H-Index: 1
(1) Background: Coreopsis lanceolata L. is a perennial plant of the family Asteraceae, and its flower is known to contain flavonoids with various bioactivities. We evaluated the effect of Coreopsis lanceolata L. flower (CLF) extracts on H2O2-induced oxidative stress (OS) in neuronal cells and mouse neurons. (2) Methods: The flowering part of CL was used as CLF1 (70% ethanol extract) and CLF2 (water extract), and 10 types of phenolic compounds were quantified using high-performance liquid chromat...
#1Poonam Kumari (CSIR: Council of Scientific and Industrial Research)H-Index: 1
#2Ujala (CSIR: Council of Scientific and Industrial Research)H-Index: 1
Last. Bhavya Bhargava (CSIR: Council of Scientific and Industrial Research)H-Index: 2
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Abstract Demand for more attractive and high quality food is growing every day. The increasing interest in functional foods and nutraceuticals has exaggerated exploration into new foods that have positive effects on human wellbeing. Even more we see edible flowers as a new way of nutritional health. Edible flowers are non-poisonous, giving any dish new colour, texture and freshness, and apart from the “alluring” factor, they are potential sources of phytochemicals. Various phytochemicals such as...
#1Bo-Ram Kim (Chonnam National University)H-Index: 9
#2Ah-Reum HanH-Index: 7
Last. Ik-Soo Lee (Chonnam National University)H-Index: 30
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Flavonoids are plant secondary metabolites that are well known for their health-promoting properties as nutraceuticals in diets. Bioavailability and biological activities of flavonoids vary among t...
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