• Plant Breeding and Biotechnology
• /
• v.6 no.4
• /
• pp.404-412
• /
• 2018

The influenza neuraminidase (NA, E.C. 3.2.1.18), an antiviral, has been the target of high pharmaceutical companies due to its essential role in viral replication cycle. Perilla frutescens (P. frutescens) is used in traditional Chinese medicine for various diseases, such as cold due to wind-cold, headache and cough. In this context, four major polyphenolic compounds including rosmarinic acid-3-O-glucoside (1), rosmarinic acid (2), luteolin (3), and apigenin (4) isolated from P. frutescens were evaluated for their inhibitory effect on recombinant virus H1N1 neuraminidase (rvH1N1 NA). Among the test compounds, rosmarinic acid and luteolin inhibited the rvH1N1 NA with an $IC_{50}$ of 46.7 and $8.4{\mu}M$, respectively. The inhibition kinetics analyzed by the Dixon plots indicated that rosmarinic acid and luteolin were noncompetitive inhibitors and that the inhibition constant, $K_I$, was established as 43.9 and $14.3{\mu}M$, respectively. In addition, 578 genetically diverse accessions and 39 cultivars of P. frutescens were analyzed using HPLC to characterize the diversity of polyphenolic composition and concentration. The individual and total compositions exhibited significant difference (P < 0.05), especially rosmarinic acid which was detected as the predominant metabolite in all accessions (58.8%) and cultivars (62.8%). Yeupsil and Sangback cultivars exhibited the highest rosmarinic acid ($3,393.5{\mu}g/g$) and luteolin ($383.3{\mu}g/g$) content respectively. YCPL177-2 with the high concentration ($889.8{\mu}g/g$) of luteolin may be used as a genetic resource for breeding elite cultivars.

• Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
• /
• 2003.04a
• /
• pp.149-149
• /
• 2003

홍화의 식품재로로서 이용성을 높이고자 홍화의 부위별 성분분석 및 DPPH radical 소거 활성을 조사하였다. 단백질은 어린싹 부위에 28.39%, 지방은 씨 부위에 20.47%로 많이 함유되어 있었다. Glucose는 어린싹에 1,253.6 mg%, fructose는 이린싹에 970.7 mg%, sucrose는 꽃봉오리 부위에 912.0 mg%로 많이 함유되어 있었다, Succinic acid는 꽃잎 부위에 2,795.3 mg%, malic acid는 잎과 어린싹 부위에 각각 2,054.8 mg%와 934.2 mg%로 많이 함유하고 있었다. 무기질로는 K이 잎과 어린싹 부위에 각각 2,826.8 mg%와 l1999.8 mg%, Ca 또한 잎과 어린싹 부위에 각각 2,613.6 mg%와 1160.9 mg%로 많이 함유하고 있었다. 불포화지방산인 linoleic acid는 어린싹과 씨 부위에 각각 80.01%와 78.21%로 가장 많이 함유하고 있었다. 총페놀함량은 꽃잎, 어린싹, 잎 부위에 각각 5.8%, 4.4% 및 2.5%, 총플라보노이드 함량은 꽃잎, 어린싹, 잎 부위에 각각 4.7%, 6.5% 및 2.0%로 많이 함유하고 있었다. Serotonin(5-bydrnxyoyptamine, 5-HT)화합물인 serotonin-I은 홍화씨 부위에 147.7 mg%, serotonin-II 또한 홍화씨 부위에 155.4 mg%를 함유하고 있었고, flavonoid화합물인 acacetin도 홍화씨 부위에 116.5 mg%을 함유하고 있었다. 또한, luteolin은 어린싹 부위에 388.3 mg%, luteolin 7-glucoside은 잎 부위에 692.3 mg%로 많이 함유하고 있었다. DPPH radical 소거 활성은 꽃잎과 잎의 80% 에탄을 추출물이 114.2%와 113.6%의 높은 활성을 나타내어 기존의 합성항산화제인 BHA 100 ppm 농도의 88.05%의 활성 보다 높은 항산화 활성을 가지고 있음을 확인하였다.

• Natural Product Sciences
• /
• v.13 no.3
• /
• pp.186-189
• /
• 2007

The aerial parts of Verbascum sinaiticum Benth. (Scrophulariaceae) yielded two iridoids that were idenified as ajugol 3 and aucubin 4. Also, investigation of the flavonoid constituents revealed the isolation and identification of luteolin 1 and chrysoeriol-7-glucoside 2. All the isolated compounds were identifid by spectroscopicmethods (UV, MS, $^{1}H-NMR$ and $^{13}C-NMR$) and in comparison with the literature data. Both alcohol and methylene chloride/methanol extracts (1 : 1) exhibited a hepatoprotective effect by $CCl_{4}challenge$ test.

• Journal of Food Hygiene and Safety
• /
• v.32 no.5
• /
• pp.371-380
• /
• 2017

In this study, 17 kinds of polyphenols and 5 kinds of anthocyanins were analyzed to compare the contents of polyphenols and anthocyanins in 76 colored agricultural products. A total of 17 polyphenols were analyzed simultaneously by 9 phenolic acids (gallic acid, protocatechuic acid, chlorogenic acid, vanillic acid, caffeic acid, syringic acid, p-coumaric acid, t-ferulic acid, t-cinnamic acid) and 8 flavonoids ((+)catechin, syringic aldehyde, rutin, epicatechin gallate, naringin, luteolin, naringenin, kaempferol) and 5 anthocyanins (delphinidin-3-glucoside, delphinidin-3-rutinoside, cyanidin-3-galactoside, cyanidin-3-glucoside, cyanidin-3-arabinoside) were simultaneously analyzed. The total content of 17 polyphenols was determined as seoritae $255.1{\pm}7.5{\mu}g/g$, seomoktae $275.8{\pm}5.3{\mu}g/g$, black rice $78.5{\pm}4.6{\mu}g/g$, black sesame $75.8{\pm}3.2{\mu}g/g$, blueberry $143.3{\pm}5.5{\mu}g/g$, aronia $195.2{\pm}4.9{\mu}g/g$ and blackcurrent $131.6{\pm}3.2{\mu}g/g$, the highest content was found in the order of seomoktae > seoritae > aronia > blueberry > blackcurrant > black rice > black sesame. The total content of 5 anthocyanins was determined as seoritae $82.4{\pm}17.2{\mu}g/g$, seomoktae $95.2{\pm}6.1{\mu}g/g$, black rice $74.1{\pm}9.7{\mu}g/g$, black sesame were not detected, blueberry $110.8{\pm}1.9{\mu}g/g$, aronia $218.9{\pm}6.1{\mu}g/g$ and blackcurrent $209.7{\pm}4.0{\mu}g/g$, the highest content was found in the order of aronia > blackcurrant > blueberry > seomoktae > seoritae > black rice. These results indicated that seomoktae and aronia possessed the high level of functional components and further study will be needed to develop high value-added foods based on the colored agricultural products.

• Journal of Microbiology and Biotechnology
• /
• v.19 no.4
• /
• pp.387-390
• /
• 2009

Microbial UDP-glycosyltransferases can convert many small lipophilic compounds into glycons using uridine-diphosphate-activated sugars. The glycosylation of flavonoids affects solubility, stability, and bioavailability. The gene encoding the UDP-glycosyltransferase from Bacillus cereus, BcGT-3, was cloned by PCR and sequenced. BcGT-3 was expressed in Escherichia coli BL21(DE3) with a glutathione S-transferase tag and purified using a glutathione S-transferase affinity column. BcGT-3 was tested for activity on several substrates including genistein, kaempferol, luteolin, naringenin, and quercetin. Flavonols were the best substrates for BcGT-3. The enzyme dominantly glycosylated the 3-hydroxyl group, but the 7-hydroxyl group was glycosylated when the 3-hydroxyl group was not available. The kaempferol reaction products were identified as kaempferol-3-O-glucoside and kaempferol-3,7-O-diglucoside. Kaempferol was the most effective substrate tested. Based on HPLC, LC/MS, and NMR analyses of the reaction products, we conclude that BcGT-3 can be used for the synthesis of kaempferol 3,7-O-diglucose.

• Journal of Applied Biological Chemistry
• /
• v.64 no.1
• /
• pp.25-32
• /
• 2021

Phytochemicals include plant-derived natural products that promote and improve the human metabolism and physiological activity, and there is a lot of research to find the value of the molecules is in progress. Likewise, we obtained 288 fractions of Capsicum annuum L. extract in less than 20 h using HPLC/SPE/HPLC coupling experiment through Sepbox system, an effective separation system to search for active substances in natural resources and ensure efficacy and reliability. Therefore, this experiment allowed rapid identification of biologically active molecules from the extract compared to traditional separation processes. Of the above fractions, eight fractions showed the α-glucosidase inhibitory (AGI) activity and subsequent LC-MS analysis revealed one of the active molecules as luteolin 7-O-glucoside. In addition, we proved the increase in AGI activity according to deglycosylation of flavonoid glycoside. Therefore, this study suggests that the Sepbox system can quickly separate and identify active components from plant extract, and is an effective technique for finding new active substances.

• Natural Product Sciences
• /
• v.14 no.2
• /
• pp.100-106
• /
• 2008

Column chromatographic separation of the MeOH extract from the aerial parts of Schizonepeta tenuifolia Briquet led to the isolation of twelve terpenes (1 - 11 and 17), four phenolics (13 - 16) and a hexenyl glucoside (12). Their structures were determined by spectroscopic means to be (-)-pulegone (1), piperitenone (2), p-cymene-3,8-diol (3), schizonepetoside A (4), schizonepetoside C (5), (+)-spatulenol (6), ursolic acid (7), $2{\alpha}$,$3{\alpha}$,$24{\alpha}$,-trihydroxyolean-12en-28oic acid (8), $5{\alpha}$,$8{\alpha}$-epidioxyergosta-6,22-diol-$3{\beta}$-ol (9), stigmast-4-en-3-one (10), ${\beta}-sitosterol$ (11), (Z)-3-hexenyl-1-O-${\beta}$-D-glucopyranoside (12), rosmarinic acid (13), apigenin-7-O-${\beta}$-D-glucopyranoside (14), luteolin-7-O-${\beta}$-D-glucuronopyranoside (15), hesperidin (16) and trans-phytol (17). Compounds 2, 3, 8, 9 and 12 were for the first time isolated from S. tenuifolia Briq.

• Proceedings of the Plant Resources Society of Korea Conference
• /
• 2018.04a
• /
• pp.13-13
• /
• 2018

The anti-inflammatory (INF) compounds (1-15) were isolated from Agrimonia pilosa Ledeb. (APL) by activity-guided isolation technique. The isolated compounds (1-15) were identified as quercetin-7-O-rhanmoside (1), apigenin-7-O-glycoside (2), kaempferol-7-O-glycoside (3), apigenin-7-O-[6"-(butyl)-glycoside] (4), querceitn (5), kaempferol (6), apigenin (7), apigenin-7-O-[6"-(pentyl)-glycoside] (8), agrimonolide (9), agrimonolide-6-O-glucoside (10), desmethylagrimonolide (11), desmethylagrimonolide-6-O-glucoside (12), luteolin (13), vitexin (14) and isovitexin (15). Flavonoids, compound 2, 3, 11, and 14-15 have been found in APL for the first time. Furthermore, two novel flavone derivatives, compound 4 and 8, have been isolated inceptively in plant. In the no cytotoxicity concentration ranges of $0-20{\mu}M$, nitric oxide (NO) production level of 1-15 was estimated in LPS-treated Raw 264.7 macrophage cells. The flavone aglycones, 7 (apigenin, $IC_{50}=3.69{\pm}0.34{\mu}M$), 13 (luteolin, $IC_{50}=4.62{\pm}0.43{\mu}M$), 6 (kaempferol, $IC_{50}=14.43{\pm}0.23{\mu}M$) and 5 (quercetin, $IC_{50}=19.50{\pm}1.71{\mu}M$), exhibited excellent NO inhibitory (NOI) activity in dose-dependent manner. In the structure activity relationship (SAR) study of apigenin-derivatives (APD), apigenin; Api, apigenin-7-O-glucoside; Api-G, apignenin-7-O-[6"-(butyl)-glycoside]; Api-BG and apignenin-7-O-[6"-(pentyl)-glycoside]; Api-P, from APL on INF activity was investigated. The INF mediators level such as NO, INF-cytokines, NF-KB proteins, iNOS and COX-2 were sharply increased in Raw 264.7 cells by LPS. When pretreatment with APD in INF induced macrophages, NOI activity of Api was most effective than other APD with $IC_{50}$ values of $3.69{\pm}0.77{\mu}M$. And the NOI activity was declined in the following order: Api-BG ($IC_{50}=8.91{\pm}1.18{\mu}M$), Api-PG ($IC_{50}=13.52{\pm}0.85{\mu}M$) and API-G ($IC_{50}=17.30{\pm}0.66{\mu}M$). The NOI activity of two novel compounds, Api-PG and Api-BG were lower than their aglycone; Api, but more effective than Api-G (NOI: Api-PG and Api-BG). And their suppression ability on INF cytokines such as $TNF-{\alpha}$, $IL-1{\beta}$ and IL-6 mRNA showed the similar tendency. Therefore, the anti-INF mechanism study of Api-PG and Api-BG on nuclear factor-kappa B ($NF-{\kappa}B$) pathway, representative INF mechanism, was investigated and Api was used as positive control. Api-BF was more effectively prevent the than phosphorylation of $pI{\kappa}B$ kinase (p-IKK) and p65 than Api-PG in Raw 264.7 cells. In contrast, Api-PG and Api-BG were not reduced the phosphorylation of inhibitor of kappa B alpha ($I{\kappa}B{\alpha}$). Moreover, pretreatment with Api-PG and Api-BG, dose-dependently inhibited LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNAs and proteins in macrophage cells, and their expression were correlated with their NOI activity. Therefore, APL can be utilized to health promote agent associated with their AIN metabolites.

• Journal of Pharmacopuncture
• /
• v.26 no.4
• /
• pp.319-326
• /
• 2023

Objectives: The study's goal was to find out whether Chrysanthemum rubellum extract has anti-diabetic properties by concentrating on α-glucosidase and the PTP-1B signaling pathway. C. rubellum flowers were used for extraction using Methanol/water (80/20) as solvent. Methods: LC-MS techniques was used to check the presence of phytoconstituents present in C. rubellum extract. In vitro antidiabetic activity was evaluated using α-glucosidase inhibitory activity and PTP-1B signaling pathway. On Streptozotocin (STZ)-induced rats with diabetes, the in vivo antidiabetic efficacy was assessed using a test for oral glucose tolerance. Results: The phytoconstituents identified in the extract of C. rubellum were apigenin, diosmin, myricetin, luteolin, luteolin-7-glucoside, and Quercitrin as compound 1-6, respectively. Results showed that diosmin exhibited highest α-glucosidase inhibitory activity i.e. 90.39%. The protein level of PTP-1B was lowered and the insulin signalling activity was directly increased by compounds 1-6. The maximum blood glucose levels were seen in all groups' OGTT findings at 30 minutes following glucose delivery, followed by gradual drops. In comparison to the control group, the extract's glucose levels were 141 mg/dL at 30 minutes before falling to 104 mg/dL after 120 minutes. The current study has demonstrated, in summary, that extract with phytoconstituents reduce blood sugar levels in rats. Conclusion: This finding suggests that extract may reduce the chance of insulin resistance and shield against disorders like hyperglycemia.

• Natural Product Sciences
• /
• v.11 no.4
• /
• pp.233-239
• /
• 2005

The aerial parts of Gomphocarpus sinaicus Boiss. yielded four flavonoids that were identified as isorhamnetin 3-O-rhamnoglucoside (1), luteolin-7-O-glucoside-3-O-rhamnoside (2), rutin (3) and rutin-7-O-rhamnoside (4). All of the isolated flavonoids were identified by spectroscopic methods (UV, FAB-MS, $^1H-NMR\;&\;^{13}C-NMR$) and in comparison with the literature data. The isolated flavonoids 1, 2 and 4 are reported here for the first time from Gomphocarpus sinaicus Boiss. Three sets of experiments were carried out using the defatted alcoholic extract of Gomphocarpus sinaicus Boiss: the $1^{st}$ experiment indicated that the $LD_{50}$ was 49.82 mg/100 g b.wt. of intraperitoneally (i.p.) injected mice. The toxic signs were recorded within the first 24 hr post-injection. The $2^{nd}$ experiment revealed that the extract of the plant exhibited significant anti-inflammatory effects in normal rats. The $3^{rd}$ experiment was found that the tested doses of the extract in diabetic rats induced a significant decrease in serum glucose, AST, ALT, triglycerides, cholesterol and LDL, while HDL caused a significant increase.