• Natural Product Sciences
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• 제28권3호
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• pp.115-120
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• 2022

Ten compounds, consisting of neoflavonoids (1-5), isoflavonoids (6 and 7), flavanone (8), and chalcones (9 and 10) were isolated from the ethyl acetate and n-butanol-soluble fractions of the heartwood of Dalbergia melanoxylon. The chemical structures were identified on the basis of spectroscopic evidence and compared to previously reported spectra. Compounds 1-10 were evaluated for cytotoxicity against HCT116 human colorectal cancer, MDA-MB-231 human metastatic breast cancer, and A2058 human melanoma cell lines. Among them, compounds 3 and 10 showed the strongest cytotoxic activity with IC₅₀ values of 11.92±1.07 μM, 10.83±1.02 μM, and 14.37±1.02 μM, 13.62±1.09 μM against HCT116 and MDA-MB-231 cell lines, respectively. Compounds 9 and 10 also had cytotoxic activity with IC₅₀ values of 13.49±1.18 μM and 9.82±0.91 μM against A2058 cell lines, respectively. To the best our knowledge, compounds 2 and 5-10 were isolated from this source for the first time.

• Natural Product Sciences
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• 제28권2호
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• pp.58-61
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• 2022

Three isoprenylated flavanones were isolated from the leaves of Flemingia lineata (L.) Aiton. Among them are two new flavanones, flemilineatins A and B (1-2), along with 6-isoprenyl eridioctyol (3). Their structures were determined using HRESIMS data and NMR spectra. Flavanones 1 - 3 were assayed in the HeLa cancer cells. Compound 1 showed moderate activity with an IC₅₀ value of 11.2 μM.

• Natural Product Sciences
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• 제28권1호
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• pp.40-43
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• 2022

Three isoprenylated flavanones were isolated from the leaves of Flemingia lineata (L.) Aiton. Among them are two new flavanones, flemilineatins A and B (1-2), along with 6-isoprenyl eridioctyol (3). Their structures were determined using HRESIMS data and NMR spectra. Flavanones 1-3 were assayed in the HeLa cancer cells. Compound 1 showed moderate activity with an IC₅₀ value of 11.2 μM.

• Nutrition Research and Practice
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• 제10권2호
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• pp.131-138
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• 2016

BACKGROUND/OBJECTIVES: Citrus and its peels have been used in Asian folk medicine due to abundant flavonoids and usage of citrus peels, which are byproducts from juice and/or jam processing, may be a good strategy. Therefore, the aim of this study was to examine antioxidant and anti-inflammatory effects of bioconversion of Jeju Hallabong tangor (Citrus kiyomi ${\times}$ ponkan; CKP) peels with cytolase (CKP-C) in RAW 264.7 cells. MATERIALS/METHODS: Glycosides of CKP were converted into aglycosides with cytolase treatment. RAW 264.7 cells were pre-treated with 0, 100, or $200{\mu}g/ml$ of citrus peel extracts for 4 h, followed by stimulation with $1{\mu}g/ml$ lipopolysaccharide (LPS) for 8 h. Cell viability, DPPH radical scavenging activity, nitric oxide (NO), and prostagladin $E_2$ ($PGE_2$) production were examined. Real time-PCR and western immunoblotting assay were performed for detection of mRNA and/or protein expression of pro-inflammatory mediators and cytokines, respectively. RESULTS: HPLC analysis showed that treatment of CKP with cytolase resulted in decreased flavanone rutinoside forms (narirutin and hesperidin) and increased flavanone aglycoside forms (naringenin and hesperetin). DPPH scavenging activities were observed in a dose-dependent manner for all of the citrus peel extracts and CKP-C was more potent than intact CKP. All of the citrus peel extracts decreased NO production by inducible nitric oxide synthase (iNOS) activity and $PGE_2$ production by COX-2. Higher dose of CKP and all CKP-C groups significantly decreased mRNA and protein expression of LPS-stimulated iNOS. Only $200{\mu}g/ml$ of CKP-C markedly decreased mRNA and protein expression of cyclooxygenase-2 in LPS-stimulated RAW 264.7 cells. Both 100 and $200{\mu}g/ml$ of CKP-C notably inhibited mRNA levels of $interleukin-1{\beta}$ ($IL-1{\beta}$) and IL-6, whereas $200{\mu}g/ml$ CKP-C significantly inhibited mRNA levels of $TNF-{\alpha}$. CONCLUSIONS: This result suggests that bioconversion of citrus peels with cytolase may enrich aglycoside flavanones of citrus peels and provide more potent functional food materials for prevention of chronic diseases attributable to oxidation and inflammation by increasing radical scavenging activity and suppressing pro-inflammatory mediators and cytokines.

• Journal of Applied Biological Chemistry
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• 제58권2호
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• pp.153-155
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• 2015

뽕나무(Morus alba L.) 뿌리껍질을 실온에서 80% MeOH 수용액으로 추출하고 이 추출물을 EtOAC, n-BuOH, 그리고 $H_2O$ 분획으로 나누었다. EtOAc 및 n-BuOH 분획에 대하여 silica gel, ODS 및 Sephadex LH-20 column chromatography를 반복 실시하여 4종의 phenolic 화합물을 분리, 정제하였다. NMR, IR, 및 EI/MS 등을 해석하여, norartocarpanone (1), 2',4',7-trihydroxy-(2S)-flavanone (2), methyl-${\beta}$-resorcylate (3), 그리고 (Z)-oxyresveratrol-4-O-${\beta}$-$\small{D}$-glucopyranoside (4)로 각각 구조동정하였다. 화합물 (Z)-oxyresveratrol-4-O-${\beta}$-$\small{D}$-glucopyranoside (4)는 상백피로부터는 이번 실험에서 처음으로 분리되었다.

• Nutrition Research and Practice
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• 제9권6호
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• pp.599-605
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• 2015

BACKGROUND/OBJECTIVES: Citrus flavonoids have a variety of physiological properties such as anti-oxidant, anti-inflammation, anti-cancer, and anti-obesity. We investigated whether bioconversion of Citrus unshiu with cytolase (CU-C) ameliorates the anti-adipogenic effects by modulation of adipocyte differentiation and lipid metabolism in 3T3-L1 cells. MATERIALS/METHODS: Glycoside forms of Citrus unshiu (CU) were converted into aglycoside forms with cytolase treatment. Cell viability of CU and CU-C was measured at various concentrations in 3T3L-1 cells. The anti-adipogenic and lipolytic effects were examined using Oil red O staining and free glycerol assay, respectively. We performed real time-polymerase chain reaction and western immunoblotting assay to detect mRNA and protein expression of adipogenic transcription factors, respectively. RESULTS: Treatment with cytolase decreased flavanone rutinoside forms (narirutin and hesperidin) and instead, increased flavanone aglycoside forms (naringenin and hesperetin). During adipocyte differentiation, 3T3-L1 cells were treated with CU or CU-C at a dose of 0.5 mg/ml. Adipocyte differentiation was inhibited in CU-C group, but not in CU group. CU-C markedly suppressed the insulin-induced protein expression of CCAAT/enhancer-binding protein ${\alpha}$ ($C/EBP{\alpha}$) and peroxisome proliferator-activated receptor gamma ($PPAR{\gamma}$) as well as the mRNA levels of $CEBP{\alpha}$, $PPAR{\gamma}$, and sterol regulatory element binding protein 1c (SREBP1c). Both CU and CU-C groups significantly increased the adipolytic activity with the higher release of free glycerol than those of control group in differentiated 3T3-L1 adipocytes. CU-C is particularly superior in suppression of adipogenesis, whereas CU-C has similar effect to CU on stimulation of lipolysis. CONCLUSIONS: These results suggest that bioconversion of Citrus unshiu peel extracts with cytolase enhances aglycoside flavonoids and improves the anti-adipogenic metabolism via both inhibition of key adipogenic transcription factors and induction of adipolytic activity.

• 생물환경조절학회지
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• 제25권1호
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• pp.9-15
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• 2016

고온은 사과(Malus domestica Borkh) 과실의 품질에 영향을 끼치는 가장 중요한 환경 요인 중 하나이다. 착색기의 '홍로' 사과 과실을 3단계로 구분하여 Real-time PCR을 통해 온도조건에 따른 안토시아닌 합성과 당 축적 관련 유전자의 발현 차이를 조사하였다. 당 합성관련 유전자인 ${\beta}$-amylase(BMY)와 polygalacturonase(PG)의 발현은 변색 시작단계보다 마지막 단계에서 월등히 높았다. 과피의 착색과 관련있는 phenylalanine ammonia-lyase(PAL), chalcone synthase(CHS), flavanone 3-hydroxylase(F3H)와 malate dehydrogenase(MDH)유전자는 변색 초기작단계에서는 고온 처리 24시간후에 발현이 증가하는 경향을 보였으며 변색 중간단계에서는 점차 증가하는 경향을 보였다. 변색단계별로 보았을 때 $25^{\circ}C$처리구가 다른 온도처리구보다 발현 정도가 더 높았으며, 변색 시작단계보다 마지막 단계에서의 발현이 강하게 유도되었다. 본 연구의 결과로 착색 초기단계의 과실이 고온스트레스가 가장 영향을 끼치므로 착색초기단계의 과실을 이용하여 전사체를 분석하면 분자생물학적 수준에서 사과의 성숙대사에서 유용한 정보를 얻을 수 있을 것으로 사료된다.

• Archives of Pharmacal Research
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• 제16권1호
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• pp.25-28
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• 1993

Our previous report demonstrated that certain flavonoid aglycones such as apigenin (flavone), quercetin, morin (flavonols), and biochanin A (isoflavone) showed in vivo antiinflammatory activity via topical and oral routes of adminstation. As a continual study, the various flavonoid glycosides have been evaluated in mouse ear edema assay using archidonic acid or croton-oil as a inflammagen. Flavonoids were orally administered (2 mg/mouse) and ear edema inhibition was measured. Significant antiinflammatory activities were found esepcially in flavone and flavonol glycosides (15-29% inhibition) although the flavonoid derivatives tested showed less antiinflammatory activity than hydrocortisone or indomethacin. Chalcone and flavanone derivatives were not significantly active. And in general, flavonol glycosides of kaempferol-type were found to have a higher oral antiinflammatory activity than that of flavonol glycosides of quercetin-type in mice.

• 동의신경정신과학회지
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• 제3권1호
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• pp.84-90
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• 1992

Solvent and TLC-fractionations of the root of Salvia miltiorrhiza have yielded the results as follows ; Solvent fractions Petr. ether Ether Ethy1 acetate Water Control 100uL 0 0.2 35.1 41.9 43.0 50ul 0.7 3.7 37.2 42.0 TLC-fractionation and the Cytotoxic activity Fractions I II III IV V VI Petr. ehter Control 100uL13.0 7.1 16.8 1.2 30.9 23.2 0.5 48.3 50uL 37.1 26.1 30.0 20.1 45.7 27.2 29.7 Among the solvent fractions the petroleum ehter fraction corresponding to the concentration of 20ug/ml has showed the strongest Cytotoxic activity. (no cell survived) A double dilution of the fraction(10ug/ml) still showed strong activity.(0.2 cells survived) The ether fraction contained strong activity. Of the fraction which have veen obtained by a prcparative silicagel TLC I, II, III & IV were cytotoxic, but V and VI were inactive Howevcr, it is worthwhile to note that no one of these has no strong Cytotoxicity as the pertoleum ether fraction itself. This observation says that the active fractions could be additive or synergic to each other. The most active fraction, IV, was scrached out from the TLC and its UV-spectrum taken. The absorption maxima were 207 and 272 nm, indicating the presence of a flavanone strucuture.

• Natural Product Sciences
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• 제10권6호
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• pp.344-346
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• 2004

Eight phenolic compounds (1-8) which were isolated from the barks of Ulmus macrocarpa were evaluated for their inhibitory activities on nitric oxide (NO) and prostagrandin $E_2$ (COX-2) production in $interferon-{\gamma}\;(INF-{\gamma})$ and lipopolysaccharide (LPS)-activated RAW 264.7 cells in vitro. NO and COX-2 levels were moderately reduced by the addition of compounds (1-8). Among them 3,4,5,6,7 and 8 inhibited NO production in a dose dependent manner with an $IC_{50}$ of 92.2, 97.3, 36.1, 43.5, 32.8, 39.4 and 37.1 ${\mu}g/ml$, respectively (positive control, L-NMMA; 36.4 ${\mu}g/ml$), and 3,4,5,6,7 and 8 reduced the COX-2 level in a dose dependent manner with an $IC_{50}$ of 43.2, 24.8, 24.8, 33.4, 44.8 and 22.7 ${\mu}g/ml$, respectively (positive control, indomethacin; 23.4 ${\mu}g/ml$). These results suggest that the phenolic compounds may be developed as potential anti-inflammatory and cancer chemopreventive agents.