• Archives of Pharmacal Research
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• 제25권3호
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• pp.313-319
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• 2002

A total of eight flavonoids (1-8), including a novel $quercetin-7-o-(6"-o-acetyl)-{\beta}-D-glucopyranoside$ (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin $7-o-{\beta}-D-glucopyranoside$ (3), $luteolin-7-o-(6"-Ο-acetyl)-{\beta}-D-glucopyranoside$ (4) quercetin $7-o-{\beta}-D-glucopyranoside$ (5), acacetin 7-o-{\beta}-D-glucuronide (7) and apigenin-6-C-{\beta}-D-glucopyrano $syl-8-C-{\beta}-D-glucopyranoside$ (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.

• 생약학회지
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• 제31권1호
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• pp.105-108
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• 2000

Impatiens textori Miquel (Balsaminaceae) is an annual plant growing in most parts of Korea. The herb of this plant has been used for the external application of snake poison and the bruise. Previous investigations conducted with the herbs have demonstrated it to contain three flavones and three flavone glycosides. Continuing to previous reports, quercetin, kaempferol and acacetin $7-O-{\beta}-D-glucoside$ were isolated from the herbs of this plant.

• 한국식품저장유통학회:학술대회논문집
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• 한국식품저장유통학회 2003년도 춘계총회 및 제22차 학술발표회
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• pp.22-39
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• 2003

Biological activity of phenolic compounds in seeds and leaves of safflower (Carthamu tinctorius L.) were evaluated using several in vitro and in vivo assays. Six phenolic constituents were isolated from the seeds and identified as N-feruloylserotonia, N- (p-coumaroyl)serotonin, matairesinol, 8′-hydroxyarctigenin, acacetin 7-O-$\beta$-D-glucoside (tilianine) and acacetin. Six phenolic compounds exhibited considerable antioxidative activity, and especially two serotonins showed potent DPPH radical scavenging activity and antiperoxidative activity against rat liver microsomal lipid peroxidation induced by the hydroxyl radical generated via a Fenton-type reaction. Additionally, six phenolic compounds possessed comparable cytotoxicity against three cancer cells, Hela cell, MCF-7 and HepG2 cell, and particularly acacetin and its glycosides had the most potent cytotoxicity. Moreover, we found that feeding safflower seeds attenuated bone loss, and lowered levels of plasma and liver lipids in ovariectomized rats. Serotonins, lignans and flavones stimulated proliferation of the osteoblast-like cells in a dose-dependent manner (10$^{-15}$ ~10$^{-6}$ M), as potently as E$_2$ (17$\beta$-estradiol). Particularly, serotonins were mainly responsible for bone-protecting and lipid lowering effects in ovariectomized rats. Meanwhile, eight flavonoids, including a novel quercetin-7-O-(6"-O-acetyl)-$\beta$-D-glucopyranoside and seven kown flavonoids, luteolin quercetin, luteolin 7-O-$\beta$-D-glucopyranoside, luteolin-7-O-(6"-O-acetyl)-$\beta$-D-gluco-pyranoside, quercetin 7-O- -glucopyranoside, acacetin 7-O-$\beta$-D-glucuronide and apigenin-6-C-$\beta$-D-glucopyranosyl-8-C-$\beta$-D-glucopyranoside were first isolated and identified from safflower leaf. Among these flavonoids, luteolin-acetyl-glucoside and $\beta$quercetin- acetyl-glucoside showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin, quercetin and their corresponding glycosides also exhibited strong antioxidative activity, while acacetin glucuronide and apigenin-6, 8-di-C-glucoside were relatively less active. Finally, changes in phenolic compositions were also determined by HPLC in the safflower seed and leaf during growth stages and roasting process to produce standardized supplement powerds. These results suggest that phenolic compounds in the roasted safflower seed and leaf may be useful as potential sources of therapeutic agents against several pathological disorders such as carcinogenesis, atherosclerosis and osteoporosis.

• Journal of Applied Biological Chemistry
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• 제59권4호
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• pp.357-360
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• 2016

국화(C. morifolium)의 꽃을 80 % MeOH 수용액으로 추출한 뒤, 감압농축한 추출물을 EtOAc, n-butyl alcohol 및 물분획으로 나누었다. EtOAc 분획과 n-butyl alcohol 분획에 대하여 $SiO_2$ 및 ODS column chromatography를 반복 실시하여 4종의 flavonoid를 분리, 정제하였다. Nuclear magnetic resonance, infrared spectrometry 및 FAB-MS data를 해석하여, 화합물 1-4를 각각 apigenin, acacetin, cosmetin (apigenin-7-O-${\beta}$-$\small{D}$-glucopyranoside), acacetin-7-O-${\beta}$-$\small{D}$-glucoside으로 구조 동정 하였다.

• Food Science and Biotechnology
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• 제16권1호
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• pp.71-77
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• 2007

The antioxidant properties of twelve phenolic compounds, including matairesinol 4'-O-$\beta$-D-glucoside, 8'-hydroxyarctigenin 4'-O-$\beta$-D-glucoside, matairesinol, 8'-hydroxyarctigenin, N-feruloylserotonin 5-O-$\beta$-D-glucoside, N-(p-coumaroyl)-serotonin-5-O-$\beta$-D-glucoside, N-feruloylserotonin, N-(p-coumaroyl)serotonin, luteolin 7-O-$\beta$-D-glucoside, luteolin, acacetin 7-O-$\beta$-glucuronide, and acacetin, isolated from defatted safflower (Carthamus tinctorius L.) seeds were evaluated with regard to the DPPH, superoxide and hydroxyl radicals. Additionally, levels of phenolic compounds were determined by HPLC in two cultivars of safflower seeds. Among them, four serotonin derivatives showed potent DPPH ($IC_{50}=10.83-21.75\;{\mu}M$) and hydroxyl ($IC_{50}=75.93-374.63\;{\mu}M$) radical scavenging activities, and their activities were significantly stronger than that of ${\alpha}-tocopherol$. Four flavonoids ($IC_{50}=170.65-275.83\;{\mu}M$) and four lignans ($IC_{50}=114.22-406.10\;{\mu}M$) exhibited significant superoxide and hydroxyl radical scavenging activities, respectively, whereas these compounds contained less activity toward the DPPH and hydroxyl radicals than serotonin derivatives. The levels of serotonin derivatives, lignans and flavonoids in safflower seeds of two cultivars ranged from 49.30 to 260.40, 3.72 to 158.90, and 11.72 to 214.97 mg% (dry base), respectively. Of the two cultivars, 'Cheongsu' had somewthat higher concentrations of phenolic compounds than 'Uisan'. These results suggest that phenolic compounds in safflower seeds may playa role as protective phytochemical antioxidants against reactive oxygen-mediated pathological diseases.

• Preventive Nutrition and Food Science
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• 제11권4호
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• pp.311-317
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• 2006

Phenolic compounds in safflower seeds were recently found to stimulate bone formation and increase plasma HDL cholesterol levels in estrogen deficient rats, and to inhibit melanin synthesis. Nine phenolic compounds: $N-feruloylserotonin-5-O-{\beta}-D-glucoside,\;8'-hydroxyarctigenin-4'-O-{\beta}-D-glucoside,\;luteolin-7-O-{\beta}-D-glucoside$, N-(p-coumaroyl)serotonin, N-feruloylserotonin, 8'-hydroxy arctigenin (HAG), luteolin (LT), $acacetin-7-O-{\beta}-D-glucuronide$ (ATG) and acacetin (AT), were quantified by HPLC in safflower (Carthamus tinctorius L.) seeds during growth and processing. During growth, levels of the nine phenolic compounds in the seeds increased progressively with increasing growth stages, reached a maximum on July 30 (42nd day after flowering), and then remained relatively constant. During the roasting process, levels of phenolic compounds, except HAG, LT and AT, generally decreased with increased roasting temperature and time, whereas those of HAG, LT and AT increased progressively with increased roasting temperature and time. During the steaming process, levels of other phenolic compounds except HAG and AT generally tended to increase with increased steaming time, whereas those of HAG and AT were scarcely changed. During the microwave treatment, quantitative changes of phenolic compounds were similar to the roasting process, although there were some differences in levels of phenolic compounds between two heat treatments. These results suggest that the steamed safflower seeds after harvesting on late July may be useful as potential dietary supplement source of phenolic compounds for prevention of several pathological disorders, such as atherosclerosis and osteoporosis and aging.

• 약학회지
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• 제11권1_2호
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• pp.7-16
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• 1967

A yellowish microneedles, $C_{28}$ H$_{32}$ $O_{14}$ ${\cdot}$ I$_{1}$/$_2$, H$_{2}$O, m.p.262-$4^{\circ}$ , [${\alpha}$$_{D}^{20}$= -71,$43^{\circ}$(C = 0.42, pyridine), its acetate m.p.123-5.deg., were obtained in 0.3% yield from the leaves of Chrysanthemum sibiricum F$_{ISCHER}$. This substance is insoluble in water and the usual organic solvents except pyridine and ethylene glycol and, is not decomposed by dilute mineral acids but undergoes decomposition on being boiled in 60% H$_{2}$SO$_{4}$ or 35% HCl, giving one moel each of acacetin, glucose and rhamnose. It was not hydrolysed with a rhamnodiastase preparation obtained from the seeds of Rhamnus koraiensis. After permethylation of it, the uncrystallized product was hydrolysed and apigenin-5,4'-dimethyl ehter, m.p.$262^{\circ}$ was obtained, indicating that the disaccharide residue is at the 7 position of acacetin. Partial hydrolysis of this acacetin-7-rhamnoglucoside in cyclohexanol with formic acid gave acacetin-7-glucoside, m.p.246.deg. and rutinose, identifying them with authentic specimen on a paper chromatography. It was thus identified as linarin(acacetin-7-rutinoside) by means of mixed fusion, of paper partition chromatography and of its derivatives. Zemplen and Bognar suggested that the glucosidic linkage of linarin is .betha. by means of synthesis of this substance. But there is no evidence whether it is hydrolysed by emulsin or maltase or not. Linarin itself was not hydrolysed by an emulsin existing in the seed of Apricot or a maltase, but acacetin-7-glucoside(tilianin) which obtained from linarin gave acacetin and glucose on hydrolysis with the same emulsin and accordingly the glucosidic linkages of linarin and tilianin are thus regarded as ${\beta}$.

• 한국식품영양과학회지
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• 제37권9호
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• pp.1162-1167
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• 2008

홍화씨를 이용한 골다공증 및 고지혈증 예방용 건강기능식품을 개발하기 위한 연구의 일환으로 홍화씨의 소화성, 기능성 및 기호성을 증대시킬 수 있는 방안으로 발아홍화씨를 제조하여 일반성분 및 기능성성분(지방산, tocopherols, 수용성아미노산 및 페놀화합물)의 함량을 홍화씨와 비교 분석하였다. 홍화씨는 발아하면서 조단백질과 조지방은 감소한 반면, 가용성 무질소물, 조섬유소 및 회분은 다소 증가하는 경향을 나타내었으며, linoleic 및 oleic aicds가 약 80% 이상 거의 대부분을 차지하고 있었으며, 그 외 palmitic, stearic 및 arachidic acids가 주요 지방산으로 나타났고, 발아에 따른 지방산의 조성 비율은 거의 변화가 없었다. 홍화씨와 발아홍화씨의 $\alpha$-tocopherol 함량은 각각 744.7 및 809.0 mg%로서 발아 후 64.3 mg% 증가하였으며, 홍화씨의 주된 아미노산으로 asparagine, arginine, proline, glutamic acid가 차지하고 있었으며, 발아함에 따라 그들의 함량이 크게 증가하였고, 특히 threonine, valine, leucine, isoleucine, phenylalanine, lysine 및 histidine 등의 필수아미노산 함량이 크게 증가하였다. 홍화씨에는 3종의 리그난(8'-hydroxyarctigenin 4'-O-$\beta$-D-glucoside, 8'-hydroxyarctigenin 및 matairesinol)과 4종의 세로토닌유도체[N-feruloylserotonin 5-O-$\beta$-D-glucoside, N-feruloylserotonin, N-(pcoumaroyl)-serotonin 5-O-$\beta$-D-glucoside, N-(p-coumaroyl)serotonin] 그리고 2종의 플라보노이드(acacetin 7-O-$\beta$-D-glucuronide, acacetin) 화합물이 존재하였으며, 발아함에 따라 세로토닌유도체를 함유한 모든 페놀화합물의 함량은 다소 감소하는 경향을 나타내었다. 이와 같이 홍화씨를 발아함에 따라 섬유소 및 유용 기능성성분의 증가와 더불어 설사를 유발하는 고미성분의 감소 그리고 소화성 및 기호성을 떨어뜨리는 홍화씨 껍질의 분리 및 효율성 확대를 이룰 수 있기에 향후 발아홍화씨는 항골다공증 및 항고지혈증 건강기능식품 소재로서 개발 가능성이 높다고 사료된다.