• Natural Product Sciences
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• v.22 no.2
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• pp.117-121
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• 2016

On the phytochemical investigation of a 70% ethanol extract of the fruits of Opuntia ficus-indica, (Cacataceae), we could result in the isolation of thirteen phenolic compounds including seven flavonoids (1 - 9) and four simple phenolic glycosides (10 - 13) by column chromatographic methods. Among the isolated compounds, picein (11), androsin (12), and $1-O-feruloyl-{\beta}-{\small{D}}-glucopyranoside$ (13) were isolated for the first time from O. ficus-indica; additionally, this is the first report $benzyl-O-{\beta}-{\small{D}}-glucopyranoside$ (10) from the genus Opuntia. The structures of the compounds were determined by spectral data analysis which included 1D, 2D NMR spectrum and ESIMS.

• Archives of Pharmacal Research
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• v.21 no.1
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• pp.17-23
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• 1998

Flavonoid glycosides were metabolized to phenolic acids via aglycones by human intestinal microflora producing ${\alpha}$-rhamnosidase, exo-${\beta}$-glucosidase, endo- ${\beta}$-glucosidase and/or ${\beta}$-glucuronidase. Rutin, hesperidin, naringin and poncirin were transformed to their aglycones by the bacteria producing ${\alpha}$-rhamnosidase and ${\beta}$-glucosidase or endo- ${\beta}$-glucosidase, and baicatin, puerarin and daidzin were transformed to their aglycones by the bacteria producing ${\beta}$glucuronidase, C-glycosidase and ${\beta}$-glycosidase, respectively. Anti-platelet activity and cytotoxicity of the metabolites of flavonoid glycosides by human intestinal bacteria were more effective than those of the parental compounds. 3,4-Dihydroxyphenylacetic acid and 4-hydroxyl-phenylacetic acid were more effective than rutin and quercetin on anti-platelet aggregation activity. 2,4,6-Trihydroxybenzaidehyde, quercetin and ponciretin were more effective than rutin and ponciretin on the cytotoxicity for tumor cell lines. We insist that these flavonoid glycosides should be natural prodrugs.

• Journal of the Korean Wood Science and Technology
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• v.34 no.6
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• pp.51-60
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• 2006

Juglans mandshurica barks were collected, extracted with acetone-$H_2O$ (7:3, v/v), fractionated with n -hexane, $CH_2Cl_2$, and EtOAc, and freeze dried to give some dark brown powder. The EtOA cand $H_2O$ soluble fractions were chromatographe d on a Sephadex LH-20 column using $H_2O$-MeOH and EtOH-hexane mixture as eluents. Spectrometric analysis such as NMR and MS, including TLC,were performed to characterize the structures of the isolated compounds. From the EtOAc and $H_2O$ soluble fractions, three flavanols (1~3), three flavonols (4~6) and five flavonol glycosides (7~11) were isolated and elucidated.

• Journal of the Korean Wood Science and Technology
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• v.43 no.5
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• pp.591-599
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• 2015

Cercidiphyllum japonicum leaves were collected, air-dried and extracted with 70% aqueous acetone, then concentrated and sequentially fractionated using n-hexane, methylene chloride ($CH_2Cl_2$), ethylacetate (EtOAc), and $H_2O$. A portion of EtOAc fraction (10 g) was chromatographed on a Sephadex LH-20 column, by the successively elution with various aqueous $MeOH-H_2O$ (1:9, fraction $1-2{\rightarrow}3:7$, fraction $3-5{\rightarrow}1:1$, fraction $6-9{\rightarrow}7:3$, fraction $10-13{\rightarrow}9:1$, fraction 14-16). Compound 2 was isolated from fraction 6 and compound 1 was separated from fraction 11 and 12. Compound 3 and 4 were purified from fraction 13. The isolated compounds were elucidated as quercetin-3-O-${\alpha}$-L-rhamnopyranoside (1), chlorogenic acid (2), quercetin-3-O-${\alpha}$-L-arabinofuranoside (3) and quercetin-3-O-${\beta}$-D-xylopyranoside (4) by the spectral and literature data, and by comparison with the authentic samples. These compounds were reported, for the first time, from the extracts of C. japonicum leaves. Also chlorogenic acid (2) has never been reported before in domestic tree species and can be used as an index compound for C. japonicum.

• Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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• 2003.04a
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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 Ginseng Research
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• v.14 no.3
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• pp.437-441
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• 1990

The investigation of UV absorbing compounds in saponin fraction of Pnm.1. Kiairnk root was carried out by thin layer chromatography, semipreparative HVLC. l3C, 1H-NMR, mass spectrometry and chemical characteristics in searching plant for growth regulatony substances such as phenolic glycoside. Drying of fresh ginseng at 15 $^{\circ}C$ decreased not only number but also size of UV absorbing sports on TLC. One of the relatively large spots in fresh ginseng was isolated and identified as adenosine, which is subjected for growth stimulatory activity Detection of phenolic glycosides failed in dried root bolt was highly probable in fresh ginseng even with the insufficient amount of sample.

• Natural Product Sciences
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• v.2 no.1
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• pp.14-18
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• 1996

A new phenolic glycoside named mussaendoside L (1), along with four known iridoidal glycosides $(2{\sim}5)$ were isolated from the aerial parts of Mussaenda pubescens Ait.f. Their structures were elucidated on the basis of chemical and spectroscopic evidence.

• Archives of Pharmacal Research
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• v.19 no.3
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• pp.231-234
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• 1996

Two acetophenone glycosides, 2, 4-dihydroxy-6-methoxy acetophenone $4-O-\beta-D-glucopyranoside(I)$, 2, 4, 6-trihydroxy acetophenone $2-O-\beta-D-glucopyranoside(II)$, together with coniferin(III) were isolated from the aerial parts of Artemisia stolonifera (Max.) Kom. The structures of the compounds were elucidated on the basis of spectroscopic evidence. Compound IIwas also confirmed as a new phenolic glycoside from natural sources. In addition, compound I induced cytostatic activity of macrophasges, while compounds II and III did not.

• Archives of Pharmacal Research
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• v.21 no.1
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• pp.24-29
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• 1998

To search for the anti-diabetic principle from the stem bark of Kalopanax pictus, seven kinds of chemical constituents including hederagenin glycosides and phenolic glycosides wre isolated. The anti-diabetic evaluation of these isoltes in the streptozotocin-induced diabetic rats exhibited that kalopanaxsaponin A has a potent anti-diabetic activity in contrast to a mild activity of hederagenin. In addition, significant hypocholesterolemic and hypolipidemic activities of kalopanaxsaponin A and hederagenin were observed. The structure-activity relationship of kalopanaxsaponin A was also investigated in the present work.

• Journal of the Korean Society of Food Science and Nutrition
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• v.35 no.6
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• pp.713-720
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• 2006

This study was designed to investigate the possible utilization of Ligustrum japonicum leaves as a source of functional ingredients. Contents of total phenolic compounds and condensed tannin were $0.89{\sim}1.53%$ and $0.10{\sim}0.13%$, respectively. The major flavonoid compounds in the leaves of L. japonicum were luteolin, apigenin and their glycosides. Tyrosol, t-cinnamic acid, p-hydroxybenzoic acid, vanillic acid, shikimic acid and protocatecuic acid were detected in free phenolic acid, while tyrosol, t-cinnamic acid, ferulic acid, esculetin, caffeic acid, p-coumaric acid and hydroxytyrosol were detected in esterified phenolic acid. The insoluble phenolic acid contained tyrosol, t-cinnamic and p-caoumaric acid.