• 생약학회지
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• 제22권4호
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• pp.211-214
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• 1991

Two compounds were isolated from the methanolyzate of the butanol-soluble fraction obtained from the whole plants of Melandrium firmum (Caryophyllaceae) and identified as $3-{\beta}-D-glucuronopyranosylmelandrigenin$ methyl ester and $2{\beta},\;21{\beta}-dihydroxy-16,\;23-dioxo-28-norolean-13(18)-ene$.

• Archives of Pharmacal Research
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• 제14권2호
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• pp.160-164
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• 1991

The existence in nature of two isomers of 28-nortriterpenes is known. One is normal D/E cis form and the other is $17\alpha$-hydrogen D/E trans form. Since the latter cannot exist with ring D in the chair conformation, the chiroptical method is not applicable to determination of the absolute configuration. The stereochemical assignment would now be made by NMR data. Confirmation of this view could be provided by the synthesis of $3\beta, 21\beta-{dihydroxy-16-keto-28-nor-17}\alpha, \;18\beta-{olean-12-ene}$ as a model compound.

• Natural Product Sciences
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• 제21권2호
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• pp.111-121
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• 2015

The root of Panax ginseng, is a Korea traditional medicine, which is used in both raw and processed forms due to their different pharmacological activities. As part of a continued chemical investigation of ginseng, the focus of this research is on the isolation and identification of compounds from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, semi-preparative-high performance liquid chromatography, Fast atom bombardment mass spectrometric, and nuclear magnetic resonance. Dammarane-type triterpenoid saponins were isolated from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, and semi-preparative-high performance liquid chromatography. Their structures were identified as protopanaxadiol ginsenosides [gypenoside-V (1), ginsenosides-Rb1 (2), -Rb2 (3), -Rb3 (4), -Rc (5), and -Rd (6)], protopanaxatriol ginsenosides [20(S)-notoginsenoside-R2 (7), notoginsenoside-Rt (8), 20(S)-O-glucoginsenoside-Rf (9), 6-O-[$\alpha$-L-rhamnopyranosyl(1$\rightarrow$2-$\beta$-D-glucopyranosyl]-20-O-$\beta$-D-glucopyranosyl-$3\beta$,$12\beta$, 20(S)-dihydroxy-dammar-25-en-24-one (10), majoroside-F6 (11), pseudoginsenoside-Rt3 (12), ginsenosides-Re (13), -Re5 (14), -Rf (15), -Rg1 (16), -Rg2 (17), and -Rh1 (18), and vinaginsenoside-R15 (19)], and oleanene ginsenosides [calenduloside-B (20) and ginsenoside-Ro (21)] through the interpretation of spectroscopic analysis. The configuration of the sugar linkages in each saponin was established on the basic of chemical and spectroscopic data. Among them, compounds 1, 8, 10, 11, 12, 19, and 20 were isolated for the first time from P. ginseng root.

• Food Science and Biotechnology
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• 제17권3호
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• pp.578-586
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• 2008

Phytochemicals study from the leaves of soybean [Glycine max (L.) Merr.], one of Korean edible plant materials were investigated through various chromatographic procedures. The methanolic leaves extracts of soybean yielded 16 phytochemicals, including 5 isoflavones 1-5, 3 flavones 6-8, 1 flavonol 9, 2 pterocarpans 10 and 11, 2 phenolic compounds 12 and 13, 2 phytosterols 14 and 15, and 1 sugar alcohol 16. The structures were fully characterized by analysis of physical and spectral data and were defined clearly as 4,5,7-trihydroxyisoflavone (1), 4,5,7-trihydroxyisoflavone-7-O-$\beta$-D-glucopyranoside (2), 4,7-dihydroxy-6-methoxyisoflavone (3), 4,7-dihydroxyisoflavone (4), 4,7-dihydroxyisoflavone-7-O-$\beta$-D-glucopyranoside (5), 5,7,4'-trihydroxyflavone (6), 3',4',5,7-tetrahydroxyflavone (7), 3',4',5-trihydroxyflavone-7-O-$\beta$-D-glucopyranoside (8), 3,4',5,7-tetrahydroxyflavonol (9), coumestrol (10), glyceofuran (11), 4-hydroxybenzoic acid (12), methyl-4-hydroxybenzoate (13), soyasapogenol B (14), stigmasterol (15), and D-mannitol (16), respectively. Among them, phytochemicals 7-16 were reported for the first time on the isolation and confirmation from the leaves of this species. These results suggest that the leaves extracts of soybean may possess possible health related benefits to human due to the isolated phytochemicals 1-16 which have been well known potential effects on various chronic diseases.

• 한국발생생물학회지:발생과생식
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• 제16권1호
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• pp.39-45
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• 2012

To verify the sex steroids which are involved in oocyte maturation of the blacktip grouper, $Epinephelus$ $fasciatus$, we incubated vitellogenic oocytes (0.41 and 0.50 mm in average diameter) in the presence of exogenous steroid precursor ($[^3H]17{\alpha}$-hydroxyprogesterone). Steroids were extracted, separated and identified by thin layer chromatography. The major metabolites produced were androstenedione, estradiol-$17{\beta}$, estrone and progestogens. Progestogen metabolites in the oocytes of 0.50 mm were more abundant than those of 0.41 mm. Also, we investigated the $in$ $vitro$ effects of human chorionic gonadotropin (HCG; 5, 50 and 500 $IU/m{\ell}$), $17{\alpha},20{\beta}$-dihydroxy-4-pregnen-3-one ($17{\alpha}20{\beta}P$) and $17{\alpha},20{\beta}$-trihydroxy-4-pregnen-3-one ($17{\alpha}20{\beta}21P$; 5, 50 and 500 $ng/m{\ell}$, respectively) on oocyte maturation. In the oocytes of 0.41 mm, treatment with 50 IU HCG stimulated GVBD ($55.30{\pm}1.20%$) compared with controls ($32.41{\pm}3.13%$, $p$<0.05). In the oocytes of 0.50 mm, treatment of $17{\alpha}20{\beta}P$ (50 and 500 $ng/m{\ell}$) stimulated GVBD ($50.13{\pm}2.52$ and $51.77{\pm}5.91%$, respectively) compared with controls ($36.81{\pm}2.89%$, $p$<0.05). Treatment with 500 IU HCG also stimulated GVBD ($49.59{\pm}5.15%$) compared with controls ($p$<0.05). Taken together, these results suggested that both HCG and $17{\alpha}20{\beta}P$ were effective on in vitro oocyte maturation and $17{\alpha}20{\beta}P$ may act as a maturation inducing hormone in blacktip grouper.

• The Korean Journal of Physiology and Pharmacology
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• 제2권4호
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• pp.461-469
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• 1998

Tetrahydroisoquinoline (THI) alkaloids can be considered as cyclized derivatives of simple phenylethy-lamines, and many of them, especially with 6,7-disubstitution, demonstrate relatively high affinity for catecholamines. Two -OH groups at 6 and 7 positions are supposed to be essential to exert ?${\beta}-receptor$ activities. However, it is not clear whether -OH at 6,7 substitution of THIs also shows ?${\alpha}-adrenoceptor$ activities. In the present study, we investigated whether -OH or $-OCH_3$ substitutions of 6,7 position of THIs differently affect the ?1-adrenoceptor affinity. We synthesized two 1-naphthylmethyl THI alkaloids, $1-{\beta}-naphthylmethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline$ HBr (YS 51) and $1-{\beta}-naphthylmethyl-6, 7-dimethoxy-1,2,3,4-tetrahydroisoquinoline$ HCl (YS 55), and their pharmacological actions on ?${\alpha}_1-adrenoceptor$ were compared. YS 51 and YS 55, concentration-dependently relaxed endothelium-denuded rat thoracic aorta precontracted with phenylephrine (PE, 0.1 ${\mu}M$) in which $pEC_{50}$ were $5.89{\pm}0.21$ and $5.93{\pm}0.19$, respectively. Propranolol (30 nM) did not affect the relaxation-response curves to YS 51 and YS 55. Concentration-response curves to PE were shifted to right by the pretreatment with YS 51 or YS 55. The $pA_2$ values of YS 51 and YS 55 showed $6.05{\pm}0.24$ and $5.88{\pm}0.16$, respectively. Both probes relaxed KCl (65.4 mM)-contracted aorta and inhibited $CaCl_2-induced$ contraction of PE-stimulated endothelium- denuded rat thoracic aorta in $Ca^{2+}-free$ solutions. In isolated guinea pig papillary muscle, 1 and 10 ${\mu}M$ YS 51 increased contractile force about 4- and 8- fold over the control, respectively, along with the concentration-dependent increment of cytosolic $Ca^{2+}$ ions. While, 10 ${\mu}M$ YS 55 reduced the contractile force about 50 % over the control and lowered the cytosolic $Ca^{2+}$ level, in rat brain homogenates, YS 51 and YS 55 displaced $[^3H]prazosin$ binding competitively with Ki 0.15 and 0.12 ${\mu}M$, respectively. However, both probes were ineffective on $[^3H]nitrendipine$ binding. Therefore, it is concluded that two synthetic naphthylmethyl-THI alkaloids have considerable affinity to ?1-adrenenoceptors in rat aorta and brain.