간디스토마에 작용하는 천연물 및 그 유사체

안병준(Byung Zun Ahn),이재구(Jae Ku Rhee) 대한약학회 1986 약학회지 Vol.30 No.5

Among 230 species of herbal drugs screened, thirty one show the anthelmintic activities in vitro against Clonorchis sinensis, the chinese liver fluke. The active substances have been isolated and their structures identified. Some of the active substances and their derivatives have been synthesized, followed by anthelmintic activity tests. The extracts froria the active drugs cause damages in organs of the adult worm in the hepatic duct of rabbit. Some fresh water fish, which function as bad hosts for the fluke, excrete defense substances against the cercaria of the fluke. The defense substances have been isolated from Cyprinus carpio and Cyprinus carpio nudus, followed by structural identification. The results are summarized as follows: 1) The bark of Machilus thunbergii as well as the seed of Schizandra chinensis contain meso-dihydro-guaiaretic acid as the anthelmintic component. Among derivatives synthesized, 4-phenyl-1-((3, 4-dihydroxyphenyl)-4-phenyl-1-(3-hydroxy-4-methoxyphenyl)-and 4-phenyl-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutanes show considerable activities. Administration of the bark extract mainly damages the bladder of the adult worm. 2) The active substance from the roasted fruit of Prunus mume is 2-hydroxymethylfurfural. This substance is produced during the roasting process. Administration of the fruit extract causes a damage of the bladder of the adult worm. 3) The active substance from the root of Scutellaria baicalensis is 5,2''-dihydroxy-6,7,8,6''-tetramethoxyflavone. 4) Beside alantolactone, a very strong anthelmintic component is contained in the root of Inula helenium. Administration of the root extract causes irreversible damage on the worm, affecting mainly the reproductive organs. 5) The cercaricidal substances from the epidermis of C. carpio and C. carpio nudus are ethyl linoleate and linoleic acid, respectively. 6) The cercaricidal substances from various kinds of fresh water fish have different Rf values, implying that the defense substances are species-specific. Unexpectedly, the fish with good host function, for example Pseudorasbora parva, excrete the defense substances, too. The defense substances are possibly organ-specific in individual species; the organs essential for the existence of the species excrete the defense substances, allowing other parts to be invaded by the cercaria. 7) The cercaricidal fraction of Carassius carassius is detected only in the fish which have been collected during the summer time from May to September. Its secretion is not dependent on water temperature. Thus, it seems to be possible that the secretion of the defense substance would be stimulated through a contact between the fish and cercaria.

Catechin 이합체

안병준(Byung Zun Ahn) 한국생약학회 1979 생약학회지 Vol.10 No.2

A 6`, 8a-bonded catechin dimer was synthesized by action of phenoloxidase on 2 ㏖ (+)-catechins. The same dimer and other two dimers which are also 6`, 8a-bonded were isolated from the fresh cortex of Quercus robur. The 4, 8a-bonded and the etherified 4, 8a-bonded dimers were isolated from it. It was discussed about the meaning of the enzymatically produced 6`, 8a-bonded dimers in plant cell. The isolated dimers are as following: 1. 6`, 8a-bonded dimers: (+)-catechin-(+)-catechin-6`, 8a-dimer (IX), (+)-catechin-(+)-gallocatechin-6`, 8a-dimar (XIII), (+)-gallocatechin-(+)-catechin-6`, 8a-dimer(XIV). 2. 4,8a-bonded dimers: (+)-catechin-(+)-catechin-4, 8a-dimer(X), (-)-epicatechin-(+)-catechin-4, 8a-dimer (XI), (+) -galloatechin-(+)-catechin-4, 8a-dimer (XII). 3. 4,8a-bonded dimers with ether linkage: etherified(+)-catechin-(+)-catechin-4, 8a-dimer (XV), etherifid (+)-catechin-(+)-gallocatechin-4, 8a-dimer (XVI), etherified (+)-gallocatechin-(+)-catechin-4, 6a-dimer (XVII).

Phenol성 화합물의 ¹³C- 핵자기 공명(Ⅱ) : Phenol 성 Coumarine 유도체의 Chemical Shift에 관하여

안병준(Byung-Zun Ahn) 한국생약학회 1977 생약학회지 Vol.8 No.1

The ¹³C-chemical shifts of the phenolic coumarine derivatives, aesculetin, daphnetin and herniarin were studied on the basis of my previous report. All spectral data found in this report could be utilized to the structure elucidation of the unknown phenolic coumarine derivatives and other phenolic compounds. In addition, it is suggested that a long range coupling may occur in the follwing structure as represented by arrow.

Phenol계 성분

안병준(Byung-Zun Ahn) 한국생약학회 1978 생약학회지 Vol.9 No.2

Phenol성 화합물의 ¹³C-핵자기 공명(Ⅰ) : Phenol성 화합물의 Chemical Shift에 관한 연구

안병준(Byung-Zun Ahn) 한국생약학회 1977 생약학회지 Vol.8 No.1

¹³C-NMR behaviors of phenolic compounds such as phenol, catechol, pyrogallol, resorcine, phoroglucine and hydroquinone were studied. From the study on the effects of OH-substitution on benzene and its dervatives it was found that the additivity rule can be applied to the ortho-and para-effect but not to the meta-effect for the OH-function. The empirically calculated chemical shifts regarding the o-and p-effects coincide very well with the results of measurement. The chemical shifts of the phenolic compunds can be classified into three types. 1) Catechol-type C-1 and C-2 145 ppm C-3 and C-6 116-107 ppm 2) Pyrogallol-type C-1 132ppm C-2 and C-6 146ppm C-3 and C-5 106ppm 3) Resorcin-type C-1 and C-3 159ppm C-2 103-95ppm C-4 and C-6 107ppm

6-(1-하이드록시 또는 아실옥시알킬)-5,8-디알콕시-1,4-나프토퀴논 유도체의 합성, DNA Topoisomerase-I에 대한 억제, 세포독성 및 항암활성

김용,최수라,명평근,안병준,Kim, Yong,Choi, Su-La,Myung, Pyung-Keun,Ahn, Byung-Zun 대한약학회 2000 약학회지 Vol.44 No.2

A new synthetic method of 6-(1-oxyalkyl)-5,8-dimethoxy-1,4-naphthoquinones was developed, 2-formyl-1,4,5,8-tetramethoxynaphthalene was oxidized to form 6-formyl-5,8-dimethoxy-1,4-naphthoquinone(DMNQ). This was selectively reduced and benzylated to produce 6-formyl-5,8-dimethoxy-1,4-dibenzyloxynaphthalene, to which various alkylmagnesium halide were added, followed by debenzylation and oxidation in sequence, yielding 6-(1-hydroxyalkyl)-DMNQ derivatives. 6-(1-hydroxyalkyl)-5,8-diethoxy-1,4-naphthalene (DENQ) derivatives were synthesized by similar procedure. 1'-OH of the naphthoquinone derivatives was acylated with various alkanoic acids to give 6-(1-acyloxyalkyl)-DMNQ or DENQ derivatives. TOPO-I inhibitory activity and cytotoxicity of DENQs were less potent than that of DMNQs. Among the DMNQ and DENQ analogues, the ones with alkyl group being heptyl were most potent in TOPO-I inhibition $IC_{50}$/; 30.1, 36.4 $\mu$M). DUNQ derivatives with a longer side chain exhibited a weaker cytotoxicity. A correlation between size of the alkyl side chain and cytotoxicity was not observed for DENQ derivatives. Acylation of 1'-hydroxyl group, in general, decreased both TOPO-I inhibitory activity and cytotoxicity T/C (%) values of the DENQ derivatives on S-180 intraperitoneal tumor were larger than those of DMNQ derivatives. Among the compounds synthesized,6-(1-hydroxyheptyl)-DENQ and 6-(1-hex-anoyloxyoctyl)-DMNQ showed the highest T/C values of 183% and 182%, respectively.

Flavone의 합성 중간체인 2-Aroxyloxyacetophenone류의 새로운 합성법

송규용(Gyu Yong Song),안병준(Byung Zun Ahn) 대한약학회 1994 약학회지 Vol.38 No.1

We have synthesized some 2-(2-benzyloxybenzoyloxy)-and 2-(2,6-dibenzyloxybenzoyloxy)-acetophenones as intermediates for flavone synthesis. The reaction of polyoxygenated 2-hydroxyacetophenones with 2-benzyloxybenzoic acid or 2,6-dibenzyloxybenzoic acid in the presence of dicyclohexylcarbodiimide and p-dimethylaminopyridine resulted in a good yield(70-89%) of 2-(2-benzvloxybenzovloxy)-acetophenones or 2-(2,6-dibenzyloxybenzoyloxy)-acetophenones under milder conditions and in shorter time than the previous methods. This new methods using benzoic acids instead of benzoyl chlorides saves one reaction step of acid chlorination in comparision of the previous methods.

2,3-Alkyl Aziridinecarboximidate류의 합성 및 항암효과 평가

정상헌(Sang Hun Jung),안병준(Byung Zun Ahn) 대한약학회 1991 약학회지 Vol.35 No.4

Seven drivatives of 2,3-alkyl substituted aziridinecarboximidates were prepared from alkyl substituted alkene and cyanamide. Their ED50 values against L1210 cell in vitro were evaluated as 1.5 to 4 mcg/ml.

L1210 세포에 대한 제라닐화 후라본의 세포독성

백경업(Kyeong Up Baik),안병준(Byung Zun Ahn) 대한약학회 1988 약학회지 Vol.32 No.2

Geranylation of some synthetic and natural flavones have yielded cytotoxic products against L1210 cell; 5,2''-dihydroxy-6,7,8-trimethoxy-6''-geranyloxyflavone 4(8.5mcg/ml), 5,6-dihydroxy-7-gerenyloxyflavone 9(2.3mcg/ml). 2 has showed the same range of cytotoxicity as the starting material, 5,2''-dihydroxy-6,7,8-trimethoxy-6''-benzyloxyflavone(17.0mcg/ml). The cytotoxicity of 4 was lower than its starting substance, 5,2'',6''-trihydroxy-6,7,8-trimethoxyflavone(4.5mcg/ml), On geranylating 5,6,7-trihydroxyflavone(baicalein, 15.0mcg/ml) the cytotoxic activity has been strongly potentiated(2.3mcg/ml of 9). The presence of at least a free hydroxy group in B-ring of SkullkApflavone II-type flavones was essential for a high activity. A larger RD-group than methoxy in the B-ring has weakened the activity. The cytotoxicities of baicalein series could not be correlated to their structures.

털진득찰의 L1210 세포독성물질 Pubetalin의 분리

김선희(Seon-Hee Kim),안병준(Byung-Zun Ahn) 한국생약학회 1988 생약학회지 Vol.19 No.4

A cytotoxic sesquiterpene against L1210 cell, named pubetalin. was isolated from the herb of Siegesbeckia pubescens Makino. Its structure was identified as 6-formyl-2, 3, 3a, 4, 5, 8, 9, 11α-octahydro-l0-hydroxymethyl-5-methoxy-3-methylene -2-oxocyclodeca[β] furan-4-ylester of 2-methyl-2-propenoic acid.