• Archives of Pharmacal Research
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• 제19권6호
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• pp.543-550
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• 1996

Analogues of $2(S)-5, 2^{l}, 5^{l}$-trihydroxy-7, 8-dimethoxyflavanone, a naturally-occurring compound, which had been reported to have potent antitumor activity, were synthesized and examined for the cytotoxicity against three cancer cell lines. Among the intermediate chalcones and synthetic 5-hydroxy-7, 8-dimethoxyflavanone analogues, $({\pm})2^{l}, 5^{l}-dibenzyloxy-5, 7, 8-trimethoxyflavanone$ exhibited about 2-8 times stronger activity than $2(S)-5, 2^{l}, 5^{l}$-trihydroxy-7, 8-dimethoxyflavanone against L1210, K562 and A549 cancer cell lines. In the structure-activity relationship, it is suggested that among analogues of 5-hydroxy-7, 8-dimethoxyflavanone, the existence of two oxygenated groups of para-relation at $C-2^{I} and C-5^{I}$ positions on flavanone B-ring, may be necessary to exhibit effective cytotoxic activity.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1994년도 춘계학술대회 and 제3회 신약개발 연구발표회
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• pp.245-245
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• 1994

From the active fraction, cytotoxic constituents 1-5 were isolated and identified to be 2(S)-5,7-dihydroxy-8,2'-dimethoxyflavanone (1), wogonin (5,7-dihydroxy-8-methoxyflavone, 2), 5,7-dihydruxy-8,2'-dimethoxyflavone (3), 2(5) -5,7,2'-trihydroxy-8-methoxyflavanone (4), 2(S) - 5,2',5'-trihydroxy-7,8-dimethoxyflavanone (5), respectively, with those of specimens$\^$1-2)/

• 한국식품영양과학회지
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• 제20권4호
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• pp.369-375
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• 1991

홍합과 진주담치 근육의 carotenoid를 TLC, column chromatography로 분리하고, $NaBH_4$에 의한 환원반응, $I_2$에 의한 이성화반응 및 UV-visible spectro-photometer로 비교하여 다음과 같은 결론을 얻었다. 혼합 근육의 총 carotenoid함량은 수컷이 0.4mg%, 암컷은 2.7mg%이며, 주 cartenoid는 수컷이 3, 4, 3'-trihydroxy-7', $8'-didehydro-{\beta}-carotene$ 26.3%, pectenoxanthin 24.8% 및 mytiloxanthin 23.4%였고, 그외 pectenolone 14.0%, diatoxanthin 5.1%의 순으로 함유하며, 암컷은 mytiloxanthin 33.4%, pecteno-xanthin 22.8% 및 3, 4, 3'-trihydroxy-7', $8'-didehydro-{\beta}-carotene$ 22.5%였고, 그외 pectenolone 9.9%, diatoxanthin 6.1%의 순으로 함유하여 서로 유사하였다. 진주담치 근육의 총 carotenoid함량은 수컷이 1.1mg%, 암컷은 3.2mg%이며, 주 carotenoid는 수컷이 mytiloxanthin 33.8%, pectenoxanthin 28.4%였고, 그외 diatoxanthin 18.1%, pectenolone 9.7%, 3, 4, 3'-trihydroxy-7', $8'-didehydro-{\beta}-carotene$ 5.5%의 순으로 함유하며, 암컷은 pectenolone 8.7%, diatoxanthin 5.0% 및 3, 4, 3'-trihydroxy-7', $8'-didehydro-{\beta}-carotene$ 3.1%의 순으로 함유하여 서로 유사하였다. 그러나 홍합과 진주담치의 근육 carotenoid는 암컷이 수컷보다 총 carotenoid 함량이 높은 함량치를 보였고, diatoxanthin과 3, 4, 3'-trihydroxy-7', $8'-didehydro-{\beta}-carotene$의 함량에서 차이를 보였다.

• Archives of Pharmacal Research
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• 제20권4호
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• pp.368-371
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• 1997

In an effort to increase of the antitumor activity of 2(S)-$2^{I}$,$5^{I}$-trihydroxy-7, 8-dimethoxyflavanone isolated from Scutellaria indica, we synthesized its analogues, II, III and IV. They showed potent cytotoxicity in vitro against cancer cell lines, L1210, K562 and A549. On the basis of $ED_50$ values against the cancer cell lines, III exhibited about 2-7 times stronger activity than I against various cell lines. We tested the antitumor activity of the analogues against Sarcoma 180 cells in vivo and evaluated the structure-activity relationship. The antitumor activity appeared to be related to the hydrogen bond between carbonyl group at C-4 and hydroxyl group at C-5, in contrast to cytotoxic action.

• Bulletin of the Korean Chemical Society
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• 제27권7호
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• pp.995-1000
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• 2006

Three new compounds orizaanthracenol (1-methoxyanthracen-2-ol, 1), 1-hydroxy-7-((2S,3R,4R,5S)-2'',3'',4''-trihydroxy-5''-(hydroxymethyl)tetrahydro-2H-pyran-1-yloxy)anthracen- 2-yl 3',7'-dimethyloctanoate (2) and 1-hydroxy-7-((2S,3R,4R,5S)-2'',3'',4''-trihydroxy-5''-(hydroxymethyl)tetrahydro-2H-pyran-1-yloxy)anthracen- 2-yl 3',7',11',15',19'-pentamethyltricosanoate (3) have been isolated and determined from the rice hulls of Oryza sativa. The structures of the compounds were elucidated using 1D and 2D NMR spectral methods, viz: 1H-NMR, 13C-NMR, DEPT, COSY and HSQC, and HMBC aided by IR, EIMS and FAB-MS. These isolated compounds were tested in bioassay on germination of radish to detect their inhibitory activities, in which compound 1 exhibited the most inhibition at the concentration of 40 ppm was 50.96% of total dry weight. Furthermore, germination and growth of radish were reduced by 27 to 48%, and dry weight of shoot and root were arranged from 50 to 52%, whilst compounds 2 and 3 exhibited weak inhibition than 1.

• Natural Product Sciences
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• 제12권4호
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• pp.205-209
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• 2006

The structures of flavonoids, 2(S)-5,7-dihydroxy-8,2'-dimethoxyflavanone (1), wogonin (2), 2(S)-5,7, 2'-trihydroxy-8-methoxyflavanone (3), and 2(S)-5,2',5'-trihydroxy-7,8-dimethoxyflavanone (4), isolated from Scutellaria indica were revised on the basis of 2D NMR spectroscopy, including to gCOSY, gHSQC, and gHMBC. Compounds 1-4 were tested in vitro protein tyrosine phosphatase 1B (PTP1B) inhibitory activity. Compounds 2 and 4 exhibited weak PTP1B inhibitory activity with $IC_{50}$ values of 208 and $337{\mu}M$, respectively.

• 대한화장품학회지
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• 제43권1호
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• pp.11-18
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• 2017

Ethyl (4-(2,3-dihydro- 1H-indene-5-carboxyamido) benzoate)는 노화방지 효과가 있으나 난용성 및 결정화 특성을 가지고 있어 제형화 및 2차 가공을 통해 입자내 활성성분을 담지시키는데 어려움이 있으며, 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone는 플라보노이드(flavonoid)류의 일종으로 미백기능을 가지고 있으나 복합제형에 사용할 경우 제형의 착색을 일으키는 물질 중 하나이다. 본 연구에서는 전기방사법을 이용하여 유용성/난용성 생리활성성분인 ethyl (4-(2,3-dihydro-1H-indene-5-carboxyamido) benzoate)와 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone 성분을 각각 poly (methyl methacrylate)와 polycaprolactone 고분자 입자 내에 담지 시키고 이를 화장품 제형에 적용했을 때 나타나는 효과에 대해서 기술하였다. 입자내 활성성분을 담지시킨 고분자 입자를 제조하는 과정에는 고분자의 농도, 노즐의 구조, 그리고 고분자와 생리활성 성분의 상용성이 중요한 역할을 하였다. 아울러 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone가 캡슐화된 polycaprolactone 고분자 입자를 금속산화물이 포함된 화장품 제형과 혼합하였을 경우, 고분자 입자는 캡슐화 되지 않은 flavonoid가 제형에 포함되었을 경우 나타나는 착색현상을 방지하는 데 효과적일 수 있다는 결과를 확인하였다.

• Preventive Nutrition and Food Science
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• 제3권4호
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• pp.315-319
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• 1998

Previously, the methanolic extract of Paeonia moutan seeds was found to potently inhibit soybean lipoxy-genase (SLO). Hence to isolate SLO inhibitor, the defattd methaniolic extract of the seeds was consecutively partitioned wiht ether, ethyl acetate,n-butanol ,adn water. The ether souble fraction showing strong inhibitory activity against SLO was further fractionated into a strongly acidic, a weakly acidic, and a neutral fractions. The strongly acidic components of the ether extract were successively subjected to chromatography on a silica gel, Sephadex LH-20, and preparative HPLC. Four phenolic compounds were isolated , and twio of them showing a strong SLO inhibition activity were identified as luteolin (IC50=2.32$\mu\textrm{g}$/ml) and 5,6,4'-trihydroxy-7,3'- dimethoxylflavone (IC50=0.31$\mu\textrm{g}$/ml) by UV, IR, 1H-& 13C-NMR, and MS spectroscopy. In addition, two flavonoids showed significantly antioxidative activity as strong as that of of $\alpha$-tocopherol (p<0.05) in the autoxidation system of linoleic acid. These results suggest that luteolin and 5,6,4'-trihydroxy-7,3'-dimethoxy-flavone may be used as a potential source of anti-inflammatory agents with antioxidative activity.

• 식물조직배양학회지
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• 제24권3호
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• pp.149-152
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• 1997

토양 방선균(Streptomyces sp.)으로부터 페튜니아 캘러스의 생장을 억제하는 물질을 탐색하기 위하여 400 균주의 배양액을 대상으로 활성을 조사하였다. 방선균 9602 균주의 배양액으로부터 캘러스 생장억제물질을 용매분획과 2차의 실리카겔 칼람 크로마토그라피를 사용하여 활성물질을 분리하였다. 활성물질은 1H-NMR, EI-MS, IR, UV 등을 사용하여 2,5,7-trihydroxy-3-(5'-hydroxyhexyl)-1,4-naphthoquinone(3-OH NQ)으로 동정하였다. 3-OH NQ는 페튜니아 캘러스 생장을 $32\mu\textrm{g}$/mL 농도에서 50% 억제하였다.

• 한국약용작물학회지
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• 제14권4호
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• pp.212-216
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• 2006

황금 (Scutellaria baicalensis Gergi)에 함유된 항산화 억제활성 물질을 분리하고 항산화 효과에 대하여 조사한 결과는 다음과 같다. 1. 황금 500g을 100% MeOH로 추출하여 150g의 수율을 얻었으며, 다시 분획하여 Ethyl ether 13.2g과 n-BuOH 10.3g, Water 126.5g을 얻었다. 2. Ethyl ether 분획을 Column chromatography, TLC 및 HPLC를 이용하여 xanthine oxidase 억제활성을 가진 compound I을 분리하였다. 3. $^1H-NMR,\;^{13}C-NMR$, MS spectrometer 등 분광학적 방법을 이용하여 Compound I의 구조를 규명한 결과, flavonoid 물질로서 compound I은 구조식이 3,5,7-trihydroxy-2'-methoxy-flavanone로 확인되었다.