• Natural Product Sciences
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• 제19권3호
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• pp.201-205
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• 2013

Thirteen phenolic compounds, 1,4-dimethoxybenzene (1), 3,4-dihydroxybenzaldehyde (2), (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylaldehyde (3), 3,7-dihydroxy-4H-chromen-4-one (4), 2,3-dihydroxy-1-(3,4-dihydroxyphenyl)propan-1-one (5), 4-hydroxy-3-methoxybenzoic acid (6), 4-hydroxy-3,5-dimethoxybenzoic acid (7), methyl 3,4-dihydroxybenzoate (8), 4-hydroxy-3,5-dimethoxybenzaldehyde (9), 3,4-dihydroxybenzoic acid (10), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (11), 2,4,6-trihydroxybenzaldehyde (12) and benzene-1,2,4-triol (13) were isolated from the heartwood of Caesalpinia sappan. Their anti-inflammatory activity was evaluated against LPS-induced NO production in macrophage RAW264.7 cells. Among them, compounds 3 and 8 showed strong inhibitory activities toward the LPS-induced NO production in macrophage RAW264.7 cells with $IC_{50}$ values of 14.5 and 21.5 ${\mu}M$, respectively.

• Archives of Pharmacal Research
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• 제27권4호
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• pp.381-385
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• 2004

Nine phenolic ($1\~9$) and two furan type (10, 11) compounds, were isolated from the methanolic extract of the tuber of Gastrodia elata Blume (Orchidaceae) in the course of continuing search for platelet anit-aggregating plant components. Compound 1 was identified as 4,4'-dihy-droxybenzyl sulfone, a novel compound for the best of our knowledge. Compound 10, 5-hydroxymethyl-2-furancarboxaldehyde, was isolated for the first time from this plant. Compound 1 ($IC_{50};\;83{\mu}M$) was about four times more inhibitory to U46619 induced aggregation than ASA ($IC_{50};\340{\mu}M$). Compound 9, 4,4'-dihydroxy-dibenzylether, ($IC_{50};\;5{\mu}M$, $3{\mu}M\;and\;33{\mu}M$, respectively) was $10\~}80$ fold more potent than ASA ($IC_{50};\;420\;{\mu}M,\;53\;{\mu}M\;and\;340\;{\mu}M$ respectively) to collagen, epinephrine and U46619 induced aggregation, although it is less active than ASA to AA induced aggregation.

• Journal of Microbiology and Biotechnology
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• 제2권2호
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• pp.92-97
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• 1992

Microbial transformation of (-)kaur-l6-en-19-oic acid and (-)pimara-9(1l), 15-dien-19-oic acid from A. koreanum was investigated. Throughout the screening of the capability of metabolizing these bioactive diterpenoids, two microorganisms have chosen among various fungi and streptomycetes tested. Scale-up fermentation with Fusarium oxysporum KCTC 6051 produced two metabolites related to the precursor diterpenoids. The two metabolites were isolated by column chromatography and identified by chemical and spectroscopic methods as $2\beta$, $16\alpha$-dihydroxy kauran-19-oic acid and $16\alpha$-hydroxy kauran-19-oic acid. However any microorganisms capable to transform (-) pimara-9(11), 15-dien-19-oic acid was not screened in this condition.

• 한국수산과학회지
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• 제33권5호
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• pp.431-438
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• 2000

본 실험은 조피볼락 (Sebastes schlegeli)의 생식년주기와 생식주기에 따른 sex steroid hormone들의 계절적인 변화를 밝히기 위하여 GSI와 HSI의 연간 변동과 생식소 조직학적인 연간 변화와 sex steroid hormone ($estradiol-l7{\beta}, 17{\alpha}, 20{\beta}-dihydroxy-4-pregnen-3-one, testosterone$, 그리고 $11-ketotestosterone$)의 혈중 수준의 연간 변화를 조사하였다. 암컷의 생식주기는 다음과 같이 5단계로 구분할 수 있었다: 1) 회복기 (6월${\~}$9월): 혈중 $estradiol-l7{\beta}$의 수준이 점차 증가 하였다. 2) 난황형성기 (9월~2월): 난모세포의 난황 형성이 관찰되며, GSI 값과 혈중 $estradiol-l7{\beta}$수준이 증가하였다; 3) 임신기 (2월${\~}$4월): 난소내에 발생중인 자어가 관찰되며, 2월에서 3월에 이르러 혈중 $17{\alpha}, 20{\beta}-dihydroxy-4-pregnen-3-one$와 testosterone의 수준이 증가하였다: 4) 출산기 ($4{\~}5$월): GSI 값이 급격히 감소하면서 난소내에는 자어들의 출산된 흔적이 보였다: 5) 휴지기 ($5월$${\~}$7월) GSI값과 혈중 steroid hormone의 수준이 낮은 값을 유지하였다. 수컷의 생식년주기는 6단계로 나눌 수 있었다: 1) 정자형성 초기(4월${\~}$6월): GSI의 값과 혈중 steroid hormone의 수준이 점진적으로 증가하였으며, 정원세포의 포낭이 수가 증가하고 일부의 정모세포의 포낭들도 관찰되었다; 2) 정자형성 중기 (6월${\~}$9월): GSI의 값과 혈중 steroid hormone의 수준이 증가하고 많은 포낭내의 생식세포들이 활발하게 정자형성을 하고 있었다: 3) 정자형성기 후기 (9월${\~}$11월): GSI와 steroid hormone의 수준이 높은 값을 유지하고 있었으며, 정자들이 정세관 내강으로 방출되었다; 4) 정자 방출기 (11월${\~}$12월): 전세관의 내강이 확장되고 이 내강내에는 성숙된 정자들로 가득차 있었다: 5) 퇴화기 (12월${\~}$2월): GSI의 값이 점차로 감소하면서 정모세포의 포낭수도 점차로 감소하였다: 6) 휴지기 (2월${\~}$4월): 정소조직의 변화는 보이지 않았으며, GSI와 steroid hormone의 수준이 낮은 값을 유지하였다. 11월에 정소들의 정세관 내강에 성숙된 정자들로 가득차 있었고 난소내강에 정자괴들이 관찰되는 것으로 보아 이종의 교미시기는 11월과 12월사이라고 할 수 있다.

• Archives of Pharmacal Research
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• 제27권9호
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• pp.937-943
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• 2004

Recent investigations have shown that certain flavonoids, especially flavone derivatives, inhibit nitric oxide (NO) production by inducible NO synthase (iNOS) in macrophages, which contrib-ute their anti-inflammatory action. For the purpose of finding the optimized chemical structures of flavonoids that inhibit NO production, various A- and B-ring substituted flavones were syn-thesized and evaluated for their inhibitory activity using lipopolysaccharide-treated RAW 264.7 cells. It was found that the optimal chemical structures were A-ring 5,7-dihydroxyflavones hav-ing the B-ring 2＇,3＇-dihydroxy or 3＇,4＇-dihydroxy or 3＇,4＇-hydroxy/methoxy (methoxy/hydroxy) groups. These structurally optimized compounds were revealed to be down-regulators of iNOS induction, but not direct iNOS inhibitors. Of these derivatives that were evaluated, 2＇,3＇,5,7-tet-rahydroxyflavone and 3＇,4＇,5,7-tetrahydroxyflavone (Iuteolin) showed the strongest inhibition. The $IC_{50}$/ values for these compounds were 19.7 and 17.1 11M, respectively. Therefore, these compounds may have a potential as new anti-inflammatory agents.

• Natural Product Sciences
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• 제23권2호
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• pp.113-118
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• 2017

A new tetracyclic triterpenoid [4,4,24-trimethylcholesta-${\Delta}^{8,9;14,5;24,28}$-trien-$3{\beta},11{\beta},12{\alpha}$-triol-12-acetate, 3-sulfate] sodium salt (1), together with eight known compounds including ergosterol $5{\alpha},8{\alpha}$-endoperoxide (2), 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (3), 3-O-${\beta}$-D-2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (4), hydnocarpin (5), derrone (6), isovitexin (7), erythrinin C (8), and 5,4'-dihydroxy-2"-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone (9), were isolated from the EtOAc soluble fraction of the methanol extract of aerial part of Desmodium uncinatum collected in the western highland of Cameroon. The structures of these compounds were established by comprehensive interpretation of their spectral data mainly including 1D- ($^1H$ and $^{13}C$), 2D-NMR($^1H$-$^1H$ COSY, HMQC, HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis. The isolation of an integracide-like compound from plant origin is a very unusual finding.

• Archives of Pharmacal Research
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• 제29권7호
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• pp.548-555
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• 2006

Three diterpenes (1, 8, and 9), three triterpenes (3, 4, and 7), one saponin (11), four sterols (2, 5, 6, and 12), and one cerebroside (10) were isolated from the EtOH extract of the aerial parts of Aralia cordata by repeated silica gel column chromatography. Their chemical structures were identified by comparing their physicochemical and spectral data with those published in literatures. All isolated compounds were evaluated for their cytotoxicity against L1210, K562, and LLC tumor cell lines using MTT assay. Of which, $3{\beta},5{\alpha}-dihydroxy-6{\beta}-methoxyergosta-7,22-diene$ (6) showed a potent cytotoxicity against all cell lines with $IC_{50}$ values of 11.7, 11.9, and $15.1\;{\mu}M$, respectively, while compounds 1, 5, and 11 showed a moderate or weak cytotoxicity. These isolates were also examined for their inhibitory activity against COX-1 and COX-2. Although most compounds, except for 2, 10, and 12, showed a strong inhibitory activity against COX-1, they exhibited a moderate or weak inhibitory activity against COX-2.

• 한국식물생명공학회:학술대회논문집
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• 한국식물생명공학회 2005년도 추계학술대회 및 한일 식물생명공학 심포지엄
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• pp.27-39
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• 2005

a-Ketol linolenic acid [KODA, 9,10-ketol-octadecadienoic acid, or 9-hydroxy-10 -oxo-12(Z), 15(Z)-octadecadienoic acid] was found as a stress-induced factor in Lemna paucicostata. KODA reacts with catecholamines to generate many products that strongly induce flowering in L. paucicostata, although KODA itself was inactive. KODA contains an asymmetric carbon at the 9-position in the molecule; the 9-hydroxyl group is predominantly 9R, with an enantiomeric excess of 40% (70% 9R and 30% 9S). We analyzed two major products of the reaction between KODA and norepinephrine, named FN1 and FN2. FN1 was identified as a tricyclic a-ketol fatty acid, 9(R)-11-{(2'R,8’R,10'S,11'S)-2',8'-dihydroxy-7'-oxo-11'-[(Z)-2-pentenyl]-9'-oxa-4'-azatricyclo[6.3.1.01.5]dodec-5'en-10'-yl}-9-hydroxy-10-oxoundecanoic acid. FN2 was the C-9 epimer of FN1. FN1 was derived from 9R-type KODA and FN2 from 9S-type. FN1 showed strong flower-inducing activity, but FN2 was inactive. Pharbitis nil (violet) is a typical short-day plant; flowering can be induced by exposing a seedling cultivated under continuous light to a single 16-h dark period. We analyzed endogenous KODA levels and showed that they were closely related to flower induction: KODA sharply increased in the later part of a 16-h dark period, on the other hand, it failed to increase in the night-break experiment. In addition to it, KODA increased transiently in immature flower buds in all the plants we examined, including P. nil. No such increase of KODA was seen in foliar buds of P. nil. When KODA was sprayed on seedlings of Pharbitis, flower induction was promoted only by the (R)-form of KODA. We also found that KODA enhances flowering in garden plants such as carnations and impatienses. These phenomena indicate that KODA may be involved in flowering formationg of plants and it is potentially useful for a regulating agent for commercial plant flowering.

• Archives of Pharmacal Research
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• 제20권3호
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• pp.291-296
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• 1997

The studies were carried out to evaluate the constituents in the aerial part of Isodon excisus var. coreanus (Labiatae). From the aqueous fraction of methanol extract, compound I (${\alpha}$-[[3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-benzenepropanoic acid), compound II (9-methyl-dihydroferulic acid-4-O-.betha.-D-glucopyranosyl $(1{\rightarrow}2)$-${\alpha}$-L- rhamnopyranosyl (1.rarw.4)-.betha.-D-glucopyranoside), compound III (ent-7.alpha., 11${\alpha}$,15.betha.-trihydroxy-kaur-16-en-1-O-.betha.-D-glucopyranoside) and compound IV ($2{\alpha}$,3${\beta}$,$7{\alpha}$,23-tetrahydroxy-olean-12 -en-28-oic acid 28-O-${\beta}$-D-glucopyranoside) were isolated and identified on the basis of their physicochemical and spectroscopic evidences[IR, FAB(-)MS,$^{1}H-NMR,$$^{13}C-NMR,$$ HMQC$$^{1}H-^{1}H $COSY and HMBC (Heteronuclear Multiple Bond Connectivity)]. Especially, New compounds II and III were named Isodonin A and Isodonin B respectively.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.194-199
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• 2002

Many oxidative metabolites of tetrahydrocannabinols (THCs), active components of marijuana, were pharmacologically active, and 11-hydroxy-THCs, 11-oxo-${\Delta}^8$-THC, 7-oxo-${\Delta}^8$-THC, 8$\beta$, 9$\beta$-epoxyhexahydrocannabinol (EHHC), 9$\alpha$, l0$\alpha$-EHHC and 3'-hydroxy-${\Delta}^9$-THC were more active than THC in pharmacological effects such as catalepsy, hypothermia and barbiturate synergism in mice. Cannabidiol (CBD), another major component, was biotransfomred to two novel metabolites, 6-hydroxymethyl-${\Delta}^9$-THC and 3-pentyl-6, 7, 7a, 8, 9, lla-hexahydro-I, 7-dihydroxy-7, 1O-dimethyldibenzo[b, d]oxepin (PHDO) through 8R, 9-epoxy-CBD and 85, 9-epoxy-CBD, respectively. Both metabolites exhibited some pharmacological effects comparable to d9 - THe. Cannabinol (CBN), the other major component, was mainly metabolized to ll-hydroxy-CBN by hepatic microsomes of animals including humans. The pharmacological effects of the metabolite were higher than those of CBN demonstrating that II-hydroxylation of CBN is metabolic activation pathway of the cannabinoid as is the case in THCs. Tolerance and reciprocal cross-tolerance developed to pharmacological effects d8 - THC and ll-hydroxy-d8-THC , and the magnitude of tolerance development produced by the metabolite was significantly higher than that by d8-THC. The results indicate that ll-hydroxy-d8-THC has an important role not only in the pharmacological effects but also its tolerance development of d8 - THe. THCs and their metabolites competed to the specific binding of CP-55, 940, an agonist of cannabinoid receptor, to synaptic membrane from bovine cerebral cortex. The Ki value of THCs and their metabolites were closely paralleled to their pharmacological effects in mice. A novel cytochrome P450 (cyp2c29) was purified and identified as a major enzyme responsible for the metabolic activation of d8-THC at the II-position in the mouse liver. cDNA of CYP2C29 was cloned from a mouse cDNA library and its sequence was determined. The oxidation mechanism of THC by cyp2c29 was proposed.