• Title/Summary/Keyword: New and known compounds

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A New Cytotoxic Acyclic Diterpene from Carpesium divaricatum

  • Zee, Ok-Pyo;Kim, Dae-Keun;Choi, Sang-Un;Lee, Chong-Ock;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.22 no.2
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    • pp.225-227
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    • 1999
  • A new acylcic deterpene (1) and a known acyclic diterpene 12(S)-hydroxygeranyleraniol (2) were isolated form the aerial parts of Carpesium divaricatum. The structure of 1 was determined to be (2E, 10E)-1, 12-dihydroxy-18-acetoxy-3,7,15-trimethylhexadeca-2,10,14-triene (1) on the basis of spectroscopic studies. Compounds 1 and 2 exhibited cytotoxicity against cultured human tumor cell lines, A549, SK-OV-3, SK-MEL-2, XF498, and $HCT_{15}$, with $ED_{50}$ values ranging from 4.3-10.2 ${\mu}g/ml$ and 4.1-8.3 ${\mu}g/ml$, respectively.

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A New Sesquiterpene Hydroperoxide from the Aerial Parts of Aster oharai

  • Choi, Sang-Zin;Lee, Sung-Ok;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.26 no.7
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    • pp.521-525
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    • 2003
  • Phytochemical works on the aerial parts of Aster oharai (Compositae) led to the isolation of a new sesquiterpene hydroperoxide, 7$\alpha$-hydroperoxy-3, 11-eudesmadiene (2) and seven known compounds, teucdiol B (1), $\alpha$-spinasterol (3), oleanolic acid (4), $\alpha$-spinasterol 3-Ο-$\beta$-D-glucopyranoside (5), methyl 3,5-di-Ο-caffeoyl quinate (6), 3,5-di-Ο-caffeoylquinic acid (7), 3,4-di-Ο-caffeoylquinic acid (8). The chemical structures of 1-8 were established by chemical and spectroscopic methods. Compound 2 showed cytotoxicity against cultured human tumor cell lines in vitro, SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), and HCT15 (colon) with $ED_{50}$ values ranging from 3.86-17.21 $\mu$g/mL.

A New Sesquiterpene Lactone from Artemisia rubripes Nakai

  • Lee, Kyu-Ha;Min, Yong-Deuk;Choi, Sang-Zin;Kwon, Hak-Cheol;Cho, Ock-Ryun;Lee, Kang-Choon;Lee , Kang-Ro
    • Archives of Pharmacal Research
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    • v.27 no.10
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    • pp.1016-1019
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    • 2004
  • The chromatographic separation of a methylene chloride extract of Artemisia rubripes led to the isolation of a new sesquiterpene lactone (3), together with four known compounds, a coumarin (2) and three terpenes (1, 4, and 5). Their structures were characterized to be $1{\beta},6{\alpha}$- dihydroxy-4(15)-eudesmene (1), scopoletin (2), $1{\alpha},4{\beta}-dihydroxy-8{\alpha}$-acetoxy-guaia-2,10(14), 11(13)-triene-6,12-olide (3), $1{\alpha},4{\beta}$ -dihydroxy-8${\alpha}$-acetoxy-guaia-2,9,11(13)-triene-6,12-olide (4), and $\beta$ -sitosterol-3-O-${\beta}$-D-glycoside (5) by spectroscopic means.

A New Phenolic Compound from Lespedeza tomentosa

  • Jang, Hyeon Seok;Choi, Seong Yeon;Yang, Heejung;Kim, Myong Jo;Chun, Wanjoo;Kwon, Yongsoo
    • Natural Product Sciences
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    • v.27 no.3
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    • pp.169-171
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    • 2021
  • A new phenolic compound and three known flavonoids isolated from the MeOH extracts of Lespedeza tomentosa. Based on spectral data, the isolated compounds were identified as methyl 4,5-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)benzoate (1), 1-methoxylespeflorin G11 (2), farrerol (3) and 1-methoxylespeflorin I2 (4). Methyl 4,5-dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)benzoate (1) is newly isolated from plant source.

Antioxidative and Hepatoprotective Effects of Injinho-Tang and Osumogwa-Tang (인진호탕(茵蔯蒿湯)과 오수목과탕(吳茱木瓜湯)의 항산화(抗酸化) 및 간세포(肝細胞) 보호효과(保護效果))

  • Lee, Sang-Hyun;Kim, Young-Bok
    • Herbal Formula Science
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    • v.16 no.1
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    • pp.117-130
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    • 2008
  • Korean traditional medicine has been used for the treatment of the various diseases based on both oriental medicinal theory and clinical trials. Thus, the prescriptions of Korean traditional medicine would be useful for the development of new therapeutics. This research focuses on the fundamental study in Korean traditional prescriptions for the development of new hepatoprotective agents. We found two prescriptions. Injinho-Tang and Osumogwa-Tang, showed the significant DPPH free radical scavenging and hepatoprotective effect, respectively. It is well-known that free radical scavenging effect is related to the prevention of various pathological events including liver injury. This paper deals with hepatoprotective effects on tacrine-induced cytotoxicity in Hep G2 cells, free radicals scavenging on both DPPH and superoxide of above two prescriptions. Hot water extract of Injinho-Tang did not show the significant hepatoprotective effect on tacrine-induced cytotoxicity in Hep G2 cells, however, it shows the significant scavenging effects for both DPPH and superoxide radicals. On the other hand, all of the hot water extracts of constituent herbal drugs in Injinho-Tang exhibited the promising protective effect on tacrine-induced cytotoxicity in Hep G2 cells. Of these, water extract of Rhei Rhizoma showed the most prominent effect on tacrine-induced cytotoxicity in Hep G2 cells. Bioassay-guided fractionation of Rhei Rhizoma extract has furnished four compounds, and their chemical structures have been identified by comparison of their spectral data with those of literature as chrysophanol (1), emodin (2), 3,5-dihydroxy-4'- methoxystilbene (3), and rhapontigenin (4), respectively. Among the isolated compounds, compounds 2-4 revealed the significant hepatoprotective effect in vitro when their $EC_{50}$ values compare with that of silybin, as a positive control. It also exhibited that emodin possessed the most hepatoprotective effect among these active compounds. In case of Osumogwa-Tang, its hot water extract showed the moderate protective effect on tacrine-induced cytotoxicity in Hep G2 cells. Hot water extract of Chaenomelis Fructus, one of the constituent herbal drug of this prescription, exhibited the significant hepatoprotective effect with $EC_{50}$ value of $7.8{\pm}0.1\;{\mu}g/ml$, however, it showed strong cytotoxicity in Hep G2 cells above the concentration of $25\;{\mu}g/ml$. It was revealed that both hot water extract of Evodiae Fructus and its butanol soluble fraction showed the moderate hepatoprotective effect but concentration-dependent activity in Hep G2 assay system. Two quinolone alkaloids, evocarpine and dihydroevocarpine, also tested for their hepatoprotective effects on tacrine-induced cytotoxicity in Hep G2 cells, however, these two compounds derived from the Evodiae Fructus as the major constituents did not show in vitro hepatoprotective effect. From these results, it would be necessary to further isolation of its hepatoprotective compounds from the butanol soluble fraction of the hot water extract of Evodiae Fructus.

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A New Triterpenoid Saponin from Pulsatilla cernua

  • Fan, Wenhao;Liu, Jianyu;Gong, Yixia;Ma, Jing;Zhou, Nan;Xu, Yongnan
    • Natural Product Sciences
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    • v.19 no.2
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    • pp.150-154
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    • 2013
  • A new oleanane-type triterpenoid saponin together with six known saponins were isolated from the roots of Pulsatilla cernua. Their structures were elucidated on the basis of spectroscopic data, including 2D NMR spectra and chemical evidence. Compounds 1 and 6 are reported from this genus for the first time.

Two New Phenylpropanoid Glycosides from the Stem Bark of Acanthopanax trifoliatus

  • Kiem, Phan-Van;Minh, Chau-Van;Dat, Nguyen-Tien;Cai, Xing-Fu;Lee, Jung-Joon;Kim, Young-Ho
    • Archives of Pharmacal Research
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    • v.26 no.12
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    • pp.1014-1017
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    • 2003
  • Two new phenylpropanoid glycosides, 1-$\beta$-D-glucopyranosyl-2,6-dimethoxy-4-propenylphenol (1) and 1-[$\beta$-D-glucopyranosyl-(1$\rightarrow6)-\beta$-D-glucopyranosyl]-2,6-dimethoxy-4-propenylphenol (2) were isolated from the stem bark of Acanthopanax trifoliatus along with four known compounds (3∼6). Their structures were established on the basis of spectral and chemical evidences.

Four New Compounds From Isodon eriocalyx

  • Wang, Jia;Lin, Zhong-Wen;Shingu, Tetsuro;Sun, Han-Dong
    • Natural Product Sciences
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    • v.4 no.3
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    • pp.143-147
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    • 1998
  • Examination of the chemical constituents of the dried leaves of Isodon eriocalyx (Dunn.) Hara led to the isolation of four new diterpenoids, named maoecrystal Q-T (1-4). Their structures were elucidated as $16(R)-methoxymethyl-6{\beta},\;7{\beta}-dihydroxy-7{\alpha},20-epoxy-ent-kaur-2,3-ethenylene-1$, 15-dione(1), $1{\beta},18-diacetoxy-6{\beta},7{\beta}-dihydroxy-7{\alpha},20-epoxy-ent-kaur-16-en-15-one\;(2),\;6{\beta},\;7{\beta}-dihydroxy-15{\beta}-acetoxy-7{\alpha},20-epoxy-ent-kaur-16-en-1-one$ (3) and $7{\beta}-hydroxy-6{\beta},15{\beta}-diacetoxy-1{\alpha},11{\beta}-acetonide-7{\alpha},20-epoxy-ent-kaur-16-ene$ (4), respectively, on the basis of spectroscopic methods. Meanwhile, five known diterpeonids eriocalyxin B (5), maoecrystal B-D (6-8) and trichokaurin (9) were also obtained.

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Five New Stilbenes from the Stem Bark of Artocarpus communis

  • Chan, Susanna T.S.;Popplewell, Wendy L.;Bokesch, Heidi R.;McKee, Tawnya C.;Gustafson, Kirk R.
    • Natural Product Sciences
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    • v.24 no.4
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    • pp.266-271
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    • 2018
  • Five new prenylated stilbenes (1 - 5), along with the known compounds cudraflavone C, trans-4-isopentenyl-3,5,2',4'-terahydroxystilbene, trans-4-(3-methyl-E-but-1-enyl)-3,5,2',4'-tetrahydroxystilbene, pannokin G, cycloartobiloxanthone, artonin P, morusin, artocarpin, artonin E, kuwanon C, artobiloxanthone, and artoindonesianin C (6 - 17) were isolated from the stem bark of the tropical tree Artocarpus communis. The structures were established by NMR spectroscopic analysis, MS studies, and comparison with spectral data reported in the literature.

Steroid Components of Marine-Derived Fungal Strain Penicillium levitum N33.2 and Their Biological Activities

  • Chi K. Hoang;Cuong H. Le; Dat T. Nguyen;Hang T. N. Tran;Chinh V. Luu;Huong M. Le;Ha T. H. Tran
    • Mycobiology
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    • v.51 no.4
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    • pp.246-255
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    • 2023
  • Genus Penicillium comprising the most important and extensively studied fungi has been well-known as a rich source of secondary metabolites. Our study aimed to analyze and investigate biological activities, including in vitro anti-cancer, anti-inflammatory and anti-diabetic properties, of metabolites from a marine-derived fungus belonging to P. levitum. The chemical compounds in the culture broth of P. levitum strain N33.2 were extracted with ethyl acetate. Followingly, chemical analysis of the extract leaded to the isolation of three ergostane-type steroid components, namely cerevisterol (1), ergosterol peroxide (2), and (3β,5α,22E)-ergosta-6,8(14),22-triene-3,5-diol (3). Among these, (3) was the most potent cytotoxic against human cancer cell lines Hep-G2, A549 and MCF-7 with IC50 values of 2.89, 18.51, and 16.47 ㎍/mL, respectively, while the compound (1) showed no significant effect against tested cancer cells. Anti-inflammatory properties of purified compounds were evaluated based on NO-production in LPS-induced murine RAW264.7 macrophages. As a result, tested compounds performed diverse inhibitory effects on NO production by the macrophages, with the most significant inhibition rate of 81.37±1.35% at 25 ㎍/mL by the compound (2). Interestingly, compounds (2) and (3) exhibited inhibitory activities against pancreatic lipase and α-glucosidase enzymes in vitro assays. Our study brought out new data concerning the chemical properties and biological activities of isolated steroids from a P. levitum fungus.