• Natural Product Sciences
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• v.10 no.5
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• pp.220-222
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• 2004

A new prenylated pyranoxanthone, inophyllin B (1), was isolated from the roots of Calophyllum inophyllum (Guttiferae). Together with this compound was also isolated the known pyranoxanthone brasilixanthone B (2) and two common triterpenes friedelin (3) and sitosterol (4). Structural elucidations of these compounds were achieved through $^1H,\;^{13}C$, DEPT, COSY, HSQC and HMBC experiments. The molecular mass was determined using MS techniques. The crude extract indicated weak toxicity to the larvae of Aedes aegypti. We report here the isolation, structural elucidation and bioassay data for Inophyllin B and brasilixanthone B.

• Natural Product Sciences
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• v.10 no.6
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• pp.306-309
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• 2004

Triterpenoids were isolated from the whole plant of Orostachys japonicus (Crassulaceae) by repeated column chromatography. Their structures were identified as friedelin (1), glutinol (2), ${\beta}-sitosterol$ (3), friedelinol (4), $5{\alpha},8{\alpha}-peroxyergosterol$ (5), ${\beta}-sitostenone$ (6) and glutinone (7) by spectral analysis. Among them, compounds 5 and 6 were isolated for the first time from this plant.

• Archives of Pharmacal Research
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• v.27 no.11
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• pp.1109-1113
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• 2004

A new triterpene (1) and six known pentacyclic terpenoids (2-7) were isolated from the methanol extract of the dried leaves from Mallotus apelta. Based on the spectral and chemical evidence, their structures were determined to be 3$\alpha$-hydroxyhop-22(29)-ene (1), hennadiol (2), friedelin (3), friedelanol (4), epifriedelanol (5), taraxerone (6), and epitaraxerol (7).

• Korean Journal of Pharmacognosy
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• v.31 no.2
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• pp.224-227
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• 2000

As part of study of the constituents of bamboo grasses, the leaves of Sasa borealis (Hackel) Makino (Gramineae) were examined. Friedelin, glutinol, isoorientin and isovitexin have been reported as constituents of bamboo grasses. In this study, tricin and two flavone glycosides, tricin $7-O-{\beta}-D-glucopyranoside$ and luteolin $6-C-{\alpha}-L-arabinopyranoside$ have been isolated from EtOAc extract of S. borealis, by consecutive silica gel, Sephadex LH-20 column chromatography and a repetitive HPLC. The structures of these compounds were determined by IR, $^1H-NMR,\;^{13}C-NMR,\;^{13}C-^1H\;COSY,\;^1H-^1H\;COSY,\;HMBC$ and Mass spectral data.

• Natural Product Sciences
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• v.18 no.1
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• pp.22-25
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• 2012

Five triterpenoids, epifriedelanol (1), friedelin (2), lupeol (3), ${\beta}$-sitosterol (4), daucosterol (5), and one phenyl propanoids ester, trans-docosanoyl ferulate (6) were isolated from the whole parts of Portulaca oleracea. They were determined using a combination of spectroscopic analyses ($^1H-$, $^{13}C$-NMR, and MS data) and evaluated for their cyclooxygenase inhibitory activity. Compound 6 exhibited inhibitory effect with $IC_{50}$ values of $40.2{\mu}M$ and 1.6 mM on COX-1 and COX-2 activities, respectively.

• Natural Product Sciences
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• v.12 no.2
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• pp.89-93
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• 2006

One new sterol glucoside, $gomphsterol\;{\beta}-D-glucoside$ 1 along with known compounds, ${\beta}-sitosterol$, stigmasterol, campesterol, $stigmasterol-{\beta}-D-glucoside$, friedelin, 3-epi-friedelinol, allantoin, and $chrysoeriol-7-O-{\beta}-D-glucoside$ have been isolated from the aerial parts of Gomphrena globosa (Amaranthaceae). On the basis of spectroscopic (including 2D NMR) and chemical studies, the structure of 1 was elucidated as $(22E,24S)-24-ethylcholesta-7,9(11),22-trien-3{\beta}-ol-3-O-{\beta}-D-glucopyranoside$. Known compounds are reported for the first time from this plant species.

• Natural Product Sciences
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• v.13 no.4
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• pp.332-336
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• 2007

Five steroids and two norsesquiterpene glycosides were isolated from the methanol extract of H. japonicus. Their structures were determined by means of physio-chemical and spectral data to be friedelin (1), stigmast-5-en-3-${\beta}$-ol (${\beta}$-sitosterol) (2), 7-keto-${\beta}$-sitosterol (3), 6${\beta}$-hydroxy-4-stigmasten-3-one (4), 7${\alpha}$-hydroxy-${\beta}$-sitosterol (5), 3-hydroxy-4,4-dimethyl-4-butyrolactone (6), daucosterol (7), (6S, 9S)-roseoside (8), and (9S)-drummondol-9-O-${\beta}$-D-glucopyranoside (spinoside B) (9). The compounds 1, 3, 4, and 6 - 9 were first isolated from this plant source.

• Korean Journal of Medicinal Crop Science
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• v.16 no.1
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• pp.51-56
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• 2008

The content of two steroids-campesterol (1) and ${\beta}$-sitosterol (2), and four triterpenes-taraxetrone (5), ${\beta}$-amyrin (6), (-)-friedelin (7), glutinol (8) in the Orostachys japonicus A. Berger cultivated under various conditions was estimated and compared with those in wild one. The present investigation disclosed that there are no significant difference in their contents between cultivated Orostachys japonicus A. Berger and wild one. from viewpoint of the content of the steroids 1 and 2, and the triterpenes 5-8, the quality of cultivated Orostachys japonicus A. Berger is not inferior to the wild one.

• Korean Journal of Pharmacognosy
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• v.41 no.2
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• pp.97-102
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• 2010

Six triterpenoid compounds, friedelin (1), $3{\alpha}$-hydroxy-2-friedelanone (2), canophyllol (3), oleanolic aldehyde acetate (4), ursolic acid (5), and pachysandiol A (6) were isolated from the methylene chloride soluble fraction of the roots of A. japonica. The chemical structures of compounds 1-6 were determined by the basis of physico-chemical properties and spectroscopic methods such as 1D and 2D NMR. These compounds were isolated from this plant for the first time. For the isolated compounds (1-3), the inhibitory effect of IL-6 production in TNF-$\alpha$ stimulated MG-63 was examined. Among the isolates, $3{\alpha}$-hydroxy-2-friedelanone (2) showed potent inhibitory effect on IL-6 production in TNF-$3{\alpha}$ stimulated MG-63.

• Natural Product Sciences
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• v.17 no.3
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• pp.245-249
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• 2011

Eight compounds, squalene (1), friedelin (2), ${\beta}$-sitosterol (3), ${\beta}$-sitosterol-3-O-glucoside (4), ${\alpha}$-tocopherol (5), betulinic acid (6), trilinolein (7) and 1-O-(9Z,12Z-Octadecadienoyl)-3-nonadecanoyl glycerol (8), were isolated from the barks of Tilia amurensis. Their chemical structures were identified by comparing their physicochemical and spectral data with those published in the literature. These isolated compounds were examined for their inhibitory activities against topoisomerase I and II. Compound 7 showed significant inhibition of DNA topoisomerase I and II activities, with percent decreases in activity of 87 and 95%, respectively at a concentration of $100\;{\mu}M$. Compound 6 exhibited cytotoxicity against the human colon adenocarcinoma cell line (HT-29), the human breast adenocarcinoma cell line (MCF-7) and the human liver hepatoblastoma cell line (HepG-2), with $IC_{50}$ values of 20, 59 and $16\;{\mu}M$, respectively.