• YAKHAK HOEJI
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• 제34권4호
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• pp.219-223
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• 1990

7,8-Dihydro-6,11-dihydroxy-9(10H)benzo(b)phenazinone was prepared from 1,2,3,4-tetra-hydrophenazine as a potential isostere of anthracyclinone. The attempts to functionalize at $C_9$ were not successful due to the unstability of the above ketone.

• Natural Product Sciences
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• 제24권3호
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• pp.189-193
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• 2018

Chemical investigation of the ethyl acetate extract of Gibberella moniliformis JS1055 endophytic fungus derived from a halophyte, Vitex rotundifolia, led to the isolation of nine compounds including 7-butyl-6,8-dihydroxy-3(R)-pent-11-enylisochroman-1-one (1), 7-butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one (2), 7-butyl6,8-dihydroxy-3(R)-pentylisochroman-1-one (3), $5{\alpha},8{\alpha}$-epidioxyergosta-6,9(11),22-trien-3-ol (4), ergosterol peroxide (5), tetradecanoic acid (6), 8-O-methylfusarubin (7), nicotinic acid (8) and adenosine (9). They were identified by extensive spectroscopic data analysis including 1D, 2D ($^1H-^1H$ COSY, HSQC, HMBC) NMR, and ESIMS. All the isolates (1-9) are reported for the first time from this endophytic fungus.

• Archives of Pharmacal Research
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• 제27권10호
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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.

• YAKHAK HOEJI
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• 제45권2호
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• pp.147-152
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• 2001

The phytochemical study of the aerial parts of Artemisia sylvatica (Asteraceae) led to the isolation of nine sesquiterpene lactones, l$\alpha$-hydroperoxy-rupicolin A acetate (1), rupicolin B acetate (2), rupicolin A acetate (3), l$\alpha$-hydroxy-4$\alpha$-hydroperoxy-bishopsolicepolide (4), 1$\alpha$-hydroperoxy-4$\beta$-hydroxy-8$\alpha$-acetoxy-guaia-2,9,11 (13)-triene-6$\alpha$,12-oxide (5), 1$\alpha$-hydroperoxy-4$\alpha$-hydroxybishopsolicepolide (6), l$\alpha$,4$\beta$-dihydroxy-8$\alpha$-acetoxy-guaia-2,9,11(13)-triene-6$\alpha$,12-olive (7), rupicolin A (8) and l$\alpha$,4$\alpha$-dihydroxy-bishopsolicepolide (9). Their structures were established by chemical and spectroscopic methods.

• Journal of Applied Biological Chemistry
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• 제43권2호
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• pp.101-103
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• 2000

The synthesis and resolution of ($\pm$)-10,11-dihydroxydibenzosuberenone 3, a potential pharmaceutical compound, is described. It was synthesized from the 5H-dibenzo[a,d]cycloheptene-5-one (dibenzosuberenone) 1, and converted to diastereomeric isomers using (R)-(+)-$\alpha$-methylbenzylamine. Optical resolution of ($\pm$)-10,11-dihydroxydibenzosuberenone 3 was possible by fractional recrystallization of the diastereomer formed in ethanol. The optical resolution of 10,11-dihydroxydibenzosuberenone through formation of its phosphoamidates 5 using the (R)-(+)-$\alpha$-methylbenzylamine was achieved. These compounds provided the optical rotation of [${\alpha}]=-64.3$ for (-)-10,11-dihydroxy-dibenzosuberenone and [${\alpha}]=+61.3$ for (+)-10,11-dihydroxydibenzosuberenone. The (-)- and (+)-enantiomers were prepared in five steps from dibenzosuberenone with overall yields of 11.66% and 9.38%, respectively.

• Archives of Pharmacal Research
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• 제27권10호
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• pp.1023-1028
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• 2004

A new 12a-dehydrorotenoid 1, 11-dihydroxy-9, 10-methylenedioxy-12a-dehydrorotenoid (1), together with a new isoflavonoid glycoside tectorigenin-7-O-${\beta}$-glucosyl-4'-O-${\beta}$-glucoside (3), were isolated and identified from the rhizomes of I. spuria (Zeal). In addition, 4 known compounds, tectorigenin (2) tectorigenin-7-O-${\beta}$-glucosyl $(1{\leftrightarrow}6)$ glucoside (4), tectoridin (a tectorigenin- 7-O-${\beta}$-glucoside) (5) and tectorigenin-4'-O-${\beta}$-glucoside (6) were isolated and identified for the first time from this plant. The structures of the isolated compounds were determined by spectroscopic methods (UV, IR, $^1H,\;^{13}C$NMR, DEPT, HMQC, NOESY, and HMBC experiments and MS spectrometry) and by comparison with literature data of known compounds. Compounds 2, 4, 5, and 6 are reported for the first time from this plant through the present study.

• Applied Chemistry for Engineering
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• 제9권6호
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• pp.842-845
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• 1998

Four new lactones and one dibenzo crown ether were synthesized by reaction of dihydroxy compound with oxalyl chloride and with ${\alpha}$,${\omega}$-dibromo compound, respectively. 5,6,11,12-Tetracarbonyl-2,2,3,3,8,8,9,9-octaphenyl-1,4,7,10-tetraoxacyclodode- cane(1), 5,6,11,12-tetracarbonyl-2,2,3,3,8,8,9,9-octamethyl-1,4,7,10-tetraoxacyclododecane(2), 7,8,15,16-tetracarbonyl-1,6,9,14-tetraoxacylclohexadecane(3), and 5,6,11,12-tetracarbonyl- 2,3,8,9- tetraphenyl-1,4,7,10-tetraoxacyclododecane(4) were prepared by reaction of oxalyl chloride with benzopinacol, pinacol, 2,2'-dihydroxybiphenyl and hydrobenzoin, respectively, in the presence of pyridine. Dibenzo-13-crown-4 (5) was obtained by reaction of catechol with 1,3-dibromopropane/1,2-dibromoethane.

• Natural Product Sciences
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• 제4권3호
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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.

• Archives of Pharmacal Research
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• 제18권6호
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• pp.440-448
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• 1995

Fitty two flavones were synthesized from polyoxygenated dibenzoylmethanes which were obtained by a modified Baker-Venkatarman rearrangement, of 2-benzoyl oxyacetophenones. The following flavones among them showed good cytotoxic activities against L1210 and HL60 cells ; 2'-benzoyloxy-5,7-dimethoxyflavone $(8.2{\mu}g/ml,{\;}5.0 {\mu}g/ml)$, 2'-benzyloxy-5,7,8-trimethoxyflavone $(5,9 {\mu}g/ml,{\;}11.0{\mu}g/ml,{\;}2.7{\mu}g/ml)$, 2'-hydroxy-5,7,8-trimethoxyflavone $(9.8{\mu}/ml,{\;}6.2{\mu}g/ml)$, 2'-benzyloxy-5-hydroxyflavone $(5.2 {\mu}g/ml,{\;}3.6{\mu}g/ml)$, and 5,2'-dihydroxyflavone $(5.1{\mu}g/ml,{\;}4.0{\mu}g/ml)$. Presence of 5-methoxy group potentiated the cytotoxic activity, while the existence of 7-methoxy group decreased the activity. 5-Hydroxy or methoxy activates 4-carbonyl group, while 7-methoxy group deactivates the acrbonyl group. From these observation it was concluded that the activation of carbonyl group at C-4 of a flavone is important for the enahncement of the cytotoxic activity. The presence of both 5-hydroxy and 2-benzyloxy-or 2-hydroxy group enhanced the antitumor activity; 2'-benzyloxy-5-hydroxy-7-methoxyflaone 9T/C=144%), 5.2'-dihydroxy-7-methoxyflavone (T/C=132%) and 5,2'-dihydroxy-6,78,6' trtramethoxyflvone (T/C = 172%) 2'hexanolytion of 5,2'-dihydroxy-flavones did not improve the natitumor activity; 2' hexanoyloxy-5-hydroxy-7-methoxyflavone showed T/C = 132%, about the same as that of 5,2'-dihydroxy-7-methoxyflvone (T/C=130%)

• Natural Product Sciences
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• 제26권2호
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• pp.151-157
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• 2020

Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5'-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4'-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B₅ (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B₂ (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.