Macrocarpals: HIV-RTase inhibitors of Eucalyptus globulus

Nishizawa, Masatoyo; Emura, Makoto; Kan, Yukiko; Yamada, Hidetoshi; Ogawa, Koji; Hamanaka, Nobuyuki

doi:10.1016/s0040-4039(00)79578-5

Cited by 90 publications

(69 citation statements)

References 14 publications

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“…20,21 Thus, the antiviral effects of compounds 1-7 against respiratory syncytial virus (RSV) were evaluated in HEp-2 cells using the cytopathic effect (CPE) reduction assay. Compounds 3, 5, and 7 exhibited moderate inhibitory activities against RSV A2 strain with IC 50 values ranging from 11.67 AE 0.95 to 15.85 AE 3.02 mM, while the IC 50 value of the positive control ribavirin was 10.20 AE 0.90 mM.…”

Section: -11mentioning

confidence: 99%

Myrtucomvalones A–C, three unusual triketone–sesquiterpene adducts from the leaves of Myrtus communis ‘Variegata’

Chen

et al. 2017

RSC Adv.

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Section: -11mentioning

confidence: 99%

Myrtucomvalones A–C, three unusual triketone–sesquiterpene adducts from the leaves of Myrtus communis ‘Variegata’

Chen

et al. 2017

RSC Adv.

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“…The AcOEt fraction was subjected to various column chromatographies (CC) and semipreparative HPLC to yield 33 compounds. The known compounds were determined as guaiacylglycerol [5], 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one [6], caffeic acid, (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid [7], (7 [10], garcimangosone [11], phloracetophenone 2'-glucopyranoside [12], eucalmainosides D and E [4], (þ)-taxifolin 3-O-a-l-rhamnopyranoside [13], engelitin [14], (þ)-aromadendrin [14], eriodictyol [14], (þ)-taxifolin [14], (þ)-catechin [7], resveratrol [15], piceatannol [16], 3,4,5-trihydroxyphenol [17], tachioside, gallic acid, 3-Omethylellagic acid 3'-O-a-l-rhamnopyranoside [4], macrocapals A and G [18], ( AE )-oleuropeic acid, b-sitosterol [7], icariside B 4 [19], eucalmaidin A [3], and glycerol, on the basis of detailed spectroscopic analyses, together with the comparison of their spectroscopic and physical data with those in the literature 1 H-COSY spectra of 2, a partial structure of ÀCH 2 ÀCH(OH)ÀCH 2 ÀCH 2 À from C(2) to C(5) could be elucidated. In the HMBC spectrum of 2, correlations of the signals of HÀC (2) and HÀC (3) with that of the carboxy C-atom, and of HÀC (5) with those aromatic C-atoms C(1'), C(2') and C(6') positioned the partial structure ÀCH 2 ÀCH(OH)ÀCH 2 ÀCH 2 À between the carboxy Catom and the aromatic ring (Fig.…”

Section: Phenolic Compounds From the Branches Of Eucalyptus Maidenimentioning

confidence: 99%

Phenolic Compounds from the Branches of Eucalyptus maideni

Tian

et al. 2012

Chemistry & Biodiversity

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Three new phenolic compounds, eucalmaidin F (1), (3S)-5-guaiacyl-3-hydroxypentanoic acid (2), and 8-β-C-glucopyranosyl-5,7-dihydroxy-2-isobutylchromone (3), were isolated from the branches of E. maideni, together with 30 known compounds, including four phenylpropanoids, three lignans, four phloroglucinol glucosides, five dihydroflavonoids, seven simple phenolic compounds, six terpenoids, and glycerol. The new structures were established by spectroscopic studies (MS, and 1D- and 2D-NMR), chemical degradation, and modified Mosher's method. Compounds 3, guaiacylglycerol, 3-hydroxy-1-(4-hydroxyphenyl)propan-1-one, caffeic acid, (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid, (7'S,8R,8'R)-lyoniresinol, (+)-lyoresinol 3α-O-α-L-rhamnopyranoside, garcimangosone, phlorocetophenone 2'-glucopyranoside, (+)-taxifolin 3α-O-α-L-rhamnopyranoside, (+)-aromadendrin, (+)-taxifolin, resveratrol, piceatannol, 3,4,5-trihydroxyphenol. Tachiaside, gallic acid, macrocapals A und G, and oleuropeic acid were evaluated for their cytotoxicities against five human cancer cell lines. Resveratrol, piceatannol, gallic acid, and macrocapal G exhibited moderate inhibitory effects on human myeloid heukemia HL-60 cell, with IC(50) values of 22.05, 22.05, 7.75, and 31.93 μM, respectively; and only macrocapal G showed inhibitory effect on hepatocellular carcinoma SMMC-7721 cell, with an IC(50) value of 26.75 μM.

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“…Formylated phloroglucinols have also proved to be therapeutically and/or pharmacologically significant (EBV inhibitory (Takasaki et al 1990), anti-bacterial (Satoh et al 1992), HIV-RT inhibitory (Nishizawa et al 1992), aldose reductase inhibitory (Satoh et al 1992), anti-protozoal (Bharate et al 2006. The dimeric derivative, sideroxylonal A, has proved to act as a potent marine anti-fouling agent comparable to the most active compound 2,5,6-tribromo-1-methyl-gramine (Singh et al 1996).…”

Section: Potential Usesmentioning

confidence: 99%