Synthese von (+)‐Taxodion

Haslinger, Ernst; Michl, Günter

doi:10.1002/jlac.198919890212

Cited by 13 publications

(12 citation statements)

References 38 publications

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“…Further purification by a combination of silica gel CC, and preparative and semipreparative RP-HPLC afforded 17 abietane, icetexane, and isopimarane diterpenoids. Fourteen of them were identified as known compounds, including 12-hydroxy-20-norabieta-8,11,13-triene (1) [21], carnosol (3) [22], 7α-ethoxyrosmanol (4) [23], miltirone (5) [24], Δ 9 -dehydro-ferruginol (7) [25], ferruginol (8) [26], miltiodiol (10) [22], and galdosol (17) [23] (▶ Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Antiprotozoal Diterpenes from Perovskia abrotanoides

et al. 2018

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As part of a screening for new antiparasitic natural products from Iranian plants, -hexane and ethyl acetate extracts from the aerial parts of were found to exhibit strong inhibitory activity against and. The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1: -17: ), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5,10)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2: ), 12-hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6: ), and 12-methoxybarbatusol (9: ) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one- and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism). The antiprotozoal activity of the isolated compounds was evaluated against , and. Selectivity indexes (SI) were calculated in comparison to cytotoxicity on rat myoblast (L6) cells. Particularly active were 7-ethoxyrosmanol (4: ) with an IC of 0.8 µM against (SI 14.9) and an IC of 1.8 µM (SI 6.9) against , ferruginol (8: ) with an IC of 2.9 µM (SI 19.2) against , and miltiodiol (10: ) with an IC of 0.5 µM (SI 10.5) against . None of the compounds exhibited selective toxicity against (SI ≤ 1.6).

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Section: Resultsmentioning

confidence: 99%

Antiprotozoal Diterpenes from Perovskia abrotanoides

et al. 2018

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“…20,21 Oxidation of 1 in the presence of sulfuric acid followed by methylation gave the known compounds methyl 12oxoabietate ( 6), methyl 7-oxodehydroabietate ( 7), methyl 7-hydroxydehydroabietate (8), and 5. Compound 6 was obtained by synthesis, 22,23 but literature NMR data of 6 are incomplete, and therefore full NMR signal assignments have been made (Tables 1 and 2). NMR data for 7 corresponded well with those reported by Krohn et al, 24 who isolated 7 and 8 after photolysis of methyl dehydroabietate.…”

Section: Resultsmentioning

confidence: 99%

“…Fraction 4 (30 mg) [R f 0.77-0.87, cyclohexane-EtOAc-glacial acetic acid (1:9:0.01)] was purified by HPLC on RP-18 eluting with MeOH-H2O ((8:2) flow rate 1 mL/min, detection at 254 nm) to afford 2. 29), 315 [m/z 333 -H2O] + (8), 314 (22), 307 [M -COOCH3] + (7), 289 (11), 263 (11), 255 (18), 247 (100), 229 (25), 211 (13), 199 (11), 183 (17), 165 (11), 159 (12), 146 (17), 123 (40), 121 (29), 109 (28), 107 (28), 95 (18), 81 (18), 79 (18), 55 (18), 43 (28), 41 (14)…”

Section: Methodsmentioning

confidence: 99%

Oxidation Products of Abietic Acid and Its Methyl Ester

et al. 2002

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Abietic acid (1) and its methyl ester (2) were investigated under various storage conditions to provide an indication of their preferred oxidation mechanisms and to investigate the most susceptible positions for modification in the abietane skeleton. Six known compounds, methyl 7alpha,13beta-dihydroxyabiet-8(14)-enoate (4a), methyl 7alpha,13alpha-dihydroxyabiet-8(14)-enoate (4b), methyl 12-oxoabietate (6), methyl 7-oxodehydroabietate (7), methyl 7alpha-hydroxydehydroabietate (8), and 13,14-seco-13,14-dioxoabiet-7(8)-enoic acid (11), were identified. Compounds 7 and 8 are regarded as potent allergens. In addition, six new oxidation products were isolated, methyl 13beta-ethoxy-7alpha-hydroxyabiet-8(14)-enoate (3a), methyl 13alpha-ethoxy-7alpha-hydroxyabiet-8(14)-enoate (3b), methyl 7alpha-hydroperoxy-13alpha-hydroxyabiet-8(14)-enoate or methyl 13alpha-hydroperoxy-7alpha-hydroxyabiet-8(14)-enoate (5), 7alpha,13beta-dihydroxyabiet-8(14)-enoic acid (9a), 7alpha,13alpha-dihydroxyabiet-8(14)-enoic acid (9b), and 7alpha,15-dihydroxydeydroabietic acid (10). Their structures were characterized on the basis of spectroscopic data interpretation. The cytotoxicity of several compounds against KB cells was evaluated, and weak activity was observed for 6, 7, and 8 with IC(50) values of 12.5, 4.5, and 5.8 microg/mL, respectively.

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“…Moreover, H-6 also exhibited HMBC correlation with the other dehydroxyferruginol aromatic C-12Ј (d C 153.1). The second moiety of 2 was identified as a 6,7-dehydroferruginol 10) since the NMR spectral data are similar to those of 1 and 4 (Tables 1, 2). Hence 2 is 7a-butoxyethoxy-12-hydroxyabieta-6a-yl 6,7-dehydroabieta-8,11,13-trien-12-yl ether.…”

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confidence: 91%