Obliquin derivatives and other constituents from Australian Helichrysum species

Jakupovic, Jasmin; Pathak, V. P.; Bohlmann, Ferdinand; King, Robert M.; Robinson, Harold

doi:10.1016/s0031-9422(00)84791-3

Cited by 49 publications

(36 citation statements)

References 14 publications

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“…Yield 28%; colourless liquid; spectral data are in accordance with data reported in ref. [33]. (27) Propanoic acid (700 mg, 4.66 mmol) was dissolved in NEt 3 (3.2 mL, 5 eq.)…”

Section: Cinnamic Acid Menthyl Estermentioning

confidence: 99%

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

et al. 2014

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Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC 50 = 48.8 µM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.

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“…Yield 28%; colourless liquid; spectral data are in accordance with data reported in ref. [33]. (27) Propanoic acid (700 mg, 4.66 mmol) was dissolved in NEt 3 (3.2 mL, 5 eq.)…”

Section: Cinnamic Acid Menthyl Estermentioning

confidence: 99%

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

et al. 2014

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“…A similar compound with cis configuration at C(2) and C(3), 3-(angeloyloxy)-12-hydroxytremetone, has been previously isolated from the roots of Helichrysum stirlingii [16].…”

mentioning

confidence: 97%

“…In contrast, C(5)-substituted obliquin derivatives are specific markers for the tribe Gnaphalieae sensu Anderberg [23]. These substances have been detected so far in the genera Helichrysum [16] . Spectra and physical data in accordance with literature data [22].…”

mentioning

confidence: 99%

New Lignan, Benzofuran, and Sesquiterpene Derivatives from the Roots of Leontopodium alpinum and L. leontopodioides

Dobner

Ellmerer

Schwaiger

et al. 2003

Helvetica Chimica Acta

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Three new compounds, including a benzofuran, 1‐{(2R*,3S*)‐3‐(β‐D‐glucopyranosyloxy)‐2,3‐dihydro‐2‐[1‐(hydroxymethyl)vinyl]‐1‐benzofuran‐5‐yl}ethanone (1), a lignan, [(2S,3R,4R)‐4‐(3,4‐dimethoxybenzyl)‐2‐(3,4‐dimethoxyphenyl)tetrahydrofuran‐3‐yl]methyl (2E)‐2‐methylbut‐2‐enoate (2), and a silphiperfolene‐type sesquiterpene, [(1S,2Z,3aS,5aS,6R,8aR)‐1,3a,4,5,5a,6,7,8‐octahydro‐1,3a,6‐trimethylcyclopenta[c]pentalen‐2‐yl]methyl acetate (3), together with the known coumarins obliquin (4) and its 5‐methoxy derivative 5 were isolated from the roots of Leontopodium alpinum. Another known coumarin derivative, 5‐hydroxyobliquin (6), was isolated from the roots of L. leontopodioides. The structures of these compounds were established by spectroscopic studies.

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“…Each fraction was repeatedly separated by a combination of different chromatographies to give two new compounds, 1 and 2, together with seven known compounds, 2,2-dimethyl-6-vinylchromene (3), 7) acetophenone (4), 2-prenyl-4-vinylphenol (5), 8) 3,4-dimethoxy-styrene (6), 9) 3,4-dimethoxy-allylbenzene (7), 9) 4-hydroxy-3,5-diprenylbenzaldehyde (8), 10) and (Ϫ)-spathulenol (9).…”

Section: Resultsmentioning

confidence: 99%

Isolation and Structures of Two New Compounds from the Essential Oil of Brazilian Propolis.

et al. 2001

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Obliquin derivatives and other constituents from Australian Helichrysum species

Cited by 49 publications

References 14 publications

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

New Lignan, Benzofuran, and Sesquiterpene Derivatives from the Roots of Leontopodium alpinum and L. leontopodioides

Isolation and Structures of Two New Compounds from the Essential Oil of Brazilian Propolis.

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