New Sesquiterpenes fromErigeron annus

Li, Xin; Yang, Min; Han, Yifeng; Gao, Kun

doi:10.1055/s-2005-837827

Cited by 49 publications

(36 citation statements)

References 9 publications

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“…1). Their structure was identified as 3-caffeoylquinic acid (1), 27) 3,5-di-O-caffeoylquinic acid methyl ester (2), 28) 3,5-di-O-caffeoyl-epi-quinic acid (3), 29) apigenin (4), 30) api- 38) daucosterol, 31) erigeroside, 39) and 3-hydroxypyran-4-one 40) by spectroscopic data measurement and by comparison with published values. To the best of our knowledge, this is the first report on the isolation of compounds 1, 3, 7, 9, and 11 from this plant.…”

Section: Resultsmentioning

confidence: 99%

“…11) Previous phytochemical investigations on this plant resulted in the isolation of g-pyranone derivatives, [12][13][14] cyclopentenone derivatives, 15) sesquiterpenoids, 16,17) flavonoids, 12) triterpenoids, 12) and phenolic derivatives. 13,14) Recently, a novel 2,3-dioxygenated flavanone, erigeroflavanone, as well as known flavonoids and g-pyranone derivatives, were isolated from the flowers of E. annuus by our group.…”

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confidence: 99%

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3,5-Di-O-caffeoyl-epi-quinic Acid from the Leaves and Stems of Erigeron annuus Inhibits Protein Glycation, Aldose Reductase, and Cataractogenesis

Jang

Yoo

Kim

et al. 2010

Biological & Pharmaceutical Bulletin

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In our ongoing project directed toward the discovery of novel treatments for diabetic complications from herbal medicines, sixteen compounds including three caffeoylquinic acids and four flavonoids were isolated from an EtOAc-soluble extract of the stems and leaves of Erigeron annuus. All the isolates were evaluated in vitro for inhibitory activity on the formation of advanced glycation end products (AGEs) and rat lens aldose reductase (RLAR). Of these, 3,5-di-O-caffeoyl-epi-quinic acid (3) exhibited the most potent inhibitory activity in both the AGEs and aldose reductase (AR) assays. Compound 3 markedly reduced AGEs-bovin serum albumin (BSA) cross-linking in a dose-dependent manner. Furthermore, opacity of lenses was significantly prevented when they were treated with 3 in an ex vivo experiment.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

3,5-Di-O-caffeoyl-epi-quinic Acid from the Leaves and Stems of Erigeron annuus Inhibits Protein Glycation, Aldose Reductase, and Cataractogenesis

Jang

Yoo

Kim

et al. 2010

Biological & Pharmaceutical Bulletin

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“…40 The enantiomer of lairdinol A, known as cyperusol C (ent-51), was isolated from two natural sources: the Egyptian herbal medicinal plant Cyperus longus 42 and Erigeron annus. 43 The absolute configuration of ent-51 was assigned by Yoshikawa using the Mosher's ester method.…”

Section: Isolated From Petriella Sordidamentioning

confidence: 99%

“…25 The enantiomer of 51, cyperusol C (ent-51), has been isolated from the plants Cyperous longus 42 and Erigeron annus. 43 The absolute configuration for ent-51 was determined 42 …”

Section: Scheme 24 Regioselective Oxidation Of Bis(tms Enol Ether) mentioning

confidence: 99%

Total Synthesis of Depsilairdin

Ward

Pardeshi

2010

J. Org. Chem.

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The total synthesis of depsilairdin, a host-selective phytotoxin isolated from Leptosphaeria maculans (the causal agent of blackleg disease of oilseed Brassicas), has been achieved by N-terminal extension of a suitably protected derivative of the hitherto unknown amino acid (2S,3S,4R)-3,4-dihydroxy-3-methyl-proline (Dhmp) followed by esterification with lairdinol A. The latter esterification, complicated by the sterically hindered nature of the carboxyl group, was accomplished by a novel method involving reaction of the 1-hydroxybenzotriazole (HOBt) derived active ester with the bromomagnesium alkoxide of lairdinol A. Three depsilairdin analogues were also prepared by replacing the Dhmp residue with L-proline and cis-and trans-4-hydroxy-L-proline. Phytotoxicity assays showed that the analogues were nontoxic to both blackleg-susceptible (brown mustard) and -resistant (canola) plants, suggesting that the presence of the Dhmp residue in depsilairdin is important for its host-selective toxicity toward brown mustard.

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“…The structures of other known compounds were identified to be α-rotunol (3), 5 β-rotunol (4), 5 (−)-eudesma-3,11-diene-5-ol (5), 12 ligucyperonol (6), 13 14-hydroxy-α-cyperone (7), 14 britanlin E (8), 15 and 1β,4β-dihydroxyeudesma-11-ene (9) 16 by physical (mp, [α] D ) and spectroscopic data ( C-NMR and DEPT spectra of 1 (Table 2) allowed the identification of 19 carbon atoms: six methyl groups, two methylene groups, five methine groups, and six quaternary carbon atoms. The chemical shifts of the latter indicated two ester carbonyl (δ 171.2 and 170.9), two aliphatic (δ 61.6 and 41.5), and two sp 2 carbons (δ 140.9 and 139.1).…”

mentioning

confidence: 99%