Seven Germacranolides, Eupaglehnins A, B, C, D, E, and F, and 2&amp;alpha;-Acetoxyepitulipinolide from &lt;i&gt;Eupatorium glehni&lt;/i&gt;

Tori, Motoo; Takeichi, Yoshiko; Kuga, Hiroe; Nakashima, Katsuyuki; Sono, Masakazu

doi:10.1248/cpb.50.1250

Cited by 18 publications

(26 citation statements)

References 31 publications

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“…These phenomena were observed in other germacranolides. 29,30) The unsaturated ester was 4′,5′-dihydroxytiglate, because of the presence of NOE between H-4′ and H-5′. The NOE between H-1 and H-7, as well as other NOEs shown in Fig.…”

Section: Resultsmentioning

confidence: 96%

“…[28][29][30][31] In our previous study on E. glehnii growing in Japan, especially in Obihiro (Hokkaido), Fujimi-cho (Nagano), and Tokushima, a large diversity in the chemical constituents was found, while there was no diversity in DNA sequences (atpB-rbcL intergenic region). 30) In our continuous research on the genus Eupatorium, we collected E. heterophyllum DC.…”

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confidence: 93%

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Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

et al. 2014

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Eight new hydroperoxides and a new enone of germacrane-type sesquiterpenoids were isolated from the aerial parts of eight different samples of Eupatorium heterophyllum DC. (Asteraceae) collected in P. R. China. The structures were determined based on spectroscopic analyses. Seven of the eight samples produced hiyodorilactone A as a major constituent, while one afforded neither hiyodorilactone nor hydroperoxide. The results indicated the presence of diversity within this species.

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Section: Resultsmentioning

confidence: 96%

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confidence: 93%

Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

et al. 2014

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“…However, acid sensitivity of the tertiary allylic ether (alcohol) motif cast doubt on its coexistence with the carboxylic acid functionality, and we therefore considered that the carboxyl motif could be esterified. The 13 C NMR shift for the ring CH 2 (in the original assignment) suggested a better match for a primary alcohol rather than an ether (Figure ) . As discussed earlier (Figure ), the tertiary allylic position most likely corresponds to a free alcohol, with the ethyl group being borne by a secondary alcohol and the reported 13 C shift for C(3) is more consistent for an ether rather than a free alcohol (Figure ).…”

Section: Resultsmentioning

confidence: 62%

Aruncin B: Synthetic Studies, Structural Reassignment and Biological Evaluation

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Josa-Culleré

et al. 2017

Chemistry A European J

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A ring‐closing alkene metathesis (RCM)/ oxyselenation‐selenoxide elimination sequence was established to the sodium salts E‐ and Z‐25 of the originally proposed structure for the recently isolated cytotoxin aruncin B (1), as well as to the sodium salt Z‐34 of a related ethyl ether regioisomer; however, none of their corresponding free acids could be obtained. Their acid sensitivity, together with detailed analysis of the spectroscopic data indicated that profound structural revision was necessary. This led to reassignment of aruncin B as a Z‐γ‐alkylidenebutenolide Z‐36. Although a related RCM/ oxyselenation‐selenoxide elimination sequence was used to confirm the γ‐alkylidenebutenolide motif, a β‐iodo Morita‐Baylis–Hillman reaction/ Sonogashira cross‐coupling‐5‐exo‐dig lactonisation sequence was subsequently developed, due to its brevity and flexibility for diversification. Aruncin B (36), together with 14 γ‐alkylidenebutenolide analogues, were generated for biological evaluation.

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“…The closest known analogues have been observed from natural sources. [11][12][13][14][15][16][17] These precedents also show the 10-membered carbocycle of the germacrane skeleton, but with different arrangements in functionality. Substances 1 and 2, on the other hand, are highly acylated members with oxy-isovaleryl groups being the most unusual ones.…”

Section: Resultsmentioning

confidence: 99%