3β,6β-Bis(acyloxy)furanoeremophilan-14-als and -14-oic Acids from Syneilesis palmata (<scp>Thunb</scp>.) <scp>Maxim</scp>.

Kuroda, Chiaki; Murae, Tatsushi; Tada, Mizuki; Nagano, Hajime; Tsuyuki, Takahiko; Takahashi, Takeyoshi

doi:10.1246/bcsj.55.1228

Cited by 22 publications

(37 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This compound seemed to be a precursor to compound 1 in its biosynthetic pathway. [7][8][9] Both compounds 6 and 7 had the same molecular formula of C 16 thoxy group, a trisubstituted furan, and a trisubstituted alkene moiety (Table 3). COSY correlations, including weak ones between H-3 and H-15, H-6 and H 2 -9, and H-12 and H 3 -13, indicated the same planar structure for 6 and 7 as depicted in Fig.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Eremophilanes from Ligularia hookeri Collected in China and Structural Revision of 3β-Acyloxyfuranoeremophilan-15,6-olide

Saito

Shiosaki

Fujiwara

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Chemical constituents of Ligularia hookeri (Asteraceae) collected in Yunnan and Sichuan Provinces in China were examined for the first time. Seven furanoeremophilanes, five of which were new, as well as known bisabolane-and eudesmane-type sesquiterpenoids, were isolated. Spectroscopic evidence indicates that the previously reported 3β-(2′-methylpropenoyloxy)furanoeremophilan-15,6β-olide should be revised to 3β-(2′-methylpropenoyloxy)furanoeremophilan-15,6α-olide.Key words Ligularia hookeri; Asteraceae; eremophilane; sesquiterpene; structure elucidation; internal transcribed spacerWe have been analyzing both the chemical composition and the DNA sequence of evolutionarily neutral regions of Liguralia (Asteraceae) plants, mainly from Sichuan and Yunnan Provinces in China, in order to study the mechanism of diversification of secondary metabolites.1,2) Intra-specific diversity has been revealed in most of the Ligularia species hitherto studied and found to be high in some species. The results of DNA analysis have suggested that the diversity in the chemicals has genetic origins in most cases. Furanoeremophilanes and/or eremophilan-8-ones have been isolated from most of the major Ligularia species; in particular, furanoeremophilanes are found more often than eremophilan-8-ones. In addition, most of the species that produce furanoeremophilanes appear to be more abundant than those that do not. These observations have led us to propose a hypothesis that furanoeremophilane-producing species or intra-specific populations are ecologically advantageous over eremophilan-8-one-producing ones.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Compounds 10 and 11 bearing H-6α were first reported by Bohlmann and Knoll. 5) Compound 12 was chemically derived from 3β,6β-bis(acyloxy)-15-oic acid by Kuroda et al 7,8) The H-6β structure of 12 was established from the NOE signal between H-6 and H 3 -14.…”

Section: Resultsmentioning

confidence: 99%

Eremophilanes from Ligularia hookeri Collected in China and Structural Revision of 3β-Acyloxyfuranoeremophilan-15,6-olide

Saito

Shiosaki

Fujiwara

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

show abstract

“…The known compounds 3 – 9 were identified as furanoeremophilan-10β-ol ( 3 ) (Jennings et al, 1976); 3β-angeloyloxyeremophila-7,11-dien-14β,6α-olide ( 4 ) (Li et al, 2004); furanoeremophil-3- en -14,6α-olide ( 5 ) (Kuroda et al, 1982); 10β-dihydroxyeremophilenolide ( 6 ) (Aclinqu et al, 1991); 8β,10β-dihydroxyeremophilenolide ( 7 ) (Kojima et al, 1997); 11-hydroxyvalenc-1(10)- en -2-one ( 8 ) (Savona et al, 1987); and ( 3R , 4R , 6S )-3,6-dihydroxy-1-menthene ( 9 ) (Cuenca et al, 1991), respectively, on the basis that their HRESI-MS and NMR data were consistent with the literature.…”

Section: Resultsmentioning

confidence: 99%

Phytotoxic Terpenoids from Ligularia cymbulifera Roots

et al. 2017

View full text Add to dashboard Cite

Ligularia cymbulifera is one of the predominant species in the Hengduan Mountains, China, and has led to a decrease in the amount of forage grass in this area. However, little is known about the mechanism behind its predominance. In this study, two novel eremophilane sesquiterpenes, ligulacymirin A and B (1 and 2), together with seven other known terpenoids (3–9), were isolated from the roots of L. cymbulifera. The structures of 1 and 2 were determined by spectroscopic methods and single-crystal X-ray diffraction. Each compound showed phytotoxic activities against Arabidopsis thaliana, and each was detected and identified in rhizosphere soil by UHPLC-MS. Compound 3 was the most potent phytotoxin, showing remarkable inhibition against both seedling growth (EC50 = 30.33 ± 0.94 μg/mL) and seed germination (EC50 = 155.13 ± 0.52 μg/mL), with an average content in rhizosphere soil of 3.44 μg/g. These results indicate that terpenoids in L. cymbulifera roots might be released as phytotoxins in rhizosphere soil to interfere with neighboring plants.

show abstract

“…Peak II was identified as furanoeremophil-3-en-15,6a-olide according to the literature. [24] CONCLUSIONS In combination with a suitable extraction and cleanup procedure prior to HSCCC separation, two eremophilane type sesquiterpenes including 8b-H-eremophil-3,7(11)-dien-12,8a; 15,6a-diolide and furanoeremophil-3-en-15,6a-olide from L. atroviolacea are obtained on a preparative scale. The results obtained in the present study clearly demonstrate that HSCCC is a powerful technique for the isolation of pure compounds .…”

Section: Identification Of the Separated Peaksmentioning

confidence: 99%

Purification of Eremophilane‐Type Sesquiterpenes from Ligularia atroviolacea by High Speed Countercurrent Chromatography

Shi

Zhang

Huang

et al. 2008

Journal of Liquid Chromatography & Related Technologies

View full text Add to dashboard Cite

Following an initial cleanup step on the C 18 open column chromatography, a preparative high speed countercurrent chromatography (HSCCC) method for isolation and purification of 8b-H-eremophil-3,7(11)-dien-12,8a; 15,6a-diolide, and furanoeremophil-3-en-15,6a-olide from the Chinese medicinal plant Ligularia atroviolacea was successfully established by a one-step separation, using n-hexane-ethyl acetateethanol-water (4:1:4:1, v/v/v/v) as the two phase solvent system. The upper phase was used as the mobile phase in the head to tail elution mode. HPLC analysis of the fractions collected on the preparative HSCCC of 600 mg of crude extracts showed that the purity of 8b-H-eremophil-3,7(11)-dien-12,8a; 15,6a-diolide (54.7 mg) was 98.1% and that of furanoeremophil-3-en-15,6a-olide (41.8 mg) was 98.4%. The chemical structures of the two eremophilane-type sesquiterpenes were identified by ESI-MS, 1 H-NMR, and 13 C-NMR analysis. To the best of our knowledge, 8b-H-eremophil-3,7(11)-dien-12,8a; 15,6a-diolide was obtained from L. atroviolacea for the first time, while furanoeremophil-3-en-15,6a-olide was first isolated as a natural product.

show abstract

3β,6β-Bis(acyloxy)furanoeremophilan-14-als and -14-oic Acids from Syneilesis palmata (Thunb.) Maxim.

Cited by 22 publications

References 11 publications

Eremophilanes from <i>Ligularia hookeri</i> Collected in China and Structural Revision of 3β-Acyloxyfuranoeremophilan-15,6-olide

Eremophilanes from <i>Ligularia hookeri</i> Collected in China and Structural Revision of 3β-Acyloxyfuranoeremophilan-15,6-olide

Phytotoxic Terpenoids from Ligularia cymbulifera Roots

Purification of Eremophilane‐Type Sesquiterpenes from Ligularia atroviolacea by High Speed Countercurrent Chromatography

Contact Info

Product

Resources

About