Chemical composition of the ethyl acetate extract of Ligularia alticola roots

Ponomarenko, L. P.; Калиновский, А. И.; Горовой, П. Г.; Stonik, Valentin A.

doi:10.1007/s10600-014-0810-6

Cited by 9 publications

(11 citation statements)

References 15 publications

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“…Such characteristic distribution of eremophilanes and their glycosides into different plant parts apparently points to the different functions of these natural compounds in organism producers. Noticeably, the dominant components of the eremophilane fraction from roots of L. alticola are furanoeremophilanes (Ponomarenko et al, 2014), while only glycosylated 2-keto-and 8-ketoeremophilanes have been found by us in aerial parts of the plant. Furthermore, the position of a sugar moiety attachment may vary both in 2-ketoeremophilanes and in 8-ketoeremophilanes.…”

Section: Resultsmentioning

confidence: 84%

“…Ligularia alticola Worosch. is endemic, inhabiting the highest mountains of the Sikhote-Alin, and grows in mountainous tundra of the Primorsky Territory at 1500-1700 m above sea level (Ponomarenko et al, 2014). Herein, we give new data concerning natural products of L. alticola in a continuation of our recent investigation of chemical composition of roots from this plant (Ponomarenko et al, 2014).…”

Section: Introductionmentioning

confidence: 90%

“…is endemic, inhabiting the highest mountains of the Sikhote-Alin, and grows in mountainous tundra of the Primorsky Territory at 1500-1700 m above sea level (Ponomarenko et al, 2014). Herein, we give new data concerning natural products of L. alticola in a continuation of our recent investigation of chemical composition of roots from this plant (Ponomarenko et al, 2014). We describe the isolation and structure elucidation of seven new sesquiterpene glycosides, alticolosides A-G (1-7), differing from each other and earlier known compounds in structures of the aglycones.…”

Section: Introductionmentioning

confidence: 99%

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Structures of eremophilane-type sesquiterpene glucosides, alticolosides A–G, from the Far Eastern endemic Ligularia alticola Worosch

et al. 2015

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Section: Resultsmentioning

confidence: 84%

Section: Introductionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Structures of eremophilane-type sesquiterpene glucosides, alticolosides A–G, from the Far Eastern endemic Ligularia alticola Worosch

et al. 2015

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“…Furanoeremophilanes with a 9-hydroxy (Fei et al, 2010;Saito et al, 2012) or a 9-acyloxy group (Bohlmann et al, 1977;Ponomarenko et al, 2014) have been isolated only as minor components.…”

Section: Discussionmentioning

confidence: 99%

Intra-specific diversity of the chemical composition of Ligularia lamarum in the Hengduan Mountains, China: The structures of four new eremophilanes and a new seco-eremophilane

Saito

Hidaka

Fukuda

et al. 2017

Phytochemistry Letters

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Chemical compositions and internal transcribed spacer (ITS) sequences of five samples of Ligularia lamarum collected in Sichuan Province, China, were analyzed. Fourteen compounds, including four new eremophilanes and one new seco-eremophilane, were isolated and their structures were elucidated by spectroscopic methods.Intra-specific diversity in the chemical composition was found to be higher than previously known. The result of DNA analysis suggested that one of the samples was introgressed, although its chemical composition was typical of L. lamarum. 2 IntroductionLigularia (Asteraceae) species in the Hengduan Mountains of China are highly diversified, thereby providing an opportunity for studying the diversity in secondary metabolites. We have studied the diversity of Ligularia using root chemicals and evolutionally neutral DNA sequences as indices, because the roots of Ligularia contain a variety of terpenoids. To date, we have revealed intra-specific diversity in many species with various modes. For example, many species consisted of several chemotypes (Kuroda et al., , 2014, implying that the generation mechanism of chemical diversity is complex. Furanoeremophilanes have been isolated from most of the major species of Ligularia, and other compounds such as bisabolanes, benzofurans, and phenylpropanoids have also been obtained. L. lamarum (Diels) C. C. Chang is widely distributed in the Hengduan Mountains, including the Yunnan, Sichuan, and Gansu provinces and the Xizang Autonomous Region of China and northwestern Myanmar (Liu and Illarionova, 2011). Taxonomically, the species is closely related to L. subspicata (Bureau and Franch.) Hand.-Mazz.The major morphological difference between L. lamarum and L. subspicata is the presence (L. lamarum) or absence (L. subspicata) of ray florets (Liu and Illarionova, 2011). We previously analyzed L. lamarum and L. subspicata collected in northwestern Yunnan and southwestern Sichuan, and showed that the two species were indistinguishable by our two indices (Saito et al., 2011). Eremophilanes were isolated from all of our collected samples, which were classified into two chemotypes: 1) a furanoeremophilane type and 2) an eremophilan-8-one type. Subspicatins (1β-acyloxyfuranoeremophilanes) are characteristic of the furanoeremophilane type, although not all furanoeremophilane-type samples produce subspicatin(s).Here, we report the results of analyses of L. lamarum samples collected in northern Sichuan Province, which showed further diversity within the furanoeremophilane type. Five new compounds were isolated and their structures were determined. Results SamplesFive samples of L. lamarum were collected in northern Sichuan Province (Table 1 and Figure 1): two in Hongyuan County (samples 1 and 2) and three in Dege County (samples 3-5). Samples 1 and 2 were less than 100 m apart.Sample 1 had typical ray florets, whereas sample 2 had very small ray florets. Samples 3 and 4 were collected sympatrically. The leaves of sample 3 were more cordate, whereas those of sample 4 were mor...

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“…For this reason, absolute stereochemistry of alticolosides F (26) and G (27) remained unclear so far [13]. Since all other eremophilane sesquiterpenoids from the L. alticola possess 14β and 15β methyl groups [13,14,19,20] the structures 26a and 27a are more likely. But the available data don't exclude the existence of 26b and 27b forms.…”

Section: Eremophilane-type Glycosidesmentioning

confidence: 99%