Tricyclic sesquiterpenes from Artemisia chamaemelifolia

Marco, J. Alberto; Sanz‐Cervera, Juan F.; Morante, María; García-Lliso, Vicente; Vallés-Xirau, Joan; Jakupovic, Jasmin

doi:10.1016/0031-9422(95)00702-4

Cited by 69 publications

(5 citation statements)

References 15 publications

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“…To probe this possibility in practice, we chose to investigate the postulated biosynthetic connection between caryophyllene and the presilphiperfolanol family of natural products . Three members of this family have been isolated to date: (−)-presilphiperfolan-9α-ol [(−)- 2 ], (−)-presilphiperfolan-8α-ol [(−)- 3 ], and (−)-presilphiperfolan-1β-ol [(−)- 4 ] (Figure b). , These natural products hold significant importance in the study of terpene biosynthesis, as their strained framework is believed to represent a branching point that links together a number of different biosynthetic pathways . They also exhibit interesting biological activities like antimycobacterial and insect antifeedant properties. , Their complex tricyclic skeleton has proven to be a challenging target for total synthesis; hitherto reported total syntheses of the presilphiperfolanols have required 13–17 linear steps from commercially available materials. ,, …”

Section: Introductionmentioning

confidence: 99%

Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis

et al. 2020

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Terpenes constitute one of the most structurally varied classes of natural products. A wide range of these structures are produced in nature by type I terpene cyclase enzymes, but such reactivity has proven difficult to reproduce in solution with man-made systems. Herein we report the shortest synthesis of the tricyclic sesquiterpene presilphiperfolan-1β-ol to date, utilizing the supramolecular resorcinarene capsule as catalyst for the key step. This synthetic approach also allows access to unnatural derivatives of the natural product, which would not be accessible through the biosynthetic machinery. Additionally, this study provides useful insight into the biosynthesis of the presilphiperfolanol natural products, including the first direct experimental evidence for the proposed biosynthetic connection between caryophyllene and the presilphiperfolanols.

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Section: Introductionmentioning

confidence: 99%

Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis

et al. 2020

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“…We highlighted the identification of presilperfolane and silphiperfolane derivatives as major components in the three samples by comparison of their carbon chemical shifts values with those reported in the literature [16][17][18][19][20][21][22]: 7-epi-silphiperfol-5-en-13-oic acid (4.0-20.8%) and silphiperfol-5-en-13-oic acid (4.0-10.6%) ( Table 2), 7-epi-subergorgiol (7.6-14.8%), 7β-H-silphiperfol-5-ene (1.8-14.8%), presilphiperfolan-9-α-ol (6.9-8.0%), 7-epi-silphiperfolenal (1.4-2.5%), 13-hydroxysilphiperfol-6-ene (1.2-1.9%) and 7α-H-silphiperfol-5-ene (up to 0.3%). The presence of a compound including an acid group as major component is very unusual in essential oils.…”

Section: Helichrysum Hirtum Essential Oilmentioning

confidence: 86%

“…We detailed the identification by 13 C NMR of 7-epi-silphiperfol-5-en-13-oic acid (152) and silphiperfol-5-en-13-oic acid (153) in the sample Hh1 (Table 2). For these two compounds: -all the expected signals were observed; -the chemical shift variations between the reference spectrum (Marco et al [16]) and the recorded spectrum of the sample Hh1 were low. Indeed, they were less than or equal to 0.08 ppm for at least 12 signals out of 15.…”

Section: Helichrysum Hirtum Essential Oilmentioning

confidence: 89%

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Chemical Composition of Aerial Parts Essential Oils from Six Endemic Malagasy Helichrysum Species

Rabehaja

Bezert

Rakotonandrasana

et al. 2020

Plants

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The essential oils of six endemic Malagasy Helichrysum species were investigated by GC (RI), GC–MS and 13C NMR spectrometry. In total, 153 compounds were identified accounting for 90.8% to 99.9% of the total composition. The main constituents were α-pinene for H. benthamii, 1,8-cineole for H. dubardii, (E)-β-caryophyllene for H. indutum, and H. bojerianum. H. diotoides essential oil was characterized by the presence of two lilac alcohols and four lilac acetates whereas H. hirtum essential oil exhibited an atypical composition with 7β-H-silphiperfol-5-ene, 7-epi-subergorgiol, and 7-epi-silphiperfol-5-en-13-oic acid as major components.

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“…Compound 1 displayed carbonyl characteristics in NMR and was identified as (-)-hinokinin [22]. Compound 2 was identified as (-)-O-methylcubebin (MC) previously isolated from Artemisia chamaemelifolia [23]. The NMR data of compound 3 possessed the characteristics of a lignan, and the structure was found to be (-)-cubebin [24] ( 13 C-NMR data were shown in the Supplementary Materials, Table S4).…”

Section: Regulatory Effects On Adipogenesis Of the Extracts From V Tmentioning

confidence: 98%

(-)-O-Methylcubebin from Vitex trifolia Enhanced Adipogenesis in 3T3-L1 Cells via the Inhibition of ERK1/2 and p38MAPK Phosphorylation

et al. 2019

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In this study, for the purpose of elucidation for antidiabetic components, we isolated and identified compounds that could become lead compounds for the development of antidiabetic agents from the herbal medicine Vitex trifolia, which is used for liver protection in Myanmar. Three kinds of lignan, (-)-O-methylcubebin (MC), (-)-hinokinin, and (-)-cubebin, were isolated from the ethyl acetate extract of the leaves of V. trifolia, using various chromatography. Among the three isolated compounds, MC showed the strongest effects to increase intracellular lipid accumulation in 3T3-L1 cells. From the results of the elucidation of the MC’s effects on the adipogenesis of 3T3-L1 cells, the downsizing of adipocytes and the promotion of the expression of adipogenesis-related proteins, as well as adiponectin, were observed. On the other hand, since the activity of MC was inhibited by antagonists of PPARγ and improved by inhibitors of the classical mitogen-activated protein kinase (MAPK) pathway and p38MAPK pathway, MC was considered to be an agonist of PPARγ, and furthermore promoted adipogenesis via the inhibition of extracellular signal-regulated kinase 1/2 (ERK1/2) and p38MAPK phosphorylation. Although MC showed similar effects to those of rosiglitazone (RO) used as a positive control, RO promoted the migration of GLUT4 from the cytoplasm to the cell membrane, whereas MC did not show such an effect. From the abovementioned results, it was considered that MC could be a lead compound for the development of antidiabetic drugs that does not show weight gain, which is a side effect of RO.

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Tricyclic sesquiterpenes from Artemisia chamaemelifolia

Cited by 69 publications

References 15 publications

Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis

Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis

Chemical Composition of Aerial Parts Essential Oils from Six Endemic Malagasy Helichrysum Species

(-)-O-Methylcubebin from Vitex trifolia Enhanced Adipogenesis in 3T3-L1 Cells via the Inhibition of ERK1/2 and p38MAPK Phosphorylation

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