Sesquiterpene lactones, lignans and aromatic esters from Cheirolophus species

Marco, J. Alberto; Sanz‐Cervera, Juan F.; García-Lliso, Vicente; Susanna, Alfonso; Garcia‐Jacas, Núria

doi:10.1016/s0031-9422(00)89537-0

Cited by 26 publications

(13 citation statements)

References 25 publications

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“…The molecular formula of 3 was determined by HR-EI-MS as C 21 H 22 O 6 and coincided with the data of 1 H-and 13 C-NMR analyses. In addition to the above spectral evidence, all the assignments of 3 were in accordance with the data of the previously reported lignan, (±)-7,8-didehydroarctigenin [7], except for the optical rotation value. Compound 3 showed a positive optical rotation value, [a] D : + 16.8 (MeOH; c 0.1).…”

supporting

confidence: 89%

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Antiproliferative and Apoptotic Effects of Butyrolactone Lignans fromArctium lappaon Leukemic Cells

Matsumoto¹,

Hosono-Nishiyama²,

Yamada³

2006

Planta med

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In the course of screening for pharmacologically active substances from extracts of crude drugs used traditionally in Sino-Japanese herbal medicines, it was found that the 70 % ethanol extract from the fruits of Arctium lappa L. (Compositae) showed potent antiproliferative activity against B cell hybridoma cell, MH60. By bioassay-guided purification, a new lignan, (+)-7,8-didehydroarctigenin, together with the known lignans (-)-arctigenin and (-)-matairesinol were isolated as the active ingredients from an aqueous ethanolic extract of the fruits of A. lappa. Of these active compounds, (-)-arctigenin showed the most potent antiproliferative activity against MH60 cells (IC (50) : 1.0 microM), and the activity was suggested to be due to apoptosis.

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supporting

confidence: 89%

“…Compound 3 showed a positive optical rotation value, [a] D : + 16.8 (MeOH; c 0.1). Thus, compound 3 was identified as a new lignan, (+)-7,8-didehydroarctigenin, which is an enantiomer of (±)-7,8-didehydroarctigenin [7]. Copies of the original spectra are obtainable from the author of correspondence.…”

mentioning

confidence: 99%

Antiproliferative and Apoptotic Effects of Butyrolactone Lignans fromArctium lappaon Leukemic Cells

Matsumoto¹,

Hosono-Nishiyama²,

Yamada³

2006

Planta med

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“…The molecular formula of 6 , C 42 H 44 O 12 , was obtained by HRESIMS ( m / z 741.2903 [M + H] + , calcd for C 42 H 45 O 12 741.2911). The 1D NMR spectra of 6 were similar to those of 7 and (7 E ,8′ R )-7,8-didehydroarctigenin, with the differences being that the aromatic rings on both sides were connected by a C–C bond between C-5′ of arctigenin and C-5′ of (7 E ,8′ R )-7,8-didehydroarctigenin (Table ). The absolute configuration of 6 was confirmed to be 8 R ,8′ R ,8″ R ,7‴ E through analysis of its 1D and 2D NMR data and comparison with literature data and ECD spectra.…”

Section: Resultsmentioning

confidence: 82%

Lignan Dimers from Forsythia viridissima Roots and Their Antiviral Effects

et al. 2019

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Six new dimeric lignans (1−6) and one new lignan glycoside (16) were isolated from Forsythia viridissima roots along with nine known lignans (7−15). Spectroscopic analyses and chemical methods were used to determine these new structures and their absolute configurations. Among these compounds, dimatairesinol (1) and viridissimaols A−E (2−6) were assigned as dimers of dibenzylbutyrolactone analogues. Furthermore, the isolated compounds were evaluated for their antiviral activities against coxsackievirus B3 (CVB3) and human rhinovirus 1B (HRV1B). In these tests, compounds 12 and 15 showed antiviral effects against CVB3 infection with IC 50 values of 15.4 and 36.4 μM, respectively, while 2, 3, 8, and 9 showed activities against HRV1B with IC 50 values of 45.7, 47.5, 13.0, and 43.2 μM, respectively.

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“…(Milošević Ifantis et al, 2013), the endemic Turkish plant Centaurea hermannii (Öksüz et al, 1994), the flowers of the endemic Turkish plant Centaurea helenioides Boiss. (Yayli et al, 2006), Centaurea scabiosa L. (Kaminskii et al, 2011), Centaurea phaeopappoides and C. thracica (Nowak et al, 1989), Centaurea americana (Ohno et al, 1973), Centaurea ragusina L. subspecies ragusina growing in Egypt (Mahmoud et al, 1986), Centaurea canariensis (Gonzalez et al, 1978), Centaurea repens (Stevens, 1982), Centaurea kotschyi (Oksuz and Putun, 1983), Centaurea arguta (Gadeschi et al, 1989); the roots of the Chinese plant Vladimiria denticulate (Jinyun et al, 2002), the aerial parts of Leuzea rhapontica helenifolia (Nowak et al, 1988), Leuzea carthamoides DC (Sovová et al, 2008), Acroptilon repens (Zhao et al, 2006), Cheirolophus species (Marco et al, 1994), from three species of Cheirolophus endemic to the Canary Islands (Gonzalez et al, 1993), some species of subtribe Centaureinae Dumort (Nowak et al, 1986), Volutaria abyssinica (Marzouk, 2015), the aerial parts of three species of the genus Cousinia (Marco et al, 1993), the aerial parts of Cousinia adenostica (Rustaiyan et al, 1987), Aegopordon berarioides (Izaddoost et al, 1985), Grossheimia macrocephala (Barbetti et al, 1985), Amberboa divericata (Rojatkar et al, 1997), Amberboa ramose (Harrison and Kulshreshtha, 1984), Amberboa tubuliflora (Ahmed et al, 1990), Volutarella divaricata (Forgacs et al, 1981), from Chartolepis intermedia, C. glastifolia, C. biebersteinii , and C. pterocaula, Vernonia glutinosa (Rakotoarimanga et al, 1992), Brachylaena species (Zdero et al, 1991), and Artemisia xerophytica (Tan et al, 1991). …”

Section: Sources Of Cynaropicrinmentioning

confidence: 99%

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent

2016

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The different pharmacologic properties of plants-containing cynaropicrin, especially artichokes, have been known for many centuries. More recently, cynaropicrin exhibited a potential activity against all genotypes of hepatitis C virus (HCV). Cynaropicrin has also shown a wide range of other pharmacologic properties such as anti-hyperlipidemic, anti-trypanosomal, anti-malarial, antifeedant, antispasmodic, anti-photoaging, and anti-tumor action, as well as activation of bitter sensory receptors, and anti-inflammatory properties (e.g., associated with the suppression of the key pro-inflammatory NF-κB pathway). These pharmacological effects are very supportive factors to its outstanding activity against HCV. Structurally, cynaropicrin might be considered as a potential drug candidate, since it has no violations for the rule of five and its water-solubility could allow formulation as therapeutic injections. Moreover, cynaropicrin is a small molecule that can be easily synthesized and as the major constituent of the edible plant artichoke, which has a history of safe dietary use. In summary, cynaropicrin is a promising bioactive natural product that, with minor hit-to-lead optimization, might be developed as a drug for HCV.

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Sesquiterpene lactones, lignans and aromatic esters from Cheirolophus species

Cited by 26 publications

References 25 publications

Antiproliferative and Apoptotic Effects of Butyrolactone Lignans fromArctium lappaon Leukemic Cells

Antiproliferative and Apoptotic Effects of Butyrolactone Lignans fromArctium lappaon Leukemic Cells

Lignan Dimers from Forsythia viridissima Roots and Their Antiviral Effects

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent

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