Anthraquinones and ethylcyclohexane derivatives from Sinningia speciosa “Fyfiana”

The present study investigated the effects of the ethanolic extract (ESa), fractions, and compounds isolated from Sinningia aggregata in male Swiss mice on carrageenan-induced paw edema, neutrophil migration, mechanical hyperalgesia, formalin-induced nociception, and lipopolysaccharide-induced fever. The ESa did not alter edema, neutrophil migration, or fever at any of the doses tested. However, the ESa reduced phase II of formalin-induced nociception and carrageenan-induced mechanical hyperalgesia. The petroleum ether (PE) and ethyl acetate (EA) fractions and aggregatin D (AgD; isolated from the EA fraction) reduced formalin-induced nociception. Anthraquinones from the PE fraction were ineffective. AgD also inhibited carrageenan-induced mechanical hyperalgesia. Neither the ESa nor AgD altered thermal nociception or motor performance. Local administration of AgD also reduced hyperalgesia induced by carrageenan, bradykinin, tumor necrosis factor-α, interleukin-1β, cytokine-induced neutrophil chemoattractant, prostaglandin E2, and dopamine but not hyperalgesia induced by forskolin or dibutyryl cyclic adenosine monophosphate. The positive control dipyrone reduced the response induced by all of the stimuli. Additionally, glibenclamide abolished the analgesic effect of dipyrone but not the one induced by AgD. AgD did not change lipopolysaccharide-induced nitric oxide production by macrophages or the nociception induced by capsaicin, cinnamaldehyde, acidified saline, or menthol. These results suggest that the ESa has important antinociceptive activity, and this activity results at least partially from the presence of AgD. AgD reduced mechanical hyperalgesia induced by several inflammatory mediators through mechanisms that are different from classic analgesic drugs.

show abstract

“…cardinalis [ 17 ], and ethylcyclohexane derivatives and anthraquinones were identified in S . speciosa [ 18 ]. In S .…”

Section: Introductionmentioning

confidence: 99%

Antinociceptive Activity of the Ethanolic Extract, Fractions, and Aggregatin D Isolated from Sinningia aggregata Tubers

et al. 2015

View full text Add to dashboard Cite

show abstract

“…The same fraction of S. warmingii yielded eight known compounds (3-10) (Figure 1). The known compounds were identified as 7-hydroxy--dunnione (2) [5], lapachenole (3) [6], tectoquinone (4) [7], 7methoxytectoquinone (5) [8], 1-hydroxytectoquinone (6) [9], 7hydroxytectoquinone (7) [10], aggregatin C (8) [11], aggregatin D (9) [11], halleridone (10) [12], and cedrol (11) [13]. The common mixture of steroids sitosterol and stigmasterol were also isolated from both plants [14].…”

mentioning

confidence: 99%

Chemical Constituents from Sinningia canescens and S. warmingii

Verdan

Ehrenfried

Scharf

et al. 2014

Natural Product Communications

Self Cite

View full text Add to dashboard Cite

A new naphthoquinone, 6-methoxy-7-hydroxy--dunnione (1), along with four known compounds (2, 4, 10, and 11) were isolated from Sinningia canescens (Mart.) Wiehler tubers, while S. warmingii (Hiern.) Chautems furnished eight known compounds (3-10). The known compounds were identified as 7-hydroxy--dunnione (2), lapachenole (3), tectoquinone (4), 7-methoxytectoquinone (5), 1-hydroxytectoquinone (6), 7-hydroxytectoquinone (7), aggregatin C (8), aggregatin D (9), halleridone (10), and cedrol (11). In addition, S. canescens yielded a volatile fraction, which was analyzed by GC/FID and GC/MS. This fraction was constituted mainly by sesquiterpene hydrocarbons (82.6%). The major components were -santalene (14.6%), -cedrene (10.4%), and trans-cadina-1(6)-4-diene (10.0%).

show abstract

“…Studies on chemical composition of Sinningia species showed the presence of flavonoids on Sinningia cardinalis , ethylcyclohexane derivatives and anthraquinones in Sinningia speciosa and anthraquinones and aromatic compounds with a new skeleton named aggregatins A‐D in Sinningia aggregata . In Sinningia allagophylla, lapachenol, 8ML, anthraquinones and naphthoquinones were found .…”

mentioning

confidence: 99%

“…The presence of naphthoquinones and anthraquinones in S. allagophylla and other species of Sinningia has guided us to evaluate a possible anti‐inflammatory and antinociceptive activity in this plant. The popularly described antipyretic activity of this plant, a property that is also shared by many analgesic and anti‐inflammatory drugs also pointed to this direction .…”

mentioning

confidence: 99%

Antinociceptive and Anti‐inflammatory Activities of the Ethanolic Extract, Fractions and 8‐Methoxylapachenol from Sinningia allagophylla Tubers

Barbosa

Mori

Riva

et al. 2013

Basic Clin Pharma Tox

Self Cite

View full text Add to dashboard Cite

This study investigated the antinociceptive and anti-inflammatory activities of the ethanolic extract (EESAl), fractions and the compound 8-methoxylapachenol (8ML) obtained from the tubers of Sinningia allagophylla. Male Swiss mice were treated with EESAl (3-300 mg/kg) or vehicle by oral route (p.o.) 1 hr before the injection of formalin 2.5% or carrageenan (Cg) into the hind paw. EESAl (3-30 mg/kg) reduced the inflammatory phase of the nociceptive behaviour induced by formalin (around 65% for all doses). EESAl (3-300 mg/kg, p.o.) also reduced Cg-induced mechanical hyperalgesia and oedema in a dose-dependent fashion but did not change the hot-plate latency or the motor performance of the animals. Oral administration of petroleum ether fraction (PE, 3 mg/kg), but not in the methanolic fraction (30 mg/kg), reduced both Cg-induced oedema and hyperalgesia. Compound 8ML isolated from PE (1.8 mg/kg, p.o.) abolished Cg-induced hyperalgesia but also did not change hotplate latency or motor performance of the animals. 8ML administration into the paw (0.75-750 pg) dose-dependently reduced Cg-induced hyperalgesia. 8ML (750 pg) also blocked the hyperalgesia induced by tumour necrosis factor (TNF-a), interleukin1b (IL-1b) and prostaglandin E 2 (PGE 2 ) but failed to change the hyperalgesia induced by cytokine-induced neutrophil chemoattractant-1 (CINC-1) and dopamine (Dopa). These results suggest that EESAl has an important antinociceptive and anti-inflammatory activity, the former one related, at least in part, to the reduction in the hyperalgesia. Similarly, 8ML reduced Cg-induced oedema and mechanical hyperalgesia and seems to act in peripheral sites and on the prostaglandin rather than on the sympathetic component of the Cg-inflammatory hyperalgesia.Gesneriaceae is a pantropical family of ornamental plants, with 135 genera, among these Sinningia. Sinningia genus comprises 68 species, distributed in South America, mainly in Brazil [1]. Sinningia allagophylla (Martius) Wiehler is a shrub species with the popular names of clove field, field-potato or potato-of-Partridge and is considered medicinal in Brazil. The tubers are used as an emollient and tonic, while the flowers and leaves are used as febrifuge, diuretic and cleanser [2].Studies on chemical composition of Sinningia species showed the presence of flavonoids on Sinningia cardinalis [3], ethylcyclohexane derivatives and anthraquinones in Sinningia speciosa [4] and anthraquinones and aromatic compounds with a new skeleton named aggregatins A-D in Sinningia aggregata [5]. In Sinningia allagophylla, lapachenol, 8ML, anthraquinones and naphthoquinones were found [6]. Naphthoquinones and anthraquinones are classes of natural compounds commonly associated with anti-inflammatory and antinociceptive properties. For example, vitamin K3 derivatives, plumbagin and emodin among others, are known naphthoquinones and anthraquinones, which share these properties [7][8][9].Traditionally, non-steroidal anti-inflammatory drugs are the class of compounds most widely used to t...

show abstract

Anthraquinones and ethylcyclohexane derivatives from Sinningia speciosa “Fyfiana”

Cited by 9 publications

References 17 publications

Antinociceptive Activity of the Ethanolic Extract, Fractions, and Aggregatin D Isolated from Sinningia aggregata Tubers

Antinociceptive Activity of the Ethanolic Extract, Fractions, and Aggregatin D Isolated from Sinningia aggregata Tubers

Chemical Constituents from Sinningia canescens and S. warmingii

Antinociceptive and Anti‐inflammatory Activities of the Ethanolic Extract, Fractions and 8‐Methoxylapachenol from Sinningia allagophylla Tubers

Contact Info

Product

Resources

About