Structure determination of salisomide and salisoflavan, two new secondary metabolites from <i>Salsola imbricata</i>, by 1D and 2D NMR spectroscopy

Saleem, Muhammad; Akhter, Naseem; Ali, Muhammad; Nazir, Mamona; Riaz, Naheed; Moazzam, Muhammad; Arshad, Muhammad; Jabbar, Abdul

doi:10.1002/mrc.2361

Cited by 15 publications

(12 citation statements)

References 7 publications

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“…Rosmarinic acid ( 87 ) was the only detected phenolic acid [ 67 ]. Meanwhile, alcoholic extract from aerial parts of S. imbricata yielded two secondary metabolites: salisomide ( 124 ) and salisoflavan ( 46 ) [ 73 ]. Investigation of the role of rosmarinic acid in that species and the involved biosynthetic pathways can help further agronomic and molecular approaches to improve its yield.…”

Section: Chemistry Of Salsolamentioning

confidence: 99%

Genus Salsola: Chemistry, Biological Activities and Future Prospective—A Review

Murshid

Atoum

Abou-Hussein

et al. 2022

Plants

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The genus Salsola L. (Russian thistle, Saltwort) includes halophyte plants and is considered one of the largest genera in the family Amaranthaceae. The genus involves annual semi-dwarf to dwarf shrubs and woody tree. The genus Salsola is frequently overlooked, and few people are aware of its significance. The majority of studies focus on pollen morphology and species identification. Salsola has had little research on its phytochemical makeup or biological effects. Therefore, we present this review to cover all aspects of genus Salsola, including taxonomy, distribution, differences in the chemical constituents and representative examples of isolated compounds produced by various species of genus Salsola and in relation to their several reported biological activities for use in folk medicine worldwide.

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Section: Chemistry Of Salsolamentioning

confidence: 99%

Genus Salsola: Chemistry, Biological Activities and Future Prospective—A Review

Murshid

Atoum

Abou-Hussein

et al. 2022

Plants

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“…These plant species also grow in the normal climatic zones, as well as have a higher occurrence in the salty environment owing to their better adaptation capabilities. Among the major halophytes of the region, the Salsola imbricata, and Salsola cyclophylla, which are also part of camels' feed, besides being the commonest remedy for diarrhea, is also used against worms' infestation, stomach ache, and dysentery [22]. The Tamarix aphylla and Aeluropus lagopoides are employed for wound healing, anti-diabetic, and also as pain-remover [23], whereas the Zygophyllum simplex is commonly used in the treatments of various diabetic conditions, wound-healing, and as an analgesic [24].…”

Section: Introductionmentioning

confidence: 99%

Anti-Microbial, Anti-Oxidant, and α-Amylase Inhibitory Activity of Traditionally-Used Medicinal Herbs: A Comparative Analyses of Pharmacology, and Phytoconstituents of Regional Halophytic Plants’ Diaspora

Al-Omar

Mohammed

et al. 2020

Molecules

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Halophytes are the category of plants growing under harsh conditions of super-salinity, and are wide-spread in the coastal Mediterranean climatic conditions and desert oasis. They are adept at surviving through maintaining excessive production of enzymatic, and non-enzymatic secondary metabolites, especially phenolics and flavonoids that primarily work as anti-oxidants and phytoalexins. Five major halophyte species growing in the kingdom’s Qassim’s high-salted desert regions were investigated for confirming their traditionally used biological activity of sugar-control and anti-infectious properties. In this context, the comparative presence of phenolics, and flavonoids together with anti-microbial, anti-oxidants, and the anti-diabetic potentials of the plants’ extracts were investigated through the α-amylase inhibition method. The highest concentrations of phenolics and flavonoids were detected in Salsola imbricata (360 mg/g of the extract as Gallic-Acid-Equivalents/GAE, and 70.5 mg/g of the extract as Rutin-Equivalents/RE). In contrast, the lowest concentrations of phenolics and flavonoids were detected in Salsola cyclophylla (126.6 mg/g GAE, and 20.5 mg/g RE). The halophytes were found rich in trace elements, a factor for water-retention in high-salinity plants, wherein iron and zinc elements were found comparatively in higher concentrations in Aeluropus lagopoides (4113 µg/kg, and 40.1 µg/kg, respectively), while the copper was detected in higher concentration (11.1 µg/kg) in S. imbricata, analyzed through Inductively Coupled Plasma Optical Emission Spectrometric (ICP-OES) analysis. The anti-oxidant potentials and α-amylase enzyme inhibition-based anti-diabetic activity of S. imbricata was significantly higher than the other halophytes under study, wherein S. cyclophylla exhibited the lowest level of α-amylase inhibition. The maximum DPPH radicals’ (52.47 mg/mL), and α-amylase inhibitions (IC50 22.98 µg/mL) were detected in A.lagopoides. The anti-microbial activity against the Methicillin-Resistant Staphylococcus aureus was strongly exhibited by Zygophyllum simplex (33 mm Inhibition Zone-Diameter, 50 µg/mL Minimum-Inhibitory-Concentration), while Escherichia coli, Enterococcus faecalis, and Candida albicans growths were moderately inhibited by Tamarix aphylla. The current findings exhibited significant differences among the locally distributed halophytic plants species with regards to their bioactivity levels, anti-oxidant potentials, and the presence of trace elements. The ongoing data corroborated the plants’ traditional uses in infections and diabetic conditions. The enhanced local distribution of the plants’ diaspora and higher density of occurrence of these plants species in this region, in comparison to their normal climatic condition’s counterparts, seemed to be affected by humans’ use of the species as part of the traditional and alternative medicine over a period of long time.

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“…Previous phytochemical investigations of the plant were limited. A chromatographic analysis of the alcoholic extract from Salsola imbricata yielded two new secondary metabolites, salisomide and salisoflavan; their structures were established with the help of spectroscopic techniques including COSY, HMQC, and HMBC NMR experiments [ 17 ]. Later on, two triterpenoidal saponin glycosides were isolated and identified from the roots of the Egyptian plant [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Phenolic Profiling and Evaluation of Contraceptive Effect of the Ethanolic Extract of Salsola imbricata Forssk. in Male Albino Rats

Shehab

Abu‐Gharbieh

2014

Evidence-Based Complementary and Alternative Medicine

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Reported researches dealing with either composition or bioactivity of Salsola imbricata are limited. This study was conducted aiming to investigate the phenolic composition of the plant and evaluate its efficacy as male contraceptive. Polyphenols, namely, phenolic acids and flavonoids, were qualitatively and quantitatively analysed by RP-HPLC in the hydrolysed methanol extract using two different wavelengths, 280 and 330 nm. The efficiency of different solvents in extracting the plant phenolics was assessed via spectrophotometric determination of the total phenolic and flavonoid contents. Acute toxicity study was carried out on the ethanolic extract to ascertain its safety prior to biological evaluation. The contraceptive effect was assessed, in male rats, by oral administration of the extract at two doses (250 and 500 mg/kg b. wt.), over a period of 65 days. HPLC analyses allowed the identification and quantification of a total of 13 and 8 components in the hydrolysed-methanol extract; the overall phenolic composition was dominated by quercitrin (12.692%) followed by coumaric acid (4.251%). Prolonged oral administration of the ethanolic extract caused slight reduction in the testis weight only. A significant decrease in the sperm count was observed (P < 0.01) in the two treated groups while significant decrease in the epididymal sperm motility was only observed in the high dose group. Morphological abnormalities were observed in sperms of treated animals. No distinct change in serum FSH, LH, and testosterone concentration was recorded. The histopathological findings supported to a high extent these results. The male contraceptive activity of Salsola imbricata could be ascribed to its phenolic components, especially quercitrin.

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Structure determination of salisomide and salisoflavan, two new secondary metabolites from Salsola imbricata, by 1D and 2D NMR spectroscopy

Abstract: Chromatographic analysis of the alcoholic extract from Salsola imbricata yielded two new secondary metabolites, salisomide (1) and salisoflavan (2). Their structures were established with the help of spectroscopic techniques including COSY, HMQC and HMBC NMR experiments.

Cited by 15 publications

References 7 publications

Genus Salsola: Chemistry, Biological Activities and Future Prospective—A Review

Genus Salsola: Chemistry, Biological Activities and Future Prospective—A Review

Anti-Microbial, Anti-Oxidant, and α-Amylase Inhibitory Activity of Traditionally-Used Medicinal Herbs: A Comparative Analyses of Pharmacology, and Phytoconstituents of Regional Halophytic Plants’ Diaspora

Phenolic Profiling and Evaluation of Contraceptive Effect of the Ethanolic Extract of Salsola imbricata Forssk. in Male Albino Rats

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