Resin glycosides from the aerial parts of Operculina turpethum

Ding, Wenbing; Jiang, Zi‐Hua; Wu, Ping; Xu, Liangxiong; Wei, Xiaoyi

doi:10.1016/j.phytochem.2012.05.010

Cited by 25 publications

(34 citation statements)

References 29 publications

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“…In contrast, the two Operculina species and Xenostegia tridentata had hexose instead of deoxyhexose or pentose as their most preferred sugar for adding the hydroxyacyl chain. Eight previously published structures from O. macrocarpa and O. turpethum (Ding et al, 2012;Lira-Ricárdez et al, 2019) with the hydroxyacyl chain bonded to glucose agree with this finding. Based on these observations, we infer that hydroxyacyl chain addition (or at least the glycosidic bond formation) with deoxyhexoses was likely the ancestral state for RG biosynthesis, with lineage-specific shifts to hexose or pentose.…”

Section: Substantial Structural Variation Exists Among Resin Glycosidessupporting

confidence: 86%

Computational metabolomics illuminates the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family

Kruse

Bennett

Mahood

et al. 2021

Preprint

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Acylsugars are a class of plant defense compounds produced across many distantly related families. Members of the horticulturally important morning glory (Convolvulaceae) family produce a diverse sub-class of acylsugars called resin glycosides (RGs), which comprise oligosaccharide cores, hydroxyacyl chain(s), and decorating aliphatic and aromatic acyl chains. While many RG structures are characterized, the extent of structural diversity of this class in different genera and species is not known. In this study, we asked whether there has been lineage-specific diversification of RG structures in different Convolvulaceae species that may suggest diversification of the underlying biosynthetic pathways. Liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) was performed from root and leaf extracts of 26 species sampled in a phylogeny-guided manner. LC-MS/MS revealed thousands of peaks with signature RG fragmentation patterns with one species producing over 300 signals, mirroring the diversity in Solanaceae-type acylsugars. A novel RG from Dichondra argentea was characterized using Nuclear Magnetic Resonance spectroscopy, supporting previous observations of RGs with open hydroxyacyl chains instead of closed macrolactone ring structures. Substantial lineage-specific differentiation in utilization of sugars, hydroxyacyl chains, and decorating acyl chains was discovered, especially among Ipomoea and Convolvulus - the two largest genera in Convolvulaceae. Adopting a computational, knowledge-based strategy, we further developed a high-recall workflow that successfully explained ~72% of the MS/MS fragments, predicted the structural components of 11/13 previously characterized RGs, and partially annotated ~45% of the RGs. Overall, this study improves our understanding of phytochemical diversity and lays a foundation for characterizing the evolutionary mechanisms underlying RG diversification.

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Section: Substantial Structural Variation Exists Among Resin Glycosidessupporting

confidence: 86%

Computational metabolomics illuminates the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family

Kruse

Bennett

Mahood

et al. 2021

Preprint

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“…Operculina turpethum root and stem are key ingredients in more than 135 herbal formulations in both Unani and Ayurvedic medicine system which are used to treat diverse ailments including obesity, constipation, gastric ulcer, diarrhoea, asthma, uterine problem, cough splenomegaly, jaundice, anaemia, hyperlipidaemia, tumours, joint and muscle pain, paralysis and rheumatoid arthritis and tuberculosis. In addition, extensive pharmacological studies of different extracts of O. turpethum with animal models have demonstrated the antibacterial (Kiran et al 2017;Kiran et al 2018), analgesic (Ezeja et al 2015), antioxidant (Sharma and Singh 2012), anti-in ammatory, anti-cancer (Arora et al 2017), anti-diabetic (Pulipaka et al 2012), hepato-protective (Prabhakaran and Ranganayakulu 2014), anti-ulcer (Ignatius et al 2013), anti-arthritic (Tamizhmozhi and Nagavalli 2016), immune-modulatory (Tamizhmozhi and Nagavalli 2017) and anti-nephrotoxic, antispasmodic, bronchodilator (Shareef et al 2014), laxative (Onoja et al 2015) and larvicidal potential (Bhattacharya and Chandra, 2015) ascribed to their bioactive constituents including avonoids, coumarin, scopoletin, Coumaric acid derivatives (N-p-coumaryl tyramine), triterpenoid (lanosta-5-ene, cycloartenol and 24-methylene-δ-5-lanosterol) dammarane type triterpenoid saponin (operculinosides A, B, C, D) (Ding et al 2011), resin glycoside (turpethosides A, B) (Ding et al 2012), glycosidic acid (turpethic acids A-C), acrylamide, phytosterol (daucosterol and βsitosterol), betulin, lupeol, α-and β-turpethein, and steroid glycoside etc. Apart from the pharmacological application, the seeds of the plant are reported to be potential source of commercial gum (Singh et al 2003).…”

Section: Introductionmentioning

confidence: 99%

De novo Transcriptome and tissue specific expression analysis of gene associated with biosynthesis of medicinally active metabolites in a high valued medicinal plant Operculina turpethum (L.)

Biswal

Jena

Giri

et al. 2021

Preprint

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Operculina turpethum (L.) Silva Manso (Nisoth), an important medicinal plant whose root and stem tissues are found to be key ingredient in more than 135 herbal formulation in both Unani and Ayurvedic medicine system and is used for the treatment of various health disorders. It has a very high demand in the Indian Pharmaceutical industry with an annual average consumption of about 660 metric tonne (dry weight). The plant because of its wide usability is also exported to countries like Sri Lanka, Singapore, Netherlands, Japan, United States, etc. leading to a total export value of approximately 2.4 million USD. Terpenoids, steroid glycosides, resin glycosides, dammarane type triterpenoid saponins, flavonoids, coumarins are the major bioactive principles present in O. turpethum. However, overexploitation of root/root bark over the other part of the plant has caused depletion of its germplasm resources from the wild while bringing it to Near Threatened category which subsequently lead to unavailability of the requisite plant material followed by adulteration. Additionally, the limited genomics and transcriptomic resource is a major hindrance in the genetic and molecular research including elucidation of biosynthetic pathway, identification of enhanced traits and proper authentication and genetic diversity study of the plant. Hence, de novo transcriptome sequencing of root and stem tissues of O. turpethum was performed using Illumina HiSeq platform which generated a total of 64259 unigenes and 20870 CDS (coding sequence) with a mean length of 449bp and 571bp respectively. Further, 20218 and 16458 unigenes showed significant similarity with the identified proteins of NR(non-redundant) and Uniprot database respectively. The homology search carried out against publicly available database found the best match with Ipomoea nil sequences (82.6%). The KEGG (Kyoto Encyclopedia of Genes and Genomes) pathway analysis identified 6538 unigenes functionally assigned to 378 modules with phenylpropanoid biosynthesis pathway as the most enriched among the secondary metabolite biosynthesis pathway followed by terpenoid biosynthesis. Moreover, transcription factors, SSRs (Simple sequence repeats) and SNPs (single nucleotide polymorphism) were also identified in this study. Apparently, the present investigation reported the first ever transcriptome analysis of the root and stem tissues of the non-model plant O. turpethum of family Convolvulaceae, which will provide a baseline for further molecular research.

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“…Capers are widely eaten as food, and are not thought to be toxic, and the active components are very commonplace phenolic compounds (Nizar et al , ) of Fomes are thought to be polysaccharides and triterpenes (Grienke et al , ). Turpeth contains resin glycosides (Ding et al , ) which are active but not all characterized. P. harmala has cytotoxic and hallucinogenic properties when taken in high doses, and its constituent β‐carboline alkaloids harmine and harmaline inhibit the two major CYP enzymes and are thus liable to affect the metabolism of co‐administered drugs including other components of KC (Zhao et al , ).…”

Section: Methodsmentioning

confidence: 99%

Anti-Arthritic and Antiinflammatory Effects of the Traditional Uighur Formula Kursi CaperIn Vivo

et al. 2015

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Kursi Caper (KC) is a Uighur medicine based on caper which is widely used to treat arthritis and rheumatism, and preliminary studies in our laboratory showed that this traditional formula may possess potent antiinflammatory effects. This study confirms the antiinflammatory effect of KC in the adjuvant induced arthritis (AIA) model, the carrageenan and cotton-pellet induced granuloma rat models, and further investigates in vivo the mechanism of action by measuring relevant indicators of anti-arthritic activity. KC showed significant and dose-dependent anti-arthritic and antiinflammatory effects, demonstrated by reduced paw edema and arthritic scores in all animal models. Histopathological examination showed that KC reduced levels of synovial inflammatory factors in AIA rats. The overproduction of TNF-α and IL-1β was attenuated, and CAT, MDA and SOD levels were restored to normal in KC-treated rats. KC also significantly reduced LPS-induced proliferation of B lymphocytes and ConA induced proliferation of T lymphocytes in a dose-dependent manner. Flow cytometry showed that the high dose KC-treated group had a significantly decreased frequency of Th17 cells. This study indicates that KC can significantly attenuate arthritis and inflammation in rats by decreasing the levels of inflammatory cytokines, regulating oxidative stress, reducing lymphocyte proliferation and decreasing Th17. This supports the traditional use of KC as a potential modern therapeutic agent for the treatment of arthritis and related conditions.

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Resin glycosides from the aerial parts of Operculina turpethum

Cited by 25 publications

References 29 publications

Computational metabolomics illuminates the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family

Computational metabolomics illuminates the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family

De novo Transcriptome and tissue specific expression analysis of gene associated with biosynthesis of medicinally active metabolites in a high valued medicinal plant Operculina turpethum (L.)

Anti-Arthritic and Antiinflammatory Effects of the Traditional Uighur Formula Kursi CaperIn Vivo

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