Immunomodulatory pinguisane-type sesquiterpenes from the liverwort Porella cordaeana (Porellaceae): the “new old” furanopinguisanol and its oxidation product exert mutually different effects on rat splenocytes

Radulović, Niko S.; Filipović, Sonja; Zlatković, Dragan B.; Đorđević, Miljana; Stojanović, Nikola; Randjelović, Pavle J.; Mitić, Katarina; Jevtović-Stoimenov, Tatjana; Ranđelović, Vladimir

doi:10.1039/c6ra04308a

Cited by 16 publications

(12 citation statements)

References 38 publications

(63 reference statements)

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“…Dex reduced the number of cells but did not alter their ability to reduce MTT (Figure c). Previously, two liverwort furanopinguisanes were found to exhibit mutually different alterations of SPC functioning when applied without stimulators, similar to 1 – 3 …”

Section: Resultsmentioning

confidence: 93%

“…Previously, two liverwort furanopinguisanes were found to exhibit mutually different alterations of SPC functioning when applied without stimulators, similar to 1−3. 41 The effects of 1−4 on ConA-or LPS-induced SPC proliferation were further evaluated. It was found that 1−4, at all test concentrations, significantly decreased lymphocyte proliferative response to ConA, a T cell mitogen, after 48 h (Figure 4).…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

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Immunomodulatory Constituents of Conocephalum conicum (Snake Liverwort) and the Relationship of Isolepidozenes to Germacranes and Humulanes

et al. 2020

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Structural elucidation of three new sesquiterpenoids, namely, (1Z,4E)-lepidoza-1(10),4-dien-14-ol (1), rel-(1(10) Z,4S,5E,7R)-germacra-1(10),6 diene-11,14-diol (2), and rel-(1(10) Z,4S,5E,7R)-humula-1(10),5-diene-7,14-diol (3), isolated from the liverwort Conocephalum conicum, was accomplished by a combination of extensive NMR experiments, 1 H NMR simulation, and other means. Additionally, the change of the identity of bicyclogermacren-14-al, previously reported as a C. conicum constituent, to isolepidozen-14-al is proposed. Compounds 2 and 3 appear to be related to 1 via hydration involving a shared intermediate, a substituted cyclopropylmethyl cation, formed by a highly regio-and stereoselective protonation of 1, followed by a stereospecific fission of the three-membered ring. In other words, an isolepidozene derivative might be a branchpoint to humulanes and germacranes; this transformation could be of, up to now, unknown, biosynthetic and/or synthetic relevance. Multivariate statistical analysis of the compositional data of C. conicum extract constituents was used to probe the hypothesized biochemical relations. The immunomodulatory effect of 1−3 and conocephalenol (4) was evaluated in an in vitro model on both nonstimulated and mitogen-stimulated rat splenocytes. The compounds displayed varying degrees of cytotoxicity to nonstimulated splenocytes, whereas 2 and 3 were found to exert immunosuppressive effects on concanavalin A-stimulated splenocytes while not being cytotoxic at the same concentrations.

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Section: Resultsmentioning

confidence: 93%

Section: Journal Of Natural Productsmentioning

confidence: 99%

Immunomodulatory Constituents of Conocephalum conicum (Snake Liverwort) and the Relationship of Isolepidozenes to Germacranes and Humulanes

et al. 2020

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“…The standard drug, Dex, used in this study was found to reduce rat spleen cell ability to metabolize MTT, which is in accordance with our previous studies. 10,11 It is worth mentioning that Marchantia convoluta leaf extracts are found to inhibit liver and lung cancer cell proliferation using the MTT assay. 12 However, the reported results are coming from cancer cells which are different from the non-altered splenocytes, which potentially indicates that the tested compounds might be less toxic to non-cancer cells.…”

Section: Resultsmentioning

confidence: 99%

Revisiting the Effect of 3 Sesquiterpenoids From Conocephalum conicum (Snake Liverwort) on Rat Spleen Lymphocyte Viability and Membrane Functioning

Filipović

Stojanović

Mitić

et al. 2022

Natural Product Communications

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Previously 3 sesquiterpenoids from Conocephalum conicum (L.) Dum. (Conocephalaceae) were found to modulate lymphocyte response to different stimuli, suggesting their immunomodulatory potential. Herein we evaluated the impact of low concentrations of these sesquiterpenoids on rat splenocyte viability and membrane permeability, as well as lactate dehydrogenase (LDH) activity, in order to, possibly, shed light on their mechanism of action. After a 24 h incubation of splenocytes with the sesquiterpenoids (from 10−8 to 10−6 M), MTT and trypan blue (TB) assays, as well as histochemical staining for LDH, were performed. The tested compounds were shown not to reduce the ability of cells to metabolize MTT; however, cell membrane permeability to TB was altered, suggesting that a certain percentage of cells were dead. Histochemical staining for LDH presence releveled that only 2, out of the 3 sesquiterpenoids, decreased the staining intensity, indicating either LDH leakage or its inhibition. In conclusion, having in mind the already proven modulatory potential of the tested sesquiterpenoids, the present results suggest that through the changes in the cell membrane function and leakage/inhibition of LDH in unaltered immune cells, some of the tested compounds could be considered promising candidates for further research as anticancer agents.

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“…For 1 H NMR (CDCl 3 , 400 MHz) and 13 C NMR (CDCl 3 , 100.6 MHz) data, see Tables 2 and 1. EIMS m/z [M] + 306 (52), 131 (47), 117 (62), 105 (42), 91 (100), 79 (51), 73 (40), 67 (34), 55 (43), 41 (37) 13 C NMR (CDCl 3 , 100.6 MHz) data, see Tables 2 and 1, respectively. EIMS m/z: [M] + 348 (21), 131 (17), 117 (26), 115 (52), 105 (19), 91 (37), 79 (19), 55 (14), 43 (100), 41 (22) 13 C NMR (CDCl 3 , 100.6 MHz) data, see Tables 2 and 1.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Constituents of Bupleurum praealtum and Bupleurum veronense with Potential Immunomodulatory Activity

et al. 2020

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In this investigation, chromatographic separations of the diethyl ether extracts of two European annual Bupleurum taxa, B. praealtum and B. veronense, yielded nine new natural products, namely, a series of esters of stereoisomeric tetradeca-5,7,9,11tetraen-1-ols (1−4 and 8), a tetra-unsaturated γ-tetradecalactone (5), a dibenzylbutyrolactone lignan (7-oxoarcitin, 6), a falcarinolrelated 17-membered macrolide (7) possessing a conjugated diyne-system, and an acylphloroglucinol derivative (9). All these new compounds were fully characterized by NMR, IR, UV, MS, and optical rotation measurement, including 1 H NMR full spin spectral simulation, whereas the absolute configurations of 1, 5, and 9 were determined via chemical correlations and NMR analysis of Mosher esters. The in vitro potential immunomodulatory activities of 1, 4, 5, and (+)-arcitin were assessed by determining their effects on the functional properties of isolated rat splenocytes and peritoneal macrophages. The results obtained support the known immunomodulatory ethnomedicinal usage of Bupleurum species.

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Immunomodulatory pinguisane-type sesquiterpenes from the liverwort Porella cordaeana (Porellaceae): the “new old” furanopinguisanol and its oxidation product exert mutually different effects on rat splenocytes

Abstract: α-Furanopinguisanol and furanopinguisanone, two new pinguisane-type sesquiterpenes from the liverwortPorella cordaeana, exert mutually different effects on rat splenocytes.

Cited by 16 publications

References 38 publications

Immunomodulatory Constituents of Conocephalum conicum (Snake Liverwort) and the Relationship of Isolepidozenes to Germacranes and Humulanes

Immunomodulatory Constituents of Conocephalum conicum (Snake Liverwort) and the Relationship of Isolepidozenes to Germacranes and Humulanes

Revisiting the Effect of 3 Sesquiterpenoids From Conocephalum conicum (Snake Liverwort) on Rat Spleen Lymphocyte Viability and Membrane Functioning

Constituents of Bupleurum praealtum and Bupleurum veronense with Potential Immunomodulatory Activity

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