RESUMEN
Eleven new seco-iridoids, valeridoids G-Q (1-6 and 8-12), along with four known products, 9-epi-valtral C (7), desacylbaldrinal (13), 11-methoxyviburtinal (14) and baldrinal (15), were obtained from Valeriana jatamansi. Among them, the new compounds were identified by their NMR, HR-ESI-MS spectroscopic data and ECD calculation. Moreover, valeridoid N and O were a pair of C3 epimers, whose ether bonds between C-1 and C-3 opened, and new ether bonds formed between C-3 and C-6. Valeridoid Q belonged to the C-1 degradation of seco-iridoids. As a result, 9-epi-valtral C displayed significant inhibition on Streptococcus agalactiae, Staphylococcus aureus, Staphylococcus argenteus, Shigella flexneri and Klebsiella pneumoniae, and valeridoid Q exhibited the most significant inhibition against Salmonella enteritidis. 9-Epi-valtral C and baldrinal selectively inhibited the growth of human glioma stem cells. Valeridoid Q exhibited significant anti-influenza activity, while valeridoid O inhibited nitric oxide production.
Asunto(s)
Valeriana , Éteres , Humanos , Iridoides/química , Estructura Molecular , Óxido Nítrico , Raíces de Plantas/química , Valeriana/químicaRESUMEN
Eight new iridoids, jatavaleridoids A-H (1-8), were isolated from the roots and rhizomes of Valeriana jatamansi. Their structures and absolute configurations were elucidated based on NMR and HRESIMS spectroscopic data, as well as quantum chemical calculation. Structurally, compounds 1-5 and 8 were rare iridoids with long-chain fatty acid esters at C-10. In addition, compound 7 showed cytotoxicity, while compounds 1 and 2 exhibited inhibition on NO production.
Asunto(s)
Nardostachys , Valeriana , Ácidos Grasos/análisis , Iridoides/química , Iridoides/farmacología , Estructura Molecular , Raíces de Plantas/química , Rizoma , Valeriana/químicaRESUMEN
Twenty-one new iridoids, jatamansidoids A-U (1-12, 21-26, 32, 35 and 36), two new natural ones, jatamansidoids V (37) and W (38), eighteen known ones (13-20, 27-31, 33 and 34), together with three patchoulol-type sesquiterpenoids (39-41), were isolated from the roots and rhizomes of Valeriana jatamansi. Structurally, compounds 1-7 were the first examples of iridoids from V. jatamansi with unique α, ß, γ, δ-unsaturated aldehyde fragment between C-11, C-4, C-5, C-9 and C-8; compound 8 was an unprecedented iridoid derivative with a methyl group (Me-10) at C-1, rather than C-8, and its plausible biogenetic pathway was proposed in this paper; compounds 22 and 23 were the first examples of Δ4(5)-iridoids simultaneously replaced by oxygen-containing groups at C-3, C-6 and C-7; compound 24 was the first iridoid with both 6,7- and 1,10-epoxy fragments. The structures and absolute configurations of new compounds were elucidated based on extensive spectroscopic techniques and quantum chemical calculation. Furthermore, compounds 13-15 and 39-41 exhibited potent anti-influenza virus activities with H1N1 and H3N2 strains, with IC50 values of 0.21-1.48 µM.
Asunto(s)
Subtipo H1N1 del Virus de la Influenza A , Nardostachys , Sesquiterpenos , Valeriana , Subtipo H3N2 del Virus de la Influenza A , Iridoides/química , Iridoides/farmacología , Estructura Molecular , Raíces de Plantas/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Valeriana/químicaRESUMEN
A new norsesquiterpene, wilfordonol E (1), and a new lignan, dipsalignan E (3), together with a known norsesquiterpene and eleven known lignans were isolated from the roots and rhizomes of Valeriana jatamansi. The structures of new compounds were determined by their NMR and HR-ESI-MS spectra. Additionally, some compounds were evaluated for their anti-influenza A virus effects.
Asunto(s)
Lignanos , Valeriana , Iridoides/química , Lignanos/análisis , Lignanos/farmacología , Estructura Molecular , Raíces de Plantas/química , Valeriana/químicaRESUMEN
An undescribed iridoid (valeridoid A) and five undescribed bis-iridoids (valeridoids B-F), along with four known ones, were isolated from the roots and rhizomes of Valeriana jatamansi. Their structures were elucidated based on 1D and 2D NMR, as well as HRESIMS spectroscopic data. In addition, 8,9-didehydro-7-hydroxydolichodial and valeridoid F were found to inhibit the growth of three human glioma stem cells (GSC-3#, GSC-12# and GSC-18#).
Asunto(s)
Nardostachys , Valeriana , Humanos , Iridoides , Estructura Molecular , Células Madre Neoplásicas , Raíces de PlantasRESUMEN
Glioblastoma is one of the most malignant tumors with very poor prognosis. Glioma stem cells (GSCs) occupy a small proportion in glioma, but they are closely associated with radiotherapy and chemotherapy resistance, promoting tumor angiogenesis, hypoxia response, invasion and recurrence. Therefore, GSCs have become a new target for tumor treatment and are used in drug screening. Rupesin E is a natural compound obtained from Valeriana jatamansi, and its antitumor activity has not been reported. In the present study, the antitumor activity of rupesin E was investigated, and the results demonstrated that it inhibited the proliferation of GSCs (GSC-3#, GSC-12#, GSC-18#) with the IC50 values of 7.13±1.41, 13.51±1.46 and 4.44±0.22 µg/ml, respectively. In addition, immunofluorescence cell staining and flow cytometry techniques demonstrated that rupesin E inhibited GSC proliferation and induced apoptosis. Furthermore, rupesin E inhibited the ability of GSC colony formation, indicating its antitumor activity against GSCs in vitro.
RESUMEN
Twelve 3,8-epoxy iridoids, including four new compounds, jatamanins R-U (1-4), and eight known compounds (5-12), were obtained from the roots and rhizomes of Valeriana jatamansi. The structures were elucidated from analysis of spectroscopic data. The absolute configurations of 1-4 were determined by comparison of experimental and literature ECD spectra. Moreover, the compounds were evaluated for cytotoxic effects against glioma stem cells, inhibition of NO production, activity against influenza A virus and reversal of multidrug resistance of HepG2/ADR cells. Compounds 9 and 12 showed significant cytotoxic potency against GSC-18# (IC50 =1.351 and 4.439â µg ml-1 , respectively) and GSC-3# (IC50 =10.88 and 6.348â µg ml-1 , respectively) glioma stem cells, while compound 12 was also slightly less potent against GSC-12# (IC50 =13.45â µg ml-1 ) glioma stem cell growth. In addition, compounds 9 and 12 displayed obvious inhibition of NO production (IC50 =4.6 and 15.8â µm, respectively).
Asunto(s)
Iridoides/química , Valeriana/química , Animales , Proliferación Celular/efectos de los fármacos , Dicroismo Circular , Resistencia a Antineoplásicos/efectos de los fármacos , Células Hep G2 , Humanos , Iridoides/aislamiento & purificación , Iridoides/farmacología , Lipopolisacáridos/toxicidad , Macrófagos/citología , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Espectroscopía de Resonancia Magnética , Ratones , Conformación Molecular , Óxido Nítrico/metabolismo , Raíces de Plantas/química , Raíces de Plantas/metabolismo , Células RAW 264.7 , Relación Estructura-Actividad , Valeriana/metabolismoRESUMEN
Onosmanones A (1) and B (2), two novel quinonoid xanthenes with two geranyl groups, have been isolated from the whole plants of Onosma paniculatum. Their structures were elucidated on the basis of one- and two-dimensional NMR techniques.
Asunto(s)
Boraginaceae/química , Xantenos/química , China , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Xantenos/aislamiento & purificaciónRESUMEN
Three new compounds (1â-â3), including a sesterterpenoid, aspterpenacid C (1), with an unusual 5/3/7/6/5 pentacyclic skeleton, together with seven known ones (4â-â10), were isolated from the ethanol extract of the traditional Chinese medicinal plant Swertia bimaculata. Their structures were elucidated on the basis of the methods of spectroscopic NMR, MS, and computational chemistry. The structure of 1 was further confirmed by single-crystal X-ray diffraction analysis. Compounds 1â-â10 were tested for activities on the inhibition of nitric oxide production and HIV-1 replication in vitro. Compound 1 exhibited moderate activity in inhibiting nitric oxide production (IC50 = 16.1 µM) and HIV-1 replication (EC50 = 1.35 µM).