Sesqui- and Diterpenoids from the Radix of <i>Curcuma aromatica</i>

Dong, Shengjuan; Li, Baocai; Dai, Wenwen; Wang, Dong; Qin, Yi; Zhang, Mi

doi:10.1021/acs.jnatprod.6b01100

Cited by 29 publications

(13 citation statements)

References 45 publications

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“…And some sesquiterpenes in C. aromatica Salisb. have been found to display antioxidant activities [31]. The chemical analysis by UPLC-Q-TOF-MS revealed the major constituents in those active extracts are sesquitepenoids and diarylheptanoids, which may act together as the antioxidants and are worthy of further study based on our current study.…”

Section: Discussionmentioning

confidence: 54%

Curcuma kwangsiensis Extracts Produced Antioxidant Effects Against Injury Induced by H2O2 on PC12 Cells

Ju-xiang¹,

Zhang²,

Zhang³

et al. 2019

Rec.Nat.Prod.

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The radix of Curcuma kwangsiensis S. G. Lee & C. F. Liang (Zingiberaceae) is a traditional medicine in China, and used for treating qi stagnation and blood stasis. Previous chemical study showed it is rich in sesquiterpenoids and diarylheptanoids, similar to those in Curcuma longa L., which showed obviously protective effects against oxidative damage. However, the antioxidant and underlying mechanism of C. kwangsiensis has not been studied yet. In current study, the antioxidant activities of C. kwangsiensis extracts (ECWs), including 95 % EtOH extract (HCECW), 75 % EtOH extract (MCECW), methanol extract (MECW), dichloromethane extract (DECW) and petroleum ether extract (PECW), and their possible mechanisms, were studied on the model of H2O2-induced PC12 cell damage in vitro. The results showed different concentrations (1, 10, 50 µg/mL) of HCECW, MCECW and DECW could increase damaged PC12 cell viability significantly. In the extract-treated groups, the release rate of LDH significantly decreased, while SOD, CAT, and GSH markedly increased. In the meantime, the intracellular Ca 2+ and cell apoptosis decreased significantly, while MMP increased and apoptosis morphology was clearly improved. Compared with the model group, they produced effects on up-regulating of Bcl-2, down-regulating of Bax and Caspase-3. Further, the chemical analysis of those five extracts by UPLC-DAD-Q-TOF-MS showed their major constituents were sesquiterpenoids and diarylheptanoids, indicating both of them presented in ECWs are antioxidant substances in this plant. This study provided an experimental basis for the future development of antioxidants from the genus Curcuma.

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Section: Discussionmentioning

confidence: 54%

Curcuma kwangsiensis Extracts Produced Antioxidant Effects Against Injury Induced by H2O2 on PC12 Cells

Ju-xiang¹,

Zhang²,

Zhang³

et al. 2019

Rec.Nat.Prod.

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“…The 1 H NMR spectrum (Table 1) exhibited characteristic signals for two methyl singlets at δ H 1.04 and 1.99, two oxymethylene protons at δ H 4.00 and 4.42, two oxymethine protons at δ H 4.36 and 4.69, and a terminal double bond at δ H 4.85 and 4.87. In the 13 C NMR spectrum (Table 2), 15 Accordingly, the structure of a 5/7/6 tricyclic skeleton with an oxygen bridge was established, representing a 9,13-epoxyguaiane-type sesquiterpenoid. The NOESY cross-peaks (Figure 2) of H 3 -15/H-3β, H-3α/H-5, H-5/H-7, and H-4/H-2 supported the relative configuration of 1 as 2R*, 4S*, 5S*, 7R*, and 9R*.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Chromatographic separation of the roots of the D. genkwa led to 17 sesquiterpenoids, including 11 new guaiane-type sesquiterpenoids, genkwanoids A–K ( 1 – 11 ). Compounds with a guaiane-type skeleton, which have a 5,7-fused hydroazulene framework, have recently attracted attention because of their extensive biological activities including cytotoxic and neuroprotective effects. − The putative biosynthetic pathway of the isolated sesquiterpenoids was also proposed in the present investigation. Furthermore, the neuroprotective effects of 1 – 17 on a H 2 O 2 -induced human neuroblastoma SH-SY5Y cell injury model were assessed.…”

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confidence: 78%

Guaiane-Type Sesquiterpenoids from the Roots of Daphne genkwa and Evaluation of Their Neuroprotective Effects

Ren¹,

Zhao²,

Shi³

et al. 2019

J. Nat. Prod.

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Chromatographic purification of the roots of Daphne genkwa led to 11 new guaiane-type sesquiterpenoids (1–11), named genkwanoids A–K, and six known analogues (12–17). A comprehensive set of spectroscopic methods including IR, UV, HRESIMS, and 1D/2D NMR were used to elucidate the structures and relative configurations of 1–11. The absolute configurations were determined by the optical rotation calculations and the modified Mosher’s method. The possible biosynthetic pathways for 1–11 are proposed. Furthermore, the neuroprotective effects of 1–17 on H2O2-induced damage in human neuroblastoma SH-SY5Y cells were screened using an MTT assay. Compounds 9, 10, and 16 exhibited moderate neuroprotective effects, with survival rates of 79.34%, 79.94%, and 75.64% after treatment with 12.5 μM, values that were comparable to the positive control, Trolox (78.65%). Furthermore, annexin V-FITC/PI staining of cells treated with 9, 10, and 16 showed that the neuroprotective effects of these compounds may arise from inhibiting cell apoptosis.

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“…Many Lactarius species are edible; chemically, these mushrooms are appreciated for their metabolites, including sesquiterpenes, steroids, nitrogen-containing compounds and other secondary metabolites with e.g. antitumor or antiviral activities [1, 2]. Lactarius deliciosus , L .…”

Section: Introductionmentioning

confidence: 99%

New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus

Tala

Qin

Ndongo

et al. 2017

Nat. Prod. Bioprospect.

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In the 1H NMR-guided fractionation of extracts from the edible mushroom Lactarius deliciosus, two new azulene-type sesquiterpenoids, 7-isopropenyl-4-methyl-azulene-1-carboxylic acid (1) and 15-hydroxy-3,6-dihydrolactarazulene (2), together with seven known compounds were characterized. Their structures were determined on basis of spectroscopic evidence, as well as by comparing with literature data. Amongst the known metabolites, the 13C NMR assignment of 15-hydroxy-6,7-dihydrolactarazulene (3) is reported here for the first time. Moreover, 7-acetyl-4-methylazulene-1-carbaldehyde (5) displayed a moderate antibacterial activity against Staphylococcus aureus.Graphical Abstract*Digital image of L. deliciosus. Retrieved March 17, 2017 from https://upload.wikimedia.org/wikipedia/commons/e/e3/Lactarius_deliciosus_1_(1).jpg .Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-017-0130-1) contains supplementary material, which is available to authorized users.

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Sesqui- and Diterpenoids from the Radix of Curcuma aromatica

Cited by 29 publications

References 45 publications

Curcuma kwangsiensis Extracts Produced Antioxidant Effects Against Injury Induced by H2O2 on PC12 Cells

Curcuma kwangsiensis Extracts Produced Antioxidant Effects Against Injury Induced by H2O2 on PC12 Cells

Guaiane-Type Sesquiterpenoids from the Roots of Daphne genkwa and Evaluation of Their Neuroprotective Effects

New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus

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