Anti-inflammatory guaiane-type sesquiterpenes from the fruits of Pittosporum undulatum

Mendes, Sofia Alexandra Carreiro; Mansoor, Tayyab A.; Rodrigues, António; Bruges-Armas, Jácome; Ferreira, Maria‐José U.

doi:10.1016/j.phytochem.2013.06.019

Cited by 27 publications

(16 citation statements)

References 26 publications

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“…To comprehensively identify the active components of this plant, we will further phytochemically characterise additional extracts with anti-inflammatory properties via activity-guided fractionation and prep-HPLC/LC-MS/MS. Since several sesquiterpene glycosides such as undulatumosides A have been reported to suppress NO production with an IC 50 value of 16.4 μM (Mendes et al, 2013), particularly, we will also isolate sesquiterpene glycoside-type compounds from this extract to confirm their role as anti-inflammatory principles.…”

Section: No Production (% Of Controlmentioning

confidence: 99%

In vitro and in vivo anti-inflammatory activity of Phyllanthus acidus methanolic extract

Hossen

Jeon

Kim

et al. 2015

Journal of Ethnopharmacology

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Section: No Production (% Of Controlmentioning

confidence: 99%

In vitro and in vivo anti-inflammatory activity of Phyllanthus acidus methanolic extract

Hossen

Jeon

Kim

et al. 2015

Journal of Ethnopharmacology

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“…The strong NOESY correlation of H‐3β/H‐5β revealed that these protons were β‐orientated. While there was no apparent spectroscopic evidence to assign the orientation of hydroxyisopropyl connected to C‐7, it could also be deduced to be a β orientation, as it was found in almost all guaiane sesquiterpenes from plants with a known stereochemistry . The ECD spectrum of 2 exhibited a positive Cotton effect at 249 (+2.93) nm with the UV λ max at 245 nm, which corresponded to the π − π* transition of the conjugated diene chromophore .…”

Section: Resultsmentioning

confidence: 96%

“…While there was no apparent spectroscopic evidence to assign the orientation of hydroxyisopropyl connected to C-7, it could also be deduced to be a β orientation, as it was found in almost all guaiane sesquiterpenes from plants with a known stereochemistry. 10,[18][19][20] The ECD spectrum of 2 exhibited a positive Cotton effect at 249 (+2.93) nm with the UV λ max at 245 nm, which corresponded to the π À π* transition of the conjugated diene chromophore. 21,22 On the basis of the determined relative configuration and the allylic axial chirality rule for conjugated dienes, 23 the 4S,5R,7S configuration of 2 was assigned.…”

Section: Resultsmentioning

confidence: 99%

Enantiomeric Neolignans and a Sesquiterpene from Solanum erianthum and Their Absolute Configuration Assignment

Peng

Yang

et al. 2016

Chirality

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One pair of new C-8-C-3'/C-7-O-C-4' linked neolignan enantiomers (1a/1b) and one new guaiane sesquiterpene (2) first featuring the 1(2),9(10)-conjugated double bond were isolated from the stems of Solanum erianthum (Solanceae). Their structures were characterized on the basis of extensive spectroscopic analyses, especially from their 2D nuclear magnetic resonance (NMR) spectra. The absolute configurations of 1a/2b were rigorously elucidated by electronic circular dichroism (ECD) experiments combined with the reversed helicity rule for the 2,3-dihydrobenzo[b]furan chromophore, and compound 2 is the first report on the sterochemical assignment of a guaiane sesquiterpene by using the allylic axial chirality rule for the conjugated diene chromophore in combination with the calculated ECD spectrum.

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“…This family is represented in New Caledonia by 45 endemic species belonging to Pittosporum genus. Species from this genus have been widely studied in the world, mainly for terpenoids, saponins, and essential oils ( e.g ., ). In New Caledonia, only Pittosporum pancheri was investigated.…”

Section: Asteridsmentioning

confidence: 97%

New Caledonia: A Hot Spot for Valuable Chemodiversity Part 3: Santalales, Caryophyllales, and Asterids

Coulerie

Poullain

2016

Chemistry & Biodiversity

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The flora of New Caledonia encompasses more than 3000 plant species and an endemism of almost 80%. New Caledonia is even considered as one of the 34 'hot spots' for biodiversity. Considering the current global loss of biodiversity and the fact that several drugs and pesticides become obsolete, there is an urgent need to increase sampling and research on new natural products. In this context, here, we reviewed the chemical knowledge available on New Caledonian native flora from economical perspectives. We expect that a better knowledge of the economic potential of plant chemistry will encourage the plantation of native plants for the development of a sustainable economy which will participate in the conservation of biodiversity. This review is divided into three parts, and the third part which is presented here summarizes the scientific literature related to the chemistry of endemic santalales, caryophyllales, and asterids. We show that the high rate of endemism is correlated with the originality of phytochemicals encountered in New Caledonian plants. A total of 176 original natural compounds have been identified from these plants, whereas many species have not been investigated so far. We also discuss the economic potential of plants and molecules with consideration of their medicinal and industrial perspectives. This review finally highlights several groups, such as Sapotaceae, that are unexplored in New Caledonia despite the high chemical interest in them. These plants are considered to have priority in future chemical investigations.

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Anti-inflammatory guaiane-type sesquiterpenes from the fruits of Pittosporum undulatum

Cited by 27 publications

References 26 publications

In vitro and in vivo anti-inflammatory activity of Phyllanthus acidus methanolic extract

In vitro and in vivo anti-inflammatory activity of Phyllanthus acidus methanolic extract

Enantiomeric Neolignans and a Sesquiterpene from Solanum erianthum and Their Absolute Configuration Assignment

New Caledonia: A Hot Spot for Valuable Chemodiversity Part 3: Santalales, Caryophyllales, and Asterids

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