Search results for "Terpenoid"

Acid-induced rearrangement of epoxygermacra-8,12-olides: synthesis and absolute configuration of guaiane and eudesmane derivatives from artemisiifolin

2010

A study on the acid-induced rearrangement of 4,5-epoxy- and 1,10-epoxygermacra-8,12-olides was carried out. From a 4,5-epoxy derivative, guaianes were obtained, whereas 1,10-epoxy derivatives furnished, depending on the stereochemistry of the C-1/C-10 epoxy ring, trans-5β,10α- or trans-5α,10β-eudesmanolides.

ChemInform Abstract: Regiospecific and Stereoselective Ene Reaction of the A-Ring Methylcyclohexene Moiety of Polycyclic Terpenoid Systems with Dimet…

2010

Regiospecific and stereoselective ene reaction of the A-ring methylcyclohexene moiety of polycyclic terpenoid systems with dimethyl acetylenedicarbox…

2001

Polycyclic terpenoid compounds with a methylcyclohexene moiety at the A-ring, such as 1 and 7, give a regio- and stereoselective ene reaction when heated at low temperatures with dimethyl acetylenedicarboxylate. The structure and stereochemistry of the compound formed in the case of 1, e.g. 5, is determined by X-ray analysis.

Coscinolactams A and B: new nitrogen-containing sesterterpenoids from the marine sponge Coscinoderma mathewsi exerting anti-inflammatory properties

2009

Abstract Investigation of the marine sponge Coscinoderma mathewsi led to the isolation of two novel nitrogen-containing cheilanthane sesterterpenoids, coscinolactams A and B, together with known suvanine. The structures were elucidated by extensive spectroscopic measurements including NOE experiments to deduce the stereochemistry. The natural compounds, as well as a semisynthetic derivative, showed moderate anti-inflammatory activity measured as their capability to inhibit PGE2 and NO production. The suvanine aldehyde derivative 4 inhibited inducible nitric oxide protein expression with an IC50 value of 7.3 μM.

The impact of winter flooding with saline water on foliar carbon uptake and the volatile fraction of leaves and fruits of lemon (Citrus limon) trees

2012

We investigated the consequences of recurrent winter flooding with saline water on a lemon (Citrus × limon (L.) Burm.f.) orchard, focussing on photosynthesis limitations and emission of secondary metabolites (isoprenoids) from leaves and fruits. Measurements were carried out immediately after flooding (December), at the end of winter (April) and after a dry summer in which plants were irrigated with optimal quality water (September). Photosynthesis was negatively affected by flooding. The effect was still visible at the end of winter, whereas the photosynthetic rate was fully recovered after summer, indicating an unexpected resilience capacity of flooded plants. Photosynthesis inhibition by…

Terpenoid treatment in osteoporosis: this is where we have come in research.

2021

Lower bone resistance to load is due to the imbalance of bone homeostasis, where excessive bone resorption, compared with bone formation, determines a progressive osteopenia, leading to a high risk of fractures and consequent pain and functional limitations. Terpenoids, with their activities against bone resorption, have recently received increased attention from researchers. They are potentially more suitable for long-term use compared with traditional therapeutics. In this review of the literature of the past 5 years, we provide comprehensive information on terpenoids, with their anti-osteoporotic effects, highlighting molecular mechanisms that are often in epigenetic key and a possible p…

Chemical composition of lipophilic extractives from grey alder (Alnus incana)

2013

The chemical composition of the lipophilic extractives in the hexane extracts from grey alder bark, knotwood, and cones has been investigated by gas chromatography and gas chromatography-mass spectrometry. The efficiency of two extraction methods was compared. The highest amount of lipophilic extractives (about 9% of o.d. material) was observed in grey alder cone, while the lowest (about 3%) was found in knotwood. The three different morphological parts of alder showed significant differences not only in the content but also in composition of extractives, namely fatty acids, triglycerides, and triterpenes. The main identified compounds were triterpenoids (lupen-3-one, lupeol, betulone, betu…

Two new biologically active triterpenoidal saponins acylated with salicylic acid from Albizia adianthifolia

2003

International audience; Two new oleanane-type triterpene saponins, adianthifoliosides A (1) and B (2), were isolated from a 95% ethanolic extract of roots of Albizia adianthifolia. Their structures were elucidated mainly by using a combination of 600 MHz 1D and 2D NMR techniques (COSY, NOESY, TOCSY, HSQC, and HMBC) and by FABMS and HRESIMS. Compounds 1 and 2 were characterized as glycosides of acacic acid acylated by an o-hydroxybenzoyl unit. The crude saponin mixture (CSM), compounds 1 and 2 together with 3 and 4 (prosapogenins obtained from the mild alkaline hydrolysate of the CSM), were evaluated for immunomodulatory activity on the Jurkat T cell line and for hemolytic property against s…

Hastifolins A-G, antefeedant neo-clerodane diterpenoids from Scutellaria hastifolia

2010

From the aerial parts of Scutellaria hastifolia, family Lamiaceae (Labiatae), seven neo-clerodane diterpenoids (hastifolins A-G) were isolated. The products are similar to the known scuteparvin and are characterized by being trans-cinnamoyl derivatives. Structures and stereochemistry were determined by intensive NMR investigation. Six of the products form three pairs of epimers at C-13. Hastifolins A-C showed significant antifeedant activity.

Acetylcholinesterase and antioxidant evaluation of C18-functionalized ferruginol analogues

2019

Nearly 200 years ago, the study of the chemistry of terpenoids started with the analysis of turpentine oil, investigating the first resin acid, abietic acid from pine oleoresin.[1] Abietic acid occurs in plants of the genus Abies and is the first member of a class of plant metabolites, the abietane-type diterpenoids. They are characterized by a tricyclic ring system and have shown a wide range of chemical diversity and biological activity. [2,3] Medicinal chemists have studied derivatives of two readily available materials such as dehydroabietic acid and dehydroabietylamine. [3] To date, there is only one commercial drug, Ecabet® [ecabet sodium], based on abietanes, which is used for the tr…