Terpenoid Esters Research Articles

Metabolite profile of tree marigold (Tithonia diversifolia (Hamsley) A. Grey) leaves

Tree marigold or Tithonia diversifolia (Hemsley) A. Grey) also known as Insulin leaves has traditionally been used as an herb for the treatment of diabetes mellitus (DM). Tree marigolds contain various metabolite compounds, which have various bioactivities, so research was carried out to study metabolite profiles using a non-target metabolism approach using a GC-MS (Gas Chromatography-Mass Spectrometry) instrument. The results of GC-MS analysis of Tree marigold ethanol extract showed 30 peaks in the chromatogram, of which 7 were dominant metabolite compounds including 1-butanol, 3-methyl acetate (28.11%), Thunbergol (14.28%), Geranyl acetate (12.13%). ), D-Limonene (6.64%), 4H-Pyran-4-one, 2,3-Dihydro-3,5-dihydroxy-6 -methyl (5.05%), acetic acid (4.10%), 7.8-epoxy-α-ionone (2.91%). The various categories of metabolites consist of the monoterpene class followed by fatty acids, terpenes, and sesquiterpenoids, as well as other compounds in the terpenoid esters class, alkanoic acids, fatty acids, proteins, amino acids, furanoids, ketones, and others. These metabolite compounds have antidiabetic, antioxidant, anti-inflammatory, antimicrobial, antibacterial, anticancer, and antitumor effects so they have potential as antidiabetic therapy.

Design, synthesis, and insecticidal activity of novel terpenoid ester compounds containing bicyclo[2.2.1] heptane against Aphis gossypii Glover

To discover novel and efficient compounds against Aphis gossypii Glover, a series of novel terpene ester derivatives containing the structure of bicyclo[2.2.1]heptane were designed and synthesized using tschimganin as the lead compound. Bioactivity assays showed that most tschimganin analogs exhibited moderate to outstanding insecticidal activity against A. gossypii. In particular, compound 56 (LC50 = 0.28 μg mL−1), identified as (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl nicotinate, exhibited the best activity, which was significantly superior to that of imidacloprid (LC50 = 0.54 μg mL−1) and sulfoxaflor (LC50 = 0.70 μg mL−1). The precise and dependable 3D-QSAR model suggests a promising direction for further design of more active tschimganin-based insecticides. Metabolomics showed that compound 56 disrupted detoxification, amino acid biosynthesis, and energy metabolism and may affect the central nervous system of A. gossypii. The results of this study indicated that tschimganin analogs are a potential new class of green insecticides that can be used for the integrated management of A. gossypii.

Plasticization of poly(3-hydroxybutyrate) with biobased terpenoid esters of geraniol

Plasticization of poly(3-hydroxybutyrate) with biobased terpenoid esters of geraniol

Terpenoid Esters Are the Major Constituents From Leaf Lipid Droplets of Camellia sinensis.

Lipid droplets (LDs) have been widely found from diverse species and exhibit diverse functions. It remains unexplored what potential roles they played in tea. To address this question, we analyzed the chemical composition and the dynamic changes of cytosolic LDs during leaf growth and diurnal cycle. Using TopFluor cholesterol and Nile Red staining we demonstrated that cytosolic LDs were heterogeneous in tea tree (Camellia sinensis cv. Tieguanyin); the size and number of LDs increased with leaf growth. Compositional analysis showed that terpenoid esters and diacylglycerol are the major components of cytosolic LDs. The contents of total sterol esters (SEs) and β-amyrin esters increased with leaf expansion and growth; individual SE also showed diurnal changes. Our data suggest that cytosolic LDs from tea tree leave mainly serve as storage site for free sterols and triterpenoids in the form of esters. Cytosolic LDs were not the major contributors to the aroma quality of made tea.

Effect of esters based on terpenoids and GABA on fluidity of phospholipid membranes

The influence of esters based on gamma-aminobutyric acid (GABA) and mono-/bicyclic terpenoids on membrane structure was investigated. The mechanism of action for terpenoid esters on phospholipids of artificial membranes and lipids isolated from the rat stratum corneum was studied by fluorescence and FT-IR spectroscopy. We report here, that inclusion of monocyclic terpenoid esters in phospholipid liposomes leads to growth of excimer to monomer ratio (IE/IM) indicating a decrease of membrane microviscosity. Another mechanism of influence on biomembranes was proposed for ester of bicyclic borneol - in this case a high ratio of vibronic peak intensities (I1/I3) was revealed. The addition of terpenoid esters appears in the FT-IR spectra as intensity reduction of absorption bands associated with C = O, P = O and P–O–С groups of lecithin phospholipids. Similar results were obtained after esters addition to lipids isolated from stratum corneum indicating a decrease of hydrogen bonds number between polar groups of lipids. Thus, the influence of terpenoid esters on molecular organization of the lipid matrix substantiates the feasibility of their use after transdermal delivery in vivo.

Transdermal delivery of novel terpenoid esters in pain management

Transdermal delivery of novel terpenoid esters in pain management

Synthesis and Pharmacological Properties of Novel Esters Based on Monoterpenoids and Glycine.

Esters based on mono- and bicyclic terpenoids with glycine have been synthesized via Steglich esterification and characterized by 1H-NMR, IR, and mass spectral studies. Their analgesic and anti-inflammatory activities were investigated after transdermal delivery on models of formalin, capsaicin, and AITC-induced pain, respectively. Glycine esters of menthol and borneol exhibited higher antinociceptive action, whereas eugenol derivative significantly suppressed the development of the inflammatory process. The mechanism of competitive binding between terpenoid esters and TRPA1/TRPV1 agonists was proposed explaining significant analgesic effect of synthesized derivatives. For an explanation of high anti-inflammatory activity, competitive inhibition between terpenoid esters and AITC for binding sites of the TRPA1 ion channel has been suggested.

Composition of cuticular waxes coating flag leaf blades and peduncles of Triticum aestivum cv. Bethlehem

The work herein presents comprehensive analyses of the cuticular wax mixtures covering the flag leaf blade and peduncle of bread wheat (Triticum aestivum) cv. Bethlehem. Overall, Gas Chromatography-Mass Spectrometry and Flame Ionization Detection revealed a wax coverage of flag leaf blades (16 μg/cm2) a third that of peduncles (49 μg/cm2). Flag leaf blade wax was dominated by 1-alkanols, while peduncle wax contained primarily β-diketone and hydroxy-β-diketones, thus suggesting differential regulation of the acyl reduction and β-diketone biosynthetic pathways in the two analyzed organs. The characteristic chain length distributions of the various wax compound classes are discussed in light of their individual biosynthetic pathways and biosynthetic relationships between classes. Along with previously reported wheat wax compound classes (fatty acids, 1-alkanols, 1-alkanol esters, aldehydes, alkanes, β-diketone, hydroxy-β-diketones, alkylresorcinols and methyl alkylresorcinols), esters of 2-alkanols and three types of aromatic esters (benzyl, phenethyl and p-hydroxyphenethyl) are also reported. In particular, 2-heptanol esters were identified. Detailed analyses of the isomer distributions within 1-alkanol and 2-alkanol ester homologs revealed distinct patterns of esterified acids and alcohols, suggesting several wax ester synthases with very different substrate preferences in both wheat organs. Terpenoids, including two terpenoid esters, were present only in peduncle wax.

ChemInform Abstract: A Hydroxylated Lupeol‐Based Triterpenoid Ester Isolated from the Scurrula parasitica Parasitic on Nerium indicum

Abstractisolation, structure elucidation and cytotoxic activity of the new terpenoid ester (I) and sixteen known compounds

Further iridoid glucosides in the genus Manulea (Scrophulariaceae)

From Manulea altissima (Scrophulariaceae) were isolated five known secoiridoid glucosides sweroside, eustomoside, eustoside, secoxyloganin and secologanoside as well as the 4″-O-rhamnopyranosyl-feruloyl ester of adoxosidic acid, named altissimoside. Also, the caffeoyl phenylethanoid glycoside verbascoside was isolated. In addition two previously unknown terpenoid esters of 6β-hydroxy 8-epi-boschnaloside, named manucoside A and B were isolated from a formerly obtained fraction from the work-up of Manulea corymbosa. The distribution of iridoid glucosides in the Scrophulariaceae is discussed.

Improvement of Ylang-Ylang Essential Oil Characterization by GC×GC-TOFMS

A single fraction of essential oil can often contain hundreds of compounds. Despite of the technical improvements and the enhanced selectivity currently offered by the state-of-the-art gas chromatography (GC) and mass spectrometry (MS) instruments, the complexity of essential oils is frequently underestimated. Comprehensive two-dimensional GC coupled to time-of-flight MS (GC×GC-TOFMS) was used to improve the chemical characterization of ylang-ylang essential oil fractions recently reported in a previous one-dimensional (1D) GC study. Based on both, the enhanced chromatographic separation and the mass spectral deconvolution, 161 individual compounds were identified and labeled as potentially characteristic analytes found in both low and high boiling fractions issued from distillation of mature ylang-ylang flowers. Compared to the most recent full GC-MS characterization, this represents 75 new compounds, essentially consisting of terpenes, terpenoid esters, and alcohols.

Rubrivivaxin, a new cytotoxic and cyclooxygenase-I inhibitory metabolite from Rubrivivax benzoatilyticus JA2

A new phenol terpenoid ester metabolite was isolated from the culture supernatant of Rubrivivax benzoatilyticus JA2 when the organism grown on L-phenylalanine as sole source of nitrogen under photoheterotrophic condition. The compound was characterized by HPLC, LCMS, IR, NMR (1H, 13C) and Mass spectrometry, as a 3, 4-dihydroxybenzoyl-terpenoid ester [IUPAC: 3, 4-dihydroxy, 5-carboxy, 3-methylpentyl ester], which has a molecular mass (m/z) of 298 and we designated as rubrivivaxin. The significance of cyclooxygenase-I (COX-I) inhibitory, antimicrobial, cytotoxic activities against U937 (Human leukemic monocyte lymphoma) and Jurkat (T lymphocyte) cell lines conferred by rubrivivaxin.

Estrogen activity of terpenoids from plants of the genus Ferula

The relationship between chemical structure and estrogen activity of a series of terpenoid esters with aromatic and aliphatic acids was studied. The studied compounds were isolated from the underground and aerial organs of Ferula tenuisecta, F. akitschkensis, F. lapidosa, F. juniperina, F. ceratophylla, F. pallida, F. tschimganica, and F. prangifolia. The estrogen activity was determined in vivo tests at a dose of 1 mg/kg.

A Review of Aromatic Herbal Plants of Medicinal Importance from Nigeria

Nigeria is blessed with a rich source of aromatic flora, many of which have not been previously investigated for their chemical constituents and biological potentials. This flora constitutes a rich source of potential spices or flavoring, ingredients of formulae intended for pharmaceutical administration, and for perfumery. Interestingly, essential oil constituents such as 1,8-cineole, precocene, 6,10,14-trimethylpentadecan-2-one, eugenol, β-caryophyllene, α-pinene, α-terpineol and even hitherto uncommon compounds such as zerumbone and rare terpenoid esters have been isolated and characterized from these plants. In addition, some of the studied volatile oils have exhibited biological activities of importance such as antimicrobial and cytotoxicity. The majority of these aromatic plants occur either as perennial or annual herbs which are suitable for cultivation purposes in herbal gardens, traditional medicinal centers, parks, research institutes and forest reserves. This paper presents a review of some of the endemic aromatic and medicinal plants of Nigeria with a view to ascertaining their suitability as raw materials for the pharmaceutical and perfumery applications.

Molecular modelling and QSAR analysis of the estrogenic activity of terpenoids isolated from Ferula plants

The relationship between chemical structure and estrogenic activity in a series of terpenoid esters with aromatic and aliphatic acid substituents isolated from Ferula plants, was studied. The fragments of the terpenoid structure that are potentially responsible for estrogenic activity were revealed. A quantitative structure-estrogenic activity study has been carried out using the QSAR approach with use of data derived from quantum-chemical calculations as well as data generated from three-dimensional structures of terpenoids. A number of molecular descriptors was obtained from the density functional theory (DFT) at the B3LYP/6-31G(d, p) level of calculation. Comparative analysis of the quantum-chemical computational data was also performed to confirm hypothesis concerning importance of the distance between the oxygen of alcohol hydroxyl group and the functional group in the para-position of the benzene ring (the hydroxyl or methoxy group). Use of the Genetic Algorithm in the QSAR analysis allowed the structural and physicochemical parameters of the terpenoids responsible for estrogenic activity to be determined. A significant QSAR model was obtained with an r 2 value of 0.892. The resulting model showed a reliable dependence of estrogenic activity of the terpenoids on such parameters as molecular shape, number of phenolic groups, surface polarity and the energy of the highest occupied molecular orbital.

Rhodestrin: A Novel Indole Terpenoid Phytohormone from Rhodobacter sphaeroides

A new phytohormone was isolated as a metabolite of anthranilate photobiotransformation by Rhodobacter sphaeroides OU5. It was identified by MS and NMR ((1)H, (13)C) as an indole terpenoid ester [(2E,4E,6E,8E,10E,12E,14E,16E,18E)24-hydroxy-2,6,10,14,19 pentamethyl tetrecosa-2,4,6,8,10,12,14,16,18 nonenyl-2(hydroxy methyl)-1H-indole-3-carboxylate] and is named as rhodestrin. Rhodestrin at 50 nM: gave positive test in auxin bioassay and initiated more profuse and early rooting in tissue-cultured plants than other auxins at 5 microM.

Secondary Metabolites from the Marine Alga Caulerpa brownii (Chlorophyta)

The green seaweed Caulerpa brownii (Chlorophyta, Caulerpaceae) occurs in Tasmania in two morphological forms (branched and unbranched) and each form has a different profile of diterpenoid secondary metabolites. Unbranched specimens gave rise to the novel secondary metabolites 11, 13, 14, 17, and 18, the secondary metabolite 8 that has been isolated for the first time as a natural product, as well as the known compounds 1 and 3–7. Branched specimens of C. brownii yielded the novel terpenoid esters 21 and the known compounds 1 and 2.

Rare terpenoid esters from Hyparrhenia rufa (Nees) Stapf. growing wild in Nigeria

AbstractThe volatile oil of Hyparrhenia rufa (Nees) Stapf. grown in Nigeria was obtained by hydrodistillation and analysed by GC, GC–MS, 1H‐ and 13C‐NMR. The main components found were τ‐cadinol (17.43%) and β‐selinene (11.64%). The most interesting characteristic of the oil was the presence of four unusual and rarely occurring terpenoid esters: (E,E)‐methyl farnesoate (1.01%), (E,E)‐methyl‐10,11‐epoxyfarnesoate (12.17%), methyl (2E,6E)‐10‐hydroxy‐3,7,11‐trimethyldodeca‐2,6,11‐trienoate (4.3%) and methyl (2E,6E)‐3,7,11‐trimethyl‐10‐oxododecadienoate (2.25%). Copyright © 2004 John Wiley & Sons, Ltd.

Juvenile Hormone Diol Kinase: I. PURIFICATION, CHARACTERIZATION, AND SUBSTRATE SPECIFICITY OF JUVENILE HORMONE-SELECTIVE DIOL KINASE FROM MANDUCA SEXTA

Manduca sexta juvenile hormone diol kinase (JHDK) catalyzes the conversion of juvenile hormone (JH) diol to JH diol phosphate. JHDK may be the first example of a phosphotransferase directly involved in the catabolism and inactivation of a lipid-soluble hormone. JHDK is an enzyme crucial for secondary metabolism of JH and possesses high specificity and catalytic efficiency for JH diol. In this study, the purification and characterization of native JHDK are described; its enzymatic properties are examined; and its role in cellular JH metabolism is explored. Using a variety of potential substrates, we show that JHDK has a preference for ATP, but will catalyze the formation of JH diol phosphate with GTP as the phosphate donor. JHDK has a nanomolar K(m) for JH I diol and a low micromolar value for MgATP. JH II and III diols also serve as phosphate acceptors with low micromolar K(m), whereas other diol derivatives of terpenoid esters structurally similar to JH metabolites are not phosphorylated. The reaction proceeds via a sequential Bi Bi mechanism. JHDK is active as a homodimer with a subunit molecular mass of 20 kDa. JHDK binds 5'-p-fluorosulfonylbenzoyladenosine and is inhibited by micromolar levels of Ca2+.

Structure and stereochemistry of nardostachysin, a new terpenoid ester constituent of the rhizomes of Nardostachys jatamansi.

The structure and stereochemistry of a new terpenoid ester, nardostachysin (1), isolated from the rhizomes of Nardostachys jatamansi, were established as the 7',8'-dihydroxy-4'-methylene hexahydrocyclopenta[c]pyran-1'-one-8'-methyl ester of 7, 9-guaiadien-14-oic acid, by spectral and chemical studies.