Triterpenoids

doi:10.1016/0031-9422(83)80198-8

Phytochemistry

Volume 22, Issue 5, 1983, Pages 1071-1095

https://doi.org/10.1016/0031-9422(83)80198-8 Get rights and content

Abstract

Triterpenoids isolated from various sources are reviewed. The newer techniques used in their isolation and structure elucidation are discussed. A compi

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n-Alkane and terpenoid fingerprints of modern biomass producers unveil floral changes recorded in postglacial alpine lake sediments, Tatra Mountains, Slovakia
2023, Organic Geochemistry
Sediments of two alpine lakes in Tatra Mts., Slovakia, record the environmental history of their catchments from deglaciation in Late Glacial warming up to the Subboreal period. We present a biomarker-based reconstruction of changes in the surrounding biota of two contrasting lakes – a relic lake in open fen Trojrohé pleso (TROJ) and a tarn lake Batizovské pleso (BAT). Taking advantage of young unaltered sediments, well-known source area, and main biomass producers, we used an actualistic approach and interpreted sedimentary lipid distributions using fingerprints of modern plant groups. Four chemostratigraphic units were defined in TROJ lake and five units in BAT lake, with boundaries and environmental changes roughly conforming to paleoclimatic intervals of the Holocene. The dry climate was recorded in the period 13,200 BP–11,500 BP, coincident with Younger Dryas stadial. In the sediment of TROJ lake at ca. 5,200 BP a sharp spike in the abundance of the aromatic terpenoid retene, decoupled from the trend of other abietane-type diterpenoids, may best be explained by episodic flooding due to the rise of the water table. Diploptene as a biomarker for bacterial activity is suggested to indicate the development of soil cover at the end of the B/A interstadial and its gradual increase in abundance in the Holocene most reflecting an extension of vegetated area and more complex development of soil cover. Based on the absence of conifer biomarkers in the sediments of BAT lake, the upper limit of the continuous Pinus mugo scrub never reached the altitude of 1880 m a.s.l. between 16,247 and 4,420 BP, whereas conifer canopy was permanently present around TROJ lake at 1611 m a.s.l. between 10,439 and 3,113 BP.
Synthesis, biological evaluation, molecular docking studies and In-silico ADMET evaluation of pyrazines of pentacyclic triterpenes
2022, Bioorganic Chemistry
Citation Excerpt :
Natural products are in general readily applicable, accessible, and offer acceptable therapeutic approaches with minimum cytotoxicity [4,5]. Pentacyclic triterpenes are secondary plant metabolites usually found in stem bark, leaves and fruit peel, and they are categorized according to the number and structure of the triterpene rings [6,7]. Triterpenes and their functionalized forms have been investigated for their therapeutic effects, including anti-inflammatory, antimicrobial, antiplasmodial, anticariogenic, antiviral and anti-HIV activities, among others [8,9].
The semisynthesis of novel derivatives of lupeyl palmitate and 3β-palmitoyloxy-olean-12-ene by introduction of a pyrazine at C-2 / C-3 and modifications of the relatively unexplored C-30 position of lupeol derivatives was conducted, and their cytotoxic and anti-inflammatory activities were evaluated. The derivatives 7, 10 and 11 significantly inhibited the tumor cell lines U251, K562, HCT-15, MCF-7 and SKLU-1, and compounds 7 and 11 were more active (IC₅₀ 25.4 ± 2.0 µM and 7.1 ± 0.4 µM, respectively) than the positive control (etoposide (IC₅₀ 31.5 ± 2.2 µM) in the tumor line PC-3. Introduction of the pyrazine at C-2 / C-3 in compounds 1 and 2 or modification at C-30 of compound 1 decreased the anti-inflammatory activity in the TPA-induced mouse ear edema. Following the results of the PASS online evaluation of the potential biological activity of the natural compounds and their derivatives, the inhibition of pNF-κB translocation to the prostate cancer (PC-3) cell nucleus was investigated and the binding mode of compounds 7, 10 and 11 with the human NF-κB receptor was explored by a molecular docking study. These derivatives bound directly or close to the amino acids that form the DNA recognition site. The ADMET physicochemical parameters of the fifteen compounds were further analyzed in silico using Molinspiration calculations indicating the potential of compounds 7, 10 and 11 for further investigation.
The potential of biomarker proxies to trace climate, vegetation, and biogeochemical processes in peat: A review
2019, Global and Planetary Change
Molecular fossils (biomarkers) are abundant in organic rich natural archives such as peats and lignites (fossilized peat), where their distribution is governed by their biological source, environmental factors, such as temperature and pH, and diagenetic reactions. As a result, biomarkers in peat have become an important tool to study past variations in vegetation, environment and climate in terrestrial settings, as well as biogeochemistry on time-scales of hundreds to millions of years ago. In recent years, significant progress has been made in understanding the controls on biomarker distributions, especially those derived from microorganisms and peat-forming plants, allowing for example, the quantification of past temperature and vegetation history during peat formation. Herein, we provide a review of a range of commonly applied biomarker proxies in peats, discuss the latest proxy developments, and explore the potential of using biomarkers in peat and lignite as paleoenvironmental proxies. We provide a framework for biomarker analyses in peat and identify possible future research directions.
Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin
2016, Geochimica et Cosmochimica Acta
The hydrogen isotopic composition (δD or (D/H) value) of molecular biomarkers preserved in sedimentary archives is increasingly used to provide clues about the evolution of past climatic conditions. The rationale is that intact biomarkers retain isotopic information related to the climatic conditions that prevailed at the time of their synthesis. Some of these biomarkers may be degraded during diagenesis, however. The extent to which these degradations alter the original δD value of the source biomarker is presently debated and the capacity to resolve this question by determination of compound-specific δD values alone is limited. The “bulk” or “global” δD value of any molecule is in fact a composite of δD values at each site within this molecule (δD_i or (D/H)_i with i = number of hydrogen/deuterium atoms in the considered molecule). Determination of this site-specific δD_i value in biomarkers could not only yield outstanding paleoenvironmental information but also help forecast the impacts of diagenesis and define essential steps in biosynthetic pathways.
This task is analytically challenging. Here, we examined the capabilities of natural abundance deuterium 2D-NMR (NAD 2D-NMR) using homopolypeptide liquid crystals as an NMR solvent to: (i) analyze the NAD spectra of biomakers; (ii) determine the site-specific distribution of hydrogen in the nine methyl groups (δD_Mei with i = 23–31) of miliacin, a pentacyclic triterpene of the amyrin family and key biomarker for broomcorn millet in sedimentary archives. Relative (D/H)_Mei values were established by anisotropic NAD 2D-NMR. Then absolute δD_Mei values were obtained by determining δD_Mei value of the methoxy group of miliacin using two independent approaches: isotropic NAD NMR (SNIF-NMR^™) and GC–irMS. The resulting isotope profile for miliacin shows, for the first time, large variations in δD_Mei values that can directly be explained by biosynthetic processes. This approach has also the potential to permit predicting fractionations during pentacyclic triterpene diagenesis.
Distribution of miliacin (olean-18-en-3β-ol methyl ether) and related compounds in broomcorn millet (Panicum miliaceum) and other reputed sources: Implications for the use of sedimentary miliacin as a tracer of millet
2013, Organic Geochemistry
Citation Excerpt :
C-3 oxygenated pentacyclic triterpenes are such compounds. Their potential use in medicine (Das and Mahato, 1983; Mors et al., 2000; Lin et al., 2003; Siddique and Saleem, 2011) motivated phytochemical studies that have increased understanding of their distributions in plants (Xu et al., 2004). Although compounds such as lupeol, and β- and α-amyrin are found in most angiosperms (i.e. Das and Mahato, 1983), several pentacyclic triterpenes bearing original functional groups can be more taxon specific.
Using sedimentary miliacin (olean-18-en-3β-ol methyl ether) as a molecular tracer of the history of Panicum miliaceum (broomcorn millet) cultivation depends upon broomcorn millet being sedimentary miliacin’s dominant source. It also requires knowledge of the variability in miliacin concentration in broomcorn millet. Finally, it is affected by the presence of other pentacyclic triterpene methyl ethers (PTMEs) that may exist in conjunction with miliacin in other sources but not in broomcorn millet.
Miliacin biosynthesis has been proposed for other Panicum species, Setaria italica (Italian or foxtail millet), Pennisetum sp. and Chaetomium olivaceum (an olive green mold). We found miliacin concentration in seeds of different varieties of P. miliaceum to be similarly high (with trace amounts of β- and α-amyrin methyl ethers). It was absent from hulls and roots, and nominally present in leaves and stems. The transfer of miliacin from plant to sediments is therefore mostly from seeds. It was abundant (often with larger amounts of β- and α-amyrin methyl ethers) in all other Panicum species studied, but only in some species of the genus Pennisetum and was absent from S. italica. Neither C. olivaceum nor its growth medium (rice) showed any trace of miliacin. Our results, with miliacin absent from S. italica and C. olivaceum, its high concentration in the seed of P. miliaceum relative to other PTMEs and to other grasses and, considering the high biomass that cultivated broomcorn millet has relative to other potential plant sources, support the use of sedimentary records of miliacin in some contexts to track past millet agricultural dynamics.
Methoxy-serratenes in a soil under conifers and their potential use as biomarkers of Pinaceae
2013, Organic Geochemistry
Citation Excerpt :
In addition, when transferred to sedimentary archives, either directly from plants or via soils, these biomarkers can be used to reconstruct the evolution of ecosystems through time. With the notable exception of hopanoids that are principally attributed to bacteria (e.g. Ourisson et al., 1979) and fernane/arborane derivatives, the origin of which is still debated (Hauke et al., 1995; Jaffé and Hausmann, 1995), most pentacyclic triterpenes are classically attributed to angiosperms (Das and Mahato, 1983; Cranwell, 1984). Due to their wide structural diversity, function and configuration, and to the limited number of organisms able to synthesize them, these compounds constitute valuable chemotaxonomic markers and are increasingly being used in environmental reconstruction.
In the frame of a study aimed at defining new soil molecular biomarkers that could attest to former land use and that could also be screened in lake sediments for palaeoenvironmental reconstruction, we analysed the 2–4 cm depth layer of a soil developed under a conifer forest in the Lake Aydat catchment (French Massif Central). The lipid fraction of the sample contained 12 serratenoids bearing at least a methoxyl (OMe) group at C-3 or C-21 and various additional functional groups (alcohol, ketone or acetate). A survey of the literature provided indubitable evidence that these compounds are typical for Pinaceae species, in agreement with the surrounding vegetation at the sampling site. Due to the economic and ecological importance of the taxa, the presence of these highly specific compounds in soil, sediments or peat could therefore help in unravelling the timing of forestry activity.

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reviewTriterpenoids

Abstract

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

J. Chromatogr.

J. Chromatogr.

Tetrahedron Letters

Phytochemistry

Tetrahedron

Chem. Phys. Lipids

J. Magn. Reson.

J. Magn. Reson.

Tetrahedron Letters

Tetrahedron

Tetrahedron Letters

Tetrahedron Letters

Phytochemistry

Helv. Chim. Acta

Rev. Pure. Appl. Chem.

Phytochemistry

Shoyakugaku Zasshi

Yakugaku Zasshi

Rev. Latinoam. Quim.

Khim. Prir. Soedin.

Phytochemistry

J. Indian Chem. Soc.

Indian J. Chem.

Chem. Pharm. Bull.

Chem. Pharm. Bull.

Chem. Pharm. Bull.

Chem. Pharm. Bull.

Khim. Prir. Soedin.

Khim. Prir. Soedin.

Jongnam Taehakkyo Nonmunjip Chayon Kwahak Pyon

Chem. Pharm. Bull.

Bull. Chem. Soc. Jpn.

Fitoterapia

Aust. J. Biol. Sci.

J. Chem. Res. (Synop.)

Tennenyuki Kagobutsu Toronkai Koen Yoshishu

Org. Magn. Reson.

S. Afr. J. Chem.

Chem. Letters

J. Org. Chem.

Chem. Pharm. Bull.

Org. Magn. Reson.

Gazz. Chim. Ital.

Bio-org. Chem.

review
Triterpenoids