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The Role of Plant-Based Natural Compounds in Inflammation
Published in Namrita Lall, Medicinal Plants for Cosmetics, Health and Diseases, 2022
Marcela Dvorakova, Premysl Landa, Lenka Langhansova
Triterpenes (Figure 22.6) are composed of three terpene units and include steroids, bile acids and saponins (triterpene glycosides). Among anti-inflammatory triterpenes, boswellic acids (BAs) have long been known as non-competitive and non-redox 5-LOX inhibitors (Safayhi et al., 1992). BAs are the main components of an anti-inflammatory remedy, frankincense, a resin obtained from the bark of Boswellia species, such as Boswellia serrata Roxb.ex Colebr., B. sacra Fluck (Figure 22.7A–B), B. carterii Birdw, B. papyrifera Hochst. or B. frereana Birdw. (Verhoff et al., 2014). The main structural features of BAs, important for their 5-LOX activity, include a pentacyclic triterpene ring structure, hydrophilic groups at the C4 position of the A-ring and an 11-keto group (Sharma and Jana, 2020). Especially, 3-O-acetyl-11-keto-β-boswellic acid (AKBA) has been extensively studied over the years and its reported IC50 values for 5-LOX inhibition range between 8 µM and 50 µM in cell-free assays and between 1.5 µM and 15 µM in cell-based assays (Werz, 2007).
Ursolic Acid: A Pentacyclic Triterpene from Plants in Nanomedicine
Published in Mahfoozur Rahman, Sarwar Beg, Mazin A. Zamzami, Hani Choudhry, Aftab Ahmad, Khalid S. Alharbi, Biomarkers as Targeted Herbal Drug Discovery, 2022
Monalisha Sen Gupta, Md. Adil Shaharyar, Mahfoozur Rahman, Kumar Anand, Imran Kazmi, Muhammad Afzal, Sanmoy Karmakar
Different analytical methodologies have been developed for triterpenes, with high selectivity, sensitivity, accuracy, and precision. Pharmacokinetic studies constitute an important stage during the development of new medicines. Discerning the disposition process (i.e., absorption, distribution, and elimination) of new drug candidates facilitates selecting the most appropriate administration route and best dose regimen. The pharmacokinetic parameters of UA in rats after an oral administration suggested rapid absorption, but plasmatic concentrations were extremely low (Liao et al., 2005). Additionally, a lower dose like 10 mg/kg of UA presented rapid absorption with distribution primarily through blood-supplied tissues, such as the lungs, spleen, and liver. The half-life of UA in the plasma was less than 1 h, indicating rapid elimination (Chen et al., 2011). The study of safety and pharmacokinetic parameters after administering an ascending oral dose of UA shows low and variable UA bioavailability due to the poor water solubility of this compound. This trait led to decreased intestinal absorption and rapid elimination through gut wall/liver metabolism (Hirsh et al., 2014).
Heterocyclic Drugs from Plants
Published in Rohit Dutt, Anil K. Sharma, Raj K. Keservani, Vandana Garg, Promising Drug Molecules of Natural Origin, 2020
Debasish Bandyopadhyay, Valeria Garcia, Felipe Gonzalez
Bruceantin (Figure 8.22) is a triterpene quassinoid antineoplastic antibiotic, biosynthesized by the plant Brucea antidysenterica (Simaroubaceaefamily) (Bruceantin, 2018). A triterpene is a compound having six isoprene units (C30) (Agra et al., 2015). Triterpenes like bruceantin have the ability to inhibit cell migration, cell proliferation, and also collagen deposition. Bruceantin has both antiamoebic and antimalarial activities. An antineo-plastic antibiotic is a type of anticancer drug which blocks cell growth by disrupting the genetic material, DNA in the cell (Schools & Health, 2018).
Centella asiatica prevents D-galactose-Induced cognitive deficits, oxidative stress and neurodegeneration in the adult rat brain
Published in Drug and Chemical Toxicology, 2022
Zeba Firdaus, Neha Singh, Santosh Kumar Prajapati, Sairam Krishnamurthy, Tryambak Deo Singh
Centella asiatica (CA), often referred to as Mandookaparni or Gotu kola is a perennial herbaceous creeper found in marshy areas up to the height of 1800 m throughout India. The entire plant has therapeutic significance. CA is an effective herb for the central nervous system (CNS) and is thought to increase intelligence and memory (Kapoor 1990). This herb is used often against anxiety, inflammation and depression (Firdaus and Singh 2020). The phytoconstituents of CA include a large number of compounds, but triterpenes, alkaloids and flavonoids are the major active constituents present in CA extract (Chiroma et al. 2017). Moreover, it contains a small amount of essential oil, flavonoids such as quercetin, kaempferol, and some phytosterol such as campesterol, sitosterol and stigmasterol (Oyedeji and Afolayan 2005). Most of the pharmacological effects are predominantly due to the presence of triterpenes (Srivastava et al. 1997). The triterpenes from CA are chiefly pentacyclic triterpenic acids that include asiatic acid, asiaticoside, madecassic acid, madecassoside, brahmoside, brahmic acid, brahminoside and other triterpenic glycosides of CA of the ursane or oleanane-type (Hashim et al. 2011). These phytochemicals can react with free radicals and pause the further propagation of the free radical chain reaction and thus function as a free radical scavenger (Tsao 2010).
Boswellic acids: privileged structures to develop lead compounds for anticancer drug discovery
Published in Expert Opinion on Drug Discovery, 2021
Hidayat Hussain, Iftikhar Ali, Daijie Wang, Faruck L. Hakkim, Bernhard Westermann, Luay Rashan, Ishtiaq Ahmed, Ivan R. Green
Triterpenes having six isoprene units are quite widespread and are found in many natural sources dating from ancient times. It was later determined that these compounds are synthesized via a cascade cyclization of squalene in many plants. Furthermore, over 20,000 triterpenes have been reported from various natural sources and interestingly, most of them are found in their free form while others occur as triterpene glycosides (saponins) [1–4]. Additionally, triterpenes are widespread in various medicinal plants and in particular, in their resin, fruits, leaves, seeds, and bark of the specific herbs. Furthermore, on the basis of the number of isoprene units, triterpenoids can be classified as acyclic, mono-, bi-, tri-, tetra- and pentacyclic. On the other hand, among the triterpenoids, tetracyclic triterpenes (viz., dammaranes, protostanes, euphanes, and cycloartanes) and pentacyclic triterpenes (viz., ursanes, oleananes, gammaceranes, hopanes, and lupanes) are the most studied of the triterpenes [1–4].
The beneficial effects of Ganoderma lucidum on cardiovascular and metabolic disease risk
Published in Pharmaceutical Biology, 2021
Sze Wa Chan, Brian Tomlinson, Paul Chan, Christopher Wai Kei Lam
Terpenes are a large and diverse group of naturally occurring compounds derived from the branched C5 carbon skeleton of isoprene. Triterpenes are a subclass of terpenes and are derived from squalene, a C30 hydrocarbon (Abdullah et al. 2012). They can be classified based on the number of cyclic structures making up the compounds. Up to now, more than 150 triterpenes have been identified from the spores, fruiting bodies, and mycelia of G. lucidum (Xia et al. 2014; Baby et al. 2015). The methods of extraction of triterpenes usually involve methanol, ethanol, chloroform, ether, acetone, or a mixture of these solvents. The extracts can be further purified by various separation methods such as normal and reverse-phase high-performance liquid chromatography (HPLC) (Chen et al. 1999). The majority of triterpenes identified are ganoderic acids and lucidenic acids; other important triterpenes include ganodermic acids, ganoderals, and ganoderiols (Wachtel-Galor et al. 2011). The strong bitterness of G. lucidum originates from the triterpenoid compounds and the bitterness depends on the strain, cultivation conditions and manufacturing processes (Seo et al. 2009). Triterpenoids have been reported to exhibit various biological activities including anti-hypertensive, lipid-lowering, anti-acetylcholinesterase, antioxidant, and anticancer activities, etc. (Abdullah et al. 2012; Chen et al. 2017).