Chemopreventive Agents
David E. Thurston, Ilona Pysz in Chemistry and Pharmacology of Anticancer Drugs, 2021
Diterpenes (also called diterpenoids) are a highly diverse C20-subclass of terpenoids comprised of four isoprene units. Diterpenes are biosynthesized by animals, plants, and fungi, and form the basis for biologically essential compounds including retinal, retinol, and phytol, as well as compounds with reported chemopreventive activity such as cafestol and kahweol (Figure 12.29), which are described below. Structures of the diterpenoids cafestol and kahweol.
Terpenes and Terpenoids
William J. Rea, Kalpana D. Patel in Reversibility of Chronic Disease and Hypersensitivity, Volume 4, 2017
The essential oils of plants contain an abundance of monoterpenes, sesquiterpenes, and diterpenes. The most common structural monoterpenes are derivatives of geraniol, the main constituent of geranium oil. Menthol is the chief component of peppermint oil. d-Limonene composes over 90% of lemon oil. α-Pinene is found in the oil of rosemary. Camphor is the main component of sage oil. Iridoids are interesting monoterpenes, which have been isolated from ants. Monoterpenes are used in flavor and perfume industries because of their attractive odors, high volatilities, and low molecular weights.78 Most of these are synthesized and usually trigger symptoms in individuals with chemical sensitivity. Several monoterpenes are found in turpentine. The rosin acids are diterpenes. Vitamin A is the best-known open-chain diterpene. The triterpenes that are obtainable from shark liver oil may be converted to cholesterol and many other steroids. The carotenoid pigments are the best-known tetraterpenes. The function of terpenes in plants, which has been previously described as being a protectant for heat and other organisms, is not always so clear. Terpenes sometimes possess toxic properties that link to the protection of the species. Animals do not eat some types of terpenes. The same protective properties appear to trigger and exacerbate symptoms in individuals with chemical sensitivity.
Terpenes: A Source of Novel Antimicrobials, Applications and Recent Advances
Mahendra Rai, Chistiane M. Feitosa in Eco-Friendly Biobased Products Used in Microbial Diseases, 2022
Diterpenes are naturally found chemical constituents containing the C20H32molecular formula and an important class of terpene with a broad spectrum of interesting biological properties (Yang et al. 2012). About 60 previously reported terpenoids were examined for their Minimum Inhibitory Concentration (MIC) against E. coli, S. aureus, C. albicans and P. aeruginosa. The terpenoids were divided into five groups to estimate their activity patterns. Hydrogen bond was found to be the determinant factor for the positive antimicrobial potential, while low water solubility was found to be responsible for antimicrobial inactivity (Griffin et al. 1999). The probable mechanism of action of diterpenes for antimicrobial activity was that they restricted the microbial oxygen uptake and oxidative phosphorylation. Another study reported that ent-kaurane and ent-pimarane diterpene derivatives have ability to inhibit the growth of pathogens of dental caries. The antibacterial potential was confirmed by MIC values (2–10 mg mL–1) (Ambrosio et al. 2006). Róz˙alski et al. (2007) extracted a diterpenoid salvipisone from the hairy roots of Salvia sclarea L. which prevented the cell adherence and development of biofilm of S. epidermidis and S. aureus (Rózalski et al. 2007).
Phytol Down-Regulates Expression of Some Cancer Stem Cell Markers and Decreases Side Population Proportion in Human Embryonic Carcinoma NCCIT Cells
Published in Nutrition and Cancer, 2021
Sara Soltanian, Mahboubeh Sheikhbahaei, Mahsa Ziasistani
Diterpenes are a class of chemical compounds which are biosynthesized by plants, animals and fungi (19). Diterpenes form the basis for two biologically important compounds, retinol (Vitamin A1) and phytol (20). It was shown, retinol and its analogue (retinoic acid, RA), can target and eradicate stem-like tumor cells by differentiation induction of CSCs to nonmalignant cells. Therefore, efficacy of RA to reduce proliferation and tumorigenicity of CSCs and reverse malignant progression and migration in various cancers has been demonstrated (21–26). Phytol is an acyclic diterpene alcohol that derive from metabolism of chlorophyll in some plants (27). Although, some biological activities such as anticancer (28–31), anti-microbial (32) and anti-inflammatory (33) effects were reported for phytol, its potential to eliminate CSCs and downregulate CSCs markers has not been explored until now.
Design, biological evaluation, and molecular modelling insights of cupressic acid derivatives as promising anti-inflammatory agents
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2023
Amal F. Soliman, Diaaeldin M. Elimam, Fardous F. El-Senduny, Manal A. Alossaimi, Mubarak Alamri, Fatma M. Abdel Bar
Since ancient times, plant-derived products have been used to reduce inflammation or inflammation-associated conditions 1. Araucaria trees are coniferous trees grown as ornamental plants, which upon injury, exudate an oleogum resin that protects against invading pathogens2. Few studies reported the biological activities of the oleogum resin of Araucaria heterophylla; mainly as an antiulcerogenic, cytotoxic, and antibacterial agent3. The oleogum resins, containing mainly labdane diterpenes, have been employed topically to treat bruises and dermal inflammation4. Diterpenes are natural products known to exert potent anti-inflammatory activities through various mechanisms4. Labdane-diterpenes were reported to exhibit anti-inflammatory activities in several animal and cell-based bioassays3,4. In addition, the analgesic and anti-inflammatory effects of semisynthetic terpene derivatives were previously described4. Cupressic acid derivatives are the major labdane diterpenes of the oleogum resin of Araucaria heterophylla. Previous studies by our research group reported the antiprotozoal activity of resin-isolated cupressic acids and the anti-inflammatory activities of their microbially transformed metabolites2,5.
The use of terpenes and derivatives as a new perspective for cardiovascular disease treatment: a patent review (2008–2018)
Published in Expert Opinion on Therapeutic Patents, 2019
Eric Aian P. Silva, Jéssica S. Carvalho, Adriana G. Guimarães, Rosana de S.S. Barreto, Márcio R.V. Santos, André S. Barreto, Lucindo J. Quintans-Júnior
They originate biosynthetically in the mevalonate pathway from C5 components, known as isoprenoids, sequentially joined as (C5)n structures. Therefore, they are classified by their number of isoprenoid structures as hemiterpenes (C5), monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), sesterterpenes (C25), triterpenes (C30), and tetraterpenes (C40) [11].
Related Knowledge Centers
- Chemical Compound
- Isoprene
- Mevalonate Pathway
- Retinal
- Retinol
- Terpene
- Geranylgeranyl Pyrophosphate
- Phytol
- Antimicrobial
- Anti-Inflammatory