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Hydrastis canadensis (Goldenseal) and Lawsonia inermis (Henna)
Published in Azamal Husen, Herbs, Shrubs, and Trees of Potential Medicinal Benefits, 2022
Md. Mizanur Rahaman, William N. Setzer, Javad Sharifi-Rad, Muhammad Torequl Islam
The major chemical compounds of goldenseal are found in theroots and rhizomes (Pengelly et al., 2012). The plant contains the isoquinoline alkaloids, such as hydrastine, berberine, berberastine, hydrastinine, tetrahydroberberastine, canadine, and canalidine (Weber et al., 2003).The three major alkaloids are berberine, hydrastine, and canadine (Pengelly et al., 2012). Hydrastis canadensis has been indicated to contain isoquinoline alkaloids inthe ranges of 1.5–4% hydrastine, 0.5–6% berberine, and 2–3% berberastine (Hamon, 1990). One study also found the compound 8-oxotetrahydrothalifendine (Gentry et al., 1998).
An Alternative Approach for Anti-Alzheimer’s Compounds from Plant Extracts
Published in Atanu Bhattacharjee, Akula Ramakrishna, Magisetty Obulesu, Phytomedicine and Alzheimer’s Disease, 2020
G. K. Pratap, Manjula Shantaram
Alkaloids constitute an important class of structurally diverse plant compounds that have a nitrogen atom in the heterocyclic ring, and are derived from amino acids. The term ‘alkaloids’ was coined by the German chemist Carl F. W. Meissner in 1819 and the word is derived from the Arabic name al-qali that is related to the plant from which soda was first isolated (Howes et al., 2003; Rinaldia et al., 2017). The alkaloid compounds are low-molecular-weight structures and make up about 20% of plant-based secondary metabolites and they have influenced human history profoundly, due to their wide range of physiological effects on animals and pharmacological properties on humans, such as anticancer and antibiotic properties, along with their potential exploitation as narcotics, stimulants, and poisons (Kaur and Arora, 2018). About 12,000 alkaloids have been isolated from the plant kingdom. Depending upon their biosynthetic precursor and heterocyclic ring system, alkaloids have been classified into different categories, including indole, piperidine, tropane, purine, imidazole, pyrrolidine, pyrrolizidine, quinolizidine, and isoquinoline alkaloids (Ramakrishna et al., 2012; Aniszewski, 2007; Bribi, 2018). They are classified using various signatures, such as natural source or chemical nature. The biological activity of alkaloids, like cytotoxic and CNS activity, and toxicity against herbivores, include anticarcinogenic, antibacterial, antifungal, and antiviral properties in vertebrates (Wirasathien et al., 2006; Padma Kumar et al., 2009; Ramakrishna et al., 2011).
Pharmacological actions of chemical constituents
Published in C. P. Khare, Evidence-based Ayurveda, 2019
In accordance with structural forms, the alkaloids are classified in diterpenoid alkaloids (14-O-acetylneoline, 14-O-veratroylpseudaconine, and hypaconitine), indole alkaloids (fumigaclavine C and isatin), indolonaphthyridine alkaloids (nigakinone), indoloquinazoline alkaloids (tryptanthin), isoquinoline alkaloids (berberine, boldine, cavidine, coptisine derivatives, EM012, papaverine, sanguinarine, sinomenine, tetrahydrocoptisine, and tetrandrine), phenanthroindolizidine alkaloids (NK-007 and W-8), piperidine alkaloids (piperine), purine alkaloids (caffeine), quinoline alkaloids (skimmianine) and quinolizidine alkaloids (matrine, oxymatrine, sophocarpine, and sophoridine).
Integrative Management of Pancreatic Cancer (PDAC): Emerging Complementary Agents and Modalities
Published in Nutrition and Cancer, 2022
Mustafa B. A. Djamgoz, Valerie Jentzsch
This is an isoquinoline alkaloid extracted from a variety of natural herbs (152). Its molecular targets include upregulation of tumor suppressor genes, activation of AMPK and downregulation of matrix metalloproteinase production, leading to decreased cellular proliferation and invasion (153). In vitro, berberine induced apoptosis and suppressed the CSC population in PDAC cell lines even more effectively than gemcitabine (154, 155). Another study showed that berberine inhibited PDAC cell viability by dysregulating cellular energetics by targeting citrate metabolism (156). In vivo, also, berberine could reduce tumor growth in mouse models of PDAC (157). In addition, berberine demonstrated insulin-regulating properties and could suppress PDAC also indirectly (158). Consistent with this, it could potentiate the therapeutic effect of metformin (see section 5.2) (159).
Mechanism-based inactivation of cytochrome P450 enzymes by natural products based on metabolic activation
Published in Drug Metabolism Reviews, 2020
Tingting Zhang, Jinqiu Rao, Wei Li, Kai Wang, Feng Qiu
Noscapine (Table 5), a naturally occurring isoquinoline alkaloid obtained from Papaver somniferum L., is widely considered to be a safe oral antitussive (Chen et al. 2015). Nevertheless, several clinical DDI reports related to noscapine showed that a serious adverse drug response (bleeding or increased International Normalized Ratio (INR)) happened when warfarin was coadministered (Ohlsson et al. 2008; Scordo et al. 2008). Noscapine also markedly increased the losartan phenotypic index after multiple dosing in twelve healthy subjects, indicative of CYP2C9 inhibition (Rosenborg et al. 2010). Further study showed that noscapine was a mechanism-based inhibitor of CYP2C9 and metabolic activation of the MDP section of its structure, which has been clarified in the above description ‘2.2 Lignans’ could be responsible for this effect (Zhang et al. 2013).
Application of a DSS colitis model in toxicologically assessing norisoboldine
Published in Toxicology Mechanisms and Methods, 2020
Mincong Huang, Jie Su, Zhaohuan Lou, Feng Xie, Wei Pan, Zhengbiao Yang, Liqiang Gu, Fang Xie, Zhiwei Xu, Lili Zhang, Fang Liu, Huimin Lai, Lijiang Zhang, Nengming Lin
This different presentation of NOR toxicity may have resulted from the different cellular functions or different receptor levels between the healthy mice and the DSS colitis mice. NOR, an isoquinoline alkaloid with anti-inflammatory effects, can induce cell apoptosis in vitro (Luo et al. 2014). In the DSS colitis mice, NOR (30 mg/kg and 90 mg/kg) increased the number of TUNEL-positive cells as well as the pro-inflammatory cytokine levels of TNF and IFN-γ in vivo. TUNEL is an immune enzymatic assay that is used to detect DNA fragmentation by labeling the terminal ends of nucleic acids exposed during programed cell death (PCD) (Radi et al. 2018). Apoptosis, one familiar form of PCD, has long been regarded as a noninflammatory or even anti-inflammatory mode of cell death, but recent studies suggest that certain physiological inducers of apoptosis, such as TNF and Fas, can promote the release of inflammatory cytokines. DSS can cause TNF and IFN-γ release, which may result in apoptosis (Davidovich et al. 2014). Thus, we speculated that a massive dose of NOR may increase the proinflammatory cytokine levels and aggravate the symptoms in DSS colitis mice and possibly cause animal deaths due to the excessive PCD.