Biologically active pentacyclic triterpenes and their current medicine signification
TL;DR: The therapeutic potential of three pentacyclic triterpenes (lupeol, betuline and betulinic acid) is discussed in this paper, which is a very promising compound.
About: This article is published in Journal of Applied Biomedicine.The article was published on 2003-03-31 and is currently open access. It has received 234 citations till now. The article focuses on the topics: Pentacyclic Triterpenes & Betulinic acid.
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TL;DR: Preclinical studies conducted to determine the utility of Lupeol as a therapeutic and chemopreventive agent for the treatment of inflammation and cancer suggest that it is a multi-target agent with immense anti-inflammatory potential targeting key molecular pathways.
490 citations
TL;DR: Evidence is provided for studying the chemical composition of supercritical carbon dioxide extracts of pitaya peel and their biological activity and the activities of their main components are studied.
Abstract: Hylocereus polyrhizus and Hylocereus undatus are two varieties of the commonly called pitaya fruits, and pitaya fruits have gained popularity in many countries all over the world. However, studies on chemical composition and the nutritional quality of pitaya flesh peel are limited. Extracts of pitaya (H. polyrhizus and H. undatus) peel were extracted by supercritical carbon dioxide extraction, and analyzed by gas chromatography–mass spectrometry analysis. Their cytotoxic and antioxidant activities were investigated. The main components of H. polyrhizus extract were β-amyrin (15.87%), α-amyrin (13.90%), octacosane (12.2%), γ-sitosterol (9.35%), octadecane (6.27%), 1-tetracosanol (5.19%), stigmast-4-en-3-one (4.65%), and campesterol (4.16%), whereas H. undatus were β-amyrin (23.39%), γ-sitosterol (19.32%), and octadecane (9.25%), heptacosane (5.52%), campesterol (5.27%), nonacosane (5.02%), and trichloroacetic acid, hexadecyl ester (5.21%). Both of the two extracts possessed good cytotoxic activities against PC3, Bcap-37, and MGC-803 cells (IC50 values ranging from 0.61 to 0.73 mg/mL), and the activities of their main components were also studied. Furthermore, these extracts also presented some radical scavenging activities, with IC50 values of 0.83 and 0.91 mg/mL, respectively. This paper provides evidence for studying the chemical composition of supercritical carbon dioxide extracts of pitaya peel and their biological activity.
348 citations
Cites background from "Biologically active pentacyclic tri..."
...They have been shown to possess several medicinal properties including anticancer and anti-HIV activities [11]....
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TL;DR: The major conclusion is that larger-scale use of terpenoids in modern medicine should be taken into consideration.
Abstract: Terpenes are naturally occurring substances produced by a wide variety of plants and animals. A broad range of the biological properties of terpenoids is described, including cancer chemopreventive effects, antimicrobial, antifungal, antiviral, antihyperglycemic, anti-inflammatory, and antiparasitic activities. Terpenes are also presented as skin penetration enhancers and agents involved in the prevention and therapy of several inflammatory diseases. Moreover, a potential mechanism of their action against pathogens and their influence on skin permeability are discussed. The major conclusion is that larger-scale use of terpenoids in modern medicine should be taken into consideration.
332 citations
TL;DR: Current and future applications of birch bark natural products in pharmaceuticals, cosmetics, and dietary supplements for the prevention and treatment of cancer, HIV, and other human pathogens are reviewed.
307 citations
TL;DR: The chemical composition, abundance and biological activities of triterpenoids occurring in cuticular waxes of some economically important fruits, like apple, grape berry, olive, tomato and others, are described in this review.
Abstract: The health benefits associated with a diet rich in fruit and vegetables include reduction of the risk of chronic diseases such as cardiovascular disease, diabetes and cancer, that are becoming prevalent in the aging human population. Triterpenoids, polycyclic compounds derived from the linear hydrocarbon squalene, are widely distributed in edible and medicinal plants and are an integral part of the human diet. As an important group of phytochemicals that exert numerous biological effects and display various pharmacological activities, triterpenoids are being evaluated for use in new functional foods, drugs, cosmetics and healthcare products. Screening plant material in the search for triterpenoid-rich plant tissues has identified fruit peel and especially fruit cuticular waxes as promising and highly available sources. The chemical composition, abundance and biological activities of triterpenoids occurring in cuticular waxes of some economically important fruits, like apple, grape berry, olive, tomato and others, are described in this review. The need for environmentally valuable and potentially profitable technologies for the recovery, recycling and upgrading of residues from fruit processing is also discussed.
196 citations
Cites background from "Biologically active pentacyclic tri..."
...…antiatherosclerotic, woundhealing, anticoagulant and anticarcinogenic properties, combined with relatively low toxicity (Akihisa et al. 2001; Patočka 2003; Liu 2005; Dzubak et al. 2006; Sun et al. 2006; Jäger et al. 2009; Kuo et al. 2009; Rezanka et al. 2009; Wolska et al. 2010; Bishayee…...
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...Triterpenoids have been shown to possess numerous biological activities and display various pharmacological effects such as antiinflammatory, antiulcer, antibacterial, antiviral (including anti-HIV), hepatoprotective, immunomodulatory, hypolipidemic and cholesterol-lowering, antiatherosclerotic, woundhealing, anticoagulant and anticarcinogenic properties, combined with relatively low toxicity (Akihisa et al. 2001; Patočka 2003; Liu 2005; Dzubak et al. 2006; Sun et al. 2006; Jäger et al. 2009; Kuo et al. 2009; Rezanka et al. 2009; Wolska et al. 2010; Bishayee et al. 2011; Thoppil and Bishayee 2011)....
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References
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TL;DR: As a result of bioassay–guided fractionation, betulinic acid, a pentacyclic triterpene, was identified as a melanoma–specific cytotoxic agent and antitumour activity was mediated by the induction of apoptosis.
Abstract: As a result of bioassay-guided fractionation, betulinic acid, a pentacyclic triterpene, was identified as a melanoma-specific cytotoxic agent. In follow-up studies conducted with athymic mice carrying human melanomas, tumour growth was completely inhibited without toxicity. As judged by a variety of cellular responses, antitumour activity was mediated by the induction of apoptosis. Betulinic acid is inexpensive and available in abundant supply from common natural sources, notably the bark of white birch trees. The compound is currently undergoing preclinical development for the treatment or prevention of malignant melanoma.
829 citations
"Biologically active pentacyclic tri..." refers background in this paper
...The compound was also tested in mice infected with human melanoma (Pisha et al. 1995)....
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TL;DR: The data support further preclinical studies of betulinic acid not confined to melanoma and neuroectodermal tumors independently of p53 status, and support the antineoplastic activity of this drug.
458 citations
"Biologically active pentacyclic tri..." refers background in this paper
...Being selective towards melanoma cells it does not affect normal cells (Zuco et al. 2002)....
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...…be expected that betulinic acid will be shortly accepted as a candidate for adjuvant therapy in the treatment of human melanoma (Rieber et al. 1998; Zuco et al. 2002) Betulinic acid and its derivatives have been discovered as a new class of compounds that seem to protect the cells of human…...
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TL;DR: The excellent tolerability of aescin in the clinic indicates this treatment is of definite clinical benefit in patients with clinical conditions resulting in chronic venous insufficiency, haemorrhoids or peripheral oedema formation.
364 citations
"Biologically active pentacyclic tri..." refers background in this paper
...…many free and sugar-bound triterpenes, such as oleanolic acid and its glycosides isolated from marigold (Calendula officinalis) (Szakiel et al. 1995) , escin from horsechestnut (Aesculus hippocastanum) (Sirtori 2001) or glycyrrhizin from licorice (Glycyrrhiza glabra) (Olukoga and Donaldson 2000)....
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283 citations
"Biologically active pentacyclic tri..." refers background in this paper
...Dihydrobetulinic acid was found to be the most potent HIV replication inhibitor (Kashiwada et al. 1996; Hashimoto et al. 1997)....
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Journal Article•
TL;DR: Perturbance of mitochondrial function constitutes a central coordinating event in drug-induced cell death and is demonstrated to be a critical role for mitochondria in apoptosis.
Abstract: Apoptosis mediated by anticancer drugs may involve activation of death-inducing ligand/receptor systems such as CD95 (APO-1/Fas), cleavage of caspases, and perturbance of mitochondrial functions. We investigated the sequence of these events in SHEP neuroblastoma cells transfected with Bcl-2 or Bcl-X(L) using two different drugs, namely, doxorubicin (Doxo), which activates the CD95/CD95 ligand (CD95-L) system, and betulinic acid (Bet A), which does not enhance the expression of CD95 or CD95-L and which, as shown here, directly targets mitochondria. Apoptosis induced by both drugs was inhibited by Bcl-2 or Bcl-X(L) overexpression or by bongkrekic acid, an agent that stabilizes mitochondrial membrane barrier function, suggesting a critical role for mitochondria. After Doxo treatment, enhanced CD95/CD95-L expression and caspase-8 activation were not blocked by Bcl-2 or Bcl-X(L) and were found in cells with a mitochondrial transmembrane potential (delta psi(m)) that was still normal (delta psi(m)high cells). In marked contrast, after Bet A treatment, caspase-8 activation occurred in a Bcl-2- or Bcl-X(L)-inhibitable fashion and was confined to cells that had lost their delta psi(m) (delta psi(m)low cells). Mitochondria from cells treated with either Doxo or Bet A induced cleavage of both caspase-8 and caspase-3 in cytosolic extracts. Thus, caspase-8 activation may occur upstream or downstream of mitochondria, depending on the apoptosis-initiating stimulus. In contrast to caspase-8, cleavage of caspase-3 or poly(ADP-ribose)polymerase was always restricted to delta psi(m)low cells, downstream of the Bcl-2- or Bcl-X(L)-controlled checkpoint of apoptosis. Cytochrome c, released from mitochondria undergoing permeability transition, activated caspase-3 but not caspase-8 in a cell-free system. However, both caspases were activated by apoptosis-inducing factor, indicating that the mechanism of caspase-8 activation differed from that of caspase-3 activation. Taken together, our findings demonstrate that perturbance of mitochondrial function constitutes a central coordinating event in drug-induced cell death.
250 citations