Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase.[1] It is found in the bark of several species of plants, principally the white birch (Betula pubescens)[2] from which it gets its name, but also the ber tree (Ziziphus mauritiana), selfheal (Prunella vulgaris), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum),[3] flowering quince (Pseudocydonia sinensis, former Chaenomeles sinensis KOEHNE),[4]
rosemary,[5]
and Pulsatilla chinensis.[6]
^Chowdhury AR, Mandal S, Mittra B, Sharma S, Mukhopadhyay S, Majumder HK (July 2002). "Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives". Medical Science Monitor. 8 (7): BR254–65. PMID 12118187.
^Tan Y, Yu R, Pezzuto JM (July 2003). "Betulinic acid-induced programmed cell death in human melanoma cells involves mitogen-activated protein kinase activation". Clinical Cancer Research. 9 (7): 2866–75. PMID 12855667.
^Zuco V, Supino R, Righetti SC, Cleris L, Marchesi E, Gambacorti-Passerini C, Formelli F (January 2002). "Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells". Cancer Letters. 175 (1): 17–25. doi:10.1016/S0304-3835(01)00718-2. PMID 11734332.
^Gao H, Wu L, Kuroyanagi M, Harada K, Kawahara N, Nakane T, Umehara K, Hirasawa A, Nakamura Y (November 2003). "Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells". Chemical & Pharmaceutical Bulletin. 51 (11): 1318–21. doi:10.1248/cpb.51.1318. PMID 14600382. (Chaenomeles sinensis KOEHNE is now named Pseudocydonia sinensis)
^Abe F, Yamauchi T, Nagao T, Kinjo J, Okabe H, Higo H, Akahane H (November 2002). "Ursolic acid as a trypanocidal constituent in rosemary". Biological & Pharmaceutical Bulletin. 25 (11): 1485–7. doi:10.1248/bpb.25.1485. PMID 12419966.
^Ji ZN, Ye WC, Liu GG, Hsiao WL (November 2002). "23-Hydroxybetulinic acid-mediated apoptosis is accompanied by decreases in bcl-2 expression and telomerase activity in HL-60 Cells". Life Sciences. 72 (1): 1–9. doi:10.1016/S0024-3205(02)02176-8. PMID 12409140.
Betulinicacid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a...
Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinicacid. It is widely distributed in food and plants...
bioactive derivatives, such as experimental antitumor agents. Betulinicacid Moronic acid Oleanolic acid CID 64945 from PubChem Constituents of Mirabilis jalapa...
derivative of the related triterpenoid betulinicacid, is under development as an anti-HIV drug; however, moronic acid has shown better antiviral profiles...
as the (R)-enantiomer, but racemizes at 300 °C. When warmed with mineral acid, limonene isomerizes to the conjugated diene α-terpinene (which can also...
particular note among these are sugar acids such as glucuronic acid and galacturonic acid, which are oxidized forms of glucose and galactose. Cardenolide...
ellagitannin, pedunculagin. Regiolone has been isolated with juglone, betulinicacid and sitosterol from the stem bark of J. regia. The fruits of trees in...
and monotropitoside), 17 amino acids including glutamic acid, as well as minerals, enzymes, proteins, betulinicacid and betulin, antioxidants, sugar...
PMID 19742422. Liu, Jie (December 1995). "Pharmacology of oleanolic acid and ursolic acid". Journal of Ethnopharmacology. 49 (2): 57–68. doi:10.1016/0378-8741(95)90032-2...
hydrolysis with hydrochloric acid, 4-aminophenol reacts in ammonia solution with a phenol derivate, e.g. salicylic acid, to form an indophenol dye under...
fruits contain phytochemicals, such as catechin, gallocatechin and betulinicacid. While many species of Diospyros bear fruit inedible to humans or only...
categories, such as carotenoids and polyphenols, which include phenolic acids, flavonoids, stilbenes or lignans. Flavonoids can be further divided into...
plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and...
is similar, as are the enzymes involved. Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. This is then condensed...
betanin, the simplest betacyan. In addition, betalamic acid reacts spontaneously with various amino acids or amines to form yellow-orange colored betaxanthins...
absorption A slowing of bile acid absorption in the ileum so bile acids escape through to the cecum Altered or increased bile acid metabolism in the cecum...
resist polymerization (low ceiling temperatures) but are susceptible to acid-induced carbocation formation. Selected terpenes Limonene, a monoterpene...
pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, unrelated biosynthesis...
the glial cell and degraded by fatty acid amide hydrolase (FAAH), which cleaves anandamide into arachidonic acid and ethanolamine or monoacylglycerol...
Gloria; Śliwiński, Tomasz (August 2021). "Enhanced Accumulation of BetulinicAcid in Transgenic Hairy Roots of Senna obtusifolia Growing in the Sprinkle...
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