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Saponins, also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort, a flowering plant, the soapbark tree and soybeans. They are used in soaps, medicinals, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages. Structurally, they are glycosides, sugars bonded to another organic molecule, usually a steroid or triterpene, a steroid building block. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin, licorice flavoring; and quillaia, a bark extract used in beverages.
Bacopa monnieri is a perennial, creeping herb native to the wetlands of southern and Eastern India, Australia, Europe, Africa, Asia, and North and South America. It is known by the common names water hyssop, waterhyssop, brahmi, thyme-leafed gratiola, herb of grace, and Indian pennywort. Bacopa monnieri is used in Ayurveda. In 2019, the US Food and Drug Administration (FDA) warned manufacturers of dietary supplement products containing Bacopa monnieri against making illegal and unproven claims that the herb can treat various diseases.
Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast plant steroids are produced via cycloartenol.
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.
Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.
Beesia is a genus of flowering plants in the buttercup family. It was named in 1915 after the plant nursery firm Bees of Chester, who financed the plant hunting trips of George Forrest and Frank Kingdon-Ward in China.
Gymnemic acids are a class of chemical compounds isolated from the leaves of Gymnema sylvestre (Asclepiadaceae). They are anti-sweet compounds, or sweetness inhibitors. After chewing the leaves, solutions sweetened with sugar taste like water.
Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as triterpenes, formally derived from cucurbitane, a triterpene hydrocarbon – specifically, from the unsaturated variant cucurbit-5-ene, or 19(10→9β)-abeo-10α-lanost-5-ene. They often occur as glycosides. They and their derivatives have been found in many plant families, in some mushrooms and even in some marine mollusks.
Karaviloside is any of several related cucurbitane triterpenoid glycosides found in bitter melon vine. They include:
Cucurbitane is a class of chemical compounds with formula C
30H
54. It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane, from which it differs by the formal shift of a methyl group from the 10 to the 9β position in the standard steroid numbering scheme.
Hemslecin is any of several compounds obtained from plants of the genus Hemsleya, which are used in Asian folk medicine. They are triterpene derivatives, specifically with the cucurbitane skeleton, related to cucurbitacin F.
Esculeoside A is a spirosolane-type glycoside with the molecular formula C58H95NO29. The structure of this product is 3-Ο-β-lycotetraosyl (22S,23S,25S)-23-acetoxy-3β,27-dihydroxy-5α-spirosolane 27-Ο-β-D-glucopyranoside. Fujiwara and colleagues were the first to isolate esculeoside A from the ripe fruit of the Cherry tomato in 2002. Esculeoside A, along with many other steroidal alkaloid glycosides, have been shown to possess cytotoxic activity that could result in a variety of potential health benefits for humans.
The molecule malabaricane and its derivatives, the malabaricanes, are triterpene and triterpenoid compounds found in various organisms. They are named after the rain forest tree Ailanthus malabarica, from which they were first isolated in 1967 by scientists at the National Chemical Laboratory in Pune, India. Later, great varieties of malabaricanes were discovered in other organisms, mostly in marine sponges such as Rhabdastrella globostellata.
Aesculus chinensis, the Chinese horse chestnut, is a tree species in the genus Aesculus found in eastern Asia.
Celastrol (tripterine) is a chemical compound isolated from the root extracts of Tripterygium wilfordii and Tripterygium regelii. Celastrol is a pentacyclic nortriterpen quinone and belongs to the family of quinone methides. In mice, celastrol is an NR4A1 agonist that alleviates inflammation and induces autophagy. Also in mice, celastrol increase expression of IL1R1, which is the receptor for the cytokine interleukin-1 (IL-1). IL1R1 knock-out mice exposed to celastrol exhibit no leptin-sensitizing or anti-obesity effect.
Bacoside A is a mixture of chemical compounds, known as bacosides, isolated from Bacopa monnieri. Its major constituents include the saponins bacoside A3, bacopaside II, jujubogenin isomer of bacopasaponin C, and bacopasaponin C. The mixture has been studied in in vitro experiments and animal models for its potential neuroprotectivity.
Tropoflavin, also known as 7,8-dihydroxyflavone, is a naturally occurring flavone found in Godmania aesculifolia, Tridax procumbens, and primula tree leaves. It has been found to act as a potent and selective small-molecule agonist of the tropomyosin receptor kinase B (TrkB), the main signaling receptor of the neurotrophin brain-derived neurotrophic factor (BDNF). Tropoflavin is both orally bioavailable and able to penetrate the blood–brain barrier. A prodrug of tropoflavin with greatly improved potency and pharmacokinetics, R13, is under development for the treatment of Alzheimer's disease.
Droplet countercurrent chromatography was introduced in 1970 by Tanimura, Pisano, Ito, and Bowman. DCCC is considered to be a form of liquid-liquid separation, which includes countercurrent distribution and countercurrent chromatography, that employs a liquid stationary phase held in a collection of vertical glass columns connected in series. The mobile phase passes through the columns in the form of droplets. The DCCC apparatus may be run with the lower phase stationary and the upper phase being introduced to the bottom of each column. Or it may be run with the upper phase stationary and the lower phase being introduced from the top of the column. In both cases, the work of gravity is allowed influence the two immiscible liquids of different densities to form the signature droplets that rise or descend through the column. The mobile phase is pumped at a rate that will allow droplets to form that maximize the mass transfer of a compound between the upper and lower phases. Compounds that are more soluble in the upper phase will travel quickly through the column, while compounds that are more soluble in the stationary phase will linger. Separation occurs because different compounds distribute differently, in a ratio called the partition coefficient, between the two phases.
Silene jenisseensis, is a species of flowering plant in the family Caryophyllaceae, native to Siberia, Far East and Mongolia.
References
- ↑ Liu, X; Liu, F; Yue, R; Li, Y; Zhang, J; Wang, S; Zhang, S; Wang, R; Shan, L; Zhang, W (2013). "The antidepressant-like effect of bacopaside I: Possible involvement of the oxidative stress system and the noradrenergic system". Pharmacology Biochemistry and Behavior. 110: 224–30. doi:10.1016/j.pbb.2013.07.007. PMID 23872136. S2CID 23612866.
- ↑ Chakravarty, AK; Sarkar, T; Masuda, K; Shiojima, K; Nakane, T; Kawahara, N (2001). "Bacopaside I and II: Two pseudojujubogenin glycosides from Bacopa monniera". Phytochemistry. 58 (4): 553–6. doi:10.1016/S0031-9422(01)00275-8. PMID 11576596.
- ↑ Hou, CC; Lin, SJ; Cheng, JT; Hsu, FL (2002). "Bacopaside III, bacopasaponin G, and bacopasides A, B, and C from Bacopa monniera". Journal of Natural Products. 65 (12): 1759–63. doi:10.1021/np020238w. PMID 12502309.
- 1 2 3 Chakravarty, AK; Garai, S; Masuda, K; Nakane, T; Kawahara, N (2003). "Bacopasides III-V: Three new triterpenoid glycosides from Bacopa monniera". Chemical & Pharmaceutical Bulletin. 51 (2): 215–7. doi: 10.1248/cpb.51.215 . PMID 12576661.
- 1 2 3 Zhou, Y; Shen, YH; Zhang, C; Su, J; Liu, RH; Zhang, WD (2007). "Triterpene saponins from Bacopa monnieri and their antidepressant effects in two mice models". Journal of Natural Products. 70 (4): 652–5. doi:10.1021/np060470s. PMID 17343408.
- 1 2 3 Zhou, Y; Peng, L; Zhang, WD; Kong, DY (2009). "Effect of triterpenoid saponins from Bacopa monniera on scopolamine-induced memory impairment in mice". Planta Medica. 75 (6): 568–74. doi:10.1055/s-0029-1185339. PMID 19214943.
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