565-63-9Relevant articles and documents
The Occurrence of Some Novel Diesters in Roman Camomile Oil
Thomas, Alan F.
, p. 2397 - 2400 (1981)
Three diols, 2-methylidene-1,3-propanediol, 2-methyl-1,3-propanediol and 1,3-butanediol, esterified on one hydroxyl group with isobutyric acid and on the other with angelic acid), have been isolated from Anthemis nobilis oil (Roman camomile) an synthesized.The presence of homologous esters is very probable.
Bioactive saponins and glycosides part 29. Acylated oleanane-type triterpene saponins: Theasaponins A6, A7, and B 5 from the seeds of Camellia sinensis
Morikawa, Toshio,Matsuda, Hisashi,Li, Ning,Li, Xian,Yoshikawa, Masayuki
, p. 2342 - 2348 (2007)
Three new acylated oleanane-type triterpene saponins, theasaponins A 6 (1), A7 (2), and B5 (3), were isolated from the saponin fraction of the seeds of the Japanese tea plant Camellia sinensis together with the known constituent foliatheasaponin III (4). The structures of the glycosides 1-3 were elucidated on the basis of spectroscopic, chemical, and physico-chemical evidence.
Chromones and coumarins from Saposhnikovia divaricata (Turcz.) Schischk. Growing in Buryatia and Mongolia and their cytotoxicity
Frolova, Tatyana S.,Ganbaatar, Jamsranjav,Petrova, Tatyana N.,Pokrovskii, Andrey G.,Radnaeva, Larisa D.,Rybalova, Tatyana V.,Shults, Elvira E.,Taraskin, Vasilii V.,Urbagarova, Bayarma M.
, (2020/07/23)
Ethnopharmacological relevance: Saposhnikovia divaricata (family Apiaceae) a traditional medicinal plant distributed in many provinces of China, is well known for the pharmaceutical value and has been used for rheumatic arthritis, and anxiety in children. Antiviral, antioxidant and antiproliferative activities were also mentioned. The application of this plant are recorded in the Chinese Medicine (CM) classical text the Shen Nong's Materia Medica (Shen Nong Ben Cao Jing). In this monograph S. divaricata (syn Radix Ledebouriella divaricata) is graded as a premium-grade herb, with their broad-spectrum of therapeutic applications for the treatment of cough, common cold, arthralgia, as well as in rheumatic disorders. Aim of the study: To isolate and identify chemical constituents (chromones and coumarins) from S. divaricata, collected in Buryatia and Mongolia and to study their in vitro anticancer activity against MEL-8, U-937, DU-145, MDA-MB-231 and ВТ-474 cell lines. Materials and methods: An 40% aqueous ethanol extract of the roots of S. divaricata was prepared and further successively fractionated by extraction with petroleum ether, diethyl ether, tert-butyl methyl ether and ethyl acetate. The obtained extracts were subjected to a series of chromatographic separations on silica gel for isolation of individual compounds. Isolated compounds were tested for their cytotoxicity with respect to model cancer cell lines using the conventional MTT assays. Results: Total of 15 individual compounds: coumarins scopoletin 2, bergapten 3, isoimperatorin 4, marmesin 5, (+)-decursinol 9, (?)-praeruptorin B 10, oxypeucedanin hydrate 11, chromones: hamaudol 6, cimifugin 7, 5-О-methylvisamminol 8, chromone glycosides: prim-O-glucosylcimifugin 12, sec-O-glucosylhamaudol 13, 4′-O-β-D-glucopyranosyl-5-О-methylvisamminol 14, 4′-O-β-D-glucopyranosylvisamminol (15) and also polyyne compound panaxinol 1 were isolated and characterized. The structure of dihydropyranocoumarin 10 was confirmed by X-ray diffraction analyses. HPLC-UV method was used for determination of the content of most abundant chromones 7, 12 and 14 in the roots of S. divaricata, collected in Mongolia. Compounds 3–11 and 13, 14 were evaluated for their cytotoxicity with respect to model cancer cell lines. All the compounds were non-toxic in the hemolysis test. Conclusion: This report about the phytochemical profiles of S. divaricata growing in Mongolia and Buryatia led to the identification of 14 compounds including coumarins and chromones. The available coumarins and chromones may serve as new leads for the discovery of anticancer drugs.
Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones
Hurst, Timothy E.,Deichert, Julie A.,Kapeniak, Lucas,Lee, Roland,Harris, Jesse,Jessop, Philip G.,Snieckus, Victor
supporting information, p. 3882 - 3885 (2019/06/07)
Reported is the synthesis of carboxylic acids, symmetrical ketones, and unsymmetrical ketones with selectivity achieved by exploiting the differential reactivity of sodium methyl carbonate with Grignard and organolithium reagents.
Dienolates of Cycloalkenones and α,β-Unsaturated Esters Form Diels–Alder Adducts by a Michael/Michael-Tandem Reaction Rather Than in One Step
Loesche, Ann-Christine,Brückner, Reinhard
supporting information, p. 562 - 573 (2018/12/11)
α,β-Unsaturated esters and lithium 1,3-dien-2-olates are known to furnish bicyclic lithium enolates by anionic Diels–Alder reactions. However, in principle, the respective products might form not only in a single step but also in two consecutive – or “tandem” – Michael additions, the first of which occurs intermolecularly, the second intramolecularly. Three cyclic lithium dienolates and four esters with a stereogenic Cα=Cβ bond reacted to give Diels–Alder adducts (10 times) or failed to react (2 times). Seven of the reactive combinations furnished adducts wherein the configuration of the former ester moiety had in part inverted. This precludes concerted pathways as their origins. This was a surprise since donors at C-2 of the 1,3-diene accelerate normal electron-demand Diels–Alder reactions in the order alkyl ⊕O? being a far better donor still, it is not obvious why the mechanism is non-concerted rather than concerted (and still more asynchronous).
Asymmetric dihydroxylation of esters and amides of methacrylic, tiglic, and angelic acid: No exception to the sharpless mnemonic!
Weber, Fabian,Brückner, Reinhard
, p. 2428 - 2449 (2015/04/22)
Literature findings on the facial selectivity of the Sharpless asymmetric dihydroxylation (SAD) of isobutyl angelate are contradictory and partly in conflict with the Sharpless mnemonic. We systematically screened the SAD of esters and amides of angelic, tiglic, and methacrylic acid. Enantiocontrol arose in 14 of the 15 reactions, culminating at 99 % ee for the Weinreb amide of tiglic acid. The absolute configurations of all the nonracemic products were established by (stereo)chemical correlations. Without exception, they conform to the Sharpless mnemonic.
Resin glycosides from Porana duclouxii
Ding, Wen-Bing,Zhang, Dai-Gui,Liu, Chun-Jie,Li, Guan-Hua,Li, You-Zhi
, p. 135 - 140 (2014/02/14)
A new intact resin glycoside (3) and two glycosidic acids (1 and 2), all having a common trisaccharide moiety and (11S)-hydroxytetradecanoic acid or (3S,11S)-dihydroxytetradecanoic acid as the aglycone, were obtained from the roots of Porana duclouxii. Their structures were elucidated by spectroscopic analyses and chemical correlations. These compounds represent the first examples of resin glycosides from the genus Porana.
Palladium-catalyzed synthesis of aromatic carboxylic acids with silacarboxylic acids
Friis, Stig D.,Andersen, Thomas L.,Skrydstrup, Troels
supporting information, p. 1378 - 1381 (2013/04/24)
Aryl iodides and bromides were easily converted to their corresponding aromatic carboxylic acids via a Pd-catalyzed carbonylation reaction using silacarboxylic acids as an in situ source of carbon monoxide. The reaction conditions were compatible with a wide range of functional groups, and with the aryl iodides, the carbonylation was complete within minutes. The method was adapted to the double and selective isotope labeling of tamibarotene.
Medicinal flowers. XXXVI.1) Acylated oleanane-type triterpene saponins with inhibitory effects on melanogenesis from the flower buds of Chinese Camellia japonica
Nakamura, Seikou,Fujimoto, Katsuyoshi,Nakashima, Souichi,Matsumoto, Takahiro,Miura, Tomoko,Uno, Kaoru,Matsuda, Hisashi,Yoshikawa, Masayuki
experimental part, p. 752 - 758 (2012/09/25)
Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E-H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.
Sesquiterpenes from Blumea balsamifera
Shirota, Osamu,Oribello, Jennifer M.,Sekita, Setsuko,Satake, Motoyoshi
experimental part, p. 470 - 476 (2011/05/30)
Five new guaiane sesquiterpenes, blumeaenes E1 (1), E2 (2), K (3), L (4), and M (5), and one new eudesmane sesquiterpene, samboginone (6), along with three known compounds, cryptomeridiol, 3,3′,5,7-tetrahydroxy-4′- methoxyflavanone, and austroinulin, were isolated from the leaves of the Philippine medicinal herb sambong, Blumea balsamifera. The absolute configuration of the new guaiane core was determined as 1S,7S,9S,10R by employing the modified Mosher's method. In the structure of 1, the absolute configuration of the epoxyangelic acid moiety was identified as 2S,3S using (R)-PGME as a chiral anisotropic auxiliary.
