Constituents of fruit pulp of Maytenus salicifolia and complete 1D/2D NMR data of 3β-hydroxy-D:B-friedo-olean-5-ene

Abstract

Maytenus salicifoliaReissek (Celastraceae). The structural formula and the stereochemistry of compound 6 were established by the data obtained through 1 H and 13 C NMR spectroscopy, including HMBC, and NOESY) experiments. By analysis of the spectral data, it was possible to correct seven chemical shift assignments of compound 6, which were erroneous attributed and published in the scientific literature.Plants of the Celastraceae family comprise 90 genera and 1210 species worldwide, the majority of which are found in tropical and subtropical regions [1]. In Brazil, the members of this family are distributed in four genera: Maytenus Juss., Goupia Reiss., Austroplenckia Lund., and Franhofera Mart. [2,3].In a continuing research of bioactive metabolites from species of the Celastraceae family, we investigated the chemical constituents of the fruit pulp of Maytenus salicifolia Reissek. It is a native plant found mainly in the "cerrado" (Savanna) of the states of Bahia, Minas Gerais, and Rio de Janeiro, Brazil. The leaves of this species have been used in traditional medicine for the treatment of stomach ulcers. The decoction of the leaves made together with other parts of the plant is also traditionally used in the form of a bath to alleviate symptoms of itches and allergies [4]. The pentacyclic triterpenes (PCTTs) 3E-stearyloxyursan-12-ene, friedelin, E-friedelinol, D-amyrin, E-amyrin, and lupeol were previously isolated from the leaves of M. salicifolia by Miranda et al. [5]. PCTTs of the series friedelane, oleanane, ursane, lupane, and others are compounds that are frequently isolated from other species of the Celastraceae family [5]. Sesquiterpenes [6,7], alkaloids and flavonoids [8], proanthocyanidins, and glycosylated steroids [9] are also commonly isolated. Pharmacological properties such as anti-inflammatory [10], antitumor [11], and anti-AIDS [12] have been presented for some of these PCTTs compounds. Then, the presence of PCTTs in Celastraceae species or in other plants confers to it an important chemical and therapeutic potential. The traditional medicinal use of M. salicifolia and its pharmacological potential induces us to study the phytochemical properties of different parts of this plant, including the pulp fruit. Generally, phytochemical studies of the fruit pulp of Celastraceae species lead to the isolation of sesquiterpenes [13,14] and alkaloids [15]; nevertheless, the presence of PCTTs in this part of the plant is relatively rare.

Psychotria viridis: Chemical constituents from leaves and biological properties

“…From leaves of P. viridis were identified nineteen constituents: a mixture of long chain hydrocarbons (1), 24-methylene-cycloartenol (2) (De Pascual et al 1987), squalene (3) (Valladao et al 2010), β-sitosterol (4), stigmasterol (5) (Goulart et al 1993), triacylglycerol (6) (Gunstone 1991), nonacosanal (7), nonacosanol (8) (Řezanka and Sigler 2007), hentriacontanoic acid (9), hexadecanoic acid (10), heptadenoic acid (11) (Gunstone 1991), ursolic acid (12), oleanolic acid (13) and at 1720 cm -1 indicated 7 as an aldehyde. The 1 H NMR and 13 C spectra of compound 7 showed signals at δ H 9.7 (t; J = 1.6 Hz) and at δ C 202.85 which are characteristics of aldehyde.…”

A Review on Phytochemicals of the Genus Maytenus and Their Bioactive Studies

“…The aerial parts of M. undata yielded four new 12-oleanene and 3,4- seco -12-oleanene triterpene acids, namely, 3-oxo-11 α -methoxyolean-12-ene-30-oic acid ( 104 ), 3-oxo-11 α -hydroxyolean-12-ene-30-oic acid ( 105 ), 3-oxo-olean-9(11), 12-diene-30-oic acid ( 106 ) and 3,4- seco -olean-4(23), 12-diene-3,29-dioic acid ( 107 ) [ 51 ], while 3 α -22 β -dihydroxyolean-12-en-29-oicacid ( 108 ) was obtained from the methanol extracts of the barks of M. laevis [ 52 ]. Compound olean-9(11):12-dien-3 β -ol ( 109 ) was isolated from the roots of M. acanthophylla [ 53 ] and compound 3 β -hydroxy-D:B-friedo-olean-5-ene ( 1 10 ) was isolated from M. salicifolia Reissek [ 54 ]. Compound 19 α -hydroxy-3-olean-12-en-29-oic acid ( 1 11 ) was isolated from M. austyoyunnanensis [ 55 ] ( Table 3 and Figure 3 ).…”

“…Dispemroquinone (53) was isolated from M. dispermus [33]. A new norquinonemethide triterpene with a netzahualcoyene type skeleton, scutione (54), was isolated from the root bark of M. scutioides [34]. Compounds zeylasterone (55) and demethylzeylasterone (56) were obtained from M. blepharodes [35], and compound 3,15-dioxo-21α-hydroxy friedelane (57) was isolated from the methanol extracts of M. robusta [36].…”

Pentacyclic Triterpenoids Isolated from Celastraceae: A Focus in the 13C-NMR Data

“…The following are available online, Table S1: Pentacyclic triterpenoids isolated from Celastraceae species (2001–2021) [ 257 , 258 , 259 , 260 , 261 , 262 , 263 , 264 , 265 , 266 , 267 , 268 , 269 , 270 , 271 , 272 , 273 , 274 , 275 , 276 , 277 , 278 , 279 , 280 , 281 , 282 , 283 , 284 , 285 , 286 , 287 , 288 , 289 , 290 , 291 , 292 , 293 , 294 , 295 , 296 , 297 , 298 , 299 , 300 , 301 , 302 , 303 , 304 , 305 , 306 , 307 ,…”