Oxidation and Acetylation of Ursolic and Oleanolic Acids Isolated from <i>Fragraea fragrans</i> fruits; Antiproliferation of P388 Leukemia Cells

Abstract

An interesting natural product chemistry aspect of Fragraea fragrans is that their fruits are richness with ursolic acid and its isomer oleanolic acid (3.05% of dried powder). As our continuous work on these inseparable structural isomeric triterpenes, this paper reports that 51.0% of inseparable 3-oxo-ursolic[3-oxo-oleanolic] acids and 48.6% of inseparable 3-acetyl-ursolic [3-acetyl-oleanolic] 52,8% asam 3-okso-ursolat[3-oxo-oleanolat] dan 48,6% asam 3-asetil-ursolat[3-asetil-oleanolat] telah berhasil dibuat dari triterpenoid buah tembesu sebagai bahan baku oksidasi dan asetilasi serta mengevaluasi aktivitasnya terhadap pertumbuhan sel leukemia P388. dengan nilai IC 50 = 18,6 µg/mL menunjukkan aktivitas antiproliferasi tiga kali lipat lebih kuat dari asam ursolat [oleanolat] dengan IC 50 = 53,5 µg/mL. Akan tetapi, dengan nilai IC 50 = 37,9 µg/mL hanya memberikan aktifitasnya dua kali lipat lebih kuat dibandingkan triterpenoid induknya (IC 50 = 53.5 µg/mL). Keywords: Fragraea fragrans; fruits; 3-oxo-ursolic[-oleanolic] acids; 3-acetyl-ursolic[-oleanolic] acids; P388 leukemia cells ABSTRAK Suatu aspek yang menarik dari kimia organik bahan alam tumbuhan tembesu, Fragraea fragrans adalah buahnya yang kaya dengan asam ursolat dan isomernya asam oleanolat (3.05% terhitung dari bubuk kering). Sebagai pekerjaan lanjutan terhadap triterpen yang berupa isomer struktural yang tidak terpisahkan ini, maka artikel ini melaporkan bahwa sebanyak

Alpha-glucosidase inhibitors from Nervilia concolor, Tecoma stans, and Bouea macrophylla

“…White amorphous powder. 1 H NMR (500 MHz, Acetone‑ d 6 ) and 13 C NMR (125 MHz, Acetone‑ d 6 ) data were consistent with those reported in the literature ( Basir et al, 2014 ).…”

Phytoconstituents with cytotoxic activity from Ulmus pumila L.

“…Compounds obtained as pure isolates included friedelin (compound 1) (Mann et al, 2012), 3β-acetoxyurs-11-en-13β,28-olide (compound 2) (Raza et al, 2015), betulinic acid (compound 7) (Lee et al, 2005), kaempferol-3-O-rutinoside (nicotiflorin) (compound 10) (Erosa-Rejón et al, 2010), and 3,4-dihydroxycinnamic acid (caffeic acid) (compound 13) (Zhou et al, 2017). In accordance with previous reports (Basir et al, 2014), 3β-O-acetyl ursolic acid (compound 3) was slightly contaminated with 3β-Oacetyl oleanolic acid (compound 4). Furthermore, the isolation of β-sitosterol and stigmasterol (compounds 5 and 6), methyl ursolate, and methyl oleanolate (compounds 8 and 9) as well as quercetin-3-O-β-D-glucopyranoside (isoquercetin) and quercetin-3-O-β-D-galactopyranoside (hyperoside) (compounds 11 and 12) as mixtures was in agreement with earlier studies (Furuya et al, 1987;Luhata and Munkombwe, 2015;Pereira et al, 2011).…”

“…Previous studies on genus Ulmus reported the presence of various types of phytoconstituents like terpenoids (Martín-Benito et al, 2011), steroids (Martín-Benito et al, 2011), phenolics (Zhou et al, 2017), and polysaccharides (Lee et al, 2018). From a bioactivity standpoint, Ulmus species were reported to exhibit antibiotic (You et al, 2013), antifungal (Burden and Kemp, 1984), antioxidant (Bora et al, 2017;Joo et al, 2014;Mina et al, 2016), anti-inflammatory (Joo et al, 2014;Mina et al, 2016), hepatoprotective (Boudaoud-Ouahmed et al, 2015), neuroprotective (So et al, 2019), antiangiogenic (Jung et al, 2007), cytotoxic (Wang et al, 2004;Wang et al, 2006), anticancer (Hamed et al, 2015), and antiviral (Hamed et al, 2015) effects.…”

Isolation of a New Triterpenoidal Ester, Chemical Composition and Biological Activities of Two Spp. Of Euphorbia (Euphorbiaceae) Grown in Egypt

“…The connection of an acetyl group to Oh-23 was documented from the long rang correlation of Ch3-33 and 2h-23 with the carbonyl carbon C-32 [32]. According to the comparison of its properties and spectral data with the corresponding of structurally related compounds, it was identified as 23-acetyl-3β-Omethyloleanolic acid that is a new natural product [30][31][32][33].…”

“…UPLC-MS 2 spectra in negative mode show molecular ion peaks at: 169 and 301 [m-h]-corresponding to the mFs of C 7 h 6 O 5 , and C 14 h 6 O 9 ,, respectively. The UV spectral data of 1 and 2 exhibited an absorption band (λ max 217, 272 and 253, 367) characteristic for gallic and ellagic acids [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34]. Depending on the comparison with their previously published spectral 1h and 13C-NmR data and Co-chromatography with the authentic samples, 11 and 12 were identified as gallic and ellagic acid, respectively [35 & 36].…”