Inhibitory Effect of Triterpenoids from Dillenia serrata (Dilleniaceae) on Prostaglandin E2 Production and Quantitative HPLC Analysis of Its Koetjapic Acid and Betulinic Acid Contents

Abstract

The crude methanol extracts and fractions of the root and stem barks of Dillenia serrata Thunb. showed 64% to 73% inhibition on the production of prostaglandin E2 (PGE2) in lipopolysaccharide-induced human whole blood using a radioimmunoassay technique. Three triterpenoids isolated from the root bark of the plant, koetjapic (1), 3-oxoolean-12-en-30-oic (2), and betulinic (3) acids, exhibited significant concentration-dependent inhibitory effects on PGE2 production with IC50 values of 1.05, 1.54, and 2.59 μM, respectively, as compared with the positive control, indomethacin (IC50 = 0.45 μM). Quantification of compounds 1 and 3 in the methanol extracts and fractions were carried out by using a validated reversed-phase high performance liquid chromatography (RP-HPLC) method. The ethyl acetate fraction of the stem bark showed the highest content of both compound 1 (15.1%) and compound 3 (52.8%). The strong inhibition of the extracts and fractions on cyclooxygenase-2 (COX-2) enzymatic activity was due to the presence of their major constituents, especially koetjapic and betulinic acids.

The phytochemical and anti‐inflammatory studies of Dillenia suffruticosa leaves

“…Present study, NMR 500 MHz, C 5 D 5 N‐ d 5 , 13 C measured at 125 MHz, 1 H measured at 500 MHz, compared with Kaneda et al (), C 5 D 5 N‐ d 5 , 13 C measured at 75.6 MHz. Jalil et al (), NMR 600 MHz, DMSO‐ d 6 , 13 C measured at 150 MHz 1 H measured at 600 MHz.…”

“…This class of oleananic triterpenes has been reported to inhibit various inflammatory mediators (Huguet, del Carmen Recio, Máñez, Giner, & Rıós, 2000;Rao, Fang, & Tzeng, 2008;Sandjo et al, 2017) and associated with a decrease in COXs and inducible nitric oxide synthase (iNOS) gene expression in HepG2 cells (Quang et al, 2011). 1 and 2 were also reported to exhibit marked anti-inflammatory activity through inhibiting the production of prostaglandin E 2 (PGE 2 ) in lipopolysaccharide-induced human blood assay (Jalil et al, 2015). Therefore, the biphasic nature of λ-carrageenan-induced paw oedema, where the later phase linking to the release of prostaglandins, was observed similar to the antiinflammatory potential of 1 and 2 at the later hours of λ-carrageenan injection.…”

“…The search for natural products to alleviate various inflammatory disorders as a result of fever, arthritis, injury, infection, body aches, and so forth, has been ongoing (Bellik et al, ) ever since the discovery of aspirin from the willow tree, Spiraea ulmaria (Recio, Andujar, & L Rios, ). Amongst the studies, the Dilleniaceae family have recently reported that Dillenia indica and the other species possessed anti‐inflammatory and anti‐arthritic activities (Alexandre‐Moreira, Piuvezam, Araújo, & Thomas, ; Jalil et al, ; Khare et al, ; Kushima et al, ; Yeshwante et al, ). The Dillenia plants contain mainly triterpenoids, flavonoids, and their glycosides, the anthraquinone glycosides, phenolic derivatives, and tannins (Macahig, Matsunami, & Otsuka, ; Nick, Wright, Sticher, & Rali, ; Tiwari & Srivastava, ).…”

Antibacterial and Cytotoxic Potencies of Stilbene Oligomers From Stem Barks of Baoti (Dryobalanops Lanceolata) Growing in Kendari, Indonesia

“…The plants were Dipterocarpaceae [1][2][3], Jatropha [4][5][6], Annonaceae [7], Pongamia [8], Imperata [9], Polygonum [10,11], and Dillenia [12]. In continuing our study of both aspects, Dryobalanops genera (Dipterocarpaceae) is still interesting.…”

Evaluation of Antiradical Scavenger Activity of Extract and Compounds From Etlingera Calophrys Stems

“…Our previous study included plants species from Dipterocarpaceae [1][2][3][4], Jatropha [5][6][7], Annonaceae [8], Pongamia [9], Imperata [10], Polygonum [11,12], and Dillenia [13].…”