New dammarane and ursane-type triterpenoids from the flower ofIxora coccineaLinn.

Abstract

Two new esters of dammarane triterpenoids ixorene isovalerate (1), ixorene 3',8'-dimethyloctanoate (2) and a new ursane-type triterpenoids Ixoroid acid (3) were isolated from the methanolic extract of flowers of Ixora coccinea Linn., along with the three known constituents. The structures of compounds 1 and 3 were elucidated on the basis of extensive 1D,2D NMR studies and mass spectrometry as 17β-dammara-12,20-diene-3β-isovelarate and 3β-hydroxy-18β-urs-12ene-29β-oic acid, respectively, whereas 2 was identified as 17β-dammara-12,20-diene-3β-3',8'-dimethyloctanoate through (1)H NMR and mass spectral data. Compounds 1, 2, 4 and 5 were evaluated for their in vitro cytotoxic activity, which exhibited weak activity against the 3T3, PC3 and HeLa cell lines with the IC50 value >30 μM. Antioxidant results of 1 - 5 revealed that only compound 5 showed antioxidant activity in DPPH radical scavenging inhibition with the IC50 1.31 × 10(- 6) ± 0.005 μm mL(- 1). Both activities are the first records of these isolated compounds from the flowers of Ixora coccinea Linn.

A New Dammarane Triterpenoid Compound Isolated From Ixora Finlaysoniana

“…Therefore the δ c from C-2' to C-10' suggest that 13 C NMR resonances at 48. Table(1) all data of the side chain similar to the reported data of 17β-dammara-12, 20 diene-3β-3', 8' -dimethyloctanoate previously isolated from Ixora coccinea [21] . Finally this new structure was identified as 17β-dammara-1-one -20 ene-3β-3', 8'-dimethyloctanoate or [12, 13 dihydroixoroid-1-one-3β-3', 8'-dimethyloctanoate] (1) Fig.…”

“…13 C signals were fully assigned according to heteronuclear single quantum correlation (HSQC) spectra Table (1). The NMR data of the compound skeleton were compared with related structure to those of ixorene 3-isovalarate and ixorene 3`, 8`-dimethyloctanoate [21] that show certain similarity with two exception firstly; the absence δ c 121,142 of double bond between C-12, 13 and the second difference presence of downfield shift of carbon resonance signal of C-1 (δ c 215) which confirm other oxygen substituted carbon. The side chain containing gem methyls group appear in IR spectrum at 1380 cm -1 and showing two doublet at δ 0.85 (J=6.5, H-26) and δ 0.82 (J=6.5, H-27) in NMR with the one bond correlations with δ c 22.70 and δ c 19.75 in HSQC plot.…”

“…Dammarane is a group of triterpenoids isolated from various plants and exhibited valuable biological activities such as antitumor, anti-inflammatory, immunosuppressive and antitubercular [4,21] ; so further studies are needed in order to establish the effect and action mechanisms of the isolated new compound responsible for these biological effects to obtain additional information on the structural factors needed for the potent activity. After illustrating the activities done on Ixora finlaysoniana; it could be concluded that the total alcohol extract, the total aqueous extract (as given in folk medicine) has highest biological activities compared to other fractions give Ixora finlaysoniana great potential and supporting to use it as a source of natural raw material for phytopharmaceuticals preparations as the new coming treatment since it is an effective safe as hepatoprotective, antiulcer, anticonvulsant, antioxidant and anti-diabetic herbal drug.…”

Anti-inflammatory and antiproliferative activities of Ixora brevifolia Benth. (Rubiaceae)

“…400 species; several are used in traditional medicine for treatment of diarrhoea, fever, headaches, ulcers and cancer (Nair & Panikkar 1990; 2016). Previous phytochemical and biological studies of species from Ixora genus and their isolated compounds showed the presence of phenols, terpenoids and peptides (Lee et al 2010;Chen, Zhan, et al 2016;Ikram et al 2016) and a variety of activities are related to traditional uses . Ixora brevifolia Benth.…”