Cerebrosides and a Monoacylmonogalactosylglycerol from Clinacanthus nutans

Abstract

The genus Clinacanthus consists of two species, C. nutans LINDAU and C. siamensis BREM. and belongs to the family Acanthaceae.1) Both species are small shrubs occurring throughout South East Asia. C. nutans (Thai name: phaya yo or phaya plongtong) is often confused with C. siamensis (Thai name: lin nguu hao). C. nutans has long been used in Thailand as a traditional medicine for the treatment of insectand snake-bite and skin rashes, including herpes simplex virus (HSV) and varicella-zoster virus (VZV) lesions. The anti-inflammatory activity of a n-BuOH-soluble fraction from the leaves has been reported.2) In a series of in vitro models a crude extract of the leaves showed significant inhibitory activity on VZV.3) Likewise, ethanol extracts of C. nutans were found to be virucidal against HSV-2 in vitro. 4)However, negative results have also been reported. 5)Nonetheless, clinical trials have reported the successful use of a C. nutans preparation (cream) for treatment of genital herpes and varicella-zoster lesions in patients.6-9) Previous chemical studies on C. nutans have revealed the presence of lupeol, b-sitosterol, stigmasterol and myricyl alcohol. 10,11) Six known C-glycosyl flavones, vitexin, isovitexin, shaftoside, isomollupentin 7-O-b-glucopyranoside, orientin and isoorientin have been isolated from the n-BuOH-and watersoluble portion of the methanolic extract of the stems and leaves of C. nutans collected in Thailand.12) Five sulfur-containing glucosides were isolated from the n-BuOH-soluble portion of a methanolic extract of the stems and leaves of plant material said to be C. nutans. 13)As part of our work on bioactive substances from natural sources, a mixture of cerebrosides (1) and a monoacylmonogalactosylglycerol (4) were isolated from the EtOAc-soluble fraction of the ethanolic extract of the fresh leaves of C. nutans. We are now reporting the isolation and structure elucidation of 1 and 4 by spectroscopic methods and chemical reactions.The fresh leaves of C. nutans were extracted with EtOH at room temperature. After evaporation of the extract, the residue obtained was dissolved in H 2 O and partitioned with EtOAc and then n-BuOH. The EtOAc-soluble fraction was subjected to flash column chromatography to give 13 fractions, among which fraction 9 possessed anti-HSV-1 activity with IC 50 value of 7.86 mg/ml. Further chromatographic purification of this fraction gave 1 as a colorless solid and 4 as a pale yellow wax.The Jϭ9.6, 4.8 Hz; d C 128.9, 129.2). The data were suggestive of a glycosphingolipid structure.The 13 C-NMR spectrum of 1 (Table 1) was assigned by a combination of distortionless enhancement by polarization transfer (DEPT), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond correlation January 2004 Chem. Pharm. Bull. 52(1) 27-32 (2004) 27 * To whom correspondence should be addressed.

Chemical constituents of Triticum aestivum and their effects on adipogenic differentiation of 3T3-L1 preadipocytes

“…Briefly, the following isolated compounds were identified (Fig. 1) including five glycolipids: 2-a-linolenoylglycerol 1-O-b-D-galactopyranoside (1) (Ha et al 2006), 3-a-linolenoylglycerol 1-O-b-D-galactopyranoside (2) (Tuntiwachwuttikul et al 2004), 2,3-di-a-linolenoylglycerol 1-O-b-D-galactopyranoside (3) (Ha et al 2006), 2,3-di-a-linolenoylglycerol 1-O-(6-O-linolenoyl-b-D-galactopyranoside) (4) (Ruberto and Tringali 2004), and 2,3-di-a- (Wegner et al 2000); two glycerides: trilinolenin (6) (Hui et al 2003), trilinolein (7) (Park et al 2001); four unsaturated fatty acids: a-linolenic (8) (Takaya et al 2003), a-linolenic acid methyl ester (9) (Takaya et al 2003), oleic acid (10) (Batchelor et al 1974), and 12(Z)-octadecenoic acid (11) (Batchelor et al 1974); three sterol: b-sitosterol (12), daucosterol (13), 6 0 -O-linolenlydaucosterol (14) (Luyen et al 2014); two alkaloids: (2R)-2-O-b-D-glucopyranosyl-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (15), adenosine (16) (Luyen et al 2014); and four phenolics: triticumoside (17), isoorientin (18), isoscoparin (19), and a-tocopherol (20) (Luyen et al 2014). Among them, compound 17 was determined to be a new compound, named as triticumoside (Luyen et al 2014).…”

Evaluation of Total Phenolic Compound and Cytotoxic Activity of Clinacanthus nutans

“…They are commonly rich in phenolic compounds such as flavonoids, phenolic acids, tannins, coumarins, and lignins [2] . Clinacanthus nutans has been widely used as a traditional medicinal plant in Asia for treating skin rashes, bugs and snake chomps, sores brought on by herpes simplex infection, diabetes mellitus, fever and diuretics [3] .…”

Two new ceramides from Zephyranthes candida

“…1 Since the chemical shifts of allylic methylene carbons are different when alkene double bonds are cis-oriented (δ C ≈ 27 ppm) compared with when they are trans-oriented (δ C ≈ 32 ppm) [7,8], the 13,14 alkenyl bond in compound 1 was assigned to the E configuration. The presence of 2-amino and 1,2′,3,4 tetrahydroxyl groups as well as the 13,14 double bond in the main chain was established from the ESI-MS fragmentation pattern analysis [9][10][11] [12,13], which further confirmed the position of the double bond (Fig. 2).…”