Constituents of Compositae Plants. 2. Triterpene Diols, Triols, and Their 3-O-Fatty Acid Esters from Edible Chrysanthemum Flower Extract and Their Anti-inflammatory Effects

Abstract

The n-hexane soluble and the nonsaponifiable lipid fractions of the edible flower extract of chrysanthemum (Chrysanthemum morifolium) were investigated for triterpene diol and triol constituents. These triterpenes occur as the 3-O-fatty acid esters in the n-hexane soluble fraction from which 26 new and 6 known fatty acid esters were isolated and characterized. From the nonsaponifiable lipid fraction, 24 triterpene diols and triols were isolated, of which 3 were new compounds: (24S)-25-methoxycycloartane-3beta,24-diol (11), (24S)-25-methoxycycloartane-3beta,24,28-triol (22), and 22alpha-methoxyfaradiol (23). Faradiol (9) and heliantriol C (19), present in the nonsaponifiable lipid fraction and as the 3-O-palmitoyl esters in the n-hexane soluble fraction, were the most predominant triterpene diol and triol constituents. Fourteen triterpene diols and triols and 9 fatty acid esters were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All of the triterpenes examined showed marked inhibitory activity, with a 50% inhibitory dose (ID50) of 0.03-1.0 mg/ear, which was more inhibitive than quercetin (ID50 = 1.6 mg/ear), a known inhibitor of TPA-induced inflammation in mice.

Green synthesis of silver nanoparticles by Chrysanthemum morifolium Ramat. extract and their application in clinical ultrasound gel

“…A broad absorption peak was observed at 430 nm, which is a characteristic band for the Ag, arising from the excitation of longitudinal plasmon vibrations of AgNP in the solution. 30 The absorption peak of the CM extract was observed at 373 nm, which is typical of the absorptions of flavonoids. Flavonoids, such as luteolin-7-O-β-D-glucoside and apigenin-7-O-β-D-glucoside, are the main components of CM extract.…”

“…Flavonoids, such as luteolin-7-O-β-D-glucoside and apigenin-7-O-β-D-glucoside, are the main components of CM extract. 30 Therefore, the flavonoids of CM extract may play the key roles, not only to reduce the AgNO 3 solution to AgNP, but also to stabilize the nanoparticles in the solution.…”

“…has been widely used in the People's Republic of China as a health food and medicine for thousands of years. 29 It has various biological features, including anti-inflammation, 30 antioxidant activity, 31 cardiovascular protection, 32 antitumorigenesis, 33 anti-HIV, 34 and anti-aging activities. 35 It contains a wide variety of flavonoids, 36 caffeoylquinic acids, 37 chlorogenic acid, 38 phenolic acids, 39 etc, which could be used as reductants to react with silver ions and as scaffolds to direct the formation of AgNP in solution.…”

An Up-to-Date Review of Phytochemicals and Biological Activities in Chrysanthemum spp

“…According to the literature survey more varieties of Chrysanthemums are mainly cultivated in china such as Shen-nong Sweet Chrysanthemum, Tender Huang-ju, Chamomile Flower, Hangzhou White Chrysanthemum, Florists Chrysanthemum, etc [3][4][5] . Chrysanthemum plants belong to Asteraceae family which has low molecular components include flavonoids 6 , sesquiterpenes 7 , triterpenes 8 , and unsaturated fatty acids 9 . The volatile chemical compounds of Chrysanthemum essential oil are mainly composed of monoterpenes, sesquiterpenes, aldehydes, acids, esters and alcohols [10][11][12] .…”

Administered chrysanthemum flower oil attenuates hyperuricemia: mechanism of action as revealed by DNA microarray analysis

“…Its flowers contain essential oil, sesquiterpenes, flavonoids, and their glycosides. 1,2) It has been reported that these flowers have various biological activities, such as anti-oxidation, 3) anti-inflammation, 4,5) oncogenic suppression, 6) anti-mutagenicity, 7) and anti-HIV. 8) We developed chrysanthemum flower oil (CFO; Kaneka Chrysflavone TM ) as an oily fraction containing polyphenols derived from chrysanthemum flowers.…”