Medicinal Flowers. XXIV. Chemical Structures and Hepatoprotective Effects of Constituents from Flowers of Hedychium coronarium

Abstract

Hedychium coronarium KOEN. (Zingiberaceae) is widely cultivated in Japan, India, South China, and Southeast Asian countries. The rhizomes of H. coronarium have been used for the treatment of headache, contusion inflammation, and sharp pain due to rheumatism in Chinese traditional medicine. Previously, we reported that the extract from the rhizomes of H. coronarium showed inhibitory effects on increase in vascular permeability and nitric oxide production and on the release of b-hexosaminidase from RBL-2H3 cells and the structures of various farnesane-type sesquiterpenes and labdane-type diterpene were characterized.2,3) However, the chemical constituents as well as the pharmacological properties of the flowers of H. coronarium have not been characterized. In the course of our serial studies on the bioactive constituents of medicinal flowers, 1,[4][5][6][7][8][9][10][11][12][13][14][15] the 80% aqueous acetone extract from the flowers of H. coronarium was found to show a protective effect on D-galactosamine (D-GalN)-induced cytotoxicity in primary cultured mouse hepatocytes. In addition, we have isolated two new labdane-type diterpene glycosides, coronalactosides I (1) and II (2), and a new labdane-type trinorditerpene, coronadiene (3), together with 8 known compounds including labdane-type diterpene derivatives from the extracts, which were obtained with chloroform and 80% aqueous acetone from the flowers of H. coronarium. Furthermore, we examined the protective effects of principal constituents on D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. In this paper, we describe the isolation and structure elucidation of the new constituents (1-3) and the hepatoprotective effects of principal constituents from the flowers of H. coronarium.The fresh flowers of H. coronarium were extracted with chloroform under room temperature [the yield (0.46%) was obtained from the fresh flowers]. Subsequently, the residue was extracted with 80% aqueous acetone under room temperature, followed by 80% aqueous acetone under reflux (0.75% and 0.43% were obtained, respectively). The 80% aqueous acetone extract obtained under room temperature was partitioned into an EtOAc-H 2 O mixture to furnish an EtOAc-soluble fraction (0.074%) and aqueous layer. The aqueous layer was further extracted with n-BuOH to give n-BuOH-and H 2 O-soluble fractions (0.10% and 0.56%, respectively). In the same procedure, the EtOAc-, n-BuOHand H 2 O-soluble fractions were given from the 80% aqueous acetone extract obtained under reflux (0.18%, 0.044%, and 0.21%, respectively). The chloroform extract (0.46%), EtOAcsoluble fraction given from the 80% aqueous acetone extract obtained under room temperature, and n-BuOH-soluble fraction given from the 80% aqueous acetone extract obtained under reflux were subjected to normal-phase and reversedphase column chromatographies, and finally HPLC to give coronalactosides I (1, 0.00029% from the flowers) and II (2, 0.00014%) and coronadiene (3, 0.00008%) together with 8 known compounds, (E)-labda-8(17),12-die...

Medicinal Flowers. XXVII. New Flavanone and Chalcone Glycosides, Arenariumosides I, II, III, and IV, and Tumor Necrosis Factor-.ALPHA. Inhibitors from Everlasting, Flowers of Helichrysum arenarium

“…As the chemical constituents from this herbal medicine, several a-pyrones, flavonoids, chalcones, and phthalides were isolated from the flowers 3,4) and roots. 5,6) During the course of our characterization studies on medicinal flowers, 1,[7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] we found that the methanolic extract from the flowers of H. arenarium inhibited on tumor necrosis factor-a (TNF-a)-induced cytotoxicity in L929 cells. TNF-a is known to mediate a number of forms of organ injury through its induction of cellular apoptosis.…”

Structures of Two New Phenolic Glycosides, Kaempferiaosides A and B, and Hepatoprotective Constituents from the Rhizomes of <i>Kaempferia parviflora</i>

“…ex BAKER cultivated at Loei province, Thailand were purchased from a Thai traditional drug store in Nakhonsithammarat province, Thailand on Effects on D-GalN-Induced Cytotoxicity in Primary Cultured Mouse Hepatocytes The hepatoprotective effect of the constituents were determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay using primary cultured mouse hepatocytes. [48][49][50][51][53][54][55][56] Hepatocytes were isolated from male ddY mice (30-35 g) by collagenase perfusion method. A cell suspension at 4×10 4 cells in 100 μL William's E medium containing FCS (10%), penicillin G (100 units/mL), and streptomycin (100 μg/mL) was inoculated in a 96-well microplate and precultured for 4 h at 37°C under a 5% CO 2 atmosphere.…”

“…Consequently, 30,48-57) As a continuing exploratory study for hepatoprotective agents from medicinal plants, the constituents from the rhizomes of K. parviflora were examined. As shown in Table 4, 5,3′-dihydroxy-3,7,4'-trimethoxyflavone (14, IC 50 =18.4 μM) showed higher activity than silybin (38.8 μM), 49,50,[53][54][55][56] a commercial hepatoprotective agent as a positive control.…”

Labdane-Type Diterpenoids from the Rhizomes of Hedychium coronarium Inhibit Lipopolysaccharide-Stimulated Production of Pro-inflammatory Cytokines in Bone Marrow-Derived Dendritic Cells

“…Previous phytochemical investigation of H. coronarium has resulted in the identification of a number of labdane diterpenes, which were proved to be the main components. [7][8][9][10] Labdane diterpenes occur in several plants of the Zingiberaceae family and have been reported to possess anti-inflammatory properties. 11,12) Interestingly, our extensive phytochemical study of the rhizomes of H. coronarium led to the isolation of two new and four known labdane-type diterpenoids.…”