Absolute stereostructures of novel norcadinane- and trinoreudesmane-type sesquiterpenes with nitric oxide production inhibitory activity from Alpinia oxyphylla

Four New Sesquiterpenoids from the Fruits of Alpinia oxyphylla

“…Previous chemical investigations of A. oxyphylla have reported sesquiterpenoids, some of which showed inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse peritoneal macrophages and release of b-hexosaminidase from RBL-2H3 cells. [2][3][4][5][6] In our continuing endeavor to discover new bioactive natural products from TCM, four new compounds including two 14-norcadinane-type sesquiterpenoids (1, 2) and two eudesmane-type sesquiterpenoids (3,4), together with two known compounds oxyphyllol C (5) 3) and epinootkaol (6) 7) were isolated from the fruits of A. oxyphylla (Fig. 1).…”

A New Noreudesmane-type Sesquiterpenoid from Alpinia oxyphylla

“…It has been reported that several diaryheptanoid and sesquiterpenoid from the fruits of A. oxyphylla were found to have inhibitory activity on NO production. [10][11][12][13]22 Taken together, our results suggested that A. oxyphylla may be a possible candidate for the treatment of inflammatory disease.…”

“…[7][8][9] Recently, diarylheptanoids and sesquiterpenes have been isolated from this plant, and some of which showed the inhibitory effects on nitric oxide production. [10][11][12][13] As part of our continuing search for inhibitors of nitric oxide (NO) production from medicinal plants, we investigated the active constituents of the fruits of A. oxyphylla. As a result, a new noreudesmane-type sesquiterpenoid, 4-methoxy-oxyphyllenone A (1), along with 15 known compounds was isolated and identified.…”

“…All the above data indicated that compound 1 was a noreudesmanetype sesquiterpenoid. 10 The planar structure of compound 1 was further determined by 2D NMR experiments such as COSY, HMQC, and HMBC spectra (Figure 2). The …”

In vitroantioxidant and cytotoxic properties of ethanol extract ofAlpinia oxyphyllafruits

“…The fruits of this plant have been used as a folk medicine for the treatment of intestinal disorders, urosis, diuresis, ulceration and dementia in traditional Chinese medicine (TCM) and were coded in Chinese Pharmacopoeia as an aromatic stomachic (Chinese Pharmacopoeia Commission, 2010). Previous phytochemical and biological investigations of this plant have reported the isolation of some sesquiterpenoids, and some of which showed inhibitory effects on nitric oxide production in lipopolysaccharideactivated mouse peritoneal macrophages and release of b-hexosaminidase from RBL-2H3 cells (Luo et al, 2012;Morikawa et al, 2002;Muraoka et al, 2001). Moreover, A. oxyphylla has also been reported to possess antianaphylactic (Kim et al, 2000;Shin et al, 2001), anti-inflammatory (Chun et al, 2001), antitumor (Lee et al, 1998), calciumantagonist (Shoji et al, 1984), neuroprotective (Guan et al, 2006a,b;Yu et al, 2003;Zhang et al, 2012a) and insecticidal (Miyazawa et al, 2000(Miyazawa et al, , 2001 activities.…”