Guaiane-type sesquiterpenes from<i>Curcuma wenyujin</i>and their inhibitory effects on nitric oxide production

Lou, Yan; Zhao, Feng; He, Hao; Peng, Kai‐Feng; Zhou, Xinyu; Chen, Lixia; Qiu, Feng

doi:10.1080/10286020903042358

Cited by 42 publications

(38 citation statements)

References 24 publications

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“…The isolation of CHCl 3 fraction of C . zedoaroides yielded one new guaiane sesquiterpene lactone ( 4 ), one new diarylheptanoid ( 7 ), and five known guaiane sesquiterpene lactones: gweicurculactone ( 1 ; Jiang et al, ; Phan, Tran, Phan, Matsunami, & Otsuka, ; Wu et al, ; Zhang, Ji, Ji, & Fan, ), zedoalactone B ( 2 ; Takano, Yasuda, Takeya, & Itokawa, ), phaeocaulisin C ( 3 ; Liu et al, ), zedoalactone H ( 5 ; Wu et al, ), and zedoalactone E ( 6 ; Liu et al, ; Lou et al, and Wu et al, ). The NMR data of all compounds can be seen in Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

Antiinflammation constituents from Curcuma zedoaroides

Tungcharoen

Wattanapiromsakul

Tansakul

et al. 2018

Phytotherapy Research

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Curcuma zedoaroides, a Zingiberaceae species, has been used for snake bite antidote and wound care in Thailand. Seven compounds were isolated from the bioactive chloroform extract consisted of one new guaiane sesquiterpene lactone, 5-epiphaeocaulisin A (4) and one new diarylheptanoid, 1,2,3,5-tetrahydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) heptane (7), together with five known guaiane-type sesquiterpene lactones including gweicurculactone (1), zedoalactone B (2), phaeocaulisin C (3), zedoalactone H (5), and zedoalactone E (6). The antiinflammation was investigated on NO and TNF-α production using RAW264.7 cells. In addition, the expressions of genes involved in inflammation including iNOS, COX-2, and TNF-α were assessed. The results found that Compounds 1-7 presented their antiinflammation against NO production. The most potential effects were demonstrated on Compounds 1 and 7 with IC of 27.3 and 32.6 μM, respectively. Although, Compounds 1 and 7 did not inhibit TNF-α production, their suppression on iNOS and COX-2 mRNA expression were revealed. These results support the ability of chloroform fraction, Compounds 1 and 7 on antiinflammation, whereas others exhibited moderate and mild effect.

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Section: Resultsmentioning

confidence: 99%

Antiinflammation constituents from Curcuma zedoaroides

Tungcharoen

Wattanapiromsakul

Tansakul

et al. 2018

Phytotherapy Research

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“…The first two fractions were repeatedly subjected to column chromatography over silica gel, MCI gel, ODS gel, and semipreparative HPLC to obtain 10 new terpenoids (1−10) and 17 known terpenoids (11−27). The known compounds were identified as zedoarolide B (11), 13 zedoalactone C (12), 13 phaeocaulisin B (13), 14 4βhydroxy-5β-H-guai-1 (10),7 (11),8-trien-12,8-olide (14), 13 gweicurculactone (15), 15 curdionolide A (16), 16 curdionolide B (17), 16 7,8-seco-9 (10),11 (12)-guaiadien-8,5-olide (18), 17 4α,8β-dihydroxy-5α-(H)-eudesm-7(11)-en-8,12-olide (19), 18 isogermafurenolide (20), 19 phacadinane D (21), 20 zedoarondiol (22), 13 wenyujinin B (23), 21 procurcumenol (24), 13 curcumadiol (25), 22 (E)-3-hydroxylabda-8 (17),12-dien-16,15olide (26), 23 and labda-8 (17),13( 14)-dien-15,16-olide ( 27) 24 by comparing their HRESIMS and NMR data with the corresponding data in the cited references, and their structures are shown in Figure S1 in the Supporting Information.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Sesqui- and Diterpenoids from the Radix of Curcuma aromatica

Dong

Dai

et al. 2017

J. Nat. Prod.

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Eight new sesquiterpenoids (1-8), two new diterpenoids (9 and 10), and 17 known sesqui- and diterpenoids (11-27) were isolated from the radix of Curcuma aromatica. Among these compounds, 1 is an unprecedented guaiane with unique cyclopropane and furan functionalities, and 9 is the first atisane diterpenoid isolated from a Curcuma species. Their 2D and 3D structures were established using HRESIMS and spectroscopic methods, including ECD and IECD data. The antioxidant activities of compounds 1-27 were evaluated based on their ability to protect PC12 cells against HO-induced damage, with 1, 2, 5-8, 11, 12, 14, 16, 18, and 19 exhibiting notable antioxidant effects on oxidative injury induced by HO.

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“…Accumulating researches have already identified the effects of sesquiterpenes of Curcuma zedoaria in preventing inflammatory responses. 12,30 –32 Cho et al 33 demonstrated that zedoarondiol, a compound of ZGS, dose dependently inhibited lipopolysaccharide-stimulated tumor necrosis factor α, interleukin (IL) 6, and IL-1β production in RAW 264.7 macrophage and mouse peritoneal macrophage cells by suppressing the phosphorylation of Nuclear factor-kappB (IkappB) kinase (IKK) and Mitogen-activated protein kinases (MAPKs) and subsequently by inactivating the nuclear factor-κB pathway. This demonstrates that ZES prevents inflammation.…”

Section: Discussionmentioning

confidence: 99%