Zedoalactone B

(1)H NMR-Based Metabolomics Approach Revealing Metabolite Variation of Black Turmeric (Curcuma caesia) Extracts and Correlation with Its Antioxidant and alpha-Glucosidase Inhibitory Activities.[Pubmed:37200789]

Food Technol Biotechnol. 2023 Mar;61(1):107-117.

RESEARCH BACKGROUND: Curcuma species (Zingiberaceae) are well known medicinal herbs in India and Southeast Asia. Despite various findings reporting their beneficial biological activities, very little information has been recorded on the Curcuma caesia. Thus, this study aims to determine the phenolic content, antioxidant and alpha-glucosidase inhibitory activity of both rhizome and leaves of C. caesia. EXPERIMENTAL APPROACH: Rhizome and leaves of C. caesia were dried with oven (OD) and freeze (FD)-drying methods, and extracted with different Phi(ethanol,water)=100:0, 80:20, 50:50 and 0:100. The bioactivities of C. caesia extracts were evaluated using in vitro tests; total phenolic content (TPC), antioxidant (DPPH and FRAP) and alpha-glucosidase inhibitory activity. Proton nuclear magnetic resonance ((1)H NMR)-based metabolomics approach was employed to differentiate the most active extracts based on their metabolite profiles and correlation with bioactivities. RESULTS AND CONCLUSIONS: The FD rhizome extracted with Phi(ethanol,water)=100:0 was observed to have potent TPC expressed as gallic acid equivalents, FRAP expressed as Trolox equivalents and alpha-glucosidase inhibitory activity with values of (45.4+/-2.1) mg/g extract, (147.7+/-8.3) mg/g extract and (265.5+/-38.6) microg/mL (IC(50)), respectively. Meanwhile, for DPPH scavenging activity, the Phi(ethanol,water)=80:20 and 100:0 extracts of FD rhizome showed the highest activity with no significant difference between them. Hence, the FD rhizome extracts were selected for further metabolomics analysis. Principal component analysis (PCA) showed clear discrimination among the different extracts. Partial least square (PLS) analysis showed positive correlations of the metabolites, including xanthorrhizol derivative, 1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-(6E)-6-heptene-3,4-dione, valine, luteolin, zedoardiol, beta-turmerone, selina-4(15),7(11)-dien-8-one, Zedoalactone B and germacrone, with the antioxidant and alpha-glucosidase inhibition activities, whereas curdione and 1-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-(lE,6E)-1,6-heptadiene3,4-dione were correlated with alpha-glucosidase inhibitory activity. NOVELTY AND SCIENTIFIC CONTRIBUTION: C. caesia rhizome and leaf extracts contained phenolic compounds and had varies antioxidant and alpha-glucosidase inhibitory capacities. These findings strongly suggest that the rhizomes of C. caesia are an invaluable natural source of active ingredients for applications in pharmaceutical and food industries.

Bioactive chemical constituents from Curcuma caesia Roxb. rhizomes and inhibitory effect of curcuzederone on the migration of triple-negative breast cancer cell line MDA-MB-231.[Pubmed:31726856]

Nat Prod Res. 2021 Sep;35(18):3166-3170.

Rhizomes of Curcuma caesia are traditionally used to treat cancer in India. The aim is to isolate chemical constituents from C. caesia rhizomes through bioassay-guided fractionation. The extract, hexanes and chloroform fractions showed effect on MCF-7 and MDA-MB-231cells in cell viability assay. The chromatographic separation afforded germacrone (1), zerumbone (2), furanodienone (3), curzerenone (4), curcumenol (5), zederone (6), curcumenone (7), dehydrocurdione (8) from hexanes fraction and curcuminol G (9), curcuzederone (10), (1S, 10S), (4S,5S)-germacrone-1 (10), 4-diepoxide (11), wenyujinin B (12), alismoxide (13), aerugidiol (14), zedoarolide B (15), Zedoalactone B (16), zedoarondiol (17), isozedoarondiol (18) from chloroform fraction. This is first report of compounds 2, 9-13, 15-18 from C. caesia. The study demonstrated compounds 1-4 and 10 are the bioactive compounds. The effect of curcuzederone (10) on MDA-MB-231 cell migration showed significant inhibition in scratch and Transwell migration assays. The results revealed that curcuzederone could be a promising drug to treat cancer.

Antiinflammation constituents from Curcuma zedoaroides.[Pubmed:30109745]

Phytother Res. 2018 Nov;32(11):2312-2320.

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-alpha production using RAW264.7 cells. In addition, the expressions of genes involved in inflammation including iNOS, COX-2, and TNF-alpha 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(50) of 27.3 and 32.6 muM, respectively. Although, Compounds 1 and 7 did not inhibit TNF-alpha 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.

Three new guaiane sesquiterpene lactones from rhizomes of Curcuma wenyujin.[Pubmed:23679107]

J Asian Nat Prod Res. 2013 Jul;15(7):723-30.

Three new guaiane sesquiterpene lactones (4S)-4-hydroxy-gweicurculactone (1), zedoalactone G (2), and (1R, 4R, 5S, 10S)-Zedoalactone B (3), and three known guaiane sesquiterpene lactones, including zedoarolide B (4), Zedoalactone B (5), and a new natural product (+)-zedoalactone A (6), were isolated from the rhizomes of Curcuma wenyujin Y.H. Chen et C. Ling. The structures were elucidated by spectroscopic methods including 1D and 2D NMR and HR-ESI-MS. The absolute configuration of 2 was determined via the calculated electronic circular dichroism (ECD), whereas the absolute configurations of 1 and 3 were determined via the ECD data of the [Rh2(OCOCF3)4] complex and [Mo2(OAc)4] complex, respectively. The inhibitory effects of compounds 1-6 on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. All of them exhibited weak anti-inflammatory activity.

Sesquiterpenes from Curcuma comosa.[Pubmed:18663560]

J Nat Med. 2009 Jan;63(1):102-4.

From the dried rhizomes of Curcuma comosa cultivating in Thailand, 26 known sesquiterpenes were isolated: zederone, zederone epoxide, furanodienone, isofuranodienone, 1(10)Z,4Z-furanodiene-6-one, glechomanolide, dehydrocurdione, neocurdione, curdione, 7 alpha-hydroxyneocurdione, 7 beta-hydroxycurdione, germacrone-1(10),4-diepoxide, germacrone, 13-hydroxygermacrone, curzerenone, curcolonol, alismol, alismoxide, zedoarondiol, isozedoarondiol, procurcumenol, isoprocurcumenol, aerugidiol, Zedoalactone B, curcumenone, and curcumadione. Their structures were elucidated on the basis of physicochemical evidence. Among them, glechomanolide, curzerenone, curcolonol, alismol, alismoxide, and zedoarondiol showed no significant optical activities, so they may be artifact products during the isolation or drying process.