Germacrane‐Type Sesquiterpenes from <i>Curcuma wenyujin</i>

Lou, Yan; Zhao, Feng; Wu, Zhaohua; Peng, Kai‐Feng; Wei, Xingchuan; Chen, Lixia; Qiu, Feng

doi:10.1002/hlca.200900059

Cited by 39 publications

(12 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…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.

View full text Add to dashboard Cite

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.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Sesqui- and Diterpenoids from the Radix of Curcuma aromatica

Dong

Dai

et al. 2017

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…Germacrone is a monocyclic sesquiterpenoid compound. Recently, it was found that germacrone has strong antiviral activity, as well as anti-inflammatory and other pharmacological effects potentially useful for clinical applications [31,32]. In particular, the germacrone and oseltamivir combination has a synergistic effect on the inhibition of influenza virus.…”

Section: Discussionmentioning

confidence: 99%

Antiviral Activity of Germacrone against Pseudorabies Virus in Vitro

Zhai

et al. 2019

Pathogens

View full text Add to dashboard Cite

Pseudorabies virus (PRV), a member of the Herpesviridae, is the causative agent of an acute infectious disease in a variety of animals. The emergence of a novel variant strain brought huge economic losses to the pig industry since classical vaccine strains were not completely effective against variant strains. Therefore, the development of new anti-pseudorabies virus drugs and vaccines is of great significance for the treatment and prevention of pseudorabies. In this study, we found that germacrone, one of the major components of the essential oils extracted from Rhizoma Curcuma, was able to effectively inhibit PRV replication in a dose-dependent manner in vitro. Germacrone showed antiviral activity against PRV in the early phase of the viral replication cycle. Moreover, we found that germacrone does not directly kill the virus, nor does it affect the expression of the PRV receptor protein nectin-1, nectin-2, and CD155. Our results suggest germacrone could be used as an efficient microbicide or immunomodulatory agent in the control of the emerging variant PRV.

show abstract

“…The IR spectrum exhibited absorption at 1668 cm −1 typical for an unsaturated lactam group. 15 The 1 H NMR spectrum (Table 2) exhibited signals corresponding to three quaternary methyl groups (δ H 1.00, 1.13, 1.70, each s) and one oxygenated methine proton (δ H 3.15, dd, J = 12.6, 3.2 Hz). The 13 C NMR data (Table 2) indicated the presence of a carbonyl carbon (δ C 177.4), two olefinic carbons at (δ C 125.2, 158.9), and two oxygenated carbons (δ C 72.4, 79.2).…”

Section: Organic and Biomolecular Chemistry Papermentioning

confidence: 99%

“…Recently, our research group has been examining the constituents of C. kwangsiensis, C. phaeocaulis and C. wenyujin as well as their inhibitory activities against LPS-induced nitric oxide production, and has hitherto reported the isolation and identification of several new sesquiterpenoids and diarylheptanoids. [12][13][14][15][16][17][18] We found that sesquiterpenes were mainly isolated from C. wenyujin and C. phaeocaulis, while diarylheptanoids were the major compounds from C. kwangsiensis. Moreover, guaiane-type and germacrane-type sesquiterpenes were mainly isolated from C. wenyujin, while guaiane-type and eudesmane-type sesquiterpenes were the major compounds from C. phaeocaulis.…”

Section: Introductionmentioning

confidence: 99%

Natural nitric oxide (NO) inhibitors from the rhizomes of Curcuma phaeocaulis

Zhao

Wang

et al. 2015

Org. Biomol. Chem.

Self Cite

View full text Add to dashboard Cite

An exploration we carried out for isolating nitric oxide (NO) inhibitors from the rhizomes of Curcuma phaeocaulis afforded one new salvialane-type sesquiterpene, phasalvione (1), two novel nor-sesquiterpenes, phaeocaudione (2) and phaeocauone (3), one aromatic acid 3-methyl-4-(3-oxo-butyl)-benzoic acid (4), two γ-elemene-type sesquiterpenes, 8β(H)-elema-1,3,7(11)-trien-8,12-lactam (5) and 8β-methoxy-isogermafurenolide (6), one eudesmane-type sesquiterpene, phaeusmane I (7), and one cyclic diarylheptanoid, phaeoheptanoxide (8). Their structures were established based on extensive spectroscopic analysis. The absolute configurations of compounds 1 and 2 were assigned using the circular dichroism data of the [Rh2(OCOCF3)4] complex, and the absolute configuration of 1 was further established by single crystal X-ray crystallography. It is noteworthy that compounds 5–7 were racemates analyzed by chiral HPLC. Furthermore, the inhibitory effects of the isolated compounds on nitric oxide production in LPS-activated macrophages were evaluated. Compounds 1, 3 and 4 showed strong inhibitory activities on NO production with IC50 values of 7.46 ± 0.69, 2.35 ± 0.17 and 3.49 ± 0.31 μM, respectively. A plausible biosynthetic pathway for 1–4 in C. phaeocaulis was also discussed.

show abstract

Germacrane‐Type Sesquiterpenes from Curcuma wenyujin

Cited by 39 publications

References 24 publications

Sesqui- and Diterpenoids from the Radix of Curcuma aromatica

Sesqui- and Diterpenoids from the Radix of Curcuma aromatica

Antiviral Activity of Germacrone against Pseudorabies Virus in Vitro

Natural nitric oxide (NO) inhibitors from the rhizomes of Curcuma phaeocaulis

Contact Info

Product

Resources

About