Sesquiterpenoids from the Rhizomes of <i>Curcuma phaeocaulis</i> and Their Inhibitory Effects on LPS-Induced TLR4 Activation

Abstract

Two new guaiane-type (2, 6) and one new furanogermacrane-type (11) sesquiterpenoids have been isolated along with twelve known compounds from an EtOAc-soluble extract of Curcuma phaeocaulis rhizomes. The structures of the isolated compounds were elucidated using a combination of NMR, MS, and circular dichroism (CD) spectra. The inhibitory effects of each compound on lipopolysaccharide (LPS)-induced Tolllike receptor 4 (TLR4) activation in THP-1-Blue cells were assessed, and compound 4 showed more potent inhibitory activity against LPS-stimulated TLR4 activation.

A New 4,5-Secofurancadinene from the Rhizome of Curcuma kwangsiensis

“…The rhizome of Curcuma kwangsiensis S. G. Lee et C. F. Liang is one of three base source plants of Rhizoma Curcumae indexed in Chinese Pharmacopoeia (2015 edition) [1], which has good effects on treating blood stasis, amenorrhea, indigestion and abdominal distension. Currently, seventeen sesquiterpenoids (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) were isolated from the rhizome of Curcuma kwangsiensis S. G. Lee et C. F. Liang for the first time, including a new 4,5-secofurancadinene (1) (Figure 1).…”

Study on Quality Standards and Hepatoprotective Effect of Curcuma phaeocaulis Radix

“…Its original plant and medicinal parts are shown in Figure 1 . Most current research has focused on Huangsiyujin [ 3 , 4 ], Wenyujin [ 5 ], and Guiyujin [ 6 ] or Curcuma phaeocaulis rhizome [ 7 , 8 ], but there have been few studies on Lüsiyujin.…”

Diarylheptanoids from Curcuma phaeocaulis Suppress IL-6-Induced STAT3 Activation

“…The rhizomes of C. phaeocaulis have been used as a traditional remedy for arthralgia, poor blood circulation, dysmenorrhea, and psychataxia in Asian countries including India, Korea, China, and Japan [1,2]. The main components of C. phaeocaulis are diarylheptanoids [3] and sesquiterpenoids [4,5], which possess various pharmacological activities, such as anti-inflammatory [6], hepatoprotective [7], anti-oxidant [3], anti-proliferative [8], and neuroprotective effects [9].…”

“…Binding of IL-6 to the IL-6 receptor complex, consisting of IL-6Rα and glycoprotein 130 (gp130), leads to the activation of Janus kinase family members (JAKs) responsible for the dimerization of the STAT3 protein [10]. The activation of STAT3, which forms phosphorylated dimers that can translocate into the nucleus, promotes the expression of inflammation-related gene, such as C-reactive protein (CRP), monocyte chemotactic protein 1, intercellular adhesion molecule 1 (ICAM-1), and vascular cell adhesion mol-Supporting information available online at http://www.thieme-connect.de/products ABSTR AC T Three undescribed diarylheptanoids (3)(4)(5) and six known curcuminoids (1, 2, and 6-9) were obtained from the ethyl acetate-soluble fraction of an ethanolic extract of Curcuma phaeocaulis. Their chemical structures and absolute configurations were elucidated by high-resolution electrospray ionization mass spectrometry, nuclear magnetic resonance spectroscopy, circular dichroism spectroscopy, and the modified Mosherʼs method.…”

“…In the present study, the ethyl acetate-soluble fraction of the EtOH extract of the rhizomes of C. phaeocaulis was separated using column chromatography to provide three previously undescribed diarylheptanoids (3)(4)(5) and six known compounds (1, 2, and 6-9), namely, 1,3-dihydroxy-1,7-bis(3,4-dihydroxyphenyl)-heptane-3,5-diol (1) [20], 1,7-bis(3,4-dimethoxyphenyl)-1-hepten-3,5-diol (2) [21], 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (6) [22], demethoxycurcumin (7) [23], curcumin (8) [19], and 1,5-dihydroxy-1,7-bis(4-hydroxyl-3-methoxyphenyl)-4,6-heptadiene-3-one (9) [22] (▶ Fig. 1).…”