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Sesquiterpenes from the rhizomes of Alpinia japonica and their inhibitory effects on nitric oxide production.

Published on Apr 1, 2013in Fitoterapia2.43
· DOI :10.1016/j.fitote.2013.01.015
Qiang-Ming Li3
Estimated H-index: 3
(CPU: China Pharmaceutical University),
Jian-Guang Luo23
Estimated H-index: 23
(CPU: China Pharmaceutical University)
+ 2 AuthorsLing-Yi Kong36
Estimated H-index: 36
(CPU: China Pharmaceutical University)
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Abstract
Abstract A novel norsesquiterpene ( 1 ), three new bisabolenes sesquiterpenes ( 2 – 4 ), along with 7 known compounds ( 5 – 11 ), were isolated from the rhizomes of Alpinia japonica . The structures of the new compounds were elucidated by analysis of spectroscopic data. The absolute configuration of C-1 in 3 was deduced via the circular dichroism data of the in situ formed [Rh 2 (OCOCF 3 ) 4 ] complexes. Inhibitory effects of the isolates on nitric oxide production in lipopolysaccaride-activated RAW264.7 macrophages were evaluated. Compound 6 showed significant inhibitory activity with IC 50 value of 5.3 μΜ, and compounds 1 , 3 , 5 and 7 – 10 exhibited moderate inhibitory activities with IC 50 values between 24.5 and 46.3 μM.
  • References (22)
  • Citations (11)
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References22
Newest
Published on Mar 1, 2012in Phytochemistry Letters1.34
Jian-Guang Luo23
Estimated H-index: 23
(CPU: China Pharmaceutical University),
Xiaoqing Lv2
Estimated H-index: 2
(CPU: China Pharmaceutical University)
+ 1 AuthorsLing-Yi Kong36
Estimated H-index: 36
(CPU: China Pharmaceutical University)
Abstract Three new norsesquiterpenoids, oxyphenol A ( 1 ), mandassion A ( 2 ) and mandassion B ( 3 ), along with three known compounds ( 4 – 6 ) were isolated from the fruits of Alpinia oxyphylla . Chemical structures of 1 – 3 were established by analysis of spectroscopic data. The absolute configuration of 2 and 3 was determined by the comparison of experimental electronic circular dichroism (ECD) spectroscopy and time-dependent density functional theory (TDDFT) calculations. Inhibitory effects...
Published on Jul 1, 2011in Organic Letters6.55
Chang-Shui Yang3
Estimated H-index: 3
,
Xiao-Bing Wang25
Estimated H-index: 25
+ 3 AuthorsLing-Yi Kong36
Estimated H-index: 36
An unusual katsumadain dimer via a [2 + 2] cycloaddition, katsumadain C (1), and a unique chalcone-diarylheptanoid adduct via a Diels–Alder reaction, calyxin Y (2) with novel carbon frameworks, were isolated from the seeds of Alpinia katsumadai. Their structures and relative configurations were determined by spectroscopic evidence.
Published on Mar 1, 2011in Fitoterapia2.43
Gerlânia de Oliveira Leite8
Estimated H-index: 8
,
Laura Hévila Inocêncio Leite4
Estimated H-index: 4
+ 4 AuthorsAdriana Rolim Campos13
Estimated H-index: 13
Abstract The study examined the antiinflammatory and antinociceptive effects of the sesquiterpene (−)-α-bisabolol (BISA). The antiinflammatory effect was evaluated on acute models of dermatitis induced by Croton oil, arachidonic acid, phenol and capsaicin, respectively, in mouse ear. BISA inhibited the dermatitis induced by all noxious agents, except capsaicin. BISA was assessed in two established mouse models of visceral nociception. Mice were pretreated orally with BISA, and the pain-related b...
Published on Sep 1, 2008in Tetrahedron Letters2.26
Shu-Zhen Hua2
Estimated H-index: 2
(CPU: China Pharmaceutical University),
Xiao-Bing Wang25
Estimated H-index: 25
(CPU: China Pharmaceutical University)
+ 2 AuthorsLing-Yi Kong36
Estimated H-index: 36
(CPU: China Pharmaceutical University)
Sumadains A (1) and B (2), a pair of unique isomeric sesquiterpene-chalcone conjugates with unprece- dented skeletons, were isolated from the seeds of Alpinia katsumadai. Their structures and relative con- figurations were established by NMR spectroscopy and X-ray crystallography.
Published on Jul 1, 2007in Phytochemistry2.90
Milka Todorova12
Estimated H-index: 12
(BAS: Bulgarian Academy of Sciences),
Antoaneta Trendafilova9
Estimated H-index: 9
(BAS: Bulgarian Academy of Sciences)
+ 2 AuthorsHelmut Duddeck9
Estimated H-index: 9
(Leibniz University of Hanover)
Abstract The lactone profile of six origins of Achillea collina growing in Bulgaria was studied and significant variability was observed. The reasons for the differences in the lactone composition are discussed. Twenty-five components in total were isolated and identified, while the presence of ten lactones was proved by intensive TLC analysis in comparison with reference compounds. The structures of the components 17 , 20 , 25 – 30 were established by spectroscopic methods. The structure of 7 ,...
Published on Aug 5, 1985in Chemistry Letters1.49
Akio Fukuzawa17
Estimated H-index: 17
,
Yoshiaki Takaya4
Estimated H-index: 4
+ 1 AuthorsTadashi Masamune26
Estimated H-index: 26
The structure of a new bromoditerpene named prepinnaterpene, isolated from the title alga, is described.
Published on Dec 15, 2005in Journal of Neuroscience Research4.14
Chol Seung Lim5
Estimated H-index: 5
,
Da-Qing Jin7
Estimated H-index: 7
(Inje University)
+ 5 AuthorsJung-Soo Han9
Estimated H-index: 9
(Inje University)
Xanthorrhizol, a natural sesquiterpenoid isolated from the rhizome of Curcuma xanthorrhiza Roxb (Zingiberaceae), has antibacterial activities and protective effects against cisplatin-induced hepatotoxicity. In this study, we investigated the activities of xanthorrhizol as an antioxidant or antiinflammatory agent using neuronal and microglial cells. Xanthorrhizol had potent neuroprotective effects on glutamate-induced neurotoxicity and reactive oxygen species (ROS) generation in the murine hippoc...
Published on Sep 1, 2002in Planta Medica2.75
Ling-Yi Kong36
Estimated H-index: 36
,
Min-Jian Qin2
Estimated H-index: 2
,
Masatake Niwa29
Estimated H-index: 29
Two novel bis-labdanic diterpenoids named calcaratarin D and calcaratarin E were isolated from the rhizomes of Alpinia calcarata. Their structures were elucidated as a pair of stereoisomers on the basis of the spectral evidence. 2D NMR techniques including 1 H- 1 H COSY, HMQC, HMBC, NOESY spectra and HRFABMS were extensively applied to establish the structures. The two bis-labdanic diterpenoids showed cytotoxic activity against human KB cells in vitro.
Sang Kok Lee43
Estimated H-index: 43
,
Chai-Hee Hong1
Estimated H-index: 1
+ 6 AuthorsJae-Kwan Hwang32
Estimated H-index: 32
(Yonsei University)
Prostaglandins and nitric oxide produced by inducible cyclooygenase (COX-2) and nitric oxide synthase (iNOS), respectively, have been implicated as important mediators in the processes of inflammation and carcinogenesis. These potential COX-2 and iNOS inhibitors have been considered as antiinflammatory and cancer chemopreventive agents. In this study, we investigated the effect of natural sesquiterpenoids isolated from plants of the Zingiberaceae family on the activities of COX-2 and iNOS in cul...
Published on Jan 1, 2001in Flavour and Fragrance Journal1.38
Peter Weyerstahl24
Estimated H-index: 24
(Technical University of Berlin),
Helga Marschall21
Estimated H-index: 21
(Technical University of Berlin),
Christian Christiansen8
Estimated H-index: 8
(Technical University of Berlin)
The acidic part of Brazilian lantana oil contains mainly new bisabolene and tricyclic helifolene derivatives. 3-Formyl-helifolen-12-oic acids 14, 16, 11-formyl-helifolen-15-oic acids 10, 12, 6,10-epoxybisabol-2- 18, 20, 22, 24, and -3-en-12-oic acids 19, 21, 23, 25, γ-(26) and ar-curcumen-15-oic acids (27), as well as the known ar-curcumen-12-oic acid (28) and amorpha-4,9,11-trien-12-oic acid, were characterized as their methyl esters. The bifunctionalized methyl helifolenoates 10, 12, 14, 16 we...
Cited By11
Newest
Published on May 1, 2017in Phytochemistry2.90
Chuan-Pu Shen3
Estimated H-index: 3
(CPU: China Pharmaceutical University),
Jian-Guang Luo23
Estimated H-index: 23
(CPU: China Pharmaceutical University)
+ 1 AuthorsLing-Yi Kong36
Estimated H-index: 36
(CPU: China Pharmaceutical University)
Abstract Eight lindenane dimers, chololactones A-H, along with two known compounds, were isolated from the roots of Chloranthus holostegius . Their structures were elucidated using 1D/2D NMR and HRESIMS, and their absolute configurations were determined using the ECD exciton chirality method. All isolates were tested for inhibitory effects on the NO production of the liposaccharide (LPS)-induced RAW 264.7 macrophages, and showed moderate activity with IC 50 values at 3.5–35.4 μM.
Published on Mar 1, 2017in Industrial Crops and Products4.19
Amel Toubane1
Estimated H-index: 1
(USTHB: University of Science and Technology Houari Boumediene),
Sid Ahmed Rezzoug2
Estimated H-index: 2
(University of La Rochelle)
+ 1 AuthorsKamel Daoud4
Estimated H-index: 4
(USTHB: University of Science and Technology Houari Boumediene)
Abstract Optimization of natural compounds extraction from Algerian Carthamus Caeruleus L was studied using accelerated solvent extraction (ASE). The optimization study was performed using three solvents (ethanol, methanol and hexane) and with a temperature range (40–50 °C), a static extraction time (30–50 min) and a cycle number (1–5) as independent variables. The optimum ASE conditions for a maximum extraction yield for each solvent were estimated, the plant pores shape and structures before a...
Published on Jan 1, 2017in RSC Advances3.05
Xiao-Ni Ma2
Estimated H-index: 2
(SOA: State Oceanic Administration),
Chun-Lan Xie4
Estimated H-index: 4
(SOA: State Oceanic Administration)
+ 2 AuthorsXian-Wen Yang23
Estimated H-index: 23
(SOA: State Oceanic Administration)
Alpinia species is one of the most important genera of the Zingiberaceae family. In Asia, they have been widely used as food and traditional medicines for centuries. This review focuses on their chemical constituents and their relevant biological activities with 252 references covering from 1955 to 2015. In total, 544 compounds were isolated from 35 Alpinia species. The major ones are terpenoids (207) and diarylheptanoids (143). The crude extracts and identified compounds exhibited a broad spect...
Published on Sep 1, 2016in Scientific Reports4.01
Qiang-Ming Li3
Estimated H-index: 3
,
Jian-Guang Luo23
Estimated H-index: 23
+ 4 AuthorsLing-Yi Kong36
Estimated H-index: 36
Sesquiterpenoid dimers are some naturally occurring metabolites that have C30 cores, and originate biosynthetically from two sesquiterpenoid molecules1. Cadinane dimers, as one class of sesquiterpenoid dimers, are of considerable interest due to their ability to induce diverse biological activity (e.g. male antifertility, anticancer, antiviral, and anti-inflammatory)1. Of these naturally occurring cadinane dimers, most are derived from two units of the corresponding monomers by the free-radical ...
Published on Jan 22, 2016in Journal of Natural Products4.26
Bing-Yuan Yang1
Estimated H-index: 1
,
Ling-Yi Kong36
Estimated H-index: 36
+ 4 AuthorsJian-Guang Luo23
Estimated H-index: 23
During an ongoing exploration of potential anti-inflammatory agents from medicinal plants, eight new arylalkenyl α,β-unsaturated δ-lactones, cryptoconcatones A–H (1–8), and two unusual arylalkenyl α,β-unsaturated γ-lactones, cryptoconcatones I and J (9 and 10), were identified from the leaves and twigs of Cryptocarya concinna. The structures of these compounds were established based on spectroscopic data (MS, 1D/2D NMR), and their absolute configurations were determined with Riguera’s method, th...
Published on Jun 26, 2015in Journal of Natural Products4.26
Chuan-Pu Shen3
Estimated H-index: 3
,
Jian-Guang Luo23
Estimated H-index: 23
+ 1 AuthorsLing-Yi Kong36
Estimated H-index: 36
Eight new cafestol-type diterpenoids, tricalysins A–H (1–8), along with five known analogues (9–13), were isolated from the twigs of Tricalysia fruticosa. The structures of 1–8 were elucidated by the application of spectroscopic methods. Inhibitory effects of the isolates on nitric oxide (NO) production in lipopolysaccaride-activated RAW 264.7 macrophages were evaluated, and compound 8 exhibited the most potent bioactivity, with an IC50 value of 6.6 ± 0.4 μM. It was shown further that compound 8...
Published on May 22, 2015in Journal of Natural Products4.26
Wen-Jun Xu2
Estimated H-index: 2
,
Mengdi Zhu5
Estimated H-index: 5
+ 3 AuthorsLing-Yi Kong36
Estimated H-index: 36
Hypermongones A–J (1–10), rare methylated polycyclic polyprenylated acylphloroglucinol derivatives, together with three known simple acylphloroglucinols (11–13) as their plausible biogenetic precursors, were identified from the flowers of Hypericum monogynum. The structures of 1–10 were elucidated by analysis of their 1D and 2D NMR spectroscopic data; the absolute configuration of their polycyclic skeleton was determined by the electronic circular dichroism exciton chirality method and was subse...
Published on Jan 1, 2015in Neurological Research1.98
Jianhua Ma4
Estimated H-index: 4
,
Ning Liu2
Estimated H-index: 2
+ 6 AuthorsYiwu Dai6
Estimated H-index: 6
AbstractTransplanted human umbilical cord mesenchymal stem cells (hUC-MSCs) have exhibited considerable therapeutic potential for traumatic brain injury (TBI). However, how hUC-MSCs migrating to the injury region and the mechanism of hUC-MSCs promoting functional recovery after TBI are still unclear. In this study, we investigated whether stromal cell-derived factor-1 (SDF-1) was involved in the hUC-MSCs migration and the possible mechanisms that might be involved in the beneficial effect on fun...
Published on May 4, 2014in Journal of Asian Natural Products Research1.17
Meng-Qin Bian1
Estimated H-index: 1
(Peking Union Medical College),
Jie Kang5
Estimated H-index: 5
(Peking Union Medical College)
+ 3 AuthorsCHENRuo-yun19
Estimated H-index: 19
(Peking Union Medical College)
From the seeds of Alpinia galanga Willd., three new norsesquiterpenoid racemic mixtures, galanols A–C (1–3) were isolated, along with three known sesquiterpenoids (4–6). Their structures were elucidated by means of UV, IR, HR-ESI-MS, 1D NMR and 2D NMR spectroscopic data.
View next paperA Novel Sesquiterpene Peroxide from Alpinia japonica (THUNB.) MIQ.