ABSTRACT
Guaiane-type sesquiterpenoids are a class of terpenoids with [5,7] ring-fused system as the basic skeletal structure composed of three isoprene units, which are substituted by 4,10-dimethyl-7-isopropyl. According to the difference in functional groups and degree of polymerization, they can be divided into simple guaiane-type sesquiterpenoids, sesquiterpene lactones, sesquiterpene dimers, and sesquiterpene trimers. Natural guaiane-type sesquiterpenoids are widely distributed in plants, fungi, and marine organisms, especially in families such as Compositae, Zingiberaceae, Thymelaeaceae, Lamiaceae, and Alismataceae. Guaiane-type sesquiterpenoids have good antibacterial, anti-inflammatory, anticancer, and neuroprotective effects. In this paper, the novel guaiane-type sesquiterpenoids isolated and identified in recent 10 years(2013-2022) and their biological activities were reviewed in order to provide refe-rences for the research and development of guaiane-type sesquiterpenoids.
Subject(s)
Humans , Molecular Structure , Sesquiterpenes, Guaiane , Asteraceae/chemistry , SesquiterpenesABSTRACT
Objective: To investigate the chemical constituents in whole plant of Ainsliaeafragrans. Methods: Silica gel, Sephadex LH-20 gel column chromatography, and semi-preparative HPLC were used to separate and purify the chemical constituents of ethanol extract. And the structures were elucidated on the basis of NMR and MS spectroscopic data. Results: Nine compounds were isolated and identified as zaluzanin C-3-O-β-glucopyranosyl-(1→3)-β-glucopyranosyl-(1→3)-β-glucopyranosyl-(1→3)-β-glucopyranoside (1), macrocliniside B (2), macrocliniside I (3), isochlorogenic acid C (4), 4,5-O-di-caffeoylquinic acid methyl ester (5), isochlorogenic acid A (6), 3,5-O-di-caffeoylquinic acid methyl ester (7), 3,4-O-di-caffeoylquinic acid methyl ester (8), and astragalin (9). Conclusion Compound 1 is a new guaiane sesquiterpene glycoside named as ainslifragsideA.Compounds2, 3, 5, 7, and 8are isolated from this plant for the first time.
ABSTRACT
Five sesquiterpenoids were isolated from 90% ethanol extract of Croton yunnanensis by silica gel,Sephadex LH-20 column chromatography,as well as prep-HPLC methods. Based on MS,1 D and 2 D NMR spectral analyses,the structures of the five compounds were identified as 11-methoxyl alismol(1),6β,7β-epoxy-4α-hydroxyguaian-10-ene(orientalol C,2),multisalactone D(3),arvestonol(4),and 4,5-dihydroblumenol A(5). Compound 1 was a new guaiane-type sesquiterpenoid. Compounds 2-4 were isolated from the Croton genus for the first time,and compound 5 was obtained from this plant for the first time.
Subject(s)
Croton , Magnetic Resonance Spectroscopy , Molecular Structure , Sesquiterpenes , Sesquiterpenes, GuaianeABSTRACT
Objective: To study the chemical components from Mongolian medicinal materials Ramulus syringae (the peeled roots and branches of Syringa pinnatifolia). Methods: The compounds were purified by column chromatography on silica gel, ODS, and Sephadex LH-20. Their structures were elucidated on the basis of spectroscopic methods. Results: Twenty-one compounds were isolated from R. syringae and their structures were identified as O-ethylcubebin (1), pinnatifone B (2), 3β-O-acetyl-11α,12α- epoxy-oleanan-28,13β-olide (3), coniferyl aldehydel (4), (8R,8’R,9S)-cubebin (5), isovanillic acid (6), (+)-dihydrocubebin (7), 6,10- eposoy-4α-hydroxy guaiane (8), (+)-1β,4β,6α-trihydroxyl-eudesmane (mucrolidin, 9), acutissimalignan B (10), 2-piperonylidene-3- piperonyl-1,4-butanediol (11), 4,4’-dihydroxy-3,3’,9’-triMethoxy-9,9’-epoxylignan (12), 2β-hydroxy-α-cadinol (13), cadinane-4β,5α, 10α-triol (14), larixnaphthanoe (15), lariciresinol (16), 4,4’9-trihydroxy-3,3’-dimethoxy-9,9’-epoxylignan (17), (-)-secoisolariciresino- 9,9’-acetonide (18), berchemol (19), daucosterol (20), and ecoisolariciresinol (21). Conclusion: Compounds 1, 7, 8, 9, 10, 13, 14, and 18 are isolated from the genus Syringa for the first time. Compounds 3 and 20 are isolated from S. pinnatifolia for the first time.
ABSTRACT
Objective To study the chemical constituents from rhizome of Stellera chamaejasme. Methods The compound was isolated and purified by various chromatographic techniques, and its structure was elucidated by spectroscopic analysis. Results A new sesquiterpene was obtained from 95% ethanol extract of rhizome of S. chamaejasme and identified as 1β,10β-dihydroxyguaia- 4,11-dien-3-one (1). Conclusion Compound 1 is a new guaiane sesquiterpene and named stelleraguaianone A. Meanwhile, the compound with a guaiane sesquiterpene skeleton is also obtained from the genus Stellera for the first time.
ABSTRACT
In the present study, two new trinor-guaiane sesquiterpenes, named clavuridins B (1), and A (2), along with three known sesquiterpenes (3-5), were isolated from the Xisha soft coral Clavularia viridis. Their structures and absolute configurations were determined on the basis of spectroscopic analysis, X-ray diffraction analysis with Cu Kα radiation and by comparison with related model compounds. Compounds 1 and 3-5 were evaluated for their cytotoxic activity.
Subject(s)
Animals , Anthozoa , Chemistry , Biological Products , Chemistry , Pharmacology , Magnetic Resonance Spectroscopy , Molecular Structure , Sesquiterpenes, Guaiane , Chemistry , PharmacologyABSTRACT
To study the chemical constituents of the fruits of Fructus carotae, silica gel column chromatography and preparative HPLC were used to isolate and purify the extract of Fructus carotae. The structures of obtained compounds were elucidated on the basis of physicochemical property and spectral data. Nine guaiane-type sesquiterpenes were isolated and identified as 8β-angeloyloxy-11-hydroxy-4-guaien-3-one(1), 11-acetoxy-4-guaien-3-one(2), 11-acetoxy-8β-isobutyryl-4-guaien-3-one(3), 11-acetoxy-8β-propionyl-4-guaien-3-one(4), 11-hydroxy-4-guaien-3-one(5), 11-acetoxy-8β-angeloyloxy-1β-hydroxy-4-guaien-3-one(6), 11-acetoxy-8β-angeloyloxy-4-guaien-3-one(7), 11-acetoxy-8β-hydroxy-4-guaien-3-one(8)and 8β,11-dihydroxy-4-guaien-3-one(9). Compound 1 is a new compound, compound 5 is a new natural product, and compounds 2-4 were isolated from this genus for the first time.
ABSTRACT
A new quaiane-tgpe sesquiterpene was isolated from the 95% ethanol extract of the rhizomes of Acorus calamus by silica gel and sephadex LH-20 column chromatographic methods. Structure and absolute configuration of the sesquiterpene were elucidated by spectroscopic data and X-ray crystallographic analysis, and named as 1R,5R,7S-guaiane-4R,10R-diol-6-one.
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Objective To study the roles of micheliolide on ovarian cancer cells. Methods Firstly, human ovarian cancer cell lines HeyA8, SKOV3 and A2780/DDP were treated with different concentration of micheliolide (0.25, 0.5, 1, 2.5, 5, 10, 20, 50 μmol/L) for 72 hours, then methyl thiazolyl tetrazolium (MTT) assay was used wo detect the growth of the human ovarian cancer cell lines and the stongest inhibited cell line were selected for the following test. Secondly, after HeyA8 cell line was treated with different concentration (5, 10, 20μmol/L) of micheliolide for 24 hours, the HeyA8 cell apoptosis was measured byflow cytometry. Thirdly, the expression of RelA mRNA in HeyA8 cell was detected through real-time PCR, the expressions of nuclear factor κB(NF-κB)signal pathway related protein RelA and the activited cysteinyl aspartate specific proteinase (caspase-9) were detected by western blot analysis. Results (1) The growth of HeyA8, SKOV3 and A2780/DDP cells were all significantly inhibited after being treated with different concentration of micheliolide for 72 hours and the roles of inhibition were all concentration dependant (P<0.05). The half maximal inhibitory concentration (IC50) of HeyA8, SKOV3 and A2780/DDP were (9.8±2.2), (12.0±2.1) and (12.8±1.8)μmol/L, respectively. We chose HeyA8 cell to do the following expreriments because of its best inhibited effect. (2) After HeyA8 cell was treated with micheliolide of different concentrations, as the concentration increased (20 and 0μmol/L, for example), the apoptosis rate of HeyA8 cell raised from (7.2±1.0)%to (17.4±1.1)%, the percentage of survived cells reduce from (92.8 ± 1.3)% to (82.6 ± 1.4)%,and the relative mRNA level of RelA decreased from 1.00 ± 0.13 to 0.18 ± 0.00 (P<0.01); furthermore, the expression of RelA protein was weaken and the activited caspase-9 protein expression was increased gradually. Conclusions Micheliolide plays a significantly inhibited role in HeyA8, SKOV3 and A2780/DDP cells. The inhibited role of micheliolide inovarian cancer cells might through inhibiting nuclear factor-kappa B (NF-кB) signaling pathway, and inducing the expression of activited caspase-9 protein to promoting apoptosis of HeyA8 cell.
ABSTRACT
The dried stems of Schisandra henryi var. henryi were extracted with 95% ethanol and the extracts were further subjected to partition, affording the ethyl acetate extracts(EtOAc Extrs.).The EtOAc Extrs.were separated and purified with silica gel and octadecyl-silylated silica gel column chromatography, preparative HPLC and preparative TLC. Thirteen known compounds were obtained and identified by spectral methods including MS and NMR, all of which were elucidated as t-cadinol(1), cadinane-4β,5α,10β-triol(2), cadinane-5α, 10α-diol-2-ene(3), oxyphyllenodiols A(4), 1β, 4β-dihydroxyeudesman-11-ene(5), cyperusol C(6), (7R)-opposit-4(15)-ene-1β,7-diol(7), dysodensiol E(8), epi-guaidiol A(9), aromadendrane-4β,10β-diol(10), tricyclohumuladiol(11), caryolane-1,9β-diol(12), and guaidiol A(13). Compounds 3, 5-10, and 13 were separated from the genus for the first time, while compounds 1-13 were separated from this species for the first time.
ABSTRACT
Objective: To study chemical constituents contained in the ethanol extracts from the roots of Chloranthus serratus. Methods: Fifteen compounds were separated from the roots of M. serratus by using various chromatographic techniques. Results: Their structures were identified on the basis of physicochemical properties and spectral data as 1α, 9α-dihydroxy-8,12-expoxy-eudesma-4,7,11-trien-6-one (1), 1β, 5α-guaiane-4β, 10α-diol-6-one (2), zedoalactone E (3), multistalactone C (4), 1β, 8β-dihydroxy-eudesman-3,7(11)-dien-8α, 12-olide (5), 1β, 8β-dihydroxy-eudesman-4(15), 7(11)-dien-8α, 12 olide (6), sobrerol (7), umbelliferone (8), isofraxidin (9), 5-methoxy-6,7-methylene-dioxy coumarin (10), trans-N-p-coumaroyl tyramine (11), N-trans-feruloyl tyramin (12), N-cis-feruloyl tyramin (13), catechin (14), and 7-hydroxy-5,8-dimethoxyflavanone (15). Conclusion: Compounds 2,5-7,10,14 an 15 are obtained from the plants of Chloranthus Sw. for the first time, and compounds 1,3, and 4 are isolated from C. serratus for the first time.