No full-text available
To read the full-text of this research,
you can request a copy directly from the authors.
A new arborinane-type triterpenoid glycoside and three known megastigmanes from the roots of Cyathula officinalis K.C.Kuan
Abstract
In this phytochemical study, a novel arborinane-type triterpenoid glycoside (1) and three known megastigmanes (2–4) were isolated from the dried roots of Cyathula officinalis K.C.Kuan. The structures of these compounds were elucidated using NMR spectroscopy. This is the first report of arborinane-type triterpenoids in the Amaranthaceae family. Among these known megastigmanes, compound 3 was isolated from the Amaranthaceae family for the first time, while compounds 2 and 4 were first reported from the Cyathula genus. The chemotaxonomic significance of these compounds is discussed.
ResearchGate has not been able to resolve any citations for this publication.
The genus Salsola L. (Russian thistle, Saltwort) includes halophyte plants and is considered one of the largest genera in the family Amaranthaceae. The genus involves annual semi-dwarf to dwarf shrubs and woody tree. The genus Salsola is frequently overlooked, and few people are aware of its significance. The majority of studies focus on pollen morphology and species identification. Salsola has had little research on its phytochemical makeup or biological effects. Therefore, we present this review to cover all aspects of genus Salsola, including taxonomy, distribution, differences in the chemical constituents and representative examples of isolated compounds produced by various species of genus Salsola and in relation to their several reported biological activities for use in folk medicine worldwide.
The present investigation involves the meiotic studies on three populations of Cyathula capitata Moq. (family Amaranthaceae) from west Himalaya. All the three populations uniformly revealed chromosome count of 2n=34 which is the first ever report for the species. Male meiosis was abnormal in all the populations characterized by occurrence of chromatin stickiness, laggards and bridges leading to abnormal microsporogenesis. The two populations showed the phenomenon of cytomixis resulting into heterogenous sized pollen grains.
A phytochemical study for the MeOH extract of Annona squamosa leaves led to the isolation of seven compounds. Among them there were two nitro derivative compounds (1 and 2), two phenolic glucoside compounds (3 and 4), and three sesquiterpenes (5‒7). The structures of these natural compounds were determined by the spectroscopic methods including 1D and 2D NMR methods. All the isolated compounds were assessed for the effects on the sEH inhibitory activity; of all the compounds, thalictoside (1) and arabinothalictoside (2) displayed strong inhibition of sEH activities with IC50 value of 20.2 µM and 47.1 µM, respectively. A kinetic analysis of compounds 1 and 2 revealed that both of them were competitive inhibitory action. The molecular docking increases our understanding of receptor‒ligand binding of all compounds. These results suggested that nitro derivatives from Annona squamosa leaves are potential sEH inhibitors.
Cyathulae Radix (CR), also known as “Chuanniux” is a well-known traditional Chinese herbal medicine that has been used in China for thousands of years. The present work reviewed advances in traditional uses, origin, chemical constituents, pharmacology, pharmacokinetics, and toxicity studies of CR. This work aims to provide more up-to-date references for modern study and application of this plant. Furthermore, the possible trends and perspectives for future research of this plant are also discussed. In China, the roots of CR have been widely used in clinical practice to treat orthopedic, gynecological, and urologic diseases. Currently, over 59 compounds have been isolated and identified from CR, including alkaloids and flavonoids. The extracts and compounds from CR have many pharmacological activities both in vivo and in vitro. They provide beneficial effects on the hematological system and anti-inflammatory properties. However, few studies have investigated the pharmacokinetics and toxicity of CR. Further studies should be undertaken to investigate the clinical effects, toxic constituents, and pharmacokinetics of CR; perform quality evaluation; and establish quality criteria for processed C. officinalis. Furthermore, studying the changes of raw and processed CR and the variety of this plant between different cultivated areas and cultivars will be interesting.
Breast cancer is an increasing public health problem. One of the main
causes of breast cancer is estrogen receptor alpha. Overexpression of
estrogen receptor is seen in a number of cases of breast cancer. The
aim of this study was to screen out the effective bioactive compounds
from Grevillea robusta namely 4-hydroxyacetophenone, Bisnorstriatol,
Grasshopper ketone, P-coumaric acid, which may be potential
inhibitors of estrogen receptor alpha (ER-α) for searching a drug
against the breast cancer. A wide range of docking score found during
molecular docking by Schrodinger. 4-hydroxyacetophenone,
Bisnorstriatol, Grasshopper ketone, P-coumaric acid showed the
docking score -6.49, -6.187, -7.368 and -6.103 respectively. Among all the compounds
Grasshopper Ketone showed best docking score towards estrogen receptor alpha. So,
Grasshopper Ketone is the best compounds for selective inhibitors of estrogen receptor alpha,
as it possessed the best value in Molecular docking. Further in vitro and in vivo investigation
need to identify estrogen receptor alpha inhibitory activity of isolated compounds from
Grevillea robusta.
n -Hexane, EtOAc, and BuOH fractions obtained from methanol extract of leaves of Cordia rothii Roem and Schult, yielded 1-octacosanol (1), β-sitosterol (2), stigmast-5-en-3-O-β- D -glucoside (3), (2S,1′S,2′S,3′R,7′Z)-N-1′-(O-β- D -glucopyranosyl)methyl-2′,3′-dihydroxy-heptadec-7′-enyl-2-hydroxytetracosane-amide (4), methyl 2-hydroxy-3-(4′-hydroxy)-phenyl propionate (5), (2R)-(4-hydroxyphenyl)lactic acid (6), syringaresinol mono-β- D -glucoside (7), 6-hydroxy-3-oxo-α-ionol 9-O-β- D -glucopyranoside (8), staphylionoside D (9), and 3-(3′,5′-dimethoxy-4′-O-β- D -glucopyranosyl-phenyl)-prop-2E-en-1-ol (10). To the best of our knowledge, all compounds except 2 are reported for the first time from this source. Norterpenoid, lignan, cerebroside, and megastigmane are also reported for the first time. Immunomodulatory activity was evaluated using oxidative burst; phytohaemagglutinin (PHA) stimulated T-cell proliferation and nitric oxide (NO) assays. EtOAc fraction exhibited significant inhibitory activity against ROS with IC 50 value of 29.4 ± 2.8 µg/mL.
n-Hexane fraction exhibited very strong suppressive effect on PHA stimulated T-cell proliferation with IC 50 value of 85% inhibition. Compound 7 exhibited significant inhibitory activity (IC 50 = 11.3 and 18.0 on PMN and whole blood respectively) on zymosan activated ROS generation. Eight sub-fractions showed potent inhibitory activity on the NO with >60% inhibition. These results suggest that compounds from C. rothii could be potential inhibitor for the mediators involved in innate and adaptive immune responses, and potential anti-inflammatory agents.
Garhwal Himalaya has been the reservoir of enormous natural resource including vegetational wealth. Primitive communities and tribes who live in the vicinity of forest due to being close to the nature, possess a deep practical knowledge on indigenous flora, pertaining to curatives, culture, customs, ethos, cults, religion, belief, legends, myths as well as other miscellaneous uses. The people in remote villages and tribal areas depend upon the folk medicines and household remedies to a great extent. The prevalent practice of herbal remedies has descended down from generation to generation and includes the cure from simple ailments to the most complicated one. The present communication pertains to the ethnomedicinal plants used for the treatment of various diseases and ailments like dysentery,
Cyathula prostrata (Linn) Blume (Amaranthaceae) is an annual herb widely used traditionally in the treatment of various inflammatory and pain related health disorders in Nigeria. The aim of this study is to evaluate the anti-inflammatory, analgesic and antioxidant activities of the methanolic extract of Cyathula prostrata (Linn) Blume.
The anti-inflammatory (phorbol 12-myristate 13-acetate (PMA)-induced reactive oxygen species (ROS), lipopolysaccharide (LPS) induced nitric oxide production in U937 macrophages, LPS-induced COX-2 expression, carrageenan-induced rat paw oedema, arachidonic acid-induced ear oedema and xylene-induced ear oedema), analgesic (acetic acid-induced writhing and hot plate tests) and antioxidant activities (DPPH [1,1-diphenyl-2-picrylhydrazyl] and lipid peroxidation assays) activities of the plant extract were investigated.
The methanolic extract of Cyathula prostrata did not show inhibitory activity in the in vitro PMA-induced reactive oxygen species, LPS-induced nitric oxide production and LPS-induced COX-2 expression assays. In the in vivo anti-inflammatory assays, the extract (50, 100 and 200mg/kg) showed a significant (P<0.05) dose-dependent inhibition in the carrageenan, arachidonic acid and xylene-induced tests. Cyathula prostrata produced a significant (P<0.05, 0.001) dose-dependent inhibition in the acetic acid and hot plate analgesic tests respectively. The plant extract did not exhibit any antioxidant activity in the DPPH and lipid peroxidation assays.
The results suggest that the methanolic extract of Cyathula prostrata possesses anti-inflammatory and analgesic activities and this authenticates the use of the plant in the traditional treatment of ailments associated with inflammation and pain.
The title compound isolated from Areca catechu L. (common name: arborinol methyl ether; a member of the arborane family) was established as 3α-methoxyarbor-9(11)-ene, C(31)H(52)O. Rings A/B/C/D assume a chair conformation, while ring E has an envelope conformation. The absolute configuration was determined to be (3R,5R,8S,10S,13R,14S,17S,18S, 21S) by analysis of Bijvoet pairs based on resonant scattering of light atoms, yielding a Hooft parameter y of -0.03 (3).
Four new compounds, 4-[(1-ethoxy-2-hydroxy)ethyl]phenol (1), 2,3-isopropylidene cyasterone (2), 24-hydroxycyasterone (3) and 2,3-isopropylidene isocyasterone (4), together with fourteen known compounds, have been isolated from the roots of Cyathula officinalis Kuan. Their structures have been elucidated predominantly by spectroscopic methods.
Six undescribed compounds, including four undescribed ecdysteroids (cyathsterones A-D) and two undescribed phenolic glycosides (cyathglucosides A-B), were isolated from the roots of Cyathula officinalis Kuan. Their structures were based on chemical analyses, NMR spectroscopic evidence, DP4+ calculations, and hydrolysis products. All compounds inhibited NO release in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages in vitro. Among them, cyathsterone A showed the strongest inhibitory effects. Moreover, cyathsterone A has been shown to inhibit the release of the proinflammatory cytokines TNF-α, IL-6, and IL-1β in LPS-induced RAW 264.7 macrophages in vitro. Further studies found that cyathsterone A present concentration-dependent suppression of the protein expression of iNOS and COX-2 in LPS-stimulated RAW 264.7 cells in vitro and exerted anti-inflammatory activity via the NF-κB signalling pathway.
Five previously undescribed polyacetylene glucosides, namely, four C10- and one C14-acetylenes, together with three known analogues, were isolated from the florets of Carthamus tinctorius L. The structures of these novel compounds were elucidated to be (5R)-5-acetoxy-8,10,12-tetradecatriyne-1-O-β-D-glucopyranoside, (2Z)-decaene-4,6,8-triyne-1-O-β-D-glucopyranoside, (8Z)-1-[(3-O-β-D-glucosyl)-isovaleroyloxy]-8-decaene-4,6-diyne, (8Z)-decaene-1-isovaleroyloxy-4,6-diyne-10-O-β-D-glucopyranoside, and (2E,8E)-decadiene-4,6-diyne-1-O-β-D-glucopyranoside via spectroscopic and chemical methods. All of the isolated compounds were tested for cytotoxicity against cancer cell lines, antibacterial activity, and inhibitory effects on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production. The results showed that (5R)-5-acetoxy-8,10,12-tetradecatriyne-1-O-β-D-glucopyranoside significantly inhibited LPS-induced NO production in RAW264.7 cells in a dose-dependent manner.
Phytochemical investigation of the ethyl acetate soluble part, generated from the ethanol extract of the roots of Dipsacus asper, led to the separation and identification of three undescribed triterpenoids including one arborinane type, one ursane type and one oleanane type, two unreported oleanane type triterpenoid arabinoglycosides, and 18 known analogues. Structures of these compounds were determined by comprehensive spectroscopic analyses, with the absolute configurations of 25-acetoxy-28-dehydroxyrubiarbonone E and 2α,3β-dihydroxy-23-norurs-4(24),11,13(18)-trien-28-oic acid being established by evaluation of their experimental and calculated ECD spectra. 25-Acetoxy-28-dehydroxyrubiarbonone E features an oxygenated C-25 that is the first case among arborinane type triterpenoids, while 2α,3β,24-trihydroxy-23-norurs-12-en-28-oic acid incorporates a sp³ C-24 that is a rare structural feature of 23-norursane type triterpenoids. Of these isolates, 2′,4′-O-diacetyl-3-O-α-l-arabinopyranosyl-23-hydroxyolea-12-en-28-oic acid and hederagonic acid exhibited moderate antibacterial activity against Staphylococcus aureus with IC50 values of 12.3 and 10.3 μM, respectively, while those with either a feruloyloxy group or an arabinosyl moiety at C-3 displayed potent cytotoxic activities against four tumor cell lines A549, H157, HepG2 and MCF-7.
Two diacyldaucic acids (1 and 2), an α,β-unsaturated γ-lactone-type lignan (3) and its derivatives (4-6), and 12 known compounds were isolated from a traditional East Asian vegetable, Oenanthe javanica. The absolute configuration of 1 was validated by obtaining (+)-osbeckic acid through acid hydrolysis. The absolute configurations of 3-5 were determined by comparing their experimental and computed ECD data. The conclusion was supported by applying the phenylglycine methyl ester method to 3. Compound 6 was obtained as an interconverting mixture of isomers in a 3:1 trans- cis ratio. Several water-soluble components (1, 3, and 6) showed concentration-dependent inhibitory effects on antigen-stimulated degranulation in RBL-2H3 cells without producing any direct cytotoxicity against RBL-2H3 or HeLa cells.
Four new compounds, including two butenolides (1 and 2), an arborinane-type triterpenoid (3) and a phenylethanoid glycoside (4), along with the known triterpenoids (5–17) and phenylethanoid glycosides (18–29), were isolated from whole plants of Plantago depressa. The structures of the isolated compounds were elucidated by comprehensive spectroscopic analyses and were evaluated for their anti-inflammatory or antiradical activities. Our results underlined that, among compounds 1–17, only compound 16 inhibited lipopolysaccharide-induced NO production with an IC50 equal to 5.33 ± 0.51 μM. All phenylethanoid glycosides (4, 18–29) were evaluated for their antiradical activity with a DPPH radical scavenging bioassay and showed high to moderate effect (IC50 from 2.70 to 51.51 μM).
A new sesquiterpenoid glycoside, consisting of one vetispirane-type, dmetelisproside A (1), together with two known megastigmane sesquiterpenoids, citroside A (2) and staphylionoside D (3) were isolated from the leaves of Datura metel L. The structures were determined by analysis of their MS and NMR data as well as by comparison with literature values. All isolates were evaluated for cytotoxicity toward SGC-7901, Hepg2, HeLa, MCF-7, and MDA-MB-231 cancer cell lines, and anti-inflammatory activity against nitric oxide (NO) in RAW 264.7 cells in vitro. Compounds 1 and 2 exhibited pronounced cytotoxicity against SGC-7901 and HeLa cells with IC50 values in the range of 21.43 to 29.51 μm. All three compounds displayed potential effects against NO production with IC50 values of 31.10, 34.25, and 44.31 μm, respectively. Thus, these isolated compounds in the leaves of Datura metel L were subjected to bioactivity substances for future studies on medicinal application.
Two new arborinane-type triterpenes, myrotheols A (1) and B (2), two new arborinane-type glycosides, myrothesides C (3) and D (4), together with four known diterpenes (5 – 8) were isolated from the ethyl acetate extract of the endolichenic fungus Myrothecium inundatum. The structures of new compounds 1 – 4 were elucidated by NMR and MS analyses. The absolute configuration of 1 was assigned by a single-crystal X-ray diffraction experiment. Compounds 3 and 4 represent the first two natural 4-O-methyl-α-D-mannosides. Compounds 1 – 8 exhibited cytotoxicity against K562 and RKO human cancer cell lines.
Three novel triterpenoids, 14-epiarbor-7-en-3β-ol (1), 14-epiarbor-7-en-3β-yl formate (2) and 14-epiarbor-7-en-3-one (3) were isolated from the rhizomes of Imperata cylindrica. Their structures were determined using spectroscopic methods including 2D NMR and using NMR shift reagents. These unique triterpenoid skeletons were isolated for the first time and the presence of these compounds suggests a novel biosynthetic route for triterpenoids.
Durian, known for its abundant nutrition, is a delicious fruit from Southeast Asia with increasing popularity worldwide. In this study, a series of chromatographic methods and bioactivity assays were applied to identify major compounds from durian shells. Two new triterpenoids, two new phenolics, and seven new glycoside esters, as well as sixteen known compounds, were isolated and identified. Anti-inflammatory activities were assayed and evaluated for the isolated compounds. Most of the isolated compounds exhibited pronounced inhibitory activities on lipopolysaccharides-induced NO production in RAW 264.7 cells. The results indicated that durian shells could serve as anti-inflammatory agents for functional food or medicinal use. This study additionally provided motivation for the ecological protection of durian shells.
From the leaves of Zanthoxylum ailanthoides, 4′-O-p-E-coumaric acid esters of 2-propanol β-D-glucopyranoside, megastigmane and megastigmane glucosides were isolated. Their structures were elucidated by spectroscopic evidence. The absolute configurations of the megastigmane and aglycone of megastigmane glucosides were determined by the octant rule and modified Mosher’s method after protection of carboxylic acids by p-bromophenacyl esters and primary alcohols by pivaloyl esters.
A new nitrogen-containing phenolic glycoside, moringaside A (1), and a new megastigmane glycoside, moringamegastigmane A (2), were isolated from the leaves of Moringa oleifera together with 16 known compounds. The chemical structures of the isolated compounds were elucidated on the basis of chemical and physicochemical evidence. To the best of our knowledge, there are few reports of compounds that effect acylated ghrelin secretion. Among the constituents of M. oleifera, niazirin (5) significantly stimulated the secretion of acylated ghrelin in vitro using rat primary gastric cells. This result suggests that 5 is a promising therapeutic agent for anorexia.
The abnormal proliferation and migration of vascular smooth muscle cells (VSMCs) are associated with cardiovascular diseases and related complications. Such deleterious proliferation and migration events are triggered by cytokines and growth factors, and among them, platelet-derived growth factor (PDGF) is recognized as the most potent inducer. Despite the genus Rubia being researched to identify valuable commercial and medicinal virtues, Rubia philippinensis has rarely been investigated. Nine arborinane-type triterpenoids (1-9) were identified from this underutilized plant species. In particular, 4 was identified as the first arborinane derivative carrying a ketocarbonyl motif at C-19. The presence of the cyclopentanone moiety and the associated configurational assignment were determined by utilizing NOE and coupling constant analysis. These compounds were assessed for their inhibitory potential on PDGF-induced proliferation and the migration of VSMCs. Treatment with 5 μM compound 5 (62.6 ± 10.7%) and compound 9 (41.1 ± 4.7%) impeded PDGF-stimulated proliferation without exerting cytotoxicity. Compound 7 exhibited antimigration activity in a dose-dependent manner (38.5 ± 3.0% at 10 μM, 57.6 ± 3.2% at 30 μM). These results suggest that the arborinane-type triterpenoids may be a pertinent starting point for the development of cardiovascular drugs capable of preventing the intimal accumulation of VSMCs. © 2016 The American Chemical Society and American Society of Pharmacognosy.
Three new triterpenoid glycosides, 3β-hydroxy-28-norolean-12-ene-16-one 3-O-β-d-glucopyranoside (1), 3β,17β-dihydroxy-28-norolean-12-ene-16-one 3-O-β-d-glucopyranoside (2) and 3β-hydroxy-olean-12-ene-16,28-lactone 3-O-β-d-glucopyranoside (3) together with eclalbasaponin II (4) were isolated from Acanthopanax senticosus (Rupr. & Maxim.) Harms. Their structures were elucidated on the basis of spectroscopic and physico-chemical analyses. Inhibition of NF-κB of these isolates was measured in HepG2 cells using a luciferase reporter system. Among the isolates, compounds 1, 2 and 4 inhibited NF-κB activation stimulated by TNF-α in a dose-dependent manner, with IC50 values ranging from 8.3 ± 0.7 to 13.5 ± 1.0 μM.
Five lignan glycosides, seven megastigmane glycosides, and seven phenolic compounds were isolated by repeated column chromatography from the MeOH extract of Salsola komarovii. Their structures were determined to be lariciresinol-9-O-β-D-glucopyranoside (1), alangilignoside C (2), conicaoside (3), (+)- lyoniresinol 9'-O-β-D-glucopyranoside (4), (8S,8'R,7'R)-9'-[(β-glucopyranosyl)oxy]lyoniresinol (5), blumenyl B β- D-glucopyranoside (6), blumenyl A β-D-glucopyranoside (7), staphylionoside D (8), icariside B2 (9), (6R,9S)-3- oxo-α-ionol β-D-glucopyranoside (10), 3-oxo-α-ionol 9-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (11), blumenol B 9-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (12), benzyl 6-O-β-D-apiofuranosyl-β-Dglucopyranoside (13), canthoside C (14), tachioside (15), isotachioside (16), biophenol 2 (17), 2-(3,4-dihydroxy)- phenyl-ethyl-β-D-glucopyranoside (18), and cuneataside C (19) by spectroscopic methods. All the isolated compounds 1 - 19 were reported from this source for the first time. Compounds 2, 3 and 6 upregulated NGF secretion to 118.8 ± 3.6%, 128.2 ± 9.3% and 111.1 ± 7.1% without significant cell toxicity.
Ten glycosidic compounds were isolated from an ethanol extract of Machilus wangchiana by a combination of various chromatographic techniques including column chromatography over silica gel and Sephadex LH-20 and reversed-phase flash chromatography and HPLC. Their structures were identified by spectroscopic data analysis (IR, MS, and NMR) as icariside B1 (1), boscialin-3-O-β-D-glucopyranoside (2), pisumionoside (3), isolariciresinol-9'-O-β-D-xylopyranoside (4), 5'-methoxyisolariciresinol-9'-O-β-D-xylopyranoside (5), lyoniresinol-9'-O-β-D-xylopyranoside (6), (E) -4-hydroxyphenylprop-7-ene 4-O-β-D-glucopyranoside (7), (E) - 4-hydroxy-3-methoxyphenylprop-7-ene 4-O-α-L-rhamnopyranosyl-(1 --> 6) -β-D-glucopyranoside (8), 4-hydroxy-3-methoxyphenylprop-8-ene 4-O-β-D-xylopyraosyl-(1 --> 6) -β-D-glucopyranoside (9), and 4-hydroxy-3,5-dimethoxyphenylprop-8-ene 4-O-α-L-rhamnpyranosyl-(1 --> 6)-β-D- glucopyranoside (10), respectively.
A chemical investigation of the roots of Pteroxygonum giraldii led to the isolation of a new arborane-type triterpene, pteroxygonumnol A (1), a new myricetin glycoside, myricetin 3-O-beta-D-galactopyranoside 3'-O-beta-D-xylopyranoside (2), and a group of phenolic lipids, 36, along with four known phenolic compounds, (-)-epigallocatechin, (-)-epigallocatechin gallate, gallic acid, and 2-(4-hydroxyphenyl)acetic acid. Their structures were elucidated on the basis of extensive spectroscopic analyses.
New potent piscicidal sterol acylglucosides named chrysanthosides have been obtained from the flower of Edgeworthia chrysantha, together with the previously known bis-coumarin and grasshopper ketone and their structures characterized to be sitosterol-3-O-6-linoleoyl- and sitosterol-3-O-6-linolenoyl-β-d-glucopyranosides by spectral data and synthesis. The natural and synthetic chrysanthosides possess potent piscicidal activity against killie-fish which was killed within 3 hr at a concentration of 0.1 ppm.
Blumenols A, B, and C, new compounds from Podocarpus blumei, are shown to have structures (1), (2), and (3), respectively, with the opposite stereochemistry to that of abscisic acid (4) at the ring chiral centre.
Four new pseudoguaianolides (1-4), one new guaianolide (5), together with ten known compounds (6-15) were isolated from the aerial parts of Inula hupehensis. Their structures were elucidated mainly on the basis of 1D and 2D spectroscopic methods and circular dichroism analysis. In addition, compounds 1-10 and 13 were tested for their inhibitory effects against LPS-induced NO production in RAW264.7 macrophages. Compounds 2, 6, 8 and 9 exhibited significant inhibitory activities with IC50 values in the range of 0.6-6.6 μM.
HRGC and HRGC-MS identifications of glycosidically bound Riesling leaf constituents were achieved after extraction with MeOH, Amberlite XAD-2 adsorption, and subsequent enzymatic hydrolysis of the glycoconjugates. Among the enzymatically liberated aglycons 23 bound C-13 norisoprenoids were identified. With the aid of multilayer coil countercurrent chromatography (MLCCC) five major C-13 glycosides were purified, and their structures were elucidated by high-field NMR, i.e., the beta-D-glucopyranosides of vomifoliol, 4,5-dihydrovomifoliol, 3-hydroxy-5,6-epoxy-beta-ionone, grasshopper ketone, and 3-oxo-megastigman-9-ol. The latter glucoside with a saturated megastigmane skeleton is reported here for the first time. In addition, the P-D-glucopyranosides of benzyl alcohol and raspberry ketone have been isolated.
Twelve new arborinane-type triterpenoids (1-12) and four new anthraquinones (13-16), together with 50 known compounds, were isolated from the roots of Rubia yunnanensis. The structures of 1-16 were elucidated by spectroscopic data analysis and chemical methods. All compounds were evaluated for their cytotoxic, antibacterial, and antifungal activities. Rubiyunnanol C (5) is the first example of an arborinane-type triterpenoid with a double bond at C-8-C-9. © 2011 The American Chemical Society and American Society of Pharmacognosy.
Three conjugates of the abscisic acid derivative (2Z,4E)-5-[(1S,3S,5R,8S)-3,8-dihydroxy-1,5-dimethyl-7-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid and phenolic glucosides (1-3), and an eremophilane-type sesquiterpene glucoside (4), along with ten known compounds, were isolated from the roots of Lindera strychnifolia. The structures of all compounds were elucidated by means of spectroscopic analysis, and by application of the modified Mosher's method for the methyl ester of the abscisic acid derivative and the octant rule for 4.
A hydrophilic interaction chromatography (HILIC) and reverse-phase liquid chromatography (RPLC) coupled with electrospray TOF MS method was developed for the analysis and characterization of constituents in the radix of Cyathula officinalis Kuan. Separation parameters of HILIC such as buffer pH, mobile phase strength, and organic modifier were evaluated. Fructose, glucose, and sucrose were identified by HILIC-ESI/TOF MS. Reverse-phase liquid chromatography-ESI/TOF MS were applied for quick and sensitive identification of major saponins in Cyathula officinalis. In-source collision-induced dissociation has been performed to elucidate the fragmentation pathways of oleanane-, hederagenin-, and gypsogmin-type saponins. Twelve saponins were characterized in this plant for the first time, and four of them were presumed to be new compounds. In addition, one phytoecdysteroid (cyasterone) and one coumarin (6,7-dimethoxycoumarin) were detected at the same time. The present method was capable of rapid characterizing and providing structure information of constituents from herbal drugs.
Plants and certain bacteria use a non-mevalonate alternative route for the biosynthesis of many isoprenoids, including carotenoids. This route has been discovered only recently and has been designated the deoxyxylulose phosphate pathway or methylerythritol phosphate (MEP) pathway. We report here that colonisation of roots from wheat, maize, rice and barley by the arbuscular mycorrhizal fungal symbiont Glomus intraradices involves strong induction of transcript levels of two of the pivotal enzymes of the MEP pathway, 1-deoxy-D-xylulose 5-phosphate synthase (DXS) and 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR). This induction is temporarily and spatially correlated with specific and concomitant accumulation of two classes of apocarotenoids, namely glycosylated C13 cyclohexenone derivatives and mycorradicin (C14) conjugates, the latter being a major component of the long-known 'yellow pigment'. A total of six cyclohexenone derivatives were characterised from mycorrhizal wheat and maize roots. Furthermore, the acyclic structure of mycorradicin described previously only from maize has been identified from mycorrhizal wheat roots after alkaline treatment of an 'apocarotenoid complex' of yellow root constituents. We propose a hypothetical scheme for biogenesis of both types of apocarotenoids from a common oxocarotenoid (xanthophyll) precursor. This is the first report demonstrating (i) that the plastidic MEP pathway is active in plant roots and (ii) that it can be induced by a fungus.
A fructan named CoPS3 was isolated from Cyathula officinalis Kuan. The structure of CoPS3 was determined by methylation, by the reductive-cleavage method combined with GC-MS analysis, and both 1D and 2D 1H and 13C NMR spectroscopy. These results show that CoPS3 is a graminans-type fructan that is comprised of a beta-D-fructofuranosyl backbone having residues linked (2-->1)- and (2-->6) with branches and an alpha-D-glucopyranose residue on the nonreducing end of the fructan chain. Each branch is terminated by a beta-D-Fruf residue. Bioassay showed that it could inhibit growth of Lewis pulmonary carcinoma implanted in mice.
In the course of our study on the isolation and structure determination of constituents in tropical plants, we focused on Peucedanum japonicum Thunb., belonging to the family Umbelliferae. In this study, a new C(13) norisoprenoid glucoside, (3S)-O-beta-d-glucopyranosyl-6-[3-oxo-(2S)-butenylidenyl]-1,1,5-trimethylcyclohexan-(5R)-ol (1), and two new phenylpropanoid glucosides, 3-(2-O-beta-d-glucopyranosyl-4-hydroxyphenyl)propanoic acid (3) and methyl 3-(2-O-beta-d-glucopyranosyl-4-hydroxyphenyl)propanoate (4), were isolated from the n-butanol soluble fraction of this plant's leaves, together with five known compounds. The structures of these compounds were determined on the basis of spectroscopic evidence. In addition, all isolated compounds were examined for scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical and inhibitory activity against mushroom tyrosinase. These results suggested that 2-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol (7) and 3-O-beta-d-glucopyranosyl-2-(4-hydroxy-3-methoxyphenyl)propanol (8) showed an appreciable activity in both assay systems.
Two cytotoxic rocaglate derivatives possessing an unusual dioxanyloxy unit, silvestrol (1) and episilvestrol (2), were isolated from the fruits and twigs of Aglaia silvestris by bioassay-guided fractionation monitored with a human oral epidermoid carcinoma (KB) cell line. Additionally, two new baccharane-type triterpenoids, 17,24-epoxy-25-hydroxybaccharan-3-one (3) and 17,24-epoxy-25-hydroxy-3-oxobaccharan-21-oic acid (4), as well as eleven known compounds, 1beta,6alpha-dihydroxy-4(15)-eudesmene (5), ferulic acid (6), grasshopper ketone (7), apigenin, cabraleone, chrysoeriol, 1beta,4beta-dihydroxy-6alpha,15alpha-epoxyeudesmane, 4-hydroxy-3-methoxyacetophenone, 4-hydroxyphenethyl alcohol, ocotillone, and beta-sitosterol 3-O-beta-D-glucopyranoside, were also isolated and characterized. The structures of compounds 1-4 were elucidated by spectroscopic studies and by chemical transformation. The absolute stereochemistry of silvestrol (1) was established by a X-ray diffraction study of its di-p-bromobenzoate derivative, and the structure of 3 was also confirmed by single-crystal X-ray diffraction. The isolates and chemical transformation products were evaluated for cytotoxicity against several human cancer cell lines, and silvestrol (1) and episilvestrol (2) exhibited potent in vitro cytotoxic activity. Silvestrol (1) was further evaluated in vivo in the hollow fiber test and in the murine P-388 leukemia model.
Chemical investigation of ecdysteroidal constituents of the roots and stems of Cyathula officinalis led to the isolation of two cyasterone stereoisomers, 2 and 3, together with the known cyasterone 1. The structures of compounds 2 and 3 were determined to be 28-epi-cyasterone and 25-epi-28-epi-cyasterone, respectively, by means of spectroscopic analysis. X-Ray structures of 1 and 2 confirmed the 24S,25S,28R configuration for 1 and 24S,25S,28S for 2.
Chemical constituents from Pilea aquarum subsp. brevicornuta
- Zhou