A new ent-kaurane diterpenoid from Ixora amplexicaulis

A new ent-kaurane diterpenoid, 6α,16α-dihyroxy-ent-kaurane (1), was isolated from the stems of Ixora amplexicaulis, together with (24R)-6β-hydroxy-24-ethyl-cholest-4-en-3-one (2), 7β-hydroxysitosterol (3), maslinic acid (4), 3,3′-bis(3,4-dihydro-4-hydroxy-6-methoxy-2H-1-benzopyran) (5) and protocatechuric acid (6). Their structures were established by extensive spectroscopic analysis, including 2D NMR techniques. Compounds 2–5 were isolated from the genus Ixora for the first time and 6 obtained originally from I. amplexicaulis.     

Hautriwaic Acid from Pulicaria salviifolia

A diterpene acid was isolated from the aerial part of Pulicaria salviifolia. Spectral data and chemical transformations identify it as hautriwaic acid.     

一个新的藏药臭蚤草二萜苷

从藏药臭蚤草的95%甲醇提取物中分离得到了2个二萜苷类化合物,采用IR,MS,1H NMR,13C NMR,ESI及HR-ESI等方法鉴定其结构分别为2-0-(2-0-Isovaler-β-D-glucopyranosyl)atraetyligenin(1)和2-O-[2-O-Isovaleryl-3-β-D-apio...     

Chemical composition and biological activities of the essential oil from Pulicaria undulata (L.) C. A. Mey. growing wild in Egypt

Abstract

Pulicaria undulata is used as a traditional herbal remedy in Egypt. We used gas chromatography-mass spectrometry for analysis of essential oil of this plant growing wild in Egypt and 64 compounds were identified. The oil was rich in oxygenated monoterpenes (64.0%) and aromatic derivatives (18.8%). The major components were carvacrol (46.5%), xanthoxylin (18.1%) and carvotanacetone (8.7%). The oil of the Egyptian plant showed significant differences from the oil results reported on this species derived from different accessions. Antioxidant activity was performed by FRAP, DPPH and ABTS assays, and the oil demonstrated a powerful antioxidant properties. Furthermore, cytotoxicity was assessed using MTT assay against three cell lines (A375, T98G, HCT116) and the oil showed moderate results with IC₅₀ of 18.53, 40.64 and 22.23?μg/ml; respectively. The oil showed a good anti-acetylcholinesterase activity (IC₅₀?=?139.2?μg/ml) using Ellman method. In conclusion, the studied oil exhibited a peculiar fingerprint and promising biological activities.     

Phytochemical Characterization,In Vitro Anti-Inflammatory,Anti-Diabetic,and Cytotoxic Activities of the Edible Aromatic Plant; Pulicaria jaubertii

Pulicaria jaubertii is a medicinal herb that alleviates inflammations and fever. Chromatographic separation, phytochemical characterization, and in vitro biological activities of the plant n-hexane extract were conducted for the first time in this study. Six compounds were isolated for the first time from the n-hexane fraction of Pulicaria jaubertii aerial parts and were identified on the bases of NMR and MS analyses as pseudo-taraxaterol (1), pseudo-taraxasterol acetate (2), 3β-acetoxytaraxaster-20-en-30-aldehyde (3), calenduladiol-3-O-palmitate (4), stigmasterol (5), and α-tocospiro B (6). Compound (6) was a rare tocopherol-related compound and was isolated for the first time from family Asteraceae, while compound (3) was isolated for the first time from genus Pulicaria. The total alcoholic extract and n-hexane fraction were tested for their anti-inflammatory, antidiabetic, and cytotoxic activities. The n-hexane fraction has dose dependent red blood cells (RBCs) membrane stabilization and inhibition of histamine release activities with IC₅₀: 60.8 and 72.9 µg/mL, respectively. As antidiabetic activity, the alcoholic extract exerted the most inhibition on the activity of yeast α-glucosidase, with an IC₅₀: 76.8 µg/mL. The n-hexane fraction showed cytotoxic activity against hepatocarcinoma (HepG-2), breast carcinoma (MCF-7), and prostate carcinoma (PC-3) cell lines with IC₅₀: 51.8, 90.8 and 62.2 µg/mL, respectively. In conclusion, the anti-inflammatory effect of Pulicaria jaubertii might be attributed to the triterpenoid constituents of the n-hexane extract of the plant.     

A new ent-kaurane diterpenoid from Isodon japonica

<正>One new ent-kaurane diterpenoid,named maoyecrystal L was isolated from the EtOAc extract of the dried leaves of lsodon japonica.Its structure was established by various spectroscopic means and confirmed by X-ray crystallographic analysis.     

A Rarely Reported Trinorsesquiterpene‐Type Structure in an Isolate from Pulicaria insignis

A trinorsesquiterpene, 1 , and its possible precursor sesquiterpene 2 were obtained from the Tibetan folk medicine Pulicaria insignis (Ming?chen?serpo). Their structures were elucidated on the basis of spectral methods including 2D‐NMR. The trinorsesquiterpene skeleton of 1 is the second example of this type of structure found in a plant, after a first compound of this type was isolated from bird's nest fungi (Cyanthus bulleri).     

Chemical composition of the essential oil from Pulicaria vulgaris var. graeca (Sch.-Bip.) Fiori (Asteraceae) growing wild in Sicily and its antimicrobial activity

In this study the chemical composition of the essential oil from aerial parts of Pulicaria vulgaris var. graeca (Sch.-Bip.) Fiori collected in Sicily was evaluated by GC and GC–MS. The main components of P. vulgaris var. graeca oil were hexadecanoic acid (21.7%), β-caryophyllene (14.3%) and geranyl propionate (8.2%). The comparison with other studied oils of genus Pulicaria is discussed. Antibacterial activity against several bacteria, including some ones infesting historical art craft, was also determined.     

Buddledin C from Pulicaria prostrata and selective synthesis of its epoxy derivative

The structure of the sesquiterpene ketone buddledin C isolated from Pulicaria prostrata (Gilib.) Aschers., was confirmed by XSA. The stereochemistry of its epoxide, which was formed selectively by treating it with hydrogen peroxide in alkaline solution, was proposed based on quantum-chemical and molecular-mechanical calculations. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 34–37, January–February, 2006.     

The antioxidant compounds isolated from the fruits of chinese wild raspberry Rubus Chingii Hu

Abstract

Raspberry, the fruit of Rubus Chingji Hu, is a widely distributed economic staple food in China. It has long been used as a traditional medicine in mainland China to treat kidney enuresis, nocturnal emission and premature ejaculation in clinic. In this paper, six known compounds (1?–?6) were purified from the fruits of Rubus chingji. Their structures were elucidated as (16α)-16,17-dihydroxy-ent-kauran-2-one17-O-β-D-glucopyranoside (1), (16R) -16,17-dihydroxy-ent-kaurane-2-one (2), 3,3′-di-O-methylellagic acid 4-(5′′-acetyl)-α-L-arabinofuranoside (3), quercilicoside A (4), esculetine (5) and ethyl-β-D-glucoside (6). All the compounds were isolated from Rubus Chingji Hu for the first time. Compounds 3 and 5 shown distinctive free radical scavenging activities in DPPH and FRAP assays. In addition, no cytotoxicity was observed for compounds 3 and 5 against different cancer cells, suggesting that they might be useful as potential antioxidant agents against various reactive oxygen species.

     

A Benzofuranoid and Two Clerodane Diterpenoids from Pulicaria wightiana

Methyl 5‐formyl‐1‐benzofuran‐6‐carboxylate ( 1 ) and the two clerodane diterpenes, methyl 6‐oxocleroda‐3,13‐dien‐15,16‐olid‐18‐oate ( 2 ) and 2β‐(2‐methylbutanoyl)cleroda‐3,13‐dien‐15,16‐olid‐18‐oic acid ( 3 ), together with 15 known compounds, were isolated from the aerial parts of Pulicaria wightiana. The structures of the new compounds 1, 2 , and 3 were established by spectroscopic (mainly 1D‐ and 2D‐NMR) methods.     

Determination of the chemical composition and antioxidant,anticancer, and antibacterial properties of essential oil of Pulicaria crispa from Saudi Arabia

Essential oils obtained from plants play critical roles in food and medicine. In this study, the phytochemical composition of Pulicaria crispa essential oil, and its antibacterial, antioxidant and anticancer properties were determined in vitro. The essential oil was extracted from the aerial parts of P. crispa through hydro-distillation using a Clevenger-type apparatus, and it was analyzed with GC-MS. The most dominant chemical constituents of the essential oil were sesquiterpenes (78.26%). The higher constituents were β-caryophyllene oxide (33.97%), modephene (23.34%), geranyl propionate (6.32%), geranyl isovalerate (6.74%), 4-cadinadiene (5%), humulene (4.05%), and β-caryophyllene (2.73%). The essential oil exhibited DPPH radical activity, and it exerted antibacterial effect against gram positive bacteria (Staphylococcus aureus and methicillin-resistant Staphylococcus aureus. However, it had no antibacterial effect on gram negative bacteria (Pseudomonas aeruginosa, Shigella sonnei, Klebsiella pneumoniae and Escherichia coli). The P. crispa essential oil produced significant cytotoxic effects against Hep-G2, MCF-7, Coca-2, and HT-29 ?cells. The oil was most toxic to Hep-G2 cells, based on its IC₂₀ and IC₅₀ values. These results indicate that the essential oil from P. crispa has potent biological properties which can be useful in the food and pharmaceutical industries.     

冬凌草中的新对映-贝壳杉烷二萜化合物

对河南省济源地区产冬凌草[Isodon rubescens(Hemsl.)Hara]再次进行了深入 的研究，从其叶的乙酸乙酯提取物中分离得到了16个化合物，其中1和2为两个新的 7，20-环氧-对映-贝壳杉烷类二萜化合物，其结构通过波谱分析确定为16（S）-羟 甲基-1α，6β，7β，11β-甲羟基-7α，20-环氧-对映-贝壳杉烷-15-酮（1）和 16（R）-羟甲基-1α，6β，7β，14β-四羟基-7α，20-环氧-对映-贝壳杉烷-15- 酮（2），分别命名为冬凌草已素（1）和庚素（2）；其余的已知化合物分别鉴定 为lasiodonin（3），冬凌草甲素（oridonin，4），乙素（ponicidin），丙素（ rubescensin C），丁素（rubescensin D），牛尾草丙素（rabdoternin C），荛 花香茶菜乙素（wikstroemioidin B），enmenol-1α-O-β-D-glucoside， enmenol，胡麻素（pedalitin），水杨酸，乌索酸，β-谷甾醇和胡萝卜甙。     

Three New Diterpenoids from Isodon Eriocalyx

Isodoneriocalyxisknowntoberichinent-kaurenoids.Inspiteofthatmanyent-kaurenoidswereisolated,newent-kaurenoidswerestillisolatedfromcollectionindifferentregions'-,o.FromthedriedleavesofthisspeciescollectedinHeqingcounty,Yunnan,threenewcompounds,eriocalyxinsC-El-3,wereisolated.Inthispaper,wereportthestructureelucidationofthesenewcompoundsbyspectralanalysis.EriocaIyxinClC22H2sO7(HRMS4O4.l825calc4O4.1835),ElMS(7OeV)In/z(reI.Int%)t4O4[M1 (lO),386[M-H2O] 'lO),368IM-2H,O] (2O),344(l00),32…     

A new ent-clerodane diterpenoid from Crassocephalum bauchiense Huch. (Asteraceae)

A phytochemical investigation of the whole plant of Crassocephalum bauchiense Huch. resulted in the isolation of a new clerodane diterpenoid, ent-2β,18,19-trihydroxycleroda-3,13-dien-16,15-olide (1), together with two known flavonoids 3′,5-dihydroxy-4′,5′,6,7,8-pentamethoxyflavone (2) and 4′,5-dihydroxy-3′,5′,6,7,8-pentamethoxyflavone (3). The compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. Compound 2 showed weak activity (IC₅₀ = 10.1 g/mL) whilst compounds 1 and 3 were inactive. The structures of the compounds were elucidated by using detailed spectral analyses, especially ¹H and ¹³C NMR, ¹H–¹H COSY, NOESY, HMBC and HR-ESI-MS.     

Two New Isoprenoid Flavonoids from Sophora flavescens with Antioxidant and Cytotoxic Activities

Sophora flavescens is a regularly used traditional Chinese medicine. In an attempt to discover adequate active agents, the isoprenoid flavonoids from S. flavescens were further investigated. In this work, two new compounds (1–2, kurarinol A-B) together with 26 known ones (3–28) were isolated and elucidated on the basis of extensive NMR, UV and MS analyses. Furthermore, the antioxidant activity of all constituents was assessed through ABTS, PTIO and DPPH methodologies and also were evaluated for cytotoxic activity by three tumor cell lines (HepG2, A549 and MCF7) and one human normal cell line (LO2 cells). As a result, a multitude of components revealed significant inhibitory activity. In particular, compound 1–2 (kurarinol A-B), two new flavanonols derivatives, exhibited the most potent ABTS inhibitory activity with IC₅₀ of 1.21 µg/mL and 1.81 µg/mL, respectively. Meanwhile, the new compound 1 demonstrated remarkable cytotoxicity against three cancer cells lines with IC₅₀ values ranging from 7.50–10.55 μM but showed little effect on the normal cell. The two new isoprenoid flavonoids could be promising antioxidant and anti-tumor nature agents.     

A new abietane diterpenoid glycoside from ajuga ovalifolia var. calantha

A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2–4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3–4 showed moderate cytotoxicity against all tested cell lines with IC₅₀ values of 1.8–7.3?μM.     

A new briarane-type diterpenoid from the South China Sea Gorgonian Dichotella gemmacea

One new briarane-type diterpenoid, dichotellide V (1), along with four known analogues, gemmacolide N (2), dichotellide J (3), junceelin A (4) and junceellolide A (5), was isolated from the South China Sea gorgonian Dichotella gemmacea. All of the isolated compounds (1–5) were established by comprehensive analysis of the spectral data, especially 1D and 2D NMR (HMQC and HMBC) spectra. The cytotoxic activities of these compounds were evaluated.     

黄草乌中的新二萜生物碱

从黄草乌(Aconitum vilmorinianum Kom.)根中分离得到三个新C~1~9-二萜生物碱: 黄乌宁(vilmorinine, 1), 黄乌生(vilmorisine20和黄乌亭(vilmoritine, 3)。采用波谱分析及化学方法确定了它们的结构。     

Caralluma tuberculata N.E.Br Manifests Extraction Medium Reliant Disparity in Phytochemical and Pharmacological Analysis

Solubility of phytoconstituents depends on the polarity of the extraction medium used, which might result in the different pharmacological responses of extracts. In line with this, ethnomedicinally important food plant (i.e., Caralluma tuberculata extracts) have been made in fourteen distinct solvent systems that were then analyzed phytochemically via total phenolic amount estimation, total flavonoid amount estimation, and HPLC detection and quantification of the selected polyphenols. Test extracts were then subjected to a battery of in vitro assays i.e., antioxidants (DDPH scavenging, antioxidant capacity, and reducing power estimation), antimicrobial (antibacterial, antifungal, and antileishmanial), cytotoxic (brine shrimps, THP-1 human leukemia cell lines and normal lymphocytes), and protein kinase inhibition assays. Maximum phenolic and flavonoid contents were computed in distilled water–acetone and acetone extracts (i.e., 16 ± 1 μg/mg extract and 8 ± 0.4/mg extract, respectively). HPLC-DAD quantified rutin (0.58 µg/mg extract) and gallic acid (0.4 µg/mg extract) in methanol–ethyl acetate and methanol extracts, respectively. Water–acetone extract exhibited the highest DPPH scavenging of 36 ± 1%. Total reducing potential of 76.0 ± 1 μg/mg extract was shown by ethanol chloroform while maximum total antioxidant capacity was depicted by the acetone extract (92.21 ± 0.70 μg/mg extract). Maximal antifungal effect against Mucor sp., antileishmanial, brine shrimp cytotoxicity, THP-1 cell line cytotoxicity, and protein kinase inhibitory activities were shown by ethyl acetate-methanol (MIC: 50 µg/disc), n-hexane (IC₅₀: 120.8 ± 3.7 µg/mL), ethyl acetate (LD₅₀: 29.94 ± 1.6 µg/mL), distilled water–acetone (IC₅₀: 118 ± 3.4 µg/mL) and methanol–chloroform (ZOI: 19 ± 1 mm) extracts, respectively. Our findings show the dependency of phytochemicals and bioactivities on the polarity of the extraction solvent and our preliminary screening suggests the C. tuberculata extract formulations to be tested and used in different ailments, however, detailed studies remain necessary for corroboration with our results.