{"content"=>"Phytochemical Analysis of and -Hexane Extracts and the HPLC Quantitation of Triterpenes.", "i"=>[{"content"=>"Podospermum"}, {"content"=>"Scorzonera n"}]} (original) (raw)
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Members of Scorzonera genus are known for their potential application in both food and pharmaceutical industries. The present study reports the chemical component and bioactivity of the dichloromethane, ethyl acetate, hexane, methanol and infused extracts of Scorzonera hieraciifolia Hayek aerial parts and roots. The methanolic extracts of both aerial parts and roots were good sources of total phenolic and flavonoid content. For the aerial parts, the infused and methanolic extracts showed highest (p < 0.05) free radical scavenging (2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS)), reducing (cupric reducing antioxidant capacity (CUPRAC))and ferric reducing antioxidant power (FRAP)) and metal chelating capacities. Whilst, for the root extracts, overall most remarkable free scavenging and reducing activity was observed for the methanolic extracts (p < 0.05) while the hexane extracts showed highest metal chelating activity. The inhibitory activity of the extracts was evaluated against key enzymes. Overall, the hexane extracts of both aerial parts (acetylcholinesterase (AChE): 2.27 ± 0.04 and butyrlcholinesterase (BChE): 5.75 ± 0.48 mg galantamine equivalent (GALAE)/g) and roots (AChE: 2.44 ± 0.35 and BChE: 53.17 ± 0.22 mg GALAE/g) were most potent against AChE and BChE, suggesting a role for the more lipophilic compounds in this regard. The highest inhibitory activity against tyrosinase was displayed by methanolic extracts of aerial parts (64.70 ± 0.26 mg kojic acid equivalent (KAE)/g) and roots (63.63 ± 0.20 mg KAE/g). Modest activity was observed against α-amylase and α-glucosidase, two major enzymes implicated in the pathology of diabetes. Liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) analysis showed the presence of 40 compounds such as caffeic, ursolic, betulinic and oleanolic acid and their derivatives in the studied extracts. Multivariate analysis showed that the biological activities were dependent on the plant parts used as well as on the type of solvent used. Overall, the results showed that S. hieraciifolia is a valuable source of phytochemicals for both the nutraceutical and pharmaceutical sectors.
Triterpenoids and Flavonoid from Scorzonera undulata ssp. alexandrina
2014
A phytochemical investigation of EtOAc extract of Scorzonera undulata ssp. alexandrina (Boiss.) Maire yielded five compounds including four triterpenoids called lupeol 1, 24-methylenecycloartanol 2, 3-O-(6-O-acetyl-β-D-glucopyranosyl) βsitosterol 3 and daucosterol 4 and one flavonoid named apigenin 5. Their structures were determined using spectroscopic methods (1 H-NMR, 13 C-NMR, DEPT, HMBC, HSQC, COSY, NOESY), ESI-MS and EI-MS, values of optical rotation and chemical correlations with known compounds that have been described in the literature.
New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana
TURKISH JOURNAL OF CHEMISTRY, 2021
Introduction Treatment with plants is as old as human history. Mankind has benefited from natural herbal resources to protect health and treat against diseases. The isolation and characterization of the active compounds found in plants started to develop from the beginning of the 19th century with developing technology. Numerous natural compounds in the scientific process, compounds such as morphine, penicillin, codeine, atropine, resveratrol, and digoxin, were isolated from natural sources and took place in the treatment processes. The isolation of the compounds from natural sources and the clarification of their structures are extremely important in the scientific process as they have the potential to become a new drug-active substance. Due to the potential of natural compounds to be exemplary molecules in active substance synthesis, studies in this field are considered to be inevitable for serving humanity. Scorzonera L. species are known to be used in complementary medicine and consumed as a vegetable in the world and Turkey [1-4]. The genus Scorzonera L. is a member of tribe Cichorieae (Asteraceae), and it is represented by around 180-190 species in the worldwide [1-2]. The major center in terms of diversity is the arid and mountainous Irano-Turanian region [3]. The genus is represented by perennial herbs often having a caudex or tuber under ground [2]. There are 52 species in Turkey and 31 of them are endemic [4]. Some members of this genus are consumed as a vegetable in Turkey [5-6]. S. aucheriana known as "Buz Tekesakalı" in Turkey is caulescent, herbaceous perennial herbs endemic to Turkey [4]. Their rootstock is thick and crowned by decayed leaf remains [2]. Members of Scorzonera including S. aucheriana are characterized by a rich latex ingredient [2]. It has been stated that different Scorzonera species are used as pain relievers among the public, and scientific studies in our country have analgesic, antiinflammatory and wound-healing effects [7-11]. Scorzonera mongolica Maxim. and Scorzonera austriaca Willd. are grown in China and are used in the treatment of fever reduction, boils, and nipple inflammation [12-14]. Scorzonera divaricata Lipsch root and aboveground parts are used in the treatment of ulcers and malignant stomach tumors; Scorzonera pseudodivaricata Turcz is used in febrile conditions caused by pulmonary edema, diuretic, and viral infection [15]. Scorzonera cretica Willd., Greek cuisine is used in dishes such as savory [16]. S. pseudodivaricata and S. divaricata species grow in Mongolia and are used for medical purposes. Scorzonera hispanica is the most commonly grown and cultivated ornamental plant in Europe, as well as being used to treat colds, lung diseases, appetizing, mucolytic, stomatic, diuretic, antipyretic effects, snake bites, and it is also added to coffee [17]. Scorzonera humilis L. is used in wound healing and gastrointestinal disorders [18]. Rootstock and fresh shoots of some of the Scorzonera member grown in Turkey are consumed fresh or cooked under the name of 'manger'. It has been stated that these plants are used for the purpose of removing high blood pressure, kidney diseases, diabetes, moxibustion, infertility, and vascular stiffness [5,19].
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010
The Araliaceae family is one of the most medicinally important plant families, which include about 55 genera and 700 species of trees, shrubs, lianas and perennial herbaceous plants. Chemical and pharmacological investigations have indicated that triterpenoid saponins are important bioactive components existing in the plants of Araliaceae family. 1) Schefflera actinophylla (ENDLICHER) HARMS, (synonym: Brassaia actinophylla ENDLICHER) is an evergreen tree in the Araliaceae family and native to tropical rainforests and gallery forests in Australia, New Guinea and Java. This distinctive ornamental plant is easily recognized by the several trunks mostly unbranched, a few very large palmately compound leaves with 7-12 leaflets as in an umbrella, and the large showy clusters of many dark red or crimson flowers on 10-20 widely spreading dark purple axes, suggesting arms of an octopus. Hence, common names include umbrella tree and octopus tree. Up till now, there have been no phytochemical and bioactivities reports on this species. In this manuscript, we described the isolation and structure elucidation of three new ursane-type triterpene glycosides (1-3), two new lupane-type triterpene glucosides (4, 6), one new lupane-type triterpene (5) and one new lupane-type triterpene glucosyl ester (7), along with nine known lupanetype triterpene glycosides (8-16) that were identified by comparing their spectroscopic data with the previously reported ones. Results and Discussion The air-dried and powdered leaves of Schefflera actinophylla were extracted with 70% MeOH till exhaustion and then concentrated under reduced pressure to yield a viscous gummy material. The concentrated methanol extract was washed with n-hexane. The methanolic layer was evaporated, suspended in water and then extracted with EtOAc and 1-BuOH, successively. The 1-BuOH-soluble fraction as well as the EtOAc-soluble fraction was subjected to Diaion HP-20, silica gel, octadecylsilanized (ODS) silica gel column chromatographies (CC), droplet counter-current chromatography (DCCC), and high-performance liquid column chromatography (HPLC) to afford seven new compounds (1-7), along with nine known triterpene compounds, 3a-hydroxylup-20(29)-ene-23,28-dioic acid (8), 2) 3a-hydroxylup-20(29)ene-23,28-dioic acid 28-O-[4Љ-O-a-L-rhamnopyranosyl-6Ј-O-b-D-glucopyranosyl]-b-D-glucopyranosyl ester (9), 3) 3a,23-dihydroxylup-20(29)-en-28-oic acid 28-O-[4Љ-O-a-Lrhamnopyranosyl-6Ј-O-b-D-glucopyranosyl]-b-D-glucopyranosyl ester (10), 4) 3-epi-betulinic acid 3-O-sulfate (11), 5) 3epi-betulinic acid 3-O-b-D-glucopyranoside (12), 6) 3-epi-betulinic acid 3-O-sulphate, 28-O-[4Љ-O-a-L-rhamnopyranosyl-6Ј-O-b-D-glucopyranosyl]-b-D-glucopyranosyl ester (13), 7) 3-epi-betulinic acid 28-O-[4Љ-O-a-L-rhamnopyranosyl-6Ј-Ob-D-glucopyranosyl]-b-D-glucopyranosyl ester (14), 8) 3-epibetulinic acid 3-O-b-D-glucopyranoside, 28-O-[4Љ-O-a-Lrhamnopyranosyl-6Љ-O-b-D-glucopyranosyl]-b-D-glucopyranosyl ester (15), 9) 3-epi-betulinic acid 3-O-b-D-6Ј-acetylglucopyranoside, 28-O-[4Љ-O-a-L-rhamnopyranosyl-6Љ-O-b-Dglucopyranosyl]-b-D-glucopyranosyl ester (16) 10) (Fig. 1).
Triterpene glycosides from Agrostemma gracilis
Phytochemistry, 2010
Four triterpene saponins, agrostemmosides A-D were isolated from the methanol extract of Agrostemma gracilis. The structures of the compounds were determined as 3-O-beta-D-xylopyranosyloleanolic acid 28-O-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;2)-[beta-D-xylopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;6)]-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;6)-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;2)-beta-D-xylopyranosyloleanolic acid 28-O-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;2)-[beta-D-xylopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;6)]-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;6)-beta-D-glucopyranosyl ester, 3-O-beta-D-xylopyranosylechinocystic acid 28-O-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;2)-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;6)-beta-D-glucopyranosyl ester, 3-O-beta-D-xylopyranosylechinocystic acid 28-O-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;2)-[beta-D-xylopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;6)]-beta-D-glucopyranosyl-(1--&amp;amp;amp;amp;amp;amp;amp;amp;amp;gt;6)-beta-D-glucopyranosyl ester by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. To the best of our knowledge this is the first phytochemical report on A. gracilis, and echinocystic acid saponins were encountered for the first time in Caryophyllaceae family.
Sesquiterpenoids and tirucallane triterpenoids from the roots of Scorzonera divaricata
A sulfated guaiane sesquiterpene lactone, an unusual pyridinium alkaloid with a sulfated guaiane sesquiterpene lactone nucleus, an amino conjugate of a sulfated guaiane sesquiterpene lactone, a bis-abolane sesquiterpene, three tirucallane triterpenes, and six known compounds, were isolated from roots of Scorzonera divaricata. Their structures and absolute configurations were established based on chemical and spectroscopic methods, X-ray single crystal crystallography, and also by comparison with experimental and calculated ECD spectra. One of the tirucallane triterpenes exhibited significant cytotoxic activities against four human cancer cell lines (HL60, HeLa, HepG2, and SMMC-7721) in vitro. Two of sul-fated guaiane sesquiterpenoids also exhibited antioxidant activities by scavenging ABTS cation free radicals. Tirucallane-type and dammarane-type triterpenes were not previously known in the genus Scorzonera. The study suggests that sulfated guaiane-type sesquiterpenoids are a valuable marker for systematic chemical studies in the Lactuceae tribe of the Asteraceae.
Triterpenoids from the leaves of Alphitonia xerocarpus Baill and their biological activity
Phytochemistry, 2016
Ten previously undescribed triterpenoid saponins and a previously undescribed norlupane triterpenoid were isolated, with three known saponins, four known flavonoids, two known lupane derivatives, sitosterol and 6'-heptadecanoyl-3-O-β-D-glucopyranosylsitosterol from the leaves of Alphitonia xerocarpus (Rhamnaceae), an endemic tree of New Caledonia. The chemical structures of the purified compounds were identified by nuclear magnetic resonance and mass spectrometry. The isolated compounds were tested for their antioxidant, antityrosinase, antibacterial and cytotoxic activity. The aqueous methanol extract showed antioxidant activity (DPPH assay) due to the presence of rutin. Ceanothenic acid showed good cytotoxic activity against a KB cell line (IC50 = 2.6 μM) and antibacterial activity against Staphylococcus aureus and Enterococcus faecalis with MIC values of 8 and 16 µg/mL, respectively. The previously undescribed 29-hydroxyceanothenic acid exhibited moderate cytotoxic activity (IC50 = 10 μM), good antibacterial activity against S. aureus (MIC = 4 µg/mL) and moderate antibacterial activity against E. faecalis (MIC =16 µg/mL).