1,721,210 research outputs found
Further New Diterpenoids from Salvia miniata Fernald (Lamiaceae)
No full textIn course of our search on Salvia metabolites for the identification of new herbicides with diterpene and triterpene skeletons [1, 2] we have continued the study on Salvia miniata Fernald [3], a Mexican species whose aerial part exudate in a preliminary test showed anti-germinative activity against Papaver rhoeas L. and Avena sativa L., chosen on the basis of evaluating the seed germination response respectively of a common invasive species and of a common crop species. From Salvia miniata we had already isolated some new and known di- and triterpenes [4]; here we report two new compounds, obtained from the chromatographic separation of not previously considered fractions. The surface exudate, obtained by rinsing the plant material with CH2Cl2, and subjected to repeated column chromatography on Sephadex LH-20 and silica gel and to reversed-phase semi-preparative HPLC, yielded two new clerodane diterpenoids (1, 2) identified by IR and NMR analysis, including TOCSY, COSY, HSQC and HMBC experiments.
[1] Vyvyan JR. Allelochemicals as leads for new herbicides and agrochemicals. Tetrahedron. 2002; 58: 1631–1646. doi:10.1016/S0040-4020(02)00052-2
[2] Dayan FE, Duke SO. Trichomes and root hairs: natural pesticide factories. Pesticide Outlook. 2003; 8: 175–178. doi:10.1039/b308491b
[3] Epling C. A Revision of Salvia, subgenus Calosphace. In: Repertorium Specierum Novarum Regni Vegetabilis. Vol.110. Fedde F. Berkley, California: University of California Press,1940.
[4] Bisio A, Romussi G, Russo E, Cafaggi S, Fraternale D, De Tommasi N. New Clerodane Diterpenoids from Salvia miniata Fernald (Lamiaceae). Planta Med. 2008; 74: 1041. doi:10.1055/s-0028-108438
A new prostaglandine-like compound from Salvia adenophora Fernald.
No full textSalvia adenophora Fernald [1] is a Mexican species whose aerial part exudate showed herbicide activity against Papaver rhoeas L. and Avena sativa L. in a preliminary test [2]. The surface exudate, obtained by rinsing the plant material with CH2Cl2, was subjected to repeated column chromatography on Sephadex LH-20 and silica gel and to HPLC-MS and MS2 experiments followed by semi-preparative RP-HPLC, yielding a new prostaglandin-like (1). The new compound was identified by IR and NMR analysis, including TOCSY, COSY, HSQC, HMBC experiments, and ESI-TRAP-MS and HR-MS analysis.Bibliografia
1 Epling, C. A Revision of Salvia, subgenus Calosphace. In: Repertorium Specierum Novarum Regni Vegetabilis. Fedde F., University of California Press: Berkley, California, 1940, Vol.110.
2 Bisio, A., Fraternale, D., Giacomini, M., Giacomelli, E., Pivetti, S., Russo, E., Caviglioli, G., Romussi, G., Ricci, D., De Tommasi, N. Crop Protection, 2010, 29, 1434-144
Phytotoxic Activity of Salvia x jamensis J. Compton.
No full textIn a previous paper we described the platelet antiaggregating activity of the surface exudate of
Salvia x jamensis J. Compton [1]. This exudate also showed a good antigerminative activity
against Papaver rhoeas L. and Avena sativa L. [2]. Bioguided fractionation of the exudate with
column chromatography on Sephadex LH-20 and silica gel yielded eight active components.
These were identified as the known compounds 15, 16-epoxy-cleroda-3-en-7α, 10β-dihydroxy-
12,17; 19,18-diolide (1), isopimaric acid (2), 14-α-hydroxy-isopimaric acid (3), 3-β-hydroxyisopimaric
acid (4), 7,8-β-dihydrosalviacoccin (5), hautriwaic acid (6), betulinic acid (7), cirsiliol
(8). Various concentrations of these substances were used for dose-response studies. Seed
germinability was assessed by determining the final cumulative percentage of germination at the
end of tests; germination progress was followed by the calculation of other indices, i.e. the speed
of germination, the speed of accumulated germination and the coefficient of the rate of
germination [3]. The lethal concentrations needed to reduce germinability by 50% (LC
Dipartimento di Scienze Farmaceutiche,
Universidad de Salerno, Salerno, Italia.
50) and by
90% (LC90
[1] Bisio A, Romussi G, Russo E, De Tommasi N, Mascolo N, Alfieri A, Bonito MC, Cicala C. (2008) Platelet Antiaggregating Activity
and Chemical Constituents of Salvia x jamensis J. Compton. Natural Products Communications 3, 881-884.
) were predicted by linear interpolation between the two adjacent values
corresponding respectively to 50% and 90% response of the total germination of the seeds for
each tested substance [4]. The compounds most active in inhibiting the germination of both the
tested species were 4, 5, 6, and 7. They were not significantly different from each other, but
significantly different from the other compounds and from control.
[2] Bisio A, Russo E, Romussi G, Fraternale D, Ricci D, Giampieri L, Bucchini A., De Tommasi N, Cafaggi S.(2008) Preliminary
results of herbicidal activity of Salvia spp. against common weeds. FITOMED 2008, III Congresso Intersocietà sulle Piante
Medicinali, Salerno, 25-27 giugno 2008.
[3] Chiapusio G,Sanchez A M, Reigosa M J, Gonzalez L, Pellissier F. 1997. Do germination indices adequately reflect allelochemical
effects on the germination process?. Journal of Chemical Ecology. 23, 2445-2453
[4] Dayan FE, Romagni JG, Duke SO. 2000. Investigating the mode of action of natural phytotoxins. Journal of Chemical Ecology. 9,
2079-2094
Diterpenoids and triterpenoids of Salvia x jamensis.
No full textThe genus Salvia L. (Lamiaceae) includes over 900 species widespread all over the world. Various plants of this genus are widely used in folk medicine and some species are listed in the modern Pharmacopoeias. Interesting compounds of this genus are flavonoids, essential oils, diterpenes and triterpenes many of which possess anti-insect (antifeedant), anti-bacterial, anti-fungal, hallucinogenic and antioxidant activities. As a part of our phytochemical research on species of the genus Salvia cultivated in Italian “Riviera dei Fiori” (Liguria) we have studied the exudate of Salvia x jamensis J. Compton. From the surface exudate, obtained by immersion of the fresh aerial parts in CH2Cl2, we have isolated two triterpenoids 1 and 2 and four diterpenoids 3-6 by repeated column chromatography on Sephadex LH-20 and silica gel. Compounds 1-5 were identified as ursolic acid, betulinic acid, isopimaric acid, 14--hydroxy-isopimaric acid and 7,8-dihydrosalviacoccin respectively by comparison of their spectral data with those reported previously. 6 is a new natural compound and its structure was determined as shown (15,16-epoxy-cleroda-3-en-7,10-dihydroxy-12,17;19,18-diolide) from the 1H- and 13C-NMR spectra and on the basis of 1H-1H-COSY, TOCSY, ROESY, HSQC and HMBC correlation
Diterpenes and triterpenes from Salvia aurea L. - Part 2: Constituents of Labiatae
No full textAs a continuation of our studies on Salvia species [1] we have investigated the constituents of Salvia aurea L. The ethanolic extract of the aerial parts afforded four diterpenes and a triterpene
Phytochemical study of Tamarix africana Poir. (Tamaricaceae)
No full textTamarix genus is a tree or shrub halophytes from coastal regions and desert, relatively long-living plants that can tolerate a wide range of environmental conditions and resist to abiotic stresses such as salt, high temperature, and drought stresses (1). Tamarix spp. are employed in traditional medicine as astringent, appetizer, stimulant of perspiration, diuretic, and spleen trouble and eye remedies (2). Younos et al. (2005) indicated the importance of this genus in some old civilizations and the actual uses of Tamarix species different organs (leaves, flowers, and galls) in the traditional Asian therapy as anti-inflammatory, anti-diarrhoic, healing and antiseptic agents (3). T. africana Poir. is an ornamental and folkloric medicinal halophyte particularly abundant in Mediterranean salt marshes (2); it’s a perennial shrub with brownish branches, punctuated, opaque, oval and acuminate leaves; its bunches reaching 6 cm long, 5-6 mm wide and contained flowers with four to five petals and four stamens. The ability of halophytes to tolerate salt and to overcome oxidative stress is determined by multiple biochemical pathways that facilitate water retention and/or acquirement, protect chloroplast functions, and maintain ion homeostasis. Essential pathways include the synthesis of compatibles solutes, specific proteins and radical scavenging molecules, such as phenolic acids and flavonoids (4). In recent years, the interesting feature of halophytes as a potential source of natural antioxidants, has aroused the interest of many researchers. In fact, it’s reported a beneficial preventive and therapeutic effects of phenolic compounds against diseases associated with oxidative stress. These constituents, and more particularly the flavonoids, are endowed with important biological activities including antioxidant, anti-inflammatory, anti-ulcer and anti-tumor. Previous studies on Tamarix species reported the isolation of hydrolyzable tannins (5), flavonoids (6) and phenolic compounds (7), while in a phytochemical work on T. africana trans-coniferyl alcohol 4-sulphate was purified and other cinnamyl alcohol sulphates were detected (8). Furthermore, several researches proved antioxidant, antimicrobial and anticancer activities of some Tamarix species such as T. ramosissima (9), T. hispida (10), and T. gallica (11).
In this context, the aim of the present work was to carry out a phytochemical study of the polar extract of T. africana aerial parts to isolate and identify bioactive compounds, including some sulphated derivatives, which could be responsible of its biological activities. The plant material was collected in Gabès (Tunisia) and dried at room temperature, then extracted with Soxhlet apparatus with n-hexane, dichloromethane and then at room temperature with methanol. The MeOH extract was partitioned between n-BuOH and H2O and the n-BuOH soluble fraction was separated by Sephadex LH-20 followed by RP-HPLC. Sulphated flavonoids, including some new compounds, were purified and fully characterized by spectroscopic techniques such as 1D and 2D-NMR, and mass spectrometry
structure and in vitro antiviral activity of triterpenoid saponins from calendula arvensis
No full textAbstract
A reinvestigation of the aerial parts of Calendula arvensis afforded, in addition to the oleanolic acid glycosides 1-4(4), the new glycoside 5 whose structure was elucidated by spectral and chemical studies and determined as 3-O-{β-D-galactopyranosyl-(1→3)[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranosyl}oleanolic acid (28→1)-β-D-glucopyranosyl ester. Furthermore, some antiviral tests were performed on glycosides 1-5 and on 5a, the hydrolysis product of 5, towards vesicular Stomatitis virus (VSV) and rhinovirus (HRV) infection in cell cultures. An inhibitory effect against VSV multiplication was observed for all the Compounds tested while HRV replication was significantly affected only by compound 3
Flavonoids and triterpenoids from Salvia blepharophylla Brandegee ex Epling
No full textVerschiedene Salvia-Arten wurden seit langer Zeit in der Volksmedizin benutzt [1]. Aus dem etanolischen Extract der Blätter von Salvia blepharophylla Brandegee ex Epling isolierten wir durch SC an Sephadex®LH-20 und DCC-Chromatographie acht Flavonoide (1-8) und eine Triterpenverbindung (9).
UV- und 1NMR-Daten von 1 (Experimenteller Teil) wiesen auf eine 5,6,3',4'-Tetrahydroxy-7-methoxyflavonstruktur (Pedalitin) hin [2,3]. Die Anwesenheit von Resonanzsignalen im 13C-NMR-Spektrum, deren chemische Verschiebungen mit denen der C-Atome 2, 3, 4 und denen vom Ring B von Luteolin bzw. 8, 9, 10 von Salvigenin und 5, 6 von Scutellarein eng korrelierbar waren und von einem Signal bei = 56,2 ppm, das mit einer 7-Methoxygruppe übereinstimmte [4], bestätigte die Struktur 1.
Die Anwesenheit von Resonanzsignalen im 13C-NMR-Spektrum von 2, deren chemische Verschiebungen mit denen der C-Atome des Rings A von 1 bzw. 2, 3, 4 und denen des Rings B von Diosmetin [5] eng korrelierbar waren, wies auf eine 5, 6, 3'-Trihydroxy-7,4'-dimethoxyflavonstruktur (Nuchensin) hin. Dieser Befund wurde von dem UV- und 1NMR-Spektren bestätigt, die mit den Literaturdaten von Nuchensin übereinstimmten [3].
Die saure Totalhydrolyse von 3 lieferte Quercetin, L-Rhamnose und Galaktose. Aufgrund der UV-, 1NMR- und 13C-NMR-Daten wurde die Verbindung als Quercetin-3-O-L--rhamnopyranosyl(16)galactopyranosid identifiziert[6].
Das UV-Spektrum von 4 ließ ein Rhamnetin-3-O-gycosid vermuten [7]. Durch die saure Totalhydrolyse, die Glucose und Rhamnetin lieferte, wurde 4 als Rhamnetin-3-O-glucosid identifiziert.
Die UV-Spektren von 5 und 6 waren typisch für Apigenin-C-glycoside [7]. Aufgrund der 1NMR- und 13C-NMR-Daten wurden 5 als 8-C--D-Glucopyranosylapigenin (Vitexin) und 6 als 6-C--D-Glucopyranosyl-8-C--L-Arabinopyranosylapigenin (Schaftosid) identifiziert [8-11].
Bei direktem Vergleich mit Testsubstanzen (DC,UV,IR) ergaben sich folgende Identitäten: 7 mit Quercetin-3-O- -D-Glucopyranosid (Isoquercitrin); 8 mit Quercetin-3-O- -D-Glucuronopyranosid (Miquelianin) und 9 mit Ursolsäure.
Obwohl die Flavone die charakteristischen Flavonoidverbindungen der Labiaten sind, wurden 1 und 2 bisher in der Gattung Salvia noch nicht gefunden
Essential oil composition of two populations od Salvia samuelssonii growing in different biogeographical regions of Jordan
No full textThe composition of the essential oils of flowering aerial parts of Salvia samuelssonii Rech. fil. (Lamiaceae Section ethiopis), collected in two different biogeographical regions, has been analyzed. Sample1, collected in a Mediterranean-like region, “As-Subayhi”, contains mainly monoterpenes (54.2%), sesquiterpenes (27.6%) and phenylpropanoids (10.5%), while sample 2, collected in the Irano-Turanian region, “Al-Adasiyyah”, contains mainly phenylpropanoids (30.6%), monoterpenes (24.9%) and sesquiterpenes (21.2%). In Sample1, the most representative constituents were sabinene (21.5%), cischrysanthenyl acetate (20.8%), germacrene D (9.3%) and myristicin (5.9%), while in sample 2, myristicin (24.1%), sclareoloxide (6.3%), and germacrene D (5.7%) were main constituents. The rate of oxygenated derivatives in the Irano-Turanian sample was higher than the Mediterranean sample. Myristicin is an unusual constituent of Salvia specie
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