Guaianolides from Centaurea sinaica

Al-Easa, Hala S.; Mann, John; Rizk, Sameh A.

doi:10.1016/0031-9422(90)85455-o

Cited by 19 publications

(18 citation statements)

References 10 publications

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“…Centaurea has been the subject of numerous chemical studies many of which have been tabulated by AI-Easa and Rizk (1992) in a detailed review. Some of the information used in the present work was taken from their survey.…”

Section: Cardueaementioning

confidence: 99%

Flavonoids of the Sunflower Family (Asteraceae)

Bohm

Stuessy

2001

119

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This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. This book is dedicated to:Arthur Cronquist Outstanding plant systematist and major contributor to understanding taxonomic relationships within Asteraceae and Ralph E. Alston (1925Alston ( -1967) Visionary natural products chemist and geneticist who pioneered the use of chemical data in studies of plant systematics and evolution PrefaceCertainly many of the readers of this book will remember the early developments of chemosystematics in the late 1950s. We ourselves remember the excitement of these new data bearing on plant interrelationships. The hopes were high, the techniques were rapidly evolving, the quantities of data were large, and young workers were eagerly enthusiastic. Some even went so far as to predict that chemical data would soon replace morphological information as the basis for plant classification. These overly zealous predictions did not materialize, of course, as the history of plant systematics has amply shown during the past two centuries. If there is any distinct characteristic of systematics it is synthesis, as Lincoln Constance (1964) called it, the "unending synthesis." New tools generate new data and provide insights on additional dimensions of plant relationships. This will never change-we will continue to discover new tools and new data in the years ahead, and they will continue to be incorporated into the predictive general reference system of classification.The earlier efforts in chemosystematics focused on secondary plant products: alkaloids, betacyanins, carbohydrates, cyanogenic glycosides, glucosinolates, lipids, terpenoids, and especialiy flavonoids. The latter were particularly well suited for chemosystematic investigation for several reasons: ease of isolation and characterization, small amounts of plant material needed for analysis, stability of compounds especially through routine preparation of herbarium specimens, and low cost to obtain useful information. As a result of these considerable advantages, literally thousands of studies on use of flavonoids in plant systematics have been published. Although now with the present zest for macromolecular data from DNA restriction sites and sequences, there are fewer workers and laboratories dedicated to flavonoid chemosystematic studies; twenty years ago they were the new currency of exciting data in plant systematics.Because of many workers historically interested in the sunflower family, Asteraceae (or Compositae), in part due to its large size (approximately 23,000 species;Bremer, 1994), and because hundreds of flavonoid compounds were discovered in this family, many chemosystematic investigations have been completed on various taxa. Many studies came from the laboratories of R. A. Alston, B. L. Turner, and T. J. Mabry in the Department of Botany ...

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Section: Cardueaementioning

confidence: 99%

Flavonoids of the Sunflower Family (Asteraceae)

Bohm

Stuessy

2001

119

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“…It is also of importance to preserve and maintain knowledge about medicinal uses of available plant resources in Qatar which is a small peninsula in the Arabian Gulf. The native herbal folk medicine forms an essential part of the heritage of the herbal folk materia medica of the whole Arab peninsula and the Gulf region (AL-Easa et al, 1990;Batanouny, 1981;Rizk, 1986, Abbas et al, 1992. Several kinds of extracts and metabolites from various Qatari plants have been isolated and their chemical structure has been elucidated (Rizk, 1986;Al-Easa et al, 1990).…”

Section: Introductionmentioning

confidence: 99%

“…The native herbal folk medicine forms an essential part of the heritage of the herbal folk materia medica of the whole Arab peninsula and the Gulf region (AL-Easa et al, 1990;Batanouny, 1981;Rizk, 1986, Abbas et al, 1992. Several kinds of extracts and metabolites from various Qatari plants have been isolated and their chemical structure has been elucidated (Rizk, 1986;Al-Easa et al, 1990). However, the biological activity of such extracts and compounds against certain bacteria and fungi is poorly investigated and a literature search indicated a total absence of information about the antimicrobial activity of Qatari medicinal plants.…”

Section: Introductionmentioning

confidence: 99%

Screening of some indigenous Qatari medicinal plants for antimicrobial activity

Mahasneh

2002

Phytotherapy Research

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Aqueous, ethanol and butanol crude extracts of the aerial parts of ten plants exhibited variable degrees of antimicrobial activity against four bacterial and two fungal species. Aqueous extracts had low antimicrobial activity against E.coli, P.aeruginosa, B. cerreus, S.aureus, C.albicans and A.flavus. Avicennia marina (AM) aqueous extract exhibited a moderate antifungal activity. Ethanol and butanol crude extracts exhibited an improved antimicrobial activity. However, butanol exhibited a superior antimicrobial activity compared with aqueous and ethanol crudes. Compared with the standard antibiotics tested the butanol extract had the highest activity. Butanol extracts at 2000 microg/disc of AM, Lotus halophilus (LA), Pulicaria gnaphaloides (PG) and Capparis spinosa (CS) had a very good antibacterial activity against both gram-positive and -negative bacteria as well as moderate to good antifungal activity against C. albicans and A. flavus. Medicago laciniata (ML), Limonium axillare (LA) and (PG) butanol crude extract compared with standard chloramphenicol, tetracycline and nalidixic acid exhibited a superior antifungal activity.

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“…Compounds 1-7 were shown to be guaianolide sesquiterpene lactones, however, compounds 1, 3, 5 and 7 were chlorinated ones. Compound 1 was isolated for the first time from Centaurea repens L. [15] and frequently existed in other Centaurea species [16][17][18]. Compound 2 was known to be a zaluzanin derivative previously isolated from Ainsliaea fragrans Champ [19] and Centaurea scoparia Sieb.…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 2, 4, 5 and 6 are reported here for the first time from Centaurea aegyptiaca species. Compound 1 existed frequently in Centaurea species [15][16][17][18]. Compound 2 was isolated from Ainsliaea fragrans Champ and Centaurea scoparia Sieb.…”

Section: Introductionmentioning

confidence: 99%

Isolation of Bioactive Compounds From Centaurea Aegyptiaca

Sary

Ayoub

Singab

et al. 2018

Int J Pharm Pharm Sci

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Objective: In a previous study, Centaurea aegyptiaca ethanol and ethyl acetate extracts showed potent cytotoxic effects against laryngeal (HEP2) and hepatic (HEPG2) carcinoma cell lines. Additionally, two novel compounds were isolated and identified. The aim of this study is to continue isolating and identifying another compound (s) that may, also, be responsible for this potent biological activity. Methods:C. aegyptiaca dried aerial parts were extracted with ethanol and ethyl acetate. Both extracts were chromatographed separately to afford seven guaianolides that were identified using different spectroscopic methods. Moreover, compounds 1-7 were evaluated for their cytotoxicity (IC50, µM) against HEP2 and HEPG2 cells in comparison to the normal fibroblasts (BHK) using sulforhodamine B assay. Doxorubicin was used as a positive control.Results: Seven sesquiterpene lactones, centaurepensin, also known as chlorohyssopifolin A (1), 8α-hydroxy-11α, 13-dihydrozaluzanin C (2), chlorohyssopifolin B (3), desacylcynaropicrin (4), chlorohyssopifolin C, acroptilin (5), subluteolide (6), and solstitiolide (7) were isolated from C. aegyptiaca extracts and identified. This is the first report on the occurrence of 2, 4, 5 and 6 in C. aegyptiaca. Compounds 1-4 and 6 exhibited selective cytotoxic effects against HEP2 and HEPG2 cells. However, compounds 1 and 7 showed the highest activities against HEP2 with IC50 values of 10.6±0.02 and 10.9±0.03 µM, respectively. Moreover, compound 3 was the most potent one against HEPG2 cells with IC50 value of 13.8±0.05 µM. Conclusions:Chemical investigation of C. aegyptiaca ethanol and ethyl acetate extracts led to the isolation and identification of seven guaianolides. These compounds exhibited good cytotoxic activities against HEP2 and HEPG2 cell lines.

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Guaianolides from Centaurea sinaica

Cited by 19 publications

References 10 publications

Flavonoids of the Sunflower Family (Asteraceae)

Flavonoids of the Sunflower Family (Asteraceae)

Screening of some indigenous Qatari medicinal plants for antimicrobial activity

Isolation of Bioactive Compounds From Centaurea Aegyptiaca

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