Phytochemical and Cytotoxic Studies on Calendula Officinalis

From the leaves of Calendula officinalis (Asteraceae) two new triterpene saponins, named sophradiol 3Oα -L-C4-rhamnopyranosyl-(1'''→4'')O-β -D-C1-galactopyranosyl (1''→6')O-β-D C1galactopyranoside (10) and 23-hydroxy-3α-[(O-α-L-C4-rhamnopyranosyl-(1"→4')-O-α-LC1-arabinopyranosyl)-oxy]olean12-en-28-oic acid O-α-L-C4-rhamnopyranosyl-(1'''''→4'''')-O-β-D-C1-galactopyranosyl-(1''''→6''')-O-β-D-C1-galactopyranosyl ester (11) were isolated. In addition, nine known compounds were isolated, namely Ecaffeic acid (1), quercetin (2), 4',5-dimethoxy quercetin (3), 8sulfated apigenin (4) rutin (5), quercetin 3-O-β-D-C1-neohesperidoside (6), 3,3',4'trimethoxy quercetin (7), oleanolic acid, (8), oleanolic acid 3-Oβ-D-C1-glucopyranosyl(1''→3')O-β-D-C1glucopyranside (9), All metabolites were isolated for the first time from this plant. The structures were determined mainly by spectroscopic methods (UV, ESI-MS, H-, C-NMR,H-H COSY, HSQC and HMBC). Cytotoxic screening of the butanol, ethyl acetate and chloroform extracts was carried out on brine shrimps. In addition the investigated butanol extract and major isolates (10 and 11) were also tested against the HepG2 tumor cell line [Mona Mohamed, Olov Sterner and karl-Erik Bergquistt. Phytochemical and Cytotoxic Studies on Calendula Officinalis. Life Sci J 2015;12(1):194-201]. (ISSN:1097-8135). http://www.lifesciencesite.com. 27

[1]  Yanxiang Gao,et al.  Investigation into the antioxidant activity and chemical composition of alcoholic extracts from defatted marigold (Tagetes erecta L.) residue. , 2012, Fitoterapia.

[2]  J. Silva,et al.  Yield, essential oil and pigment content of Calendula officinalis L. flower heads cultivated under salt stress conditions , 2010 .

[3]  Hui-Chi Huang,et al.  Triterpenoidal saponins from Hydrocotyle sibthorpioides. , 2008, Phytochemistry.

[4]  C. Ao Comparative anatomy of bisexual and female florets, embryology in Calendula officinalis (Asteraceae), a naturalized horticultural plant , 2007 .

[5]  İ. Çalış,et al.  Triterpene Saponins from Calendula arvensis , 2006 .

[6]  T. Maoka,et al.  Analysis of Carotenoid Composition in Petals of Calendula (Calendula officinalis L.) , 2005, Bioscience, biotechnology, and biochemistry.

[7]  R. Faure,et al.  Triterpenoid saponins from leaves of Hedera pastuchowii. , 2004, Chemical & pharmaceutical bulletin.

[8]  Wellington Amâncio da Silva,et al.  Influencia de diferentes sistemas de solventes no processo de extracao de Calendura officinalis L. (Asteraceae) , 2004 .

[9]  J. Dalla Via,et al.  Simultaneous quantitative determination of eight triterpenoid monoesters from flowers of 10 varieties of Calendula officinalis L. and characterisation of a new triterpenoid monoester. , 2004, Phytochemical analysis : PCA.

[10]  H. Harada,et al.  Triterpenes and triterpene saponins from the stems of Akebia trifoliata. , 2003, Chemical & pharmaceutical bulletin.

[11]  L. Foo,et al.  Polyphenolics of Salvia--a review. , 2002, Phytochemistry.

[12]  H. Matsuda,et al.  Inhibitory, and Gastroprotective Principles and New Oleanane-Type Triterpene Oligoglycosides, Calendasaponins A, B, C, and D, from Egyptian Calendula officinalis , 2001 .

[13]  H. Matsuda,et al.  Medicinal flowers. III. Marigold. (1): hypoglycemic, gastric emptying inhibitory, and gastroprotective principles and new oleanane-type triterpene oligoglycosides, calendasaponins A, B, C, and D, from Egyptian Calendula officinalis. , 2001, Chemical & pharmaceutical bulletin.

[14]  H. Sakagami,et al.  Steroidal glycosides from the bulbs of Camassia leichtlinii and their cytotoxic activities. , 2001, Chemical & pharmaceutical bulletin.

[15]  J. Wansi,et al.  CONSTITUENTS OF ERYTHRINA SIGMOIDEA , 2001 .

[16]  Kun-Young Park,et al.  Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides and bisdesmosides isolated from the stem bark of Kalopanax pictus. , 2000, Planta medica.

[17]  S. Sosa,et al.  The role of triterpenoids in the topical anti-inflammatory activity of Calendula officinalis flowers. , 1994, Planta medica.

[18]  Ahmed Awad E. Ahmed,et al.  Sesquiterpene glycosides from Calendula arvensis. , 1993, Journal of natural products.

[19]  G. Cordell,et al.  Separation, structure elucidation, and bioassay of cytotoxic natural products , 1993 .

[20]  Y. Takeda,et al.  Screening of Higher Plants Reputed as Pesticides Using the Brine Shrimp Lethality Assay , 1993 .

[21]  James A. Duke,et al.  Handbook of Phytochemical Constituents of GRAS Herbs and Other Economic Plants , 1992 .

[22]  J. Chalchat,et al.  Chemical composition of essential oil of Calendula officinalis L. (pot marigold) , 1991 .

[23]  N. de Tommasi,et al.  Structure and in vitro antiviral activity of triterpenoid saponins from Calendula arvensis. , 1991, Planta medica.

[24]  I. Masterova Flavonoids in flowers of Calendula officinalis L. , 1991 .

[25]  D. Scudiero,et al.  New colorimetric cytotoxicity assay for anticancer-drug screening. , 1990, Journal of the National Cancer Institute.

[26]  G. Duménil,et al.  Antimutagenic activity of some saponins isolated from Calendula officinalis L., C. arvensis L. and Hedera helix L. , 1990, Mutagenesis.

[27]  R. Kasai,et al.  Saponins from Roots of Kalopanax septemlobus (THUNB.) KOIDZ., Ciqiu : Structures of Kalopanax-saponins C, D, E and F , 1989 .

[28]  Jeffrey B. Harborne,et al.  The Flavonoids Advances in Research Since 1986 , 1993 .

[29]  C. Pizza,et al.  Plant metabolites triterpenoid saponins from Calendula arvensis , 1987 .

[30]  O. Tanaka,et al.  Saponins from Chinese medicinal plants. (I). Isolation and structures of hemslosides. , 1984, Planta medica.

[31]  D. Pilbeam The Flavonoids: Advances in Research : Edited by J.B. Harborne and T.J. Mabry Chapman and Hall; London, New York, 1982 744 pages. £ 49.50 , 1983 .

[32]  J. Góra,et al.  CHEMICAL SUBSTANCES FROM INFLORESCENCES OF ARNICA MONTANA L. AND CALENDULA OFFICINALIS L. SOLUBLE IN ISOPROPYL MYRISTATE AND PROPYLENE GLYCOL , 1980 .