Anti-Inflammatory, Anti-Tumor-Promoting, and Cytotoxic Activities of Constituents of Marigold (Calendula officinalis) Flowers

Abstract

Ten oleanane-type triterpene glycosides, 1-10, including four new compounds, calendulaglycoside A 6'-O-methyl ester (2), calendulaglycoside A 6'-O-n-butyl ester (3), calendulaglycoside B 6'-O-n-butyl ester (5), and calendulaglycoside C 6'-O-n-butyl ester (8), along with five known flavonol glycosides, 11-15, were isolated from the flowers of marigold (Calendula officinalis). Upon evaluation of compounds 1-9 for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, all of the compounds, except for 1, exhibited marked anti-inflammatory activity, with ID50 values of 0.05-0.20 mg per ear. In addition, when 1-15 were evaluated against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA, compounds 1-10 exhibited moderate inhibitory effects (IC50 values of 471-487 mol ratio/32 pmol TPA). Furthermore, upon evaluation of the cytotoxic activity against human cancer cell lines in vitro in the NCI Developmental Therapeutics Program, two triterpene glycosides, 9 and 10, exhibited their most potent cytotoxic effects against colon cancer, leukemia, and melanoma cells.

Chemical characterization and bioactive properties of two aromatic plants: Calendula officinalis L. (flowers) and Mentha cervina L. (leaves)

“…In contrast to the lack of studies with M. cervina in this regard, there are some reports that evaluate the antitumor activity of C. officinalis extracts and isolated compounds by using in vitro and in vivo models. 7,21,22 The antitumor activity of triterpene glycosides isolated from marigold was shown by Ukiya et al, 7 and the results obtained by Matić et al 22 on marigold infusion against HeLa (GI 50 = 750 µg mL −1 ) and other tumor cell lines, are consistent with the present study. In summary, C. officinalis (marigold flowers) and M. cervina (Hart's pennyroyal leaves) contain phytochemicals that are of great interest due to their potential antioxidant and antitumor activities.…”

“…5 According to the literature, the major constituents of C. officinalis included steroids, terpenoids, triterpenoids, phenolic acids, flavonoids and carotenoids. 6 Several reports experimentally confirm the pharmacological activities of this plant and also of its isolated compounds, including anti-inflammatory, anti-edematous, anti-HIV, 10 antibacterial and antifungal 3 activities, and wound healing by in vivo assays 7,8 and clinical trials in patients with head-and-neck cancer. 9 Other reported activities include immuno-stimulating and immunomodulatory, 11 spasmolytic, spasmogenic and gastroprotective, 12,13 insecticidal, 14 heart rate decrease, 15 cardioprotective, 16 geno-toxic and antigenotoxic dose-dependent, 17 antioxidant 4,[18][19][20] and antitumoral effects.…”

Estonian folk traditional experiences on natural anticancer remedies: From past to the future

“…Cancersuppressive action has reported also for Calendula officinalis whereas the laser-activated Calendula extract induces growth inhibitory effect in various human and murine cancer cell lines (Jimenez-Medina et al, 2006). Triterpene glycosides isolated from marigold flowers exhibit the potent cytotoxic activity against human colon cancer, leukemia, and melanoma cells (Ukiya et al, 2006) and the flower extract can suppress the metastatic spread of melanoma cells to lung in mice (Preethi et al, 2010). Cytotoxic action of marigold tea is highly selective to target cancer cells being similar to the effect of chamomile tea; however, marigold tea exhibits significantly stronger cytotoxic action against malignant cell lines in comparison to chamomile tea (Matic et al, 2013;Srivastava & Gupta, 2007).…”

Produção orgânica de calêndula: um estudo de caso

“…As inflorescências são maceradas e aplicadas no local do ferimento na forma de emplasto. A utilização popular da calêndula se deve pelas suas propriedades colerética, anti-inflamatória, analgésica, antitumoral, bactericida, diurética, cicatrizante, sedativa e imunomoduladora (FRANCO, 1996), sendo que estudos científicos comprovam a propriedade antiinflamatória dessa espécie, corroborando a indicação popular (HEROLD et al, 2003;UKIYA et al, 2006;MULEY et al, 2009).…”