Marigold Metabolites: Diversity and Separation Methods of Calendula Genus Phytochemicals from 1891 to 2022

Abstract

Marigold (Calendula), an important asteraceous genus, has a history of many centuries of therapeutic use in traditional and officinal medicines all over the world. The scientific study of Calendula metabolites was initiated at the end of the 18th century and has been successfully performed for more than a century. The result is an investigation of five species (i.e., C. officinalis, C. arvensis, C. suffruticosa, C. stellata, and C. tripterocarpa) and the discovery of 656 metabolites (i.e., mono-, sesqui-, di-, and triterpenes, phenols, coumarins, hydroxycinnamates, flavonoids, fatty acids, carbohydrates, etc.), which are discussed in this review. The identified compounds were analyzed by various separation techniques as gas chromatography and liquid chromatography which are summarized here. Thus, the genus Calendula is still a high-demand plant-based medicine and a valuable bioactive agent, and research on it will continue for a long time.

Carotenoid Composition of Calendula officinalis Flowers with Identification of the Configuration of 5,8-Epoxy-carotenoids

“…With a few exceptions, we found the same carotenoids as previously described. 14,21 We detected the open-chain lycopene (8), γ-carotene (7), δ-carotene (17), as well as their cis-and di-cis-isomers, which were previously isolated and identified by Kishimoto et al 21 Among the carotene hydrocarbons, we also found α-carotene (16) and β-carotene (1) in small amounts. Monohydroxy carotenoids are represented by β-cryptoxanthin (15) and rubixanthin (6) and their cis-isomer.…”

“…The most important hydrophilic active ingredients of marigold are flavonoids (isorhamnetin, quercetin and quercetin glucosides, narcissin, calendoflavoids). , Lipophilic biomolecules of particular value to the cosmetic industry are the anti-inflammatory, antioxidant, and skin-regenerating carotenoids (β-carotene ( 1 ), (all- E )-lutein ( 2 ), (9 Z )-lutein, luteoxanthin ( 3 ), flavoxanthin ( 4 ), violaxanthin ( 5 ), rubixanthin ( 6 ), γ-carotene ( 7 ), and lycopene ( 8 ), Figure S1). − In addition, the determination of Calendula genus metabolic products has a tradition of more than a century, during which 656 characteristic molecules have been identified for taxa …”

“…14−16 In addition, the determination of Calendula genus metabolic products has a tradition of more than a century, during which 656 characteristic molecules have been identified for taxa. 17 According to the literature, the carotenoid content of calendula drug is influenced by various factors, such as variety, growing location, harvest time, soil nutrient composition, or temperature. 6 Based on the results of Andreeva, 18 dark orange calendulas can have up to 1.5% carotenoid content.…”

“…Isomerization of Lycopene, γ-, and δ-Carotene. Lycopene (8), γ- (7), and δ-carotene (17) were taken from our collection. A solution of 2 mg of carotenoid in 50 mL of toluene was isomerized in the presence of 0.02 mg of I 2 (∼2% to the carotenoid) under N 2 in scattered daylight.…”

Comparative Metabolomics of Ligulate and Tubular Flowers of Two Cultivars of Calendula officinalis L.

“…The therapeutic properties of C. officinalis are attributed to the presence of biologically active compounds. Among these, phenolic compounds and triterpenoids are the most abundant [ 5 ].…”