Crocus derivatives

Van Calsteren et al.. Spectroscopy characterization of crocetin derivatives from Crocus sativus and Gardenia jasminoides, J. Agric. Food Chem., 45, 1055, 1997. 

Colchicine is an important naturally occurring tropolone derivative. It is isolated from the autumn crocus and is used in medicine for the treatment of gout. It also has an effect on cell division and is used in plant genetic studies to cause doubling of chromosomes. The structure has been confirmed by total synthesis. 

Crocetin (C20) is a yellow (IP)2—(PI)2-derived dicarboxylic, acid (generalized structure -OOG-Gig-GOO-) from the styles of Crocus sativus (Iridaceae) (the saffron of Indian cooking and Buddhist robes). Grocin, the digentiobiose ester of crocetin, is water soluble, unlike other carotenoids which are lipophilic (fat soluble). Crocetin is a protein kinase inhibitor. Excess vitamin A (or excess pro-vitamin A) ingestion is toxic (dog liver consumption having caused the death of Sir Douglas Mawson s explorer companions in the Antarctic by this mechanism). 

This is an alkaloid derived from the autumn crocus (Colchicum). Colchicine rapidly relieves the pain and inflammation of an acute attack of gout. Such swift relief is considered to confirm the diagnosis because non-gouty arthritis is unaffected, though failure does not prove the patient is free of gout. It is most effective if given within 24 h of onset and is useful in patients in whom NSAIDs are contraindicated. It is also used in recurrent hereditary polyserositis (Familial Mediterranean Fever) when it may prevent attacks and the development of amyloid. The t) is 1 h. 

Compounds other than ionone, and without ionone-like structures, derived from carotenoids are also of commerical importance. Safranal, CioHil(0 is isolated from the styles of the autumn blooming crocus and is accompanied by a C20H2A01) yellow pigment. The fresh saf ranal oil is very unstable, but it has a very strong and pleasant odor. It is used as an additive to violet-like perfumes and the results are very satisfying. Addition of tinctures of safranal to bitter and... 

All garden enthusiasts know about the nice autumn crocus (Colchicum autumnale), which flowers in late autumn. It is not difficult to understand that this very conspicuous plant profits by containing a strong poison that protects it from pathogens and herbivores. It contains colchicine, which is very toxic and has a complicated structure. The substance is well known to plant breeders because it is used to double the number of chromosomes artificially in plants. A synthetic benzimidazole derivative, l-methyl-3-dode-cylbenzimidazolium chloride, was developed in 1960 as a curative fungicide against apple scab. Thiabendazole, another synthetic benzimidazole derivative, has been used as an anthelmintic since 1962. 

Also mentioned in the aforecited book are colchicine and colchidnamide, derived from the common autumn crocus (Colchicum autumnale), also called meadow saffron. (Colchicine, incidentally, is used in plant gaieties to artificially produce mutations.) The notable use cited is against breast cancer, but gout and arthritis also yield to treatment. It is emphasized that both these alkaloids are potent, and their use requires expert medical supervision. Another plant mentioned is cro-talaria (Crotalaria spectabilis), from which a toxic alkaloid called monocrotaline may be obtained. This substance also has antitumor properties, but acts against the liver. 

Saffron, derived from the stigma of Crocus sativum, of the family Iridaceae, is briefly mentioned as an anticancer agent in Pat Willard s book of the same name [2001] along with some other medicinal properties, about all of which Willard remains skeptical.)... 

Saffron, as derived from Crocus sativus, is noted to have antitumor effects, presumably due to the presence of caretonoids. 

Flavonoids occur in plants as mono- and di-glycosides and derive from 2-phenyl-y-benzopyrone. Their UV spectra depend on the number and substitution of the hydroxy groups in the phenol nucleus. Flavonoid derivatives have been also found in stigmata of Crocus sativus. Among them kaempherol diglycoside has been isolated and identified by mass spectra [38]. 

Tetramethylcyclohexanes.— The derivatives of 1,1,2,3-tetramethylcyclohexane are associated with saffron (the dried stigmas of Crocus sativa), and a new investigation has revealed two new members of the series, some with one carbon atom less. Of those shown below, the first four were synthesized from isophorone (224), which was also found in saffron. Saffron is somewhat similar to Tournefortia sibirica, a perennial of the boraginaceae, which also contains safranol (225). ... 

The importance of the crocus seems to derive from the abundant presence in Colchis of both the false or meadow crocus, crocus colchium,... 

Their occurrence is limited to the Liliaceae, e. g., Col-chicum, Kreysigia, anAAndrocymbium species (see table). They are readily soluble in water, chloroform, and ethanol. Colchicine is one of the few natural tropolone derivatives, see, e. g., fomentariol. It occurs together with other, structurally related alkaloids (colchamine, colchicoside, colchiceine, colchiciline, colchifoline) in meadow saffron (autumnal crocus, naked lady, Col-chicum aummnale). Colchicine is a highly potent mi-... 

Linear HomotrlsaccharidesIn connection with the characterization of an unknown trlsaccharide from crocuses, the four possible linear 6-D-glucopyranosyl derivatives of gentioblose [6-D-G1c (1 6)-D-G1c] were synthesized as their peracetates and... 

Chemically related to brazUin are the yellow mordant dyes, luteolin and morin. Both are flavone derivatives whereas the former is obtained from yellow weed or weld (Reseda luteola L.), which grows widely across Europe, the latter comes from dyer s mulberry (Madura tinctoria, syn. Morus tinctorius L.). Alum- and tin-based mordants from luteolin produce a beautiful true yellow on all textile materials. Apart from weld, saffron (Crocus sativus L.) used to be the most important yellow colourant. The ancient Greeks and Romans used the dried stigmas from this species of crocus to obtain crocin, which was absorbed onto textiles with an alum mordant. Like saffron, curcuma (also known as turmeric) serves as a colourant for foodstuffs (e.g. for mustard and curry), and as a somewhat acrid spice in Oriental and South-east Asian cuisine. Curcuma is obtained from the root nodules of, for instance. Curcuma longa L., which is cultivated in plantations in China and the East Indies. 

Results obtained in the National Cancer Institute of the USA from the study of the cytostatic activity of the (133) and bis(chloroethyl)amino derivatives on 60 tumor lines were reported [138]. Originally colchicine a soluble alkaloid was extracted from Colchicum autumnale also known as autumn crocus, meadow saffron or itkuchala in Uzbekistan which means dog poison [138]. 

Term for dyes and lake pigments based on safflower (dye derived from Carthamis tinctorius L.) as opposed to true saffron (qq.v.) derived from Crocus sativus. Sometimes also called carthame or safranum (for example, Watin, 1785). 

The title mars yellow and the mars colours that are its derivatives emerged in the eighteenth century as a literal translation of the Latin crocus martins. To alchemists, Mars symbolised iron and crocus was synonymous with saffron and hence yellow. 

The name mars is derived from the god of war, whose metal is iron. The pigment was also called crocus martius, with crocus referring to saffron or yellow for example, the seventeenth-eighteenth century chemist Boerhaave has a section in his 1727 treatise on chemistry titled Exhibiting the reduction of Vitriol of Iron to a Calx or Crocus or the preparation of Crocus Martis astringens. ... 

The term saffron in a pigment context refers to a dye derived from the stamens of the plant Crocus sativus L., prized by illuminators as the Borradailes stated in their notes to the fifteenth century Strasburg MS (Clarke MS 2000). The main dyestuff produced is crocetin. 

Saffron, derived from stigmas of the saffron crocus, is the worid s most expensive spice, its color is caused by... 

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