Isolierung und Strukturaufklärung von Neapolitanose (O‐β‐D‐Glucopyranosyl‐(1→2)‐O‐[β‐D‐glucopyranosyl‐(1→6)]‐(D‐glucose), einem neuen Trisaccharid aus den Stempeln von Gartenkrokussen (Crocus neapolitanus var.)

Abstract

Isolation and Structure Elucidation of Neapolitanose (O-P-o-GIucopyranosyl-( 1 +2)-O-~-o-glncopyranosyl-(1+6)~-D-glucose), a New Trisaccharide from the Stigmas of Garden Crocusses (Crocus neapolitanus vnr.) SummaryFrom the stigmas of Crocus neapolitanus var. 'Blue Bird' two new crocetin glycosyl esters were isolated. They contained a hitherto unknown trisaccharide. For the structure elucidation a homonuclear 2D-'H-NMR-shift-correlation experiment was carried out with the peracetate of the isolated trisaccharide. This experiment revealed that the carbohydrate is 0 -P-D-glUCOpyranOSyl-( 1 + 2)-0 -[p -D-glUCOpyranOSyl-( 1 + 6)]-~-glucose, for which we suggest the name 'neapolitanose'. The two new C,,-carotenoids from Crocus neapolitanus are crocetin @-gentiobiosyl) @-neapolitanosyl) ester (4) and crocetin diw-neapolitanosyl) ester (5). Einleitung und

Saffron, an alternative crop for sustainable agricultural systems. A review

“…Carotenoids are the most characteristic and important components of saffron stigmas, responsible for the particular colorant features of this spice. They include both fat-soluble carotenoids such as lycopene, αand β-carotene and zeaxanthin, and, mainly, the water-soluble C 20 apocarotenoid, crocetin (8,8'-diapo-8,8'-carotenedioic acid), and its ester derivatives, with one or more molecules of sugar, the trans crocetin (β-d-digentibiosyl) ester being the most important and abundant component of this class (Lozano et al, 1999;Carmona et al, 2006c;Rychener et al, 1984) (Fig. 5).…”

In‐depth analysis of crocetin ester glycosides from dried/processed stigmas of Crocus sativus L. by HPLC‐ESI‐MSn (n = 2, 3)

“…Briefly, crocins constitute a class of bis‐apocarotenoid (crocetin, a C 20 backbone) mono‐ and bis‐ester glycosides varying in the types of (oligo)saccharide residues as e.g. glucose, gentiobiose, gentiotriose and neapolitanose . These highly coloured glycosides are unique to the stigmas of the flowers of Crocus sativus L., related to some Crocus species from the eastern Mediterranean areas as well as to the fruits of Gardenia jasminoides Ellis (plant family: Rubiaceae ) originating from southeast Asia, the latter botanically not related to the genus Crocus .…”

“…glucose, gentiobiose, gentiotriose and neapolitanose. 11 These highly coloured glycosides are unique to the stigmas of the flowers of Crocus sativus L., related to some Crocus species from the eastern Mediterranean areas as well as to the fruits of Gardenia jasminoides Ellis (plant family: Rubiaceae) originating from southeast Asia, the latter botanically not related to the genus Crocus. 9,12 As Crocus sativus L. does not exist in the wild, this botanical entity can best be seen nowadays as a sterile triploid cultivar of the wild type species Crocus cartwrightianus Herb.…”

Comparison of different tandem mass spectrometric techniques (ESI‐IT, ESI‐ and IP‐MALDI‐QRTOF and vMALDI‐TOF/RTOF) for the analysis of crocins and picrocrocin from the stigmas of Crocus sativus L.

“…Chemically, saffron contains a wide variety of different constituents including carotenoids (e.g., α ‐ and β ‐carotene, lycopene and zeaxanthin), mono‐ and bis‐esters of crocetin (one of the major constituents of saffron representing C 20 ‐degradation products of carotene) with glucose, gentiobiose, gentiotriose or neapolitanose, respectively, and a rather complex essential oil (containing up to 70% safranal). Picrocrocin, another major constituent of saffron, represents a glucoside of the monoterpene hydroxyl‐β‐cyclocitral (the precursor molecule of the volatile safranal).…”