Lycoris radiata

Oxidation of Pluviine (276), isolated from Narcissus pseudonarcissus. Narcissus incomparabilis, and Lycoris radiata Herb., with benzophenone and potassium rerr-butylate yielded a red phenol-betaine 277 from which one neutral covalent form can be drawn (Scheme 90). The betaine has absorption maxima Imax (loge) in a buffer at pH 10 at 240 (4.49), 325 (4.46), 360 (3.58), 380 (3.27), and 490 (3.26) nm. In dilute HCl, a salt is formed [lmax = 260 (4.57), 295 (4.39), 340 (3.76), 355 (3.84), 400 (3.62) nm] (57CB363). The oxidation of the alkaloid Caranine gives a similar betaine, the 1,3-dioxolo derivative 278 (56CIL348). 

In 1933, Schlubach and Knoop32 isolated a di-D-fructose dianhydride from Jerusalem artichoke and tentatively identified it as difructose anhydride I [a-D-Fru/-1,2 2,1 - 3-D-Fn / (5)]. Alliuminoside ( -D-fructofuranose- -D-fructofura-nose 2,6 6,2 -dianhydride) was isolated from tubers of Allium sewertzowi by Strepkov33 in 1958. Uchiyama34 has demonstrated the enzymic formation of a-D-Fru/-1,2 2,3 -(3-D-Fru/ [di-D-fructose anhydride III (6)] from inulin by a homogenate of the roots of Lycoris radiata Herbert. 

Lycopus lucidus Turcz., L. ramosissimus (Makino) Makino var. japonicus (Matsum et Kudo) Kitam., L. parviflorus Maxim., L. lucidus Turcz. f. hirtus (Regel) Kitag., L. maackianus (Maxim.) Makino Lycoris radiata (L Her.) Herb., L. longituba Y. Han et Fan., L. aura (L Her.) Herb. 

Morns alba, M. constantinopolitana, M. indica Lycoris radiata, L. longituba, L. aura Morns alba, M. constantinopolitana, M. indica... 

Forty-five samples representing 35 species were tested nine had been known to contain alkaloids Amaryllis belladonna, Ammo-charis coranica, Crinum asiaticum, C. giganleum, Haemanthus mul-liflorus, Hippeaslrum villatum, Lycoris radiata, Narcissus pseudonarcissus, Sprekelia formosissima. 

During the course of screening plants for insect antifeedants, the extract of the bulbs of Lycoris radiata Herb, was found to exhibit antifeeding activity when tested against the larvae of the yellow butterfly Eurema hecabe mandarina (61). 

Reinvestigation of the alkaloid extracts of Lycoris radiata Herb. (62) and Narcissus tazetta L. (68) has revealed that tazettine (397), which had been previously isolated from these plants, was an artifact of the isolation procedure, and pretazettine (395) was in fact the naturally occurring alkaloid. In view of... 

Nearly equal amounts of narciclasine and lycoricidine have been detected in Lycoris radiata Herb. (78). 

Independently, lycoricidine and lycoricidinol, two lactams which presented physical and chemical properties identical with those of margetine and narciclasine, respectively, were isolated from Lycoris radiata. A different interpretation of the physical and chemical data... 

Dihydrolycorme Lycoris radiata (Amaryllidaceae) 80S PS - cell-free HeLa PS (-1000),... 

Leucojum aestiuum, Lycoris radiata, Narcissus tazetta, Pancratium biflorum, ephyranthes carinatus (Amaryllidaceae)... 

Lycoris radiata, Lycoris squamigera Narcissus tazetta, Narcissus spp. (Amaryllidaceae, Liliaceae) ... 

Lycorine (=Narcissine Lycoris radiata, (Narcissus spp. Inhibits apoptosis induced by... 

Tazettine (298) has been isolated from Crinum americanum (leaves) (76), C. giganteum (27), Hippeastrum equestre (bulbs) (40), Hippeastrum hybrids (bulbs) (42), Hymenocallis expansa (bulbs and leaves) (48), Lycoris radiata (bulbs) (60), Narcissus tazetta (90), N. cantaricus (whole plants) (65), Pancratium maritinum (bulbs) (96), and Stembergia sicula (whole plants) (103). Pretazettine (300) has been found in N. pallidiflorus (whole plants) (76), N. panizzianus (whole plants) (79) (aerial and bulbs) (80), S. culsiani (bulbs) (102), and Zephyranthes flava (fresh mature seeds) (70S). Tazettine (298), pretazettine (300), littoraline (301), and marconine (302) have been isolated... 

The first report on DFA formation in higher plants dates back to 1933, when Schlubach and Knoop [23] isolated a compound tentatively identified as a-D-fructofuranose p-o-fmctofuranose l,2 2,l -dianhydride (10, also known as DFA I) from Jerusalem artichoke. Alliuminoside, a difructofuranose 2,6 6,2 -dianhydride for which configuration at the glycosidic linkages was not determined, was isolated from tubers of Allium sewertzowi [24], However, the fact that these results have not been further confirmed throws some doubt onto whether the DFAs were actually from plant origin or were formed by the presence of microorganisms. The enzymic formation of a-o-fructofuranose p-o-fructofuranose l,2 2,3 -dianhydride (1, DFA HI) in sterilized homogenates of the roots of Lycoris radiata, a plant use in China as a traditional folk medicine, unequivocally demonstrated the capacity of this plant to produce this particular DFA [25]. The compound was further extracted from the intact bulbs by supercritical carbon dioxide and its structure unequivocally established by NMR [26]. 

A phenolic base, norpluviine, was isolated from the bulbs of Lycoris radiata (86). The alkaloid possesses the molecular formula C H N03. Methylation of norpluviine afforded pluviine, and ethylation with diazoethane gave an ethyl ether which was degraded in a manner similar to that employed for pseudolycorine (p. 321) to the phenan-thridone (LVIIc), the structure of which was verified by synthesis. From the structure of LVIIc, it follows that norpluviine is represented by structure LXXIX. It is interesting to note that the phenoUc hydroxyls of pseudolycorine and norpluviine are not in the same position. 

Three new alkaloids of the galantharaine group have been isolated. The structure of 0-deraethyllycoramine (5) from Lycoris radiata was apparent from its formation from the reaction of lycoramine with pyridine hydrochloride at 190°C. Leucojum aestivum contains leucotamine (9), which was converted with diazomethane into a second new alkaloid of this species, 0-methylleucotamine (10) the... 

H 8.01%, N 4.84%. O 16.59%. t)ne of the minor alkaloids of Lycoris radiata Herb., Amaryltidaceae Kondo, Ishiwata, Ber. 70B, 2427 (1937). From Narcissus spp. Boit et of., ibid. 90, 725 2197 (1957). Tentative structure Koba-yashi, Uyeo. Chem. Ind. (London) 1956, 177. Structure elucidation William, Rogers. Proc. Chem. Soc. 1964, 357. Synthesis of the naturally occurring (—)-form Barton. 

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