Nicandra

Solanaceae Solanoideae Atropa, Atropanthe, Cyphomandra, Datura, Hyoscyamus, Latua, Mandr agora, Nicandra, Physalis, Physochlairta, Przewalskia, Salpichroa, Scopolia, Solandra, Withania... 

The mechanism of acetoacetate coupling in the biosynthesis of hygrine (209) has been studied by feeding sodium [3-14C]- and [4-14C] acetoacetate to Nicandra physaloides 134). 

New sources of hygrine are the roots of Nicandra physaloides (L.) Gaertn. (Solanaceae) (9, JO), Dendrobium chrysanthum Wall. (Orchidaceae) (11), and Cochlearia arctica Slecht (Cruciferae) (12). Hygroline was also isolated from this latter source as well as from Carallia brachiata (Lour.) Merr. (Rhi-zophoraceae), a plant from eastern Asia, New Guinea, and Queensland (13), and... 

Although the ovipositional stimulant and the phagostlmulant are necessary to illicit their respective responses, they may not be sufficient to account for host-plant selection. In the case of Nicandra physaloldes, a member of the Solanaceae not preferred as a host plant by M. sexta, we have shown that aqueous extracts... 

Hygrine.—The alkaloid hygrine (3) is an intermediate in the formation of tropane bases. Biosynthesis is from acetic acid, plausibly via acetoacetic acid (cf. Vol. 10, p. 12), and from ornithine (1), very reasonably in the manner shown in Scheme l.1,2 Acetoacetate has been confirmed as an intact precursor for hygrine in experiments with [3-14C]- and [4-14C]-acetoacetic acid in Nicandra phys-aloides. Labelling in (3) was, respectively, of C-2 and C-3, which confirms the suspected orientation of acetoacetate in hygrine (see Scheme l).3... 

Calystegine Bi-3-O-P-D-glucopyranoside Nicandra physalodes (Solanaceae) fruits ... 

The occurrence in Solanaceae is documented for 12 genera, Atropa, Brunfelsia, Datura, Duboisia, Flyoscyamus, Lycium, Mandragora, Nicandra, Physalis, Scopolia, Solanum, and Withania [2,89]. Our group isolated and characterized calystegines A3, A5 (72), Bi, B2, and... 

The 9(10-> l9)-abeo analogue (6) of oestrone methyl ether has been shown by X-ray crystallography to have the normal 9a -configuration, but because of the chair conformation of the enlarged ring b the molecule differs considerably in shape from oestrone methyl ether. X-Ray, n.m.r., and o.r.d. data establish the structures and absolute configurations of a series of insect-repellent steroids isolated from Nicandra physaloides. The structure and conformation of the 6-sila-steroid (7) have been determined. ... 

Insecticidal properties of withanolides were first noticed on components isolated from the Peruvian plant Nicandra physaloides. Nicandrenone (Nic-1) (90), the major component isolated from this plant, was known by its bitter taste and its insecticidal properties. [58-61]... 

During an infestation by larvae of the Egyptian cotton leafworm Spodoptera littoralis (Boisd) in the summer of 1978, it was noticed that shrubs of Physalis peruviana L. (cape gooseberry) were not attacked, whereas other Physalis and Nicandra spp. suffered heavy damage. Asher and co-workers demonstrated that withanolide E (118) and 4(3-hydroxywithanolide E (119), isolated from P. peruviana, as well as several related steroids, had insect antifeedant properties. Further studies on other withanolides showed antifeedant effects and species-specific activity on three insects, S. littoralis (Boisd.) (Lepidoptera), the Mexican bean beetle, Epilachna varivestis Muls. (Coleoptera) and the red flour beetle, Tribolium castaneum (Herbst) [62]. 

Aromatisation in expanded ring D is common in Nicandra. 104-107,96b nicandcenone... 

Nicandra steroids possess a 5 -hydroxy-6 a,7a-epoxy pattern. 

Nicandra steroids are closely related to withanolides (Chart I). 

Ecdysones which are yet another closely related group of polyoxy steroids and Nicandra steroids are knwon for their powerful... 

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