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Often mis-spelled: Nicandra physaloides', (even 'Wikipedia' does it [well, they can't even spell their own name correctly as 'Wikipædia']) but it is un-like anything.
Not to be semantically confused with : Thorn-Apple or May Apple (Mandrake ) [plant which are in the same Nightshade Family]
Some similarities to : Bindweeds such as Sea Bindweed, but it is blue rather that white, pink or red. Also the seed pods look similar to those of Japanese Lantern (aka Cape Gooseberry, Winter Cherry) (Physalis alkengi).
Uniquely identifiable characteristics
Distinguishing Feature : Black stems, large leaves with small black 'dots' and a foetid odour.
No relation to : Apple , Apple Mint, Pineapple Weed or Crab Apple [plants with similar names].
Apple-of-Peru is a plant native to Peru, and is grown in the UK as an ornamental, from which it can escape into the wild. It is the only member in the Genus Nicandra and, according to some, is highly toxic. The dark coloured 'dots' that adorn the surface of the leaves are actually trichomes; sharp stiff hairs that physical defence it against herbivorous insects. It already has a highly effective chemical defence. It exudes a foetid odour which keeps flies away by paralysing them.
Its other common name is Shooo Fly which comes from its former popular use to shoo flies away; it was used as an insect repellant by rubbing the leaves and tender stems on exposed skin. The seeds are reagarded as more toxic than the other parts of the plant.
The fruits are dry, brown and encased in a brownish, loose papery net-veined covering that was the sepals.
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WITHANOLIDES
The poisonous principles in Apple-of-Peru include Withanolides (named after the Withania Genus which also belongs to the Nightshade Family) such as Nicandrenone (which is an insecticide), pyrrolidine alkaloids (the roots contain 0.1% Hygrine) and some calystegines.
All parts of the plant are considered hazardous, but ingestion of the fruits is rarely dangerous, but highly in-advised!
Note the double epoxide group on NIC-1 (and its lactone).
Withanolides, such as Withaferin A, can be regarded as multiply oxidized Cholesterol with an extra methyl group at the C-24 position, and indeed are produced by the oxidation of steroids. Withanolides are found not only in members of the Nightshade Family (Solanaceae), but also in other plant families. Over 300 withanolides have been described since they were first found in plants in 1965.
They have exhibited a wide range of pharmacological effects including anti inflammatory, immunomodulatory, hypno-sedative, anti arthritic, anti cholinesterase, anti oxidant and angiogenesis inhibition.
Withaferin A is a steroidal lactone exhibiting anti inflammatory, anti-tumour and anti angiogenic properties.
Shown are the two! Withaferin A structural formulae that are to be found on the internet. The first is on the NextBio website, the latter on the Wikipaedia website (as of 13 July 2011). The author does not have the super-powers necessary to tell which, if any, is the correct formula, but the two are very different! But they are both obviously Withanolides, and each have the same number of carbon atoms (but not of oxygen nor hydrogen). Based upon the relative number of occurrences on the internet, the latter seems favoured, but that is indeed an error-prone method of discriminating between two possibilities.
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CALYSTEGINES
A glycosidic Calystegine alkaloid (Calystegine B1-3-O-β-D -glucopyarnoside) was found in 2001. Calystegines are based upon the Tropane skeleton, and are found extensively in other members of the Nightshade Family. See Danish Scurvygrass for more information about Calystegines.
The calystegines are named from the Bindweed Genus Calistegia, indeed, Apple-of-Peru has some physical resemblance to the Bindweeds.
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ANY TEXT GOES HERE
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Nightshade [Solanaceae] 
