Piper sarmentosum

Pellitorine (1) has been isolated from several plants fruits of Piper sarmentosum [7], roots of Anacyclus pyrethrum [8] and seeds of Piper sylvaticum and presents insecticidal activity [10]. The Z-isomer (2), isolated from Piper guineense [11], has similar activity. Another component of the dried fruits of Piper sarmentosum, known in Thailand as Cha-plu , is sarmentine (3) which is used as an expectorant [7]. The corresponding piperidine derivative (4) is an Achillea amide [12]. 

S. sarmentosum contains two liquid alkaloids which are separated by fractional crystallization of the picrates. The least soluble picrate (CigHanOgNi), m.p. 159°, proved to be identical with the picrate of synthetic d(-methylisopelletierine (86). The more soluble picrate (C1BH22O8N4), m.p. 125°, is that of an optically active base C9H19ON, [a] 25.0 (abs. ethanol). On the assumption that this new base was the dihydro derivative of. A -methyl-isopelletierine (.A -methyl-l-(2-piper-idyl)-2-propanol), di-methylisopelletierine was reduced with lithium aluminum hydride and the product converted to the picrate. The two diastereoisomeric forms separated into an oily picrate and a crystalline picrate, m.p. 126° (86). The base recovered from this picrate could not be resolved (93). 

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