Lignan and amides from Piper sylvaticum

Abstract: The secondary metabolites isolated from Piper species for the period 1907 to June 1996 have been reviewed. Nearly six hundred chemical constituents belonging to different classes of bioactive compounds are listed together with their source(s) and references. © 1997 Elsevier Science Ltd

Abstract: Cultivars of sesame were screened to determine how widely lignans occur. All lines tested contained sesamin and sesamolin. Sesamin and sesamolin in other species of Sesamum varied. Some other genera in the Pedaliaceae also possessed lignans. Phytochemical evidence as well as other data support the suggestion that the progenitor of sesame occurs in India.

Abstract: Two new unsaturated amides, retrofractamides A and C, were isolated from the total above-ground parts of Piper retrofractum . Retrofractamide A was shown to be N -isobutyl-9(3′,4′-methylenedioxyphenyl)2 E ,4 E ,8 E -nonatrienamide from spectroscopic and chemical investigations. The structure 6 for retrofractamide C was suggested from spectroscopic and chemical studies and was confirmed by a total stereoselective synthesis. The presence of sesamin and 3,4,5-trimethoxydihydrocinnamic acid as well as two higher homologues of retrofractamide A, viz. pipericide (retrofractamide B) and retrofractamide D was demonstrated. The synthesis of pipericide was also achieved.

Abstract: During the past decade many new lignans and neolignans have been isolated from the Piperaceae. Lignans and neolignans are known to possess biological activity. This review summarizes the structures of lignans and neolignans presently known in the Piperaceae.

Abstract: Piper, the pepper plants or pepper vines are an economically and ecologically important genus in the family Piperaceae. It contains about 1,000-2,000 species of shrubs, herbs, and lianas, many of which are keystone species in their native habitat. Piper species have a pan tropical distribution, and are most commonly found in the understory of lowland tropical rainforests, but can also occur in clearings and in higher elevation life zones such as cloud forests. Most Piper species are either herbaceous or vines; some grow as shrubs or almost as small trees. Many species of piper have been used for treating different diseases in many traditions. E.g P. cubeba has been used in folk medicine, herbalism as well as in the early 20th century, as a cigarette flavoring. P. darienense is used medically by the Kuna people of the Panama-Colombia border region, and elsewhere it is used to intoxicate fish which then can be easily caught. Black Pepper (P. nigrum) essential oil is sometimes used in herbalism, and Long Pepper (P. longum) is similarly employed in Ayurveda, where it was an ingredient of Triphala Guggulu and (together with Black Pepper) of Trikatu pills, used for rasayana (rejuvenating and detoxifying) purposes.

Abstract: From the root of Piper longum L two new alkaloids, piperlongumine and piperlonguminine have been isolated Piperlongumine and piperlonguminine are shown to be N-(3,4,5-trimethoxycinnamoyl)-Δ 5 -piperidin-2-one and isobutylamide of piperic acid respectively

Abstract: The structure of sylvatine (1), a new alkamide from Piper sylvaticum, has been elucidated from spectroscopic studies, chemical reactions and correlation with compounds of known structures.