Amides from Piper nigrum L. with dissimilar effects on melanocyte proliferation in-vitro

Zhixiu Lin, Yonghong Liao, Radhakrishnan Venkatasamy, Robert C. Hider, Amala Soumyanath

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Melanocyte proliferation stimulants are of interest as potential treatments for the depigmentary skin disorder, vitiligo. Piper nigrum L. (Piperaceae) fruit (black pepper) water extract and its main alkaloid, piperine (1), promote melanocyte proliferation in-vitro. A crude chloroform extract of P. nigrum containing piperine was more stimulatory than an equivalent concentration of the pure compound, suggesting the presence of other active components. Piperine (1), guineensine (2), pipericide (3), N-feruloyltyramine (4) and N-isobutyl-2E, 4E-dodecadienamide (5) were isolated from the chloroform extract. Their activity was compared with piperine and with commercial piperlongumine (6) and safrole (7), and synthetically prepared piperettine (8), piperlonguminine (9) and 1-(3, 4-methylenedioxyphenyl)-decane (10). Compounds 6-10 either occur in P. nigrum or are structurally related. Compounds 1, 2, 3, 8 and 9 stimulated melanocyte proliferation, whereas 4, 5, 6, 7 and 10 did not. Comparison of structures suggests that the methylenedioxyphenyl function is essential for melanocyte stimulatory activity. Only those compounds also possessing an amide group were active, although the amino component of the amide group and chain linking it to the methylenedioxyphenyl group can vary. P. nigrum, therefore, contains several amides with the ability to stimulate melanocyte proliferation. This finding supports the traditional use of P. nigrum extracts in vitiligo and provides new lead compounds for drug development for this disease.

Original languageEnglish (US)
Pages (from-to)529-536
Number of pages8
JournalJournal of Pharmacy and Pharmacology
Volume59
Issue number4
DOIs
StatePublished - Apr 2007

Fingerprint

Piper nigrum
piperine
Melanocytes
Amides
Vitiligo
Chloroform
Piperaceae
Safrole
Complex Mixtures
Alkaloids
In Vitro Techniques
Fruit
Skin
Water

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Cite this

Amides from Piper nigrum L. with dissimilar effects on melanocyte proliferation in-vitro. / Lin, Zhixiu; Liao, Yonghong; Venkatasamy, Radhakrishnan; Hider, Robert C.; Soumyanath, Amala.

In: Journal of Pharmacy and Pharmacology, Vol. 59, No. 4, 04.2007, p. 529-536.

Research output: Contribution to journalArticle

Lin, Zhixiu ; Liao, Yonghong ; Venkatasamy, Radhakrishnan ; Hider, Robert C. ; Soumyanath, Amala. / Amides from Piper nigrum L. with dissimilar effects on melanocyte proliferation in-vitro. In: Journal of Pharmacy and Pharmacology. 2007 ; Vol. 59, No. 4. pp. 529-536.
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