Isolierung von 1‐Allyl‐2, 3‐dimethoxy‐4, 5‐methylendioxybenzol (= Dill‐Apiol)aus Heckeria umbellata (L.) Kunth (Piperaceae)

Abstract

Isolation of 1‐Allyl‐2,3‐dimethoxy‐4,5‐methylenedioxybenzene from Heckeria umbellata (L.) KUNTH (Piperaceae) From the leaves of Heckeria umbellata (L.) KUNTH an oily substance was isolated and its structure deduced. It is 1‐allyl‐2, 3‐dimethoxy‐4, 5‐methylenedioxybenzene (= Dill‐Apiol; 2) and not as previously published 1‐allyl‐2, 5‐dimethoxy‐3, 4‐methylenedioxybenzene (= Apiol; 1) [2].

Essential Oil of thePothomorphe peltata(L.) Miq.

“…In Brazil it occurs in the states of Acre, Amapá, Amazonas, Pará, Ceará and Mato Grosso (4,7,8). Phytochemical studies of the roots, leaves and of the essential oil of P. umbellata collected in Brazil show the occurrence of 4-nerolidylcatechol (9), phellandrene (10), asarone (11) and apiole (12), with the last substance being later identified as dillapiole (13). However, no chemical data for the oil of the P. peltata could be found in the literature.…”

Five New Prenylatedp-Hydroxybenzoic Acid Derivatives with Antimicrobial and Molluscicidal Activity fromPiper aduncumLeaves

“…Compound 10 (4.5g, 0.29%): 10 had identical physical and chemical properties to those of the known metabolite dillapiol(2,16), 13C-NMR (CDC13, 75.5 MHz): 102.6 (d, C-i), 144.5 (s, C-2), 135.8 (s, C-3), 137.5 (s, C-4), 144.2 (s, C-5), 125.9 (s, C-6), 33.8 (t, C-i'), 137.3 (d, C-2'), 115.3 (t, C-3'), 100.9 (t, C-i"), 61.0 (q, MeO-4), 59.7 (q, MeO-5).Myristicin (5.8 mg. 0.0004 %), humulene (120.4mg, 0.008%), humulene epoxide (120.7mg, 0.008%), and caryophyllene epoxide (80.1 mg, 0.005%) had identical physical and chemical properties to those of the known metabolites(2,(17)(18)(19)(20)(21).Results and DiscussionCompound I showed a molecular ion in its El-MS at m/z 302 [M], corresponding to the molecular formula of C19H2603. In theIR spectrum of 1 the presence of aromatic (1605 and 1500cm1) and conjugated ester carbonyl (1718 cm1) moieties were indicated.…”

Monografias de Plantas Medicinais Brasileiras e Aclimatadas: Volume II

“…Piper umbellatum folhas: dilapiol (1-alil-2,3-dimetoxi-4,5-metilenodioxibenzeno (Bernhard & Tieli, 1978, citado por Rezende & Barros, 2004. Apiol também foi reportado, contudo pode ter sido uma identificação equivocada de dilapiol (Moraes, 1986;Silva & Baver, 1972).…”