Пиперлотин D

Description

Piperlotine D is an amide alkaloid, (2Z)-1-(1-pyrrolidinyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one. The natural source is Piper lolot, a pepper plant, from the methanol extract of which a series of amides piperlotin A–L has been isolated. The molecule is built like an acrylamide: the trimethoxyphenyl ring is connected by a double bond to the carbonyl, the amide nitrogen is included in the pyrrolidine ring. Piperlotin D differs from piperlotin C in the geometry of this double bond - Z-configuration versus E for the isomer.

Basic Attributes

• CAS No.: 958296-13-4
• Chemical formula: C16H21NO4
• Molecular Weight: 291.34224
• Exact weight: 291.147
• PSA Specifications: 48
• XLogP3: 2.2
• Synonyms: Piperlotine D, (2Z)-1-(1-pyrrolidinyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one

Activity studied

• inhibition of platelet aggregation induced by arachidonic acid: IC50 = 43.4 μg/ml

Methanolic extract of Piper lolot inhibited platelet aggregation induced by arachidonic acid and platelet activating factor (PAF). Separation of the extract, monitoring activity at each step, yielded twelve new amide alkaloids, including this compound.

Scope of application

• analytical standard for studying the composition of Piper lolot and related species
• reference substance for HPLC and LC-MS techniques
• object of study of antiaggregation activity of natural amides
• structural template for work on linking double bond geometry with biological effect - paired with the E-isomer piperlotin C

Storage and handling

Research product. Store in a closed container, protected from light: the Z-configuration of the double bond is sensitive to photoisomerization. Work is carried out with gloves and safety glasses. The card does not contain data on phase transition temperatures, solubility, toxicity, GHS classification and transport codes.