Exploring Natural Products for New Taste Sensations

Abstract

This paper discusses the discovery of uncommon taste or trigeminal active compounds and their associated sensory analysis using human tasting panels with the aim of enhancing the overall taste experience whilst reducing where possible the sugar and salt content of foods. The first example outlines the discovery of the sensory quality attributes of (R)-2-(carboxymethylamino)propanoic acid, named (R)-strombine, as assessed by a panel of 47 subjects to confirm its contribution to the typical taste of scallop muscle. The second example discusses the pungency and trigeminal effect of polygodial, which is compared with piperine and capsaicin, as well as the elucidation of a new structure eliciting a trigeminal effect, (+/-)-trans-2,3,3a,7a-tetrahydro-1 H-indene-4-carbaldehyde, discovered in Amomum tsao-ko. Finally, the time intensity trigeminal effect of (-)-menthol is compared with (1R,2RS,4RS)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-2-ol, named dihydroumbellulol, a new cooling compound obtained by hemi-synthesis from umbellulone extracted from Umbellularia californica Nutt.

Rubemamine and Rubescenamine, Two Naturally Occurring N-Cinnamoyl Phenethylamines with Umami-Taste-Modulating Properties

“…Final purification was possible via crystallization from ethyl acetate. 1 (20), 194 (12), 193 (10), 192 (10), 177 (40), 151 (10), 150(100), 149 (9), 145 (14), 137 (11), 89 (8).…”

p‐Menthandiol‐vanillin acetals: synthesis and study of their chemo‐sensorial properties

“…In particular, compound 6a exhibits a definite warming effect without hot/burning activity. This feature is quite remarkable, especially in light of the increasing interest for compounds with new sensory properties . Moreover, warming/tingling compounds hold a specific interest as food and cosmetic additives where the most sought after application lies in their use as enhancers in alcoholic beverages.…”

“…This feature is quite remarkable, especially in light of the increasing interest for compounds with new sensory properties. [18] Moreover, warming/tingling compounds hold a specific interest as food and cosmetic additives where the most sought after application lies in their use as enhancers in alcoholic beverages. Although we have not investigated the stability of the prepared vanillin acetals in aqueous environments and the main part of them are not active enough to suit the strict requirements of an industrial application, the scientific study of these compounds is worthy of investigation, especially with regard to the possible discovery of new and more active derivatives.…”

Synthesis of γ-Sanshool and Hydroxy-γ-sanshool

“…The sanshools are a family of polyunsaturated fatty acid amides found in various Zanthoxylum species that has recently attracted the interest of a broad cross-section of the scientific community ( Figure 1). 1 For example, hydroxy-α-sanshool (HAS) is responsible for the numbing/tingling sensation one experiences when eating Sichuan (or Szechuan) peppercorns (huajiao), 2 and this finding has led to interest in understanding the details of its mechanism of action, 3 and in developing various medicinal, 4 agricultural, 5 food, 6 and cosmetic 7 applications for it. However, while HAS has been relatively widely studied, it is rather difficult to obtain in pure form.…”