Terpenes (general)

Sesquiterpenes in Grapes and Wines

Sabine Downer
Written by Sabine Downer

Ever wonder what gives wine its distinct and unique flavors and aromas? Plant compounds called terpenes are one of the main contributors. Terpenes are a large group of organic molecules that can be further divided based on their chemical structure. Sesquiterpenes are one of these subgroups that has been less explored when it comes to wine. However, sesquiterpenes do influence wine aroma and their presence can be altered by different winemaking practices. A recent paper [1] explores and characterizes sesquiterpenes found in wine grapes.

 

Overview of Sesquiterpenes in Wine

  • Monoterpenoids like linalool, nerol, and citronellol give wine floral, fruity, and citrus flavors.
  • Degraded carotenoid molecules (C13-norisoprenoids) also give wines and grapes aromas that are honey-like (generated by ๐›ฝ-damascenone) or raspberry-like (generated by ๐›ฝ-ionone).
  • Sesquiterpenoids like rotundone (peppery flavor in Shiraz) contribute to grape and wine aromas and may also have health benefits.
  • Potential sesquiterpene health benefits include anti-inflammatory, antimicrobial, and anticancer properties.
  • Sesquiterpenes are located in the grape skin and are influenced by the winemaking process.
  • Sesquiterpene content in wine can be enhanced up to ten times through pressing, longer maceration time, and involvement of non-grape material, enzymes, and yeast.

Most sesquiterpenes have balsamic, spicy, and woody aromas. One of the most desirable sesquiterpenoids in wine is rotundone which is considered to have a favorable aroma. Grapes and wines are rich in many terpenes and plant compounds though, so it is important to consider the influence of the over 97 other sesquiterpenes that also contribute to unique wine aromas. Here are just some of the sesquiterpenes this research team identified and their potential health benefits:

 

Acyclic Sesquiterpenes/Sesquiterpenoids

(Z, E)-๐›ผFarnesene and ๐›ฝ-farnesene: Woody scent ((E, E)-๐›ผ-farnesene has green apple scent); Antibacterial, antifungal, free radical-scavenging, and anticarcinogenic activity, with a concentration-dependent cytotoxic effect

Farnesol: Sweet floral scent; Chemopreventative, antitumor, and antibacterial properties, controversial allergic effects

Nerolidol: Woody and floral scent; Antiparasitic, antioxidant, anti-inflammatory, and anticancer

 

Monocyclic Sesquiterpenes/Sesquiterpenoids

๐›ผ-Bisabolol: Floral and woody scents; Anti-irritant, anti-inflammatory, and antimicrobial

๐›ฝ-Bisabolene: Spice and balsamic scent; Antifungal, antibacterial, antioxidant, and antitumor

๐›ผ-Curcumene: Woody scent; Cytotoxic, antifungal, and antibiotic properties

Lanceol: Sweet, creamy, woody scents; Selective antibacterial properties

Germacrene B: Woody, earthy and spice; Anti-inflammatory, antimicrobial, and antioxidant

๐›ผ-Caryophyllene: Woody scent; Antimicrobial and antioxidant

Bicyclic Sesquiterpene/Sesquiterpenoid with Eudesmane Skeleton

๐›ผ-Selinene: Weak spicy and balsamic scent; Antimalarial and antiplasmodial

๐›พ-Eudesmol: Rose and citrus scent; Cytotoxic, antiproliferation, and anticancer

Bicyclic Sesquiterpenes with Cadalane Skeleton

๐›ฟ-Cadinene: Woody and medicinal scent; Anti-proliferative and anti-cancer

Calamenene: Herbal, spicy and savory scent; Antioxidant and antimicrobial

Bicyclic Sesquiterpene/Sesquiterpenoid with Guaiane Skeleton

๐›ผ-Guaiene: Sweet, woody, balsamic, and peppery scent; Anti-inflammatory

Rotundone: Spicy and peppery scent; Flavoring and potential anti-herbivory function

Other Bicyclic Sesquiterpenes

๐›ฝ-Caryophyllene: Woody and spicy scent; Antibacterial, antifungal, and anticancer

Valencene: Citrus, green, woody scent; Antioxidant and cytotoxic against Hela cells

Tricyclic Sesquiterpene/Sesquiterpenoid

Cubebol: Spicy and minty scent; Dietary supplement and flavoring

Sesquichamene: Woody scent; Antimicrobial, anti-inflammatory, diuretic, and anti-spasmodic [1]

 

References

  1. Li Z, Howell K, Fang Z, Zhang P. Sesquiterpenes in grapes and wines: Occurrence, biosynthesis, functionality, and influence of winemaking processes. Compr Rev Food Sci Food Saf. 2020;19(1):247-281. doi:10.1111/1541-4337.12516. [Impact Factor: 12.811; Times Cited: 10 (Semantic Scholar)]

 

Image: Adonyi Gรกbor via Pexels

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Sabine Downer

Sabine Downer

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