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 𝛽-damascenone) or raspberry-like (generated by 𝛽-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)-𝛼–Farnesene and 𝛽-farnesene: Woody scent ((E, E)-𝛼-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
𝛼-Bisabolol: Floral and woody scents; Anti-irritant, anti-inflammatory, and antimicrobial
𝛽-Bisabolene: Spice and balsamic scent; Antifungal, antibacterial, antioxidant, and antitumor
𝛼-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
𝛼-Caryophyllene: Woody scent; Antimicrobial and antioxidant
Bicyclic Sesquiterpene/Sesquiterpenoid with Eudesmane Skeleton
𝛼-Selinene: Weak spicy and balsamic scent; Antimalarial and antiplasmodial
𝛾-Eudesmol: Rose and citrus scent; Cytotoxic, antiproliferation, and anticancer
Bicyclic Sesquiterpenes with Cadalane Skeleton
𝛿-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
𝛼-Guaiene: Sweet, woody, balsamic, and peppery scent; Anti-inflammatory
Rotundone: Spicy and peppery scent; Flavoring and potential anti-herbivory function
Other Bicyclic Sesquiterpenes
𝛽-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
- 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)]
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