New Dammarane Triterpenoids, Caffruones A–D, from the Cherries of Coffea arabica

Abstract

In present study, four new dammarane-type triterpenoids, namely caffruones A–D (1–4), were isolated from the cherries of Coffea arabica. Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, 1H–1H COSY, and ROESY), HRMS and IR spectra. This is the first time that tetracyclic triterpenes have been reported in genus Coffea.Graphical Abstract Electronic supplementary materialThe online version of this article (10.1007/s13659-018-0181-y) contains supplementary material, which is available to authorized users.

Review on factors affecting coffee volatiles: from seed to cup

“…Coffee has a wide range of biological activities, including refreshing, antidepressant, antioxidant, antibacterial, protecting DNA and anticancer, which are closely associated with its chemical components such as caffeine, chlorogenic acid, trigonelline, diterpenes, phenolics and volatile organic compounds (VOCs). [1][2][3][4] Since the beginning of the 20th century, there have been many reports on the chemical components of coffee, especially VOCs, which are considered to be one of the most important factors that influence coffee quality and acceptance by customers.…”

“…Although there are as many as 80 species of coffee in the world, two major coffee species are cultivated for drinking: arabica coffee and robusta coffee, which account for approximately 60% and 40% of global coffee production, respectively (https://www.ico.org/prices/po-production.pdf). Coffee has a wide range of biological activities, including refreshing, antidepressant, antioxidant, antibacterial, protecting DNA and anticancer, which are closely associated with its chemical components such as caffeine, chlorogenic acid, trigonelline, diterpenes, phenolics and volatile organic compounds (VOCs) 1‐4 . Since the beginning of the 20th century, there have been many reports on the chemical components of coffee, especially VOCs, which are considered to be one of the most important factors that influence coffee quality and acceptance by customers.…”

Relationship between the Chemical Composition and the Biological Functions of Coffee

“…16-O-methylcafeol has been used as a marker to distinguish small and medium coffee [45] detected 16-O-methylcafestol and 16-O-methylkahweol in small coffee roasting beans for the first time by using 600 MHz NMR and LC-MS. In recent years, [45][46][47] isolated and identified four new pairs of mascarosides I~II (mascarosides I~II, paniculoside VI and ofaryloside I), 1 pair of villanovane I and 7 pairs of kauri diterpenoid glycosides; five mascaroside III-V and 20-nor-Cofarylosiii diterpenoids; 8 which showed no inhibition on HL60, A549, SMMC-7721, McF-7 and SW480 tumor cell lines and were isolated from green beans. Among them, caffarolides C, D, and F showed platelet aggregation activation activity in vitro.…”

“…Triterpenes are also found in coffee. [46] isolated four new dammarane triterpenes (caffruones A~D) from dried fruits of Yunnan coffee for the first time. These results greatly enriched the types of terpenoids in coffee, and provided a lot of reference for the further study of Yunnan coffee.…”

Progress in Phytochemical and Bioactivities of Coffea arabica L.

“…Terpenes are another type of characteristic constituents in C. arabica L. 55 terpenes include the skeletons of ent-kaurane, kahweol, villanovane diterpenoid, ent-kaurane diterpenoid glucosides, dammarane and pentacyclic triterpene. These terpenes were identified ursolic acid (31), [6] caffruone A-D (32-35), [10] caffruenol A-B (36-37), [11] caffruolide A-B (38-39), [11] tricalysiolide A-E (40-43), [11] 16α,17-dihydroxyent-kauran-19-al (44), [11] 16β-17-hydroxy-ent-kauran-19-oic acid (45), [11] 16α,17-dihydroxy-ent-kauran-19-oic acid (46), [11] 9β,16α,17-trihydroxy-ent-kauran-19oic acid (47), [11] 16β-7,17dihydroxy-ent-kauran-19-oic-methyl ester (48), [11] 16α,17-dihydroxy-9(11)-ent-kauren-19-oic acid (49), [11]…”