Isolation and Characterization of Sesquiterpenoids from Cassia Buds and Their Antimicrobial Activities

Abstract

Cassia buds, the immature fruits of Cinnamomum cassia (Lauraceae), are widely consumed as a food spice, dietary supplements, flavoring agents, and preservatives. In this study, cassia buds were phytochemically investigated for the first time, leading to the isolation of 2 new sesquiterpenoids (1 and 2) and 10 known sesquiterpenoids (3-12). Their structures were determined by spectrometric and spectroscopic analyses, including nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, and circular dichroism. Cinnamosim A (1) represents the ninth example of the rare cyperane-type sesquiterpenoids. All of the compounds (1-12) isolated from cassia buds were evaluated for antimicrobial activities, with compounds 1-3, 5-8, 11, and 12 exhibiting strong antimicrobial activities against Candida albicans and compounds 6, 7, and 11 showing moderate antibacterial activities against Escherichia coli and Staphylococcus aureus. The present investigation indicated that sesquiterpenoids from cassia buds might be used as potential antimicrobial agents to preserve food.

In vitro growth‐inhibitory effect of essential oils and supercritical carbon dioxide extracts from Cinnamomum spp. barks and fruits against food bacterial pathogens in liquid and vapor phase

“…Traditionally, immature fruits of C. cassia have been used as flavoring agent in various Asian foods such as curries, pickles, chutneys, poach fruit and apple desserts and local pastries. From the sensory point of view, this commodity resembles C. cassia bark, however, minor compounds add floral, woody, nut‐like, cool and sweet impressions (mostly because of presence of γ muurolene and δ cadinene) (Guoruoluo et al, 2017; Santos et al, 2017). Moreover, chemical analysis revealed remarkably lower content of coumarin than in C. cassia bark and therefore represents lower concern regarding to the toxicity associated with potential food uses.…”

“…They are evergreen trees belonging to the Lauraceae family native to the tropical regions of South East Asia and their dried inner bark have traditionally been used as spice, food preservative and flavoring (Hameed, Altameme, & Mohammed, 2016; Jayaprakasha & Rao, 2011). Immature fruits of C. cassia , known as cassia buds, are another commodity being utilized as a flavoring food additive and are added to pickles, exquisite fruit dishes and curries (Guoruoluo et al, 2017). E‐ cinnamaldehyde has been found as the dominant compound by previous studies.…”

Terpenoids and Their Biological Activities from Cinnamomum: A Review

“…Compounds including 89, 90, 93-95, 97, 101, 102, and 117 showed significant antimicrobial activities against Candida albicans with inhibitory zone diameters ranging from 8 to 11 mm. Moreover, 90, 101, and 117 have exhibited moderate inhibitory effects on Escherichia coli and Staphylococcus aureus with inhibitory zone diameters ranging from 7 to 11 mm [51]. In another antibacterial assay, the activities of 79 and 80 against Candida glabrata were also evaluated, and the MIC values were 187.6 and 177.5, respectively [58].…”

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“…Oleic acid and linoleic acid were identified in smaller quantities. Cassia buds contain sesquiterpenoids and are used in food spice, dietary supplements, flavoring agents, and preservatives, [23] Cassia nomame is a processed nutraceutical obtained from Cassia sp. [24] C. fistula seeds are used as food by tribes.…”