Cytotoxic Sesquiterpenoids from the Stem Bark of <i>Aglaia harmsiana</i> (Meliaceae)

Abstract

Three aromadendrane-type sesquiterpenoids, spathulenol (1), 4β,10α-dihydroxyaromadendrane (2), and 4α,10α-dihydroxyaromadendrane (3) were isolated from the stem bark of Aglaia harmsiana (Meliaceae). Compound 3 was isolated for the first time from Aglaia genus. The chemical structures of isolated compounds were elucidated by various spectroscopic methods, including one and two-dimensional NMR, as well as mass spectroscopy analysis. These sesquiterpenoids 1-3 were evaluated for their cytotoxic activity against MCF-7 breast cancer cell lines. The IC50 value of compound 1-3 were 31.65 ± 0.1, 8.41 ± 0.04 and 2.80 ± 0.02 µM, respectively. Among the aromadendrane-type sesquiterpenoids, compounds 2 and 3, which do not have a double bond, showed higher activity than compound 1. Whereas, compound 3 showed the strongest activity indicate that α configuration of hydroxyl group increases the cytotoxic activity.

Sesquiterpenoids from the Stem Bark of <i>Aglaia simplicifolia</i> and Their Cytotoxic Activity against B16-F10 Melanoma Skin Cancer Cell

“…The cyclopropane ring and hydroxyl group can increase cytotoxic activity. The 4β,10α-dihydroxy aromadendrene compound from the stem bark of Aglaia harmsiana can inhibit the growth of MCF-7 breast cancer cells with an IC 50 value of 8.4 µM [3]. At the same time, the presence of an olefinic group in compound (2) decreases the cytotoxic activity.…”

“…Sesquiterpenoids were classified using the number of cyclic formed by modification of the cyclization reaction and rearrangement of the carbon skeleton. For example, acyclic, monocyclic, bicyclic, and tricyclic sesquiterpenoids, with several types of cyclic, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and cycloheptane [2][3]. The characteristic of sesquiterpenoids are oils with volatile properties but less volatile than monoterpenoids, the main components of essential oil with more pungent odors, and can be found in plants, mainly in higher plants [3].…”

“…The distributions of the Aglaia genus can be found in many countries, such as India, Thailand, Vietnam, Malaysia, and Indonesia [13][14]. Traditionally, the bark of Aglaia has been used as traditional Indonesian herbal medicine for healing fever, influenza, cough, and other skin diseases [3,[13][14].…”

Antiplasmodial and anticancer activities of xanthones isolated from Garcinia bancana Miq.

“…The anticancer activity was assayed according to a previously reported cell viability test using the PrestoBlue® reagent (Milawati et al, 2020). The evaluation was conducted against four cell lines: A549 (lung carcinoma), MCF-7 (breast adenocarcinoma), HeLa (cervical carcinoma), and B-16 (skin melanoma) from American Type Culture Collection (ATCC), with cisplatin as the positive control.…”

Sesquiterpenoids from the Stem Bark of <i>Lansium domesticum</i> Corr. Cv. Kokossan and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell Lines

“…These two compounds were isolated from the stem bark of D. parasiticum with IC 50 values for MCF-7 of 12.17 and 23.79 μM, respectively [14]. The other sesquiterpenoids isolated from the stem bark of plants from the Meliaceae family (Aglaia harmsiana) have good cytotoxic against MCF-7, namely; β-caryophyllene oxide, senecrassidiol; 4β,10α-dihydroxy aromadendrane; 4α,10α-dihydroxyaromadendrane with the IC 50 values of 0.62, 1.32, 8.41, and 2.8 μM, respectively [15][16].…”