A New Cytotoxic Phenolic Derivative from the Roots of Antidesma Acidum

Abstract

A new phenolic derivative, acidumonate (1), together with a synthetically known compound, 4-((E)-3,3-dimethylpenta-1,4-dienyl)-phenol (2), and sixteen known natural products, antidesmol (3), mellein (4), sitosterol (5), stigmasterol (6), 5-cholesten-3β-ol (7), 4-cholesten-3-one (8), 3-(1,1-dimethylallyl)scopoletin (9), (-)-5,7-dihydroxy-2-eicosyl-chromone (10), 2,5-dimethoxy-1,4-benzoquinone (11), barbatumol A (12), N-trans-feruloyltyramine (13), syringic aldehyde (14), p-hydroxybenzoic acid (15), taxifolin (16), (+)-catechin (17) and gallocatechin (18), were isolated from the roots of Antidesma acidum. The structural assignment of the new compound was based on spectroscopic methods. All isolated compounds were evaluated for their cytotoxicity (KB and HeLa cells). Compound 1 showed good cytotoxicity against both cell lines (with IC 50 values of 2.60 and 3.80 µg/mL, respectively).

Melleins—Intriguing Natural Compounds

“…Compound 1 was also isolated from the roots of Antidesma acidum, as identified by spectroscopic methods [96]. (R)-(-)-mellein (1) was also isolated from the roots of another plant Microcos tomentosa [97].…”

“…Antidesma acidum [96] Enicosanthum membranifolium [93] Ficus formosana [92] Garcinia bancana [91] Microcos tomentosa [97] Millettia leucantha [94] Rhodiola kirilowii [95] Stevia lucida [98] Zelkova serrata [100] Insects:…”

Phytochemical and Pharmacological Review of the Genus Antidesma

“…Simple phenolics from Antidesma plants usually contain only 1 benzene ring as their carbon backbone with 2-4 substituted groups of hydroxyl (OH), methoxyl (OCH 3 ), carboxylic (COOH), aldehyde (CHO), or glycosyl types. [29][30][31][32][33][34] Some compounds are also either alkylated, alkenated, or prenylated (28,29,37,38,40, and 41) (Figure 2).…”

“…The characteristic feature of Antidesma coumarins is the 1,1-dimethylallyl substitution at C-3 position ( 85 - 90 ). 29 Besides the simple coumarins, coumarinolignan derivatives, which are formed by a coumarin and a phenylpropanoid via etheric linkages, were also isolated and structurally determined ( 91 - 99 ). 29,36,39 The relative configuration of C-7′ and C-8′ usually belonged to trans type, which was determined by coupling constant value of approximately 4 to 6 Hz.…”

“…29 Besides the simple coumarins, coumarinolignan derivatives, which are formed by a coumarin and a phenylpropanoid via etheric linkages, were also isolated and structurally determined ( 91 - 99 ). 29,36,39 The relative configuration of C-7′ and C-8′ usually belonged to trans type, which was determined by coupling constant value of approximately 4 to 6 Hz. As for compounds 97 - 99 , the absolute configuration of C-7′ and C-8′ was determined by ECD quantum calculation (Figure 5).…”