Bioactive Cardinane Sesquiterpenes from the Stems of Alangium salviifolium

Abstract

A dichloromethane extract of the stems of Alangium salviifolium afforded twelve cardinane sesquiterpenes, seven of which are new alangenes A-G (1-7) and five known compounds (8-12). Their structures were elucidated on the basis of spectroscopic techniques including UV, IR, and NMR spectroscopies, and mass spectrometry. Most of the tested compounds exhibited very potent aromatase inhibition properties, especially in the case of the cardinane sesquiterpenes 1, 5-8, and 10 (IC50 values of 0.09, 0.13, 0.30, 0.06, 2.05, and 1.19 μM, respectively), which are significantly better than that of the positive control (ketoconazole, IC50 of 2.4 μM). Compounds 1 and 4 exhibited selective cytotoxicity against the MOLT-3 cancer cell line with IC50 values of 7.9 and 2.1 μg mL(-1) , respectively.

Further terpenoids from Euphorbia tirucalli

“…Calamene-type sesquiterpenes contain one benzenoid ring while cadalenes incorporate the whole naphthalene bicycle [31]. Some tricyclic analogues of cadinane sesquiterpenes also extended the chemical diversity of this structural class, leading to introduce a fused five or six-membered oxygenated heterocycle [32][33][34] Nevertheless, the 6/6/6-fused tricyclic ring skeleton of tirucadalenone comprising an 1,2-dioxane core is an unprecedented structural feature.…”

Iridium‐Catalyzed Tandem Cyclization of Benzoylacetonitriles with Diazo Compounds Leading to Substituted Naphtho[1,8‐bc]pyrans by Sequential C−H Functionalization

“…Its derivatives have attracted much attention due to their interesting optoelectronic properties . Naphtho[1,8‐ bc ]pyran moieties, in particular, have often been described as privileged structures in drug development for their wide range of biological and physiological activities, such as anti‐HIV, anti‐tumor, anti‐bacterial, and anti‐arrhythmic properties as a result of their β ‐blocking activity . Therefore, considerable efforts have been devoted to the development of efficient methods for the construction of naphtho[1,8‐ bc ]pyran derivatives and screening of biological and optoelectronic molecules.…”

“…When HOAc, adamantane-1-carboxylic acid (1-AdCO 2 H), and 2,4,6-trimethylbenzoic acid (MesCO 2 H) were used instead of PivOH in entry 3 as one of the additives, the target product 3 aa was formed in 70-76% yields (see Table S1, entries 10-12 in the ESI †). In addition, slightly lower yields were obtained when the loading of NaOAc or PivOH was decreased (entries [4][5]. Furthermore, different temperatures were investigated, and 100 8C was found to be more suitable for this transformation (entries 3, 6-Scheme 1.…”

Pharmacological Modulation of Steroid Activity in Hormone-Dependent Breast and Prostate Cancers: Effect of Some Plant Extract Derivatives

“…Alangium salviifolium, commonly known as sage-leaved alangium, is a flowering plant in the Cornaceae family. Most of the isolated cardinane sesquiterpenes are potent aromatase inhibitors [82]. The modulation of the flavonoid skeleton increases the anti-aromatase effect [83].…”

“…Melatonin [44] Naringin, apigenin, berberine, palmatine, bavachin, jatrorrhizine, bavachinin [80] Alangenes [82] Extracts of Brassaiopsis glomerulata [84] Bakuchiol [85] Extracts of Sarcococca saligna [86] Shu-Gan-Liang-Xue decoction [87,88] Aqueous extracts of white button mushrooms [90] Butein [89] Obacunone [91] 5α-reductase Finasteride [53] Dutasteride [54] Serenoa repens extracts [92] Ethanolic extracts of Epilobium angustifolium [93] (−)-epigallocatechin gallate, biochanin A, daidzein, genistein, kaempferol [94] caffeic acid, grandifloroside [95] polyphenols from Cynomorium songaricum [96] Androgen receptor (SARM) Bicalutamide [65] Enzalutamide [69] Darolutamide [71] Methanolic extract of Brosimum rubescens bark [98] 3,3 -diindolylmethane [99] Androgen receptor (SARD) Darolutamide derivatives [79] Tanshinone IIA [100] Ethanolic extracts from propolis [101] Estrogen receptor (SERM)…”