TL;DR: Bioassay-guided fractionation of C. americana extracts using the yellow fever mosquito led to the isolation of alpha-humulene, humulene epoxide II, and intermedeol and a newly isolated terpenoid (callicarpenal), which showed significant repellent activity against A. aegypti and Anopheles stephensi in bite deterrent studies.
Abstract: Essential oil extracts from Callicarpa americana and Callicarpa japonica were investigated. Bioassay-guided fractionation of C. americana extracts using the yellow fever mosquito, Aedes aegypti, led to the isolation of α-humulene, humulene epoxide II, and intermedeol and a newly isolated terpenoid (callicarpenal). Similar work involving C. japonica resulted in the isolation of an additional compound, spathulenol, as well as the four compounds isolated from C. americana. Structure elucidation was performed on all isolated compounds using a combination of gas chromatography−mass spectrometry−electron ionization, high-resolution liquid chromatography−MS−electrospray ionization, and one- and two-dimensional NMR experiments. Heretofore, 13,14,15,16-tetranorclerodane, callicarpenal, has never been identified from natural sources. Complete 1H and 13C NMR assignment data are provided for this compound. In bite deterrent studies, spathulenol, intermedeol, and callicarpenal showed significant repellent activity aga...
TL;DR: Pharmacological results have validated the use of Callicarpa species in the traditional medicine, and terpenoids and flavonoids are perhaps responsible for most of the activities shown by the plants of this genus.
TL;DR: Bioassay-guided fractionation of the combined fruits, leaves, and twigs of Callicarpa americana, collected from a plot in a forested area in southern Florida, led to the isolation of six new clerodane diterpenes (1-6) and eight known compounds.
Abstract: Bioassay-guided fractionation of the combined fruits, leaves, and twigs (fruiting branches) of Callicarpa americana, collected from a plot in a forested area in southern Florida, led to the isolation of six new clerodane diterpenes (1–6) and eight known compounds. The structures of 1–6 [12(S), 16ξ-dihydroxycleroda-3,13-dien-15,16-olide (1), 12(S)-hydroxy-16ξ-methoxycleroda-3,13dien-15,16-olide (2), 12(S)-hydroxycleroda-3,13-dien-15,16-olide (3), 16 ξ-hydroxycleroda-3,11 (E),13-trien-15,16-olide (4), 3β,12(S)-dihydroxycleroda-4(18),13-dien-15,16-olide (5), and 12(S)hydroxycleroda-3,13-dien-16,15-olide (6)] were elucidated by interpretation of spectroscopic data and chemical methods. The absolute configuration at C-12 in 1 and 3 was ascertained using the Mosher ester technique. The cytotoxicity of all isolates was tested against a panel of human cancer cell lines, and compounds 1, 4, and 6, and the known compounds genkwanin, 16ξhydroxycleroda-3,13-dien-15,16-olide, and2-formyl-16ξ-hydroxy-3-A-norcleroda-2,13dien-15,16-olide were active (ED50 <5 μg/mL). However, 1 was found to be inactive against human cancer cells implanted in mice using a hollow-fiber tumor model. Callicarpa americana L. is a shrub native to the southeastern United States. 2 Although the
TL;DR: Callicarpenal showed repellency against all colonies, and intermedeol showed significantly greater repellent than callicarPenal against both species and their hybrid.
Abstract: Callicarpenal and intermedeol are two insect-repellent terpenoids isolated from leaves of American beautyberry (Callicarpa americana L.; Verbenaceae) and Japanese beautyberry (Callicarpa japonica Thunb.). The repellency of these two terpenoids against workers of red imported fire ants, Solenopsis invicta Buren, black imported fire ants, Solenopsis richteri Forel, and a hybrid of these two species was evaluated using digging bioassays. In a multiple choice digging bioassay using two colonies from each species and their hybrid, callicarpenal showed significant repellency at concentration as low as 50 ppm against both red imported fire ant colonies and 6.25 ppm against all black imported fire ant and hybrid colonies. Intermedeol showed significant repellency at concentration as low as 1.50 ppm against both red imported fire ant colonies and 6.25 ppm against all black imported fire ant and hybrid colonies. In total, 15 colonies, five colonies from each species and the hybrid, were tested on callicarpenal and intermedeol at 50 ppm in a two-choice digging bioassay. Both callicarpenal and intermedeol showed repellency against all colonies, and intermedeol showed significantly greater repellency than callicarpenal against both species and their hybrid.
TL;DR: All of the Callicarpa leaf essential oils showed larvicidal activity, but two samples of C. candicans were particularly active with 48-h LC50 values of 2.1 and 3.8 μg/mL, which should be considered as a potential alternative mosquito control agent.
Abstract: There are around 140 species in the genus Callicarpa, with 23 species occurring in Vietnam. The Vietnamese Callicarpa species have been poorly studied. In this work, the leaf essential oils of C. bodinieri, C. candicans, C. formosana, C. longifolia, C. nudiflora, C. petelotii, C. rubella, and C. sinuata, have been obtained from plants growing in central Vietnam. The chemical compositions of the essential oils were determined using gas chromatography – mass spectrometry. Mosquito larvicidal activities of the essential oils were carried out against Aedes aegypti. All of the Callicarpa leaf essential oils showed larvicidal activity, but two samples of C. candicans were particularly active with 48-h LC50 values of 2.1 and 3.8 μg/mL. Callicarpa candicans essential oil should be considered as a potential alternative mosquito control agent.