Abstract
The ethyl acetate fraction obtained from aerial parts of L. lucidus was subjected for isolation of new bioactive compounds, which enabled isolation of five new pimarane-type diterpenoids, namely, 3β, 8β, 12β, 18-tetrahydroxy pimar-15-ene (10), 7α, 8β, 12β, 18-tetrahydroxy pimar-15-ene (11), 3β, 8β, 11β, 12α, 18-pentahydroxy pimar-15-ene (12), 12β acetoxy, 8β, 3β, 18-trihydroxy pimar-15-ene (13), and 3β acetoxy, 8β, 12β, 18-trihydroxy pimar-15-ene (14), along with nine known compounds. The structures were elucidated by spectroscopic analysis and comparison with literature data. The isolated new pimarane diterpenoids were examined for antimicrobial activity against Gram-negative and Gram-positive bacteria strains. Among them, the compound 3β, 8β, 12β, 18-tetrahydroxy pimar-15-ene (10) was most effective, exhibiting minimum inhibitory concentration (MIC) values of 15.62 µg/mL against Staphylococcus epidermidis, 31.25 µg/mL against Staphylococcus aureus, 62.5 µg/mL against Pseudomonas aeruginosa, and 125 µg/mL against Escherichia coli.
Highlights
Introduction e genus Lycopus of familyLamiaceae (Labiatae) contains around 16 species with wide distribution in Europe, Asia, and North America [1]
Major bioactive compounds that have been isolated from this plant are flavonoid and its esters, rosmarinic acid derivatives, phenylpropanoids, steroids, pentacyclic triterpenes, essential oils, oligosaccharides, polysaccharides, and diterpenoid glycosides [3, 6,7,8]. e leaf and stem of L. lucidus have been extensively used for the treatment of inflammation, cardiovascular problem, insomnia, menstrual problems, and thyroid problem, as a sedative, wound healing, pain reliving agents, herbal tea, and useful tonic [6, 8, 9]. e root of L. lucidus is known as small ginseng in China and widely used as dietary supplement [10]
Compound 10 appeared as white crystalline needles with HR-ESI-MS [M-H]- ion at m/z 337.2354 and molecular formula C20H34O4. e 1H-NMR showed three olefin protons, twelve methylene groups, two oxygenated geminal methylene protons, two oxygenated methine protons, and two other normal methine protons, along with three methyl protons. e 13C-NMR exhibited 20 carbon signals consisting of two olefin carbon signals at δC 153.4 (C-15) and 108.9 (C-16), four oxygenated carbon signals at δC 75.6 (C12), 74.9 (C-8-tertiary carbon), 68.5 (C-3), and 64.5 (C-18)
Summary
Introduction e genus Lycopus of familyLamiaceae (Labiatae) contains around 16 species with wide distribution in Europe, Asia, and North America [1]. In Asia, Lycopus lucidus is widely distributed species in Korea, China, Japan, Russia, and Taiwan. E root of L. lucidus is known as small ginseng in China and widely used as dietary supplement [10]. Many biological activities such as inhibition of superoxide radical [4], nitric oxide scavenging effect [6], inhibition of hypercholesterolemia and atherosclerosis [11], acaricidal activities [10], and hyaluronidase inhibition [5] have been explored from this plant
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