Diversified abietane family diterpenoids from the leaves of Leucosceptrum canum and their cytotoxic activity. 2019

Kai Guo, and Yan-Chun Liu, and Yan Liu, and Shi-Hong Luo, and Wen-Yuan Li, and Xiao-Nian Li, and Sheng-Hong Li
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, PR China; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming, 650201, PR China; University of Chinese Academy of Sciences, Beijing, 100049, PR China.

Twenty-four diterpenoids of abietane family, including thirteen undescribed compounds and eleven known ones, were isolated from the leaves of Leucosceptrum canum. Their structures were elucidated by comprehensive spectroscopic analyses (including 1D and 2D-NMR and HRMS), and in the case of 15-hydroxy-abieta-8,11,13-trien-3-one by single-crystal X-ray diffraction. Their frameworks are highly diversified, involving normal abietane, 9,10-epoxy-9,10-seco-abietane, 18(4 → 3)-abeo-abietane, 3,4-seco-18(4 → 3)-abeo-abietane, and 16-nor-abietane. Selected compounds were evaluated for their cytotoxic activity against three human tumor cell lines, NCI-H1975, HepG2 and MCF-7. Among them, 3β-hydroxy-abieta-8,13-diene, 3β-hydroxy-abieta-8,11,13,15-tetraene, and 3β-hydroxy-9,10-epoxy-9,10-seco-abieta-8,11,13-triene exhibited moderate cytotoxicity against all three cell lines with IC50 values ranging from 8.11 to 50.73 μM, while 3α-hydroxy-abieta-8,11,13,15-tetraene, 3β-hydroxy-abieta-8,11,13,15-tetraen-7-one, and 15-hydroxy-18(4 → 3)-abeo-abieta-3,8,11,13-tetraene were selectively active with IC50 values ranging from 28.80 to 71.29 μM.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000972 Antineoplastic Agents, Phytogenic Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. Antineoplastics, Botanical,Antineoplastics, Phytogenic,Agents, Phytogenic Antineoplastic,Botanical Antineoplastics,Phytogenic Antineoplastic Agents,Phytogenic Antineoplastics
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines
D045784 Abietanes A subclass of cyclical DITERPENES that contain the abietane ring structure. Abietane Diterpene,Abietane Diterpenoid,Abietane Diterpenoids,Diterpenes, Abietane,Isopimarane,Isopimaranes,Totarane Diterpene,Totarane Diterpenes,Totaranes,Diterpenes, Pimarane,Pimaranes,Abietane Diterpenes,Diterpene, Abietane,Diterpene, Totarane,Diterpenoid, Abietane,Pimarane Diterpenes
D018515 Plant Leaves Expanded structures, usually green, of vascular plants, characteristically consisting of a bladelike expansion attached to a stem, and functioning as the principal organ of photosynthesis and transpiration. (American Heritage Dictionary, 2d ed) Plant Leaf,Leaf, Plant,Leave, Plant,Leaves, Plant,Plant Leave
D019686 Lamiaceae The mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals). Glechoma,Labiatae,Leonotis,Mesona,Micromeria,Schizonepeta,Tetradenia,Glechomas,Leonoti,Mesonas,Micromerias,Schizonepetas,Tetradenias

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