Cuceolatins A–D: New Bioactive Diterpenoids from the Leaves of Cunninghamia lanceolata

Four new diterpenoids named cuceolatins A–D, including three labdane‐type (1–3) and one abietane‐type (4) as well as three known labdane analogs (5–7), were reported from the leaves of Cunninghamia lanceolata. Structural assignments for these compounds were conducted by analyses of spectroscopic dat...

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Bibliographic Details
Published in:Chemistry & biodiversity 2019-08, Vol.16 (8), p.e1900317-n/a
Main Authors: Yu, Jin‐Hai, Yu, Zhi‐Pu, Wu, Dong‐Xiang, Yan, Xue, Wang, Yin‐Yin, Zhang, Hua
Format: Article
Language:English
Subjects:
Antibacterial activity
Biocompatibility
biological activity
Circular dichroism
Cunninghamia lanceolata
Cytotoxicity
Density functional theory
Dichroism
Diterpenes
diterpenoid
ECD calculation
Leaves
Time dependence
Toxicity
Tumor cell lines
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Summary:Four new diterpenoids named cuceolatins A–D, including three labdane‐type (1–3) and one abietane‐type (4) as well as three known labdane analogs (5–7), were reported from the leaves of Cunninghamia lanceolata. Structural assignments for these compounds were conducted by analyses of spectroscopic data, and their absolute configurations were determined by time‐dependent density functional theory (TD‐DFT) based electronic circular dichroism (ECD) calculations. Among them, the abietane‐type diterpenoid (11‐hydroxy‐12‐methoxyabieta‐8,11,13‐trien‐3‐one (4)) showed significant cytotoxicity against human MDA‐MB‐231, MCF‐7, and HeLa tumor cell lines with IC50 measurements of 4.3, 2.8 and 4.5 μm, respectively, while the labdane‐type diterpenoids with a 4α‐carboxy group (1–3 and 5) exhibited moderate antibacterial activity towards Bacillus subtilis and Staphylococcus aureus with IC50 values all below 25 μm.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.201900317