Scopariusols L-T, nine new ent-kaurane diterpenoids isolated from Isodon scoparius

Hua-Yi Jiang; Xiao-Nian Li; Han-Dong Sun; Hong-Bin Zhang; Pema-Tenzin Puno

doi:10.1016/S1875-5364(18)30079-7

Scopariusols L-T, nine new ent-kaurane diterpenoids isolated from Isodon scoparius

Chin J Nat Med. 2018 Jun;16(6):456-464. doi: 10.1016/S1875-5364(18)30079-7.

Authors

Hua-Yi Jiang¹, Xiao-Nian Li², Han-Dong Sun², Hong-Bin Zhang³, Pema-Tenzin Puno⁴

Affiliations

¹ Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100049, China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
³ Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China. Electronic address: [email protected].
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China. Electronic address: [email protected].

PMID: 30047467
DOI: 10.1016/S1875-5364(18)30079-7

Abstract

Nine new ent-kaurane diterpenoids, named scopariusols L-T (1-9), were isolated from the aerial parts of Isodon scoparius. Their structures were characterized mainly by analyzing the NMR and HR-ESI-MS data, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compound 1 was active against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with an IC₅₀ value of 0.6 μmol·L^-1.

Keywords: Anti-inflammatory activity; Cytotoxicity; Ent-kaurane diterpenoids; Isodon scoparius; X-ray diffraction.

MeSH terms

Animals
Antineoplastic Agents, Phytogenic / chemistry*
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology
Cell Line, Tumor
Crystallography, X-Ray
Diterpenes, Kaurane / chemistry*
Diterpenes, Kaurane / isolation & purification
Diterpenes, Kaurane / pharmacology
Drug Screening Assays, Antitumor
Drugs, Chinese Herbal / chemistry*
Drugs, Chinese Herbal / isolation & purification
Drugs, Chinese Herbal / pharmacology
HL-60 Cells
Humans
Isodon / chemistry*
Lipopolysaccharides / pharmacology
Macrophages / drug effects
Mice
Molecular Structure
Nitric Oxide / biosynthesis
Nuclear Magnetic Resonance, Biomolecular
Plant Components, Aerial / chemistry
RAW 264.7 Cells

Substances

Antineoplastic Agents, Phytogenic
Diterpenes, Kaurane
Drugs, Chinese Herbal
Lipopolysaccharides
Nitric Oxide