Glechomenes A-G, diterpenoids with anti-inflammatory activities from the aerial part of Glechoma longituba

Qian Zhang; Meilong Lu; Tianzi Liu; Xiuqin Zheng; Tianqi Chen; Li Yang; Lili Ding; Yingbo Yang; Zhuzhen Han; Lihua Gu; Zhengtao Wang

doi:10.1016/j.fitote.2024.106034

Glechomenes A-G, diterpenoids with anti-inflammatory activities from the aerial part of Glechoma longituba

Fitoterapia. 2024 Jul:176:106034. doi: 10.1016/j.fitote.2024.106034. Epub 2024 May 23.

Authors

Qian Zhang¹, Meilong Lu¹, Tianzi Liu¹, Xiuqin Zheng², Tianqi Chen¹, Li Yang¹, Lili Ding¹, Yingbo Yang², Zhuzhen Han³, Lihua Gu⁴, Zhengtao Wang⁵

Affiliations

¹ The MOE Key Laboratory of Standardization of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; Shanghai R&D Center for Standardization of Chinese Medicine, Shanghai 201203, China.
² The MOE Key Laboratory of Standardization of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
³ The MOE Key Laboratory of Standardization of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; Shanghai R&D Center for Standardization of Chinese Medicine, Shanghai 201203, China. Electronic address: [email protected].
⁴ The MOE Key Laboratory of Standardization of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; Shanghai R&D Center for Standardization of Chinese Medicine, Shanghai 201203, China. Electronic address: [email protected].
⁵ The MOE Key Laboratory of Standardization of Chinese Medicines, Institute of Chinese Materia Medica, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; Shanghai R&D Center for Standardization of Chinese Medicine, Shanghai 201203, China. Electronic address: [email protected].

PMID: 38795853
DOI: 10.1016/j.fitote.2024.106034

Abstract

Ten diterpenoids including six unreported abietane-type diterpenoids Glecholmenes A-F (1-6) and an undescribed labdane-type diterpenoid Glecholmene G (9), together with three known diterpenoids (7,8,10), were firstly isolated from the aerial part of G. longituba. Their structures were established mainly by nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) methods. Electronic circular dichroism (ECD) calculations and X-ray crystallographic analyses were used for the determination of their absolute configurations. The anti-inflammatory activity of all compounds was evaluated using the classical LPS-induced NO release model in RAW264.7 cells. Compound 2 displayed significant anti-inflammatory activities with IC₅₀ values of 29.08 ± 1.40 μM (Aminoguanidine hydrochloride as the positive control, IC₅₀ = 21.84 ± 0.48 μM).

Keywords: Anti-inflammatory activity; Diterpenoids; Glecholmenes A-F; Glechoma longituba (Nakai) Kupr.; RAW264.7 cells.

MeSH terms

Abietanes / isolation & purification
Abietanes / pharmacology
Animals
Anti-Inflammatory Agents* / isolation & purification
Anti-Inflammatory Agents* / pharmacology
China
Diterpenes* / chemistry
Diterpenes* / isolation & purification
Diterpenes* / pharmacology
Lamiaceae / chemistry
Mice
Molecular Structure
Nitric Oxide / metabolism
Phytochemicals* / isolation & purification
Phytochemicals* / pharmacology
Plant Components, Aerial* / chemistry
RAW 264.7 Cells

Substances

Anti-Inflammatory Agents
Diterpenes
Phytochemicals
Nitric Oxide
Abietanes
labdane