Germacrane and humulane sesquiterpenes from the roots and rhizomes of Valeriana officinalis var. latifolia and their anti-inflammatory and anti-influenza virus activities.

Abstract

Twenty-seven sesquiterpenes, including twenty-one new germacrane-type ones (1-5, 8-16, and 19-25) and a new humulane-type one (27), were isolated from the roots and rhizomes of Valeriana officinalis var. latifolia. The structures and absolute configurations of the new compounds were elucidated using extensive spectroscopic techniques (1D and 2D NMR, and HRESIMS) and quantum chemical calculations. Structurally, compound 20 was a new germacrane-type norsesquiterpene, while compound 27 was a new humulane-type norsesquiterpene. In addition, compound 27 significantly inhibited the production of nitric oxide with an IC₅₀ value of 3.65 ± 1.06 μM. It reduced the expression of cytokines such as IL-1 and IL-6, as well as inflammation-related proteins induced by LPS or influenza A virus in macrophages, thereby exhibiting significant anti-inflammatory activity. This effect may be related to blocking the formation of the inflammasome and the activation of the NF-κB signaling pathway. Furthermore, compound 10 showed anti-influenza virus activity with an EC₅₀ value of 27.28 ± 5.63 µM. The study may provide a scientific basis for the development and utilization of functional foods and medicines derived from V. officinalis var. latifolia.