two rare N-β-D-glucopyranosyl-1H-indole-3-acetic acid conjugates, N-[2-(1-β-D-glucopyranosyl)-1Hindol-3-yl)acetyl]-L-glutamic acid (1) and N-[2-(1-β-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-aspartic acid (2) were isolated from Ginkgo biloba. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. In addition, a simplified and efficient synthetic route for compounds 1 and 2 is also disclosed to determine the absolute configurations of them. This concise syntheses of compounds 1 and 2 may facilitate studies of the biology of this type alkaloids. Compounds 1 and 2 were also tested for their cytotoxic and anti-inflammatory activities. The biological evaluation showed that compounds 1 and 2 led to the decrease of interleukin (IL)-6, nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 at mRNA level in lipopolysaccharide (LPS)-stimulated murine macrophage RAW264.7 cells. Ginkgo biloba L., one of the most well-known medicinal plants worldwide, is considered as a living fossil due to its survival over millions of years 1. Pharmacological studies have shown that extracts from its leaves and seeds exhibit antiparasitic, antifungal, antibacterial and antiviral activities. G. biloba extracts have also found broad applications in the treatment of cognitive diseases 2-5. Since the discovery of ginkgolides A-C, a lot of phytochemical and pharmaceutical studies have been conducted on the G. biloba leaves 6-8. It is well known that G. biloba leaf extracts, mainly composed of ginkgolides, flavonoids and phenolic compounds, are frequently used in the treatment of cardiovascular, cerebrovascular, and neurological diseases 9,10. The dried seeds of G. biloba (called "baiguo" in Chinese), have been reported in the Chinese Pharmacopoeia as effective treatments for cough, asthma, enuresis, alcohol misuse, pyogenic skin infections and worm infestations in the intestinal tract 11,12. In contrast to extensive studies on G. biloba leaves, the seeds of G. biloba have received much less attention. In order to find structurally interesting and bioactive components from Ginkgo seeds and provide a better understanding of their functions, we conducted a phytochemical investigation of Ginkgo seeds. As a result, two N-β-D-glucopyranosyl-1H-indole-3-acetic acid conjugates were isolated from the title plant and the concise syntheses of 1 and 2 were also enclosed to determine the absolute configurations of compounds 1 and 2 (Fig. 1). Notably, compounds 1 and 2 are naturally isolated N-glycosides, which are rarely found in natural products. To the best of our knowledge, only very few examples have been reported previouly 13-17. Although compounds 1 and 2 were detected in an alkaline hydrolysate of rice extract using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) 18 , there are no examples of their isolation, absolute configurations determination and bioactivities. Reported herein are the structural identification, concise syntheses and bioactivities of them. Results and discussion Ginkgos...