Details

Autor(en) / Beteiligte

• Kim, Jun Gu
• Le, Thi Phuong Linh
• Han, Jae Sang
• Cho, Yong Beom
• Kwon, Haeun
• Lee, Dongho
• Lee, Mi Kyeong
• Hwang, Bang Yeon

Titel

Bioactive molecular network-guided discovery of dihydro-β-agarofurans from the fruits of Celastrus orbiculatus

Ist Teil von

• Phytochemistry (Oxford), 2022-11, Vol.203, p.113349-113349, Article 113349

Ort / Verlag

Elsevier Ltd

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A bioactive molecular networking strategy has been applied to discovery of bioactive constituents from the fruits of Celastrus orbiculatus Thunb., which showed significant inhibitory effects on the α-MSH-induced melanin production in B16F0 melanoma cells. In the obtained molecular network, the nodes with relatively high bioactive scores were prioritized for isolation; as a result, 12 undescribed dihydro-β-agarofuran sesquiterpenes together with 15 known compounds were isolated from MeOH extracts of the fruits of C. orbiculatus. Their structures were elucidated based on the interpretation of NMR, HRESIMS, ECD data, and single crystal X-ray diffraction. Among the obtained isolates, celastorbin A and (1R,2S,4R,5S,7S,8S,9R,10S)-1,2,8-triacetoxy-9-cinnamoyloxydihydro-β-agarofuran, which possessed high bioactive scores in the molecular network, exhibited potent inhibitory effects on the α-MSH-induced melanin production in B16F0 cells with IC50 values of 4.1 and 2.0 μM, respectively. Twelve undescribed dihydro-β-agarofurans were isolated from Celastrus orbiculatus using a bioactive molecular networking strategy. Celastorbin A and (1R,2S,4R,5S,7S,8S,9R,10S)-1,2,8-triacetoxy-9-cinnamoyloxydihydro-β-agarofuran, which possessed high bioactive scores in the molecular network, showed potent inhibitory effects on the α-MSH-induced melanin production. [Display omitted] •A bioactivity-based molecular networking was applied to search bioactive chemicals of Celastrus orbiculatus.•Twelve undescribed dihydro-β-agarofurans were isolated by target-isolation.•Their structures were determined by NMR, HRESIMS, ECD, and single crystal X-ray diffraction.•All compounds were tested for their inhibitory effects on the α-MSH induced melanin production.