TY - JOUR
T1 - Bioactive molecular network-guided discovery of dihydro-β-agarofurans from the fruits of Celastrus orbiculatus
AU - Kim, Jun Gu
AU - Le, Thi Phuong Linh
AU - Han, Jae Sang
AU - Cho, Yong Beom
AU - Kwon, Haeun
AU - Lee, Dongho
AU - Lee, Mi Kyeong
AU - Hwang, Bang Yeon
N1 - Funding Information:
This study was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST) (No. 2020R1A2C1008406 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.
Funding Information:
This study was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST) (No. 2020R1A2C1008406). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.
Publisher Copyright:
© 2022 Elsevier Ltd
PY - 2022/11
Y1 - 2022/11
N2 - 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.
AB - 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.
KW - Celastraceae
KW - Celastrus orbiculatus
KW - Dihydro-β-agarofuran sesquiterpenes
KW - Melanogenesis
KW - Molecular networking
UR - http://www.scopus.com/inward/record.url?scp=85136087111&partnerID=8YFLogxK
U2 - 10.1016/j.phytochem.2022.113349
DO - 10.1016/j.phytochem.2022.113349
M3 - Article
C2 - 35973614
AN - SCOPUS:85136087111
SN - 0031-9422
VL - 203
JO - Phytochemistry
JF - Phytochemistry
M1 - 113349
ER -