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

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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Article number113349
JournalPhytochemistry
Volume203
DOIs
Publication statusPublished - 2022 Nov

Bibliographical note

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

Keywords

  • Celastraceae
  • Celastrus orbiculatus
  • Dihydro-β-agarofuran sesquiterpenes
  • Melanogenesis
  • Molecular networking

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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