Annoglabrins D–F, Three New ent -Kaurane Diterpenoids from the Annona glabra Fruit Pulp
9 affiliations
- 1Graduate University of Science and Technology , , ,
- 2Pham Ngoc Thach University of Medicine , , ,
- 3Duy Tan University , , ,
- 4University of Natural Resources and Environment Ho Chi Minh City , ,
- 5Vietnam National University , , , ,
- 6Research Laboratories of Saigon Hi-tech Park , , ,
- 7Vietnam Academy of Science and Technology , , ,
- 8Nguyen Tat Thanh University , , , ,
- 9Nguyen Tat Thanh University , , ,
Abstract
Annona glabra L. is a tropical fruit tree distributed across the Americas and Asia, renowned for its diverse traditional therapeutic uses and rich phytochemical profile. Despite its medicinal potential, research on its fruit remains limited, with ambiguities surrounding the distinct constituents of the seeds versus the pulp. To address this gap, the present study focused on the fruit pulp of A. glabra, resulting in the isolation of two new nor-ent-kaurane diterpenoids, annoglabrin D (1) and annoglabrin F (3), and one new ent-kaurane diterpenoid, annoglabrin E (2), along with five known compounds (4–8) of the same skeletal type. Their structures were elucidated via spectroscopic analyses (1D, 2D NMR, HR-ESI-MS) and comparison with previous literature. DP4 probability and ECD spectrum were deployed to identify the absolute configuration of compounds 1–3. The in vitro nitric oxide production inhibitory assay indicated 3 (IC50 48.1 μM) and 8 (IC50 51.8 μM) as moderate inhibitors in comparison with L-NMMA (IC50 12.9 μM), while the others were inactive. Compound 8 demonstrated potent cytotoxicity against KB (IC50 19.7 μM) and HepG2 (IC50 16.4 μM) cancer cell lines, in comparison with ellipticine (IC50 1.91, 1.95 μM, respectively). These findings were corroborated by molecular docking and molecular dynamics simulations, revealing the efficient and stable binding interactions of 3 and 8 with proteins associated with key inflammatory mediators (iNOS, IL-6, TNF-α, COX-2, IL-1β), transcription factors (NF-κB, Nrf2), and the KB and HepG2 cancer cell lines. The simulations predicted the contribution of specific functional groups in compounds 3 and 8, particularly the C-4 methyl, C-16 ketone, and acetoxymethyl carbonyl in 3, as well as the methyl ester moiety at C-16 and the carboxyl group (−COOH) at C-4 in 8, in mediating these compounds’ stable and effective interactions.
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BibTeX
@article{duong2026annoglabrins,
title = {{Annoglabrins D–F, Three New ent -Kaurane Diterpenoids from the Annona glabra Fruit Pulp}},
author = {Thi-Kim-Yen Duong and Ngoc-Van-Trang Dao and Hoang-Vinh-Truong Phan and Thi-Minh-Suong Huynh and Huynh-Nguyen-Khanh Tran and Phan-Si-Nguyen Dong and Nhan-Tam Do and Vu Nguyen-Si and Van-Tinh Vo and Dinh-Tri Mai and Van-Kieu Nguyen},
journal = {ACS Omega},
year = {2026},
month = nov,
doi = {10.1021/acsomega.6c09651},
url = {https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c09651/5465173/Annoglabrins-D-F-Three-New-ent-Kaurane},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Annoglabrins D–F, Three New ent -Kaurane Diterpenoids from the Annona glabra Fruit Pulp
AU - Thi-Kim-Yen Duong
AU - Ngoc-Van-Trang Dao
AU - Hoang-Vinh-Truong Phan
AU - Thi-Minh-Suong Huynh
AU - Huynh-Nguyen-Khanh Tran
AU - Phan-Si-Nguyen Dong
AU - Nhan-Tam Do
AU - Vu Nguyen-Si
AU - Van-Tinh Vo
AU - Dinh-Tri Mai
AU - Van-Kieu Nguyen
PY - 2026
DA - 2026/11/05
JO - ACS Omega
DO - 10.1021/acsomega.6c09651
UR - https://pubs.acs.org/acsodf/article/doi/10.1021/acsomega.6c09651/5465173/Annoglabrins-D-F-Three-New-ent-Kaurane
AB - Annona glabra L. is a tropical fruit tree distributed across the Americas and Asia, renowned for its diverse traditional therapeutic uses and rich phytochemical profile. Despite its medicinal potential, research on its fruit remains limited, with ambiguities surrounding the distinct constituents of the seeds versus the pulp. To address this gap, the present study focused on the fruit pulp of A. glabra, resulting in the isolation of two new nor-ent-kaurane diterpenoids, annoglabrin D (1) and annoglabrin F (3), and one new ent-kaurane diterpenoid, annoglabrin E (2), along with five known compounds (4–8) of the same skeletal type. Their structures were elucidated via spectroscopic analyses (1D, 2D NMR, HR-ESI-MS) and comparison with previous literature. DP4 probability and ECD spectrum were deployed to identify the absolute configuration of compounds 1–3. The in vitro nitric oxide production inhibitory assay indicated 3 (IC50 48.1 μM) and 8 (IC50 51.8 μM) as moderate inhibitors in comparison with L-NMMA (IC50 12.9 μM), while the others were inactive. Compound 8 demonstrated potent cytotoxicity against KB (IC50 19.7 μM) and HepG2 (IC50 16.4 μM) cancer cell lines, in comparison with ellipticine (IC50 1.91, 1.95 μM, respectively). These findings were corroborated by molecular docking and molecular dynamics simulations, revealing the efficient and stable binding interactions of 3 and 8 with proteins associated with key inflammatory mediators (iNOS, IL-6, TNF-α, COX-2, IL-1β), transcription factors (NF-κB, Nrf2), and the KB and HepG2 cancer cell lines. The simulations predicted the contribution of specific functional groups in compounds 3 and 8, particularly the C-4 methyl, C-16 ketone, and acetoxymethyl carbonyl in 3, as well as the methyl ester moiety at C-16 and the carboxyl group (−COOH) at C-4 in 8, in mediating these compounds’ stable and effective interactions.
SN - 2470-1343
ER -