Meroterpenoids Composed of Flavone and Cyclic Sesquiterpene from Syzygium oblanceolatum
Abstract
Phytochemical investigation of the Indonesian medicinal plant Syzygium oblanceolatum led to the isolation of three new meroterpenoids, syzygioblanes I-K (1-3). These compounds possess a unique flavanone-derived moiety fused with a sesquiterpenoid unit, further expanding the structural diversity of the syzygioblane family. Their structures and absolute configurations were established through comprehensive spectroscopic analyses. Syzygioblanes J (2) and K (3) represent new structural subclasses characterized by C-7' ketone-deficient and C-5' ketone-deficient frameworks, respectively, and plausible biosynthetic pathways for their formation are proposed. In addition, re-examination of NMR and nuclear Overhauser effect spectroscopy data led to the stereochemical revision of the previously reported syzygioblane E. Antiproliferative evaluation against a panel of human tumor cell lines, including the multidrug-resistant (MDR) DU145/TxR/CxR cell line, revealed that syzygioblane I retained collateral sensitivity toward MDR cells, although its selectivity was lower than that of syzygioblane A. These findings indicate that the structural features of the sesquiterpenoid moiety play an important role in modulating collateral sensitivity and provide further insight into the structure-activity relationships of this rare class of plant-derived spiromeroterpenoids.
Related
- Flavone-Based Anticancer Agents: Advances in Structure–Activity Relationships and Multitarget Mechanisms for Drug Design (2015–Present)
- Daturolides A-K, cytotoxic sesquiterpene lactones from Datura wrightii.
- Evaluation of a colorectal cancer screening program composed of successive waves of different tests: The experience of the French Calvados County
- Phytochemical characterization and preliminary antimicrobial evaluation of a mono- and sesquiterpene-rich essential oil of Salvia limbata C.A.Mey.
- Antiviral Sesquiterpene Lactones from Laurus nobilis L.: Inhibition of Hepatitis C Virus and Dengue Virus Replication.
BibTeX
@article{muroda2026meroterpenoids,
title = {{Meroterpenoids Composed of Flavone and Cyclic Sesquiterpene from Syzygium oblanceolatum}},
author = {Rintaro Muroda and Nona Koga and Kaede Kawashima and Chihiro Ito and Shuichi Fukuyoshi and Yohei Saito and Katsunori Miyake and Abdul Rahim and Kyoko Nakagawa-Goto},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2026},
month = sep,
doi = {10.1248/cpb.c26-00362},
url = {https://www.jstage.jst.go.jp/article/cpb/74/9/74_c26-00362/_article},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Meroterpenoids Composed of Flavone and Cyclic Sesquiterpene from Syzygium oblanceolatum
AU - Rintaro Muroda
AU - Nona Koga
AU - Kaede Kawashima
AU - Chihiro Ito
AU - Shuichi Fukuyoshi
AU - Yohei Saito
AU - Katsunori Miyake
AU - Abdul Rahim
AU - Kyoko Nakagawa-Goto
PY - 2026
DA - 2026/09/18
JO - Chemical and Pharmaceutical Bulletin
DO - 10.1248/cpb.c26-00362
UR - https://www.jstage.jst.go.jp/article/cpb/74/9/74_c26-00362/_article
AB - Phytochemical investigation of the Indonesian medicinal plant Syzygium oblanceolatum led to the isolation of three new meroterpenoids, syzygioblanes I-K (1-3). These compounds possess a unique flavanone-derived moiety fused with a sesquiterpenoid unit, further expanding the structural diversity of the syzygioblane family. Their structures and absolute configurations were established through comprehensive spectroscopic analyses. Syzygioblanes J (2) and K (3) represent new structural subclasses characterized by C-7' ketone-deficient and C-5' ketone-deficient frameworks, respectively, and plausible biosynthetic pathways for their formation are proposed. In addition, re-examination of NMR and nuclear Overhauser effect spectroscopy data led to the stereochemical revision of the previously reported syzygioblane E. Antiproliferative evaluation against a panel of human tumor cell lines, including the multidrug-resistant (MDR) DU145/TxR/CxR cell line, revealed that syzygioblane I retained collateral sensitivity toward MDR cells, although its selectivity was lower than that of syzygioblane A. These findings indicate that the structural features of the sesquiterpenoid moiety play an important role in modulating collateral sensitivity and provide further insight into the structure-activity relationships of this rare class of plant-derived spiromeroterpenoids.
SN - 1347-5223
SN - 0009-2363
ER -