Anchietins A-E: 30-norfriedelane-type triterpenes from Anchietea pyrifolia

Yukiyasu Yoneda; Tadahiro Yahagi; Kenichi Harada; Yasuko Okamoto; Sumiaki Motai; Keiichi Matsuzaki; Miwa Kubo; Yoshiyasu Fukuyama; Ayumi Ohsaki

doi:10.1016/j.phytochem.2022.113388

Anchietins A-E: 30-norfriedelane-type triterpenes from Anchietea pyrifolia

Phytochemistry. 2022 Nov:203:113388. doi: 10.1016/j.phytochem.2022.113388. Epub 2022 Sep 6.

Authors

Yukiyasu Yoneda¹, Tadahiro Yahagi², Kenichi Harada³, Yasuko Okamoto³, Sumiaki Motai⁴, Keiichi Matsuzaki², Miwa Kubo³, Yoshiyasu Fukuyama³, Ayumi Ohsaki⁵

Affiliations

¹ Department of Chemistry, College of Humanities and Sciences, Nihon University, Setagaya-ku, Tokyo 156-8550, Japan.
² School of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba, 274-8555, Japan.
³ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yashiro-cho, Tokushima, 770-8514, Japan.
⁴ Phytogalen, Avenida Pissanguaba, 1994 Planalto Paulista, São Paulo, SP, 04060-003, Brazil.
⁵ Department of Chemistry, College of Humanities and Sciences, Nihon University, Setagaya-ku, Tokyo 156-8550, Japan. Electronic address: ohsaki.ayumi@nihon-u.ac.jp.

PMID: 36075316
DOI: 10.1016/j.phytochem.2022.113388

Abstract

Five undescribed norfriedelane triterpenoids, anchietins A-E, along with three known norfriedelane triterpenoids, 21β-hydroxycaloncobalactone, and welwitschiilactones B and C, were isolated from the vine of Anchietia pyrifolia. The compounds were characterized by spectroscopic and crystallographic methods, including 2D NMR spectroscopy and single crystal X-ray crystallography. The isolated compounds were evaluated for the cytotoxic activity against HeLa and HL60 cells and for the inhibitory activity against lipopolysaccharide-induced NO production. Further, inhibitory effects on the inducible nitric oxide synthase mRNA expression levels were also assessed.

Keywords: Anchietia pyrifolia; NO production; Violaceae 30-Norfriedelane Triterpenoid; iNOS.

MeSH terms

Lipopolysaccharides / pharmacology
Molecular Structure
Nitric Oxide / metabolism
Nitric Oxide Synthase Type II / metabolism
RNA, Messenger
Triterpenes* / chemistry
Triterpenes* / pharmacology

Substances

Lipopolysaccharides
RNA, Messenger
Triterpenes
Nitric Oxide
Nitric Oxide Synthase Type II