Highly Oxygenated Triterpenoids and Diterpenoids from Fructus Rubi ( Hu) and Their NF-kappa B Inhibitory Effects

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Apr 3

PMID 33805414

Citations 2

Authors

Jiang Wan

Xiao-Juan Wang

Nan Guo

Xi-Ying Wu

Juan Xiong

Yi Zang

Chun-Xiao Jiang

Bing Han

Jia Li

Jin-Feng Hu

Affiliations

Soon will be listed here.

Abstract

During a phytochemical investigation of the unripe fruits of Hu (i.e., Fructus Rubi, a traditional Chinese medicine named "Fu-Pen-Zi"), a number of highly oxygenated terpenoids were isolated and characterized. These included nine ursane-type (, , and -), five oleanane-type (, -), and six cucurbitane-type (-) triterpenoids, together with five -kaurane-type diterpenoids (-). Among them, (4,5,8,9,10,14,17,18,19,20)-2,19α,23-trihydroxy-3-oxo-urs-1,12-dien-28-oic acid (rubusacid A, ), (2*,4*,5*,8*,9*,10*,14*,17*, 18*,19*,20*)-2α,19α,24-trihydroxy-3-oxo-urs-12-en-28-oic acid (rubusacid B, ), (5,8,9,10, 14,17,18,19)-2,19α-dihydroxy-olean-1,12-dien-28-oic acid (rubusacid C, ), and (3,5,8,9, 10,13,16)-3α,16α,17-trihydroxy--kaur-2-one (rubusone, ) were previously undescribed. Their chemical structures and absolute configurations were elucidated on the basis of spectroscopic data and electronic circular dichroism (ECD) analyses. Compounds and are rare naturally occurring pentacyclic triterpenoids featuring a special -unsaturated keto-enol (diosphenol) unit in ring A. Cucurbitacin B (), cucurbitacin D (), and 3,16,20(),25-tetrahydroxy-cucurbita-5,23- dien-2,11,22-trione () were found to have remarkable inhibitory effects against NF-B, with IC values of 0.08, 0.61, and 1.60 μM, respectively.

Citing Articles

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Cucurbitacin B Down-Regulates TNF Receptor 1 Expression and Inhibits the TNF-α-Dependent Nuclear Factor κB Signaling Pathway in Human Lung Adenocarcinoma A549 Cells.

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