A total of 12 new cycloartane- and lanostane-type triterpenoids including 16-deoxyargentatin A (), 16-deoxyisoargentatin A (), 7-oxoisoargentatin A (), 24--argentatin H (), 24---anisoylargentatin C (), 24---cinnamoylargentatin C (), 16-dehydroargentatin C (), 16,17(20)-didehydroargentatin C (), isoargentatin C (), isoargentatin H (), 3--quisquagenin (), and isoquisquagenin () together with 10 known triterpenoids (-) were isolated from the resin of AZ-2 obtained as a byproduct of Bridgestone guayule rubber production. The structures of new triterpenoids - and argentatin H (), which has previously been characterized as its diacetate (), were elucidated by extensive analysis of their spectroscopic data and chemical conversions, and the known compounds - were identified by comparison of their spectroscopic data with those reported. Of these, , , and exhibited weak cytotoxic activity for several cancer cell lines.
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http://dx.doi.org/10.1021/acsomega.1c01714 | DOI Listing |
Chem Biodivers
November 2023
Bioactive Natural Products Research Laboratory, Institute of Chemistry, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS, 79074-460, Brazil.
Sixteen triterpenoids with various skeletal types, five phenylpropanoid derivatives, and two flavonoids were isolated from a propolis sample produced by Apis mellifera collected in the Atlantic Forest of Midwest Brazil. Among these compounds, six triterpenes, namely 3β,20R-dihydroxylanost-24-en-3-yl-palmitate, (23E)-25-methoxycycloartan-23-en-3-one, 24-methylenecycloartenone, epi-lupeol, epi-α-amyrin, and epi-β-amyrin are being reported for the first time in propolis, while cycloartenone, (E)-cinnamyl benzoate, and (E)-cinnamyl cinnamate are new findings in Brazilian propolis. The presence of cycloartane- and lanostane-type triterpenoids, the latter being a class of compounds of restricted distribution in propolis worldwide, has not been reported in propolis from Midwest Brazil until now.
View Article and Find Full Text PDFJ Nat Prod
June 2023
Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai 201203, People's Republic of China.
A preliminary phytochemical investigation on the 90% MeOH extract from the twigs and needles of the vulnerable conifer led to the isolation and characterization of 17 structurally diverse triterpen-26-oic acids, including nine previously undescribed ones (fortunefuroic acids A-I, -) featuring a rare furoic acid moiety in the lateral chain. Among them, - are uncommon 9β-lanostane-type triterpenoic acids. Friedo-rearranged triterpenoids and feature a unique 17,14-friedo-lanostane skeleton, whereas possesses a rare 17,13-friedo-cycloartane-type framework.
View Article and Find Full Text PDFRSC Adv
November 2021
Department of Respiratory Medicine, The Third People's Hospital of Kunming Yunnan 650041 People's Republic of China
Eleven new 9,19-cycloartane triterpenes (1-9, 11-12) and one undescribed lanostane-type aglycone (10) were identified from the aerial parts of . The new structures were elucidated by analysis of spectroscopic data. Compounds 3-5, 7-9, and 11, without obvious cytotoxicity at 50 μM, were evaluated for inhibiting the mRNA expressions of atherosclerosis-related factors of CD147 (extracellular matrix metalloproteinase inducer, EMMPRIN), matrix metalloproteinase 2 (MMP-2) and MMP-9 in phorbol-12-myristate-13-acetate (PMA) induced Human monocytic THP-1 cells by using a quantitative real-time PCR method (q-PCR).
View Article and Find Full Text PDFBioorg Chem
July 2022
Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang 318000, PR China; Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai 201203, PR China. Electronic address:
A preliminary phytochemical investigation on the MeOH extract of the twigs and needles of Pseudotsuga gaussenii (a 'vulnerable' plant endemic to China) led to the isolation and characterization of 25 structurally diverse mono- and dimeric triterpenoids. 19 of them are previously undescribed, including eight cucurbitane-type triterpenoids (gaussenols A-H, 1-8, resp.), one serratene-type triterpene (gaussenol I, 9), and 10 triterpenic dimers (gaussenols J-S, 10-19, resp.
View Article and Find Full Text PDFACS Omega
June 2021
Southwest Center for Natural Products Research, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona, 250 E. Valencia Road, Tucson, Arizona 85706, United States.
A total of 12 new cycloartane- and lanostane-type triterpenoids including 16-deoxyargentatin A (), 16-deoxyisoargentatin A (), 7-oxoisoargentatin A (), 24--argentatin H (), 24---anisoylargentatin C (), 24---cinnamoylargentatin C (), 16-dehydroargentatin C (), 16,17(20)-didehydroargentatin C (), isoargentatin C (), isoargentatin H (), 3--quisquagenin (), and isoquisquagenin () together with 10 known triterpenoids (-) were isolated from the resin of AZ-2 obtained as a byproduct of Bridgestone guayule rubber production. The structures of new triterpenoids - and argentatin H (), which has previously been characterized as its diacetate (), were elucidated by extensive analysis of their spectroscopic data and chemical conversions, and the known compounds - were identified by comparison of their spectroscopic data with those reported. Of these, , , and exhibited weak cytotoxic activity for several cancer cell lines.
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