Acetylenes and fatty acids from Codonopsis pilosula

Abstract

Four new acetylenes (1–4) and one new unsaturated ω-hydroxy fatty acid (5), together with 5 known analogues, were isolated from an aqueous extract of Codonopsis pilosula roots. Their structures were determined by spectroscopic and chemical methods. The new acetylenes are categorized as an unusual cyclotetradecatrienynone (1), tetradecenynetriol (2), and rare octenynoic acids (3 and 4), respectively, and 3 and 4 are possibly derived from oxidative metabolic degradation of 1 and/or 2. The absolute configuration of 1 was assigned by comparison of the experimental circular dichroism (CD) spectrum with the calculated electronic circular dichroism (ECD) spectra of stereoisomers based on the quantum-mechanical time-dependent density functional theory, while the configuration of 2 was assigned by using modified Mosher׳s method based on the MPA determination rule of ΔδRS values for diols.

Shenqi Fuzheng Injection Reverses Cisplatin Resistance through Mitofusin‐2‐Mediated Cell Cycle Arrest and Apoptosis in A549/DDP Cells

“…var. modesta (Nannf) L. T. Shen, has been used for the treatment of lethargy, poor appetite, thirst, indigestion, chronic diarrhea, archoptoma, chronic anemia, and leukemia [ 14 ]. SFI was approved in 1999 by the State Food and Drug Administration of the People's Republic of China as an antitumor treatment [ 15 , 16 ].…”

Three pairs of alkaloid enantiomers from the root of Isatis indigotica

“…This differs from practical application of water decoctions of “ban lan gen”, as well as formulations containing “ban lan gen”. Therefore, as part of a program to assess the chemical and biological diversity of traditional Chinese medicines 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , we investigated a water decoction of “ban lan gen” and have reported characterization of 28 new alkaloids, including a pair of indole alkaloid enantiomers containing dihydrothiopyran and 1,2,4-thiadiazole rings, a pair of bisindole alkaloid enantiomers, seven glycosidic bisindole alkaloids, and 54 known compounds, as well as their antiviral and hepatocyte-protective activities 23 , 24 , 25 , 26 , 27 . A further in-depth investigation on the same extract led to the chiral separation of three pairs of alkaloid enantiomers (−)/(+)- 1 −(−)/(+)- 3 having diverse structural features ( Fig.…”

Sesquiterpene glycosides from the roots of Codonopsis pilosula

“…(Campanulaceae), known as “dang shen” in Chinese, are one of the most common drugs in traditional Chinese medicine and normally are used as a substitute for the much more costly Panax ginseng as tonic agents exhibiting similar therapeutic effects 1 . Although some chemical constituents and pharmacological activities have been reported, previous work was mainly carried out on ethanol or methanol extracts of this natural product 2 , which is not consistent with practical utilization of herbal medicines including various formulations containing “dang shen” by decocting with water. As part of a program to systematically study the chemical diversity of traditional Chinese medicines and their biological effects, focusing on water-soluble and minor constituents 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , an aqueous decoction of “dang shen” was investigated.…”

“…As part of a program to systematically study the chemical diversity of traditional Chinese medicines and their biological effects, focusing on water-soluble and minor constituents 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , an aqueous decoction of “dang shen” was investigated. Previously, we reported twelve new constituents from the decoction 2 , 15 , including an unsaturated ω -hydroxy fatty acid, 4 acetylenes, and 7 C 14 -polyacetylene glucosides, along with preliminary bioassays. Continuation of our investigation on the same extract led to characterization of three new minor sesquiterpene glycosides named codonopsesquilosides A−C ( 1 − 3 ) ( Fig.…”