Two New Pyrrolidine Alkaloids, Codonopsinol C and Codonopiloside A, Isolated from &lt;i&gt;Codonopsis pilosula&lt;/i&gt;

Wakana, Daigo; Kawahara, Nobuo; Goda, Yukihiro

doi:10.1248/cpb.c13-00516

Cited by 40 publications

(25 citation statements)

References 8 publications

(11 reference statements)

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“…Previous studies showed that extracts of the C. pilosula roots exhibited pharmacological effects in protecting against peptic ulceration and promoting its healing, enhancing immunity, and improving learning and memory behavior, as well as inhibiting inducible NO synthase and protein oxidation and attenuating the cardiac-impaired insulin-like growth factor II receptor pathway 2 , 3 , 4 , 5 , 6 . Meanwhile, different types of chemical constituents were isolated from the extracts, such as phytosteroids, sesquiterpenes, triterpenes, alkaloids, alkyl alcohol glycosides, phenylpropanoid glycosides, polyacetylene glycosides and polysaccharides 7 , 8 , 9 , 10 , 11 , 12 , of which only polysaccharides were biologically evaluated 13 , 14 , 15 , 16 , 17 . As part of a program to systematically study the chemical diversity of traditional Chinese medicines and their biological effects, focusing on minor small molecules 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , an aqueous decoction of the C. pilosula roots was investigated since a variety of formulations containing “Dang shen” are practically used by decocting with water.…”

Section: Introductionmentioning

confidence: 99%

Acetylenes and fatty acids from Codonopsis pilosula

Jiang

Liu

Guo

et al. 2015

Acta Pharmaceutica Sinica B

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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.

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Section: Introductionmentioning

confidence: 99%

Acetylenes and fatty acids from Codonopsis pilosula

Jiang

Liu

Guo

et al. 2015

Acta Pharmaceutica Sinica B

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“…modesta Roots [ 12 ] C. tangshen Roots [ 13 ] 6 Codonopyrrolidium B C. pilosula Roots [ 14 ] C. pilosula var. modesta Roots [ 12 ] C. tangshen Roots [ 13 ] 7 Codonopsinol A C. pilosula Roots [ 11 ] 8 Codonopsinol B C. pilosula Roots [ 11 ] 9 Codonopsinol C C. pilosula Roots [ 11 ] 10 Codonopiloside A C. pilosula Roots [ 11 ] 11 Codotubulosine B C. tubulosa Roots [ 15 ] 12 n -9-Formyl harman C. lanceolata Roots [ 16 ] 13 Norharman C. lanceolata Roots [ ...…”

Section: Chemical Constituents Of Genus Codonopsismentioning

confidence: 99%

“…modesta [ 12 , 14 ]. In addition, the pyrrolidine alkaloids codonopsinols A ( 7 ), B ( 8 ), C ( 9 ) and the glycoside, codonopiloside A ( 10 ) were obtained from the roots of C. pilosula [ 11 ]. Codotubulosine B ( 11 ) was found in the roots of C. tubulosa [ 15 ].…”

Section: Alkaloidsmentioning

confidence: 99%

The genus Codonopsis (Campanulaceae): a review of phytochemistry, bioactivity and quality control

et al. 2014

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Codonopsis, in the family Campanulaceae, is a genus containing 42 species of dicotyledonous herbaceous perennial plants, predominantly found in Central, East and South Asia. Several Codonopsis species are widely used in traditional medicine and are considered to have multiple medicinal properties. Among the Codonopsis species, Codonopsis pilosula (Franch.) Nannf. and C. lanceolata (Sieb. et Zucc.) Benth. & Hook. f. ex Trautv. are more popular than others according to the findings, especially phytochemical and bioactive studies. Phytochemical research shows that Codonopsis species contain mainly polyacetylenes, phenylpropanoids, alkaloids, triterpenoids and polysaccharides, which contribute to multiple bioactivities. However, the mechanisms of their bioactivities need to be further elucidated. The less popular Codonopsis species remain to be studied and exploited. In addition, although a series of methods for the quality evaluation of Codonopsis species have been developed, a feasible and reliable approach to the efficacious and safe use of various Codonopsis species is still needed, with considering botanical origin, chemical constituents and bioactive effects. This review aims to provide up-to-date and comprehensive information on the phytochemistry, bioactivity and quality control of medicinal plants in the genus Codonopsis and to highlight current gaps in knowledge, which is useful for the wider development of the Codonopsis genus.

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“…6,7 The phytochemical studies of this genus have shown presence of major phytocomponents like alkaloids, phenylpropanoids, organic acid, triterpenoids, polyacetylene and polysaccharides. [8][9][10] Codonopsis clematidea is one of the species of Codonopsis, reported in Ladakh region which is used in traditional medicinal systems of this region (Amchi medicinal systems). This plant has been found to produce a pungent smell with bell-shaped flowers.…”

Section: Introductionmentioning

confidence: 99%

Phytochemical Screening and Antioxidant Activity Study of Methanol Extract of Stems and Roots of Codonopsis clematidea from Trans-himalayan Region

Bhardwaj¹,

Thakur²,

Kapoor³

et al. 2019

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Aim: The present report aimed to study the therapeutic and phytochemical properties of stems and roots of trans-himalayan plant Codonopsis clematidea. Material and Methods: The crude samples of stems and roots were explored for their chlorophyll, carotenoid and carbohydrate content in order to understand the matrix of these two plant parts. The extraction of phytochemicals was carried out by three different methods viz. sonication, maceration and soxhlet in methanol to identify the best extraction method. Further, analysis of Total Flavonoid Content (TFC) and Total Polyphenolic Content (TPC) were carried out using rutin trihydrate and gallic acid as a reference standard. Antioxidant capacity was estimated using three methods viz. 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging assay and Ferric Reducing Antioxidant Power (FRAP) assay. In addition to this, GC-MS analysis was also performed for the identification of volatile constituents of Methanol Extract of Stems (MES) and Methanol Extract of Roots (MER). Results: The MES and Dimethylsulfoxide Extract of Stems (DES) were found to have higher Chlorophyll a (Ch a) content in comparison to Chlorophyll b (Ch b) and Carotenoids (C ca). Carbohydrate profile showed that stems and roots have the highest content of fructose in comparison to other sugar moieties. The soxhlet method showed the highest percentage extractive yield in the stems as well as roots. Results revealed that the MES showed higher antioxidant potential as compared to the MER. A correlation has also found to exist between the results of TPC, TFC and antioxidant assays, since TPC and TFC are key constituents responsible for the antioxidant potential. Conclusion: These results have been found to suggest the richness of MES in natural phenols, flavonoids and antioxidants. Further, study should be conducted over identification and characterization of compounds present in the extract.

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Two New Pyrrolidine Alkaloids, Codonopsinol C and Codonopiloside A, Isolated from <i>Codonopsis pilosula</i>

Cited by 40 publications

References 8 publications

Acetylenes and fatty acids from Codonopsis pilosula

Acetylenes and fatty acids from Codonopsis pilosula

The genus Codonopsis (Campanulaceae): a review of phytochemistry, bioactivity and quality control

Phytochemical Screening and Antioxidant Activity Study of Methanol Extract of Stems and Roots of Codonopsis clematidea from Trans-himalayan Region

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