A New Sesquiterpene and other Constituents from Saussurea Lappa Root

Five sesquiterpenes, dehydrocostus lactone (1), santamarine (5), β-cyclocostunolide (6), 4α-hydroxy-4β-methyldihydrocostol (7) and 10α-hydroxyl-artemisinic acid (9), along with four other compounds, β-sitosterol (2), daucosterol (3), 5-hydroxy-methyl-furaldehyde (4), and trans-syingin (8), were isolated and identified from the roots of Saussurea lappa (Compositae). Based on previous reports and our study, sesquiterpene derivatives are common and characteristic constituents of the genus Saussurea. Among the nine compounds obtained, 9 is a new sesquiterpene. It is an artemisinic acid derivative, whose structural skeleton has not been reported for Saussurea species before, but artemisinic acid is a common compound in another Compositae species, Artemisia annua. Dehydrocostus lactone (1) is present in high-content and is a possible bioprecursor of 10α-hydroxyartemisinic acid (9).

Download Full-text

Seasonal and Post-harvest Accumulation of Artemisinin, Artemisinic Acid, and Dihydroartemisinic Acid in Three Accessions of Artemisia annua Cultivated in West Virginia, USA

Planta Medica ◽

10.1055/s-2008-1075155 ◽

2008 ◽

Vol 74 (03) ◽

Cited By ~ 6

Author(s):

JFS Ferreira

Keyword(s):

West Virginia ◽

Artemisia Annua ◽

Post Harvest ◽

Artemisinic Acid ◽

Dihydroartemisinic Acid

Download Full-text

Inhibition of TNF-α-Induced Inflammation by Sesquiterpene Lactones from Saussurea lappa and Semi-Synthetic Analogues

Planta Medica ◽

10.1055/s-0043-120115 ◽

2017 ◽

Vol 84 (05) ◽

pp. 329-335 ◽

Cited By ~ 17

Author(s):

Siwattra Choodej ◽

Khanitha Pudhom ◽

Tohru Mitsunaga

Keyword(s):

High Efficiency ◽

Sesquiterpene Lactones ◽

Significant Activity ◽

Synthetic Analogues ◽

Necrosis Factor Alpha ◽

Saussurea Lappa ◽

Tnf Α ◽

Ic50 Values ◽

Reduced Toxicity ◽

Dehydrocostus Lactone

We investigated the tumor necrosis factor-alpha (TNF-α) inhibitory activity of sesquiterpenes from Saussurea lappa root extracts. According to the hexane and EtOAc extracts showing significant activity with IC50 values of 0.5 and 1.0 µg/mL, respectively, chromatographic fractionation of the extracts was performed and led to the isolation of 10 sesquiterpenes (1–10). Costunolide (1), a major compound, and dehydrocostus lactone (4) exhibited high efficiency in decreasing TNF-α levels, with IC50 values of 2.05 and 2.06 µM, respectively. In addition, sesquiterpene analogues were synthesized to establish their structure-activity relationship (SAR) profile. Among the semi-synthetic analogues, compounds 6a and 16 showed the most potent activity with IC50 values of 1.84 and 1.97 µM, respectively. More importantly, compound 6a showed less toxicity than costunolide and 16. These results provided the first SAR profile of sesquiterpene lactones and indicated that the α-methylene-γ-lactone moiety plays a crucial role in TNF-α inhibition. Additionally, the epoxide derivative 6a might represent a lead compound for further anti-TNF-α therapies, owing to its potent activity and reduced toxicity.

Download Full-text

Preparation and Application of Reversed Phase ChromatorotorTM for the Isolation of Natural Products by Centrifugal Preparative Chromatography

Natural Product Communications ◽

10.1177/1934578x1300800308 ◽

2013 ◽

Vol 8 (3) ◽

pp. 1934578X1300800 ◽

Cited By ~ 1

Author(s):

Ilias Muhammad ◽

Volodymyr Samoylenko ◽

Francis Machumi ◽

Mohamed Ahmed Zaki ◽

Rabab Mohammed ◽

...

Keyword(s):

Natural Products ◽

Artemisia Annua ◽

Polar Compounds ◽

Reversed Phase ◽

Preparative Chromatography ◽

Planar Chromatography ◽

Sorbent Layer ◽

Preparative Scale ◽

Artemisinic Acid ◽

Binder Free

A method of preparation of rotors with a reversed phase (RP) solid silica gel sorbent layer has been developed for centrifugal preparative chromatography (CPC), also known as rotational planar chromatography (RPC). The rotors consist of binder free RP solid SiO2 layers of different thicknesses packed between two supported circular glass discs and can be used in any appropriate device for centrifugal chromatography, like Chromatotron® and CycloGraph®. Polar and /or semi-polar compounds with close R f values, as well as extracts and column fractions were separated and /or purified in a preparative and / or semi-preparative scale using the RP rotors, eluted with mixtures of aqueous-based solvents. We herein report three examples of its application, using RP ChromatorotorsTM, for the isolation of the diastereoisomeric alkaloids banistenosides I and II from Banisteriopsis caapi, saponins III and IV from Fagonia cretica, and the sesquiterpenes artemisinin (V) and artemisinic acid (VI) from Artemisia annua.

Download Full-text

Dehydrocostus lactone (DHCL) isolated from the root of Saussurea lappa inhibits the migration and invasion of DU145 human prostate cancer cells

The FASEB Journal ◽

10.1096/fasebj.22.1_supplement.700.40 ◽

2008 ◽

Vol 22 (S1) ◽

Author(s):

Ji Eun Hong ◽

Eun Ji Kim ◽

Soon Sung Lim ◽

Hyun‐Kyung Shin ◽

Jong‐Sang Kim ◽

...

Keyword(s):

Prostate Cancer ◽

Cancer Cells ◽

Human Prostate ◽

Migration And Invasion ◽

Human Prostate Cancer ◽

Prostate Cancer Cells ◽

Saussurea Lappa ◽

Dehydrocostus Lactone

Download Full-text

Simultaneous Quantification of Five Sesquiterpene Components after Ultrasound Extraction in Artemisia annua L. by an Accurate and Rapid UPLC–PDA Assay

Molecules ◽

10.3390/molecules24081530 ◽

2019 ◽

Vol 24 (8) ◽

pp. 1530 ◽

Cited By ~ 3

Author(s):

Jiaqi Ruan ◽

Zhengyue Liu ◽

Feng Qiu ◽

Henan Shi ◽

Manyuan Wang

Keyword(s):

Artemisia Annua ◽

Correlation Coefficients ◽

Ultra Performance Liquid Chromatography ◽

Artemisinic Acid ◽

Artemisia Annua L ◽

Acid Aqueous Solution ◽

Photodiode Array ◽

The Stability ◽

Acquity Uplc

Objective: To develop an accurate and rapid ultra-performance liquid chromatography (UPLC) coupled with a photodiode array (PDA) method for the simultaneous determination of artemisinin (Art), arteannuin B (Art B), arteannuin C (Art C), dihydroartemisinic acid (DHAA) and artemisinic acid (AA) in Artemisia annua L. Methodology: Chromatography separation was performed on an ACQUITY UPLC BEH C18 Column with isocratic elution; the mobile phase was 0.1% formic acid aqueous solution (A) and acetonitrile (B) (A:B = 40:60, v/v). Data were recorded at an ultraviolet (UV) wavelength of 191 nm for Art, Art C, DHAA and AA, and 206 nm for Art B. Results: The calibration curves of the five sesquiterpene components were all linear with correlation coefficients more than 0.9990. The linear ranges were 31.44–1572 μg/mL, 25.48–1274 μg/mL, 40.56–2028 μg/mL, 31.44–1572 μg/mL and 26.88–1396 μg/mL for Art, Art B, Art C, DHAA and AA, respectively. The precision ranged from 0.08% to 2.88%, the stability was from 0.96% to 1.66%, and the repeatability was all within 2.42% and had a mean extraction recovery of 96.5% to 100.6%. Conclusion: The established UPLC–PDA method would be valuable for improving the quantitative analysis of sesquiterpene components in Artemisia annua L.

Download Full-text

Biosynthesis of artemisinic acid in Artemisia annua

Phytochemistry ◽

10.1016/0031-9422(90)83020-2 ◽

1990 ◽

Vol 29 (7) ◽

pp. 2129-2132 ◽

Cited By ~ 29

Author(s):

Anand Akhila ◽

Kumkum Rani ◽

Raghunath S. Thakur

Keyword(s):

Artemisia Annua ◽

Artemisinic Acid

Download Full-text

Estimation of Costunolide and Dehydrocostus Lactone in Saussurea lappa and its Polyherbal Formulations followed by their Stability Studies Using HPLC-DAD

Pharmacognosy Magazine ◽

10.4103/0973-1296.149736 ◽

2015 ◽

Vol 11 (41) ◽

pp. 180 ◽

Cited By ~ 4

Author(s):

KSuresh Babu ◽

PR Rao Vadaparthi ◽

K Kumar ◽

VankaUma Maheswara Sarma ◽

QaziAltaf Hussain

Keyword(s):

Stability Studies ◽

Saussurea Lappa ◽

Dehydrocostus Lactone

Download Full-text

Apoptosis of DU145 human prostate cancer cells induced by dehydrocostus lactone isolated from the root of Saussurea lappa

Food and Chemical Toxicology ◽

10.1016/j.fct.2008.08.038 ◽

2008 ◽

Vol 46 (12) ◽

pp. 3651-3658 ◽

Cited By ~ 32

Author(s):

Eun Ji Kim ◽

Soon Sung Lim ◽

So Young Park ◽

Hyun-Kyung Shin ◽

Jong-Sang Kim ◽

...

Keyword(s):

Prostate Cancer ◽

Cancer Cells ◽

Human Prostate ◽

Human Prostate Cancer ◽

Prostate Cancer Cells ◽

Saussurea Lappa ◽

Dehydrocostus Lactone

Download Full-text

Network Analysis, and Experimental Validation to Uncover the Mechanism of the Four Compounds in Artemisia annua (Qing Hao) Antimalarial

10.21203/rs.3.rs-61078/v2 ◽

2020 ◽

Author(s):

yuping zhao ◽

Xiao-bo Zhang ◽

Hai-yu Xu ◽

Ling Wang ◽

Lu-qi Huang

Keyword(s):

Chemical Structure ◽

Experimental Validation ◽

Artemisia Annua ◽

Similarity Theory ◽

Artemisinic Acid ◽

Combined Application ◽

Tnf Α ◽

Text Information ◽

Qing Hao ◽

Using Data

Abstract Background: Artemisinin is widely used to treat malaria, but the antimalarial mechanism and coordinative interactions governing the actions of artemisinin, scopoletin, arteannuin B and artemisinic acid have not been elucidated. Methods: Based on the existence of antimalarial drugs, the antimalaria targets of artemisinin, scopoletin, arteannuin B and artemisinic acid were investigated by molecular docking using the similarity theory of chemical structure, and the antimalaria mechanism of scopoletin and its coordinative antimalaria interactions with the other three ingredients of the mixture were subsequently examined. Results: Using the text information excavation method, the relevant proteins involved in the antimalarial effect of artemisinin were IL-6, ACHE, PC3, IPOB, CYC, TNF-α, UGT1A9, CASP3, XDH, IL-1β, VEGF, CAT, CREB, AMPK, UGT1A6, ADR, MAPK, COX2, LB24AB and CYP450. The relevant proteins involved in the antimalarial effect of scopoletin were TNF-α, PI3K, IL-8, IL- 6, VEGF, IL-1β, MAPK, CD4, SP2, CTNNB, CASP3, PRO1400, IgE, IL-4, ICAM1, p38, STAT3, TLR4 and API4. However, arteannuin B and artemisinic acid had little relevance to the abovementioned proteins. The interaction property between TNF-α and Artemisia annua was that the effect of the mixture of artemisinin, scopoletin, arteannuin B and artemisinic acid was greater than that of artemisinin alone, and the synergistic effect of the four elements was considered beneficial to the progress of antimalarial treatment. Conclusion: The antimalarial targets of Artemisia annua ingredients were examined using data mining methods, and the antimalarial effect of scopoletin may be related to TNF. The combined application of the four elements achieved the same antimalarial effect and reduced the clinical use of artemisinin and scopoletin.

Download Full-text