Structure elucidation and NMR assignments for curcuminoids from the rhizomes of <i>Curcuma longa</i>

Li, Wei; Wang, Shisheng; Feng, Jiatao; Xiao, Yuan-Sheng; Xue, Xing-Ya; Zhang, Hui; Wang, Yaqin; Liang, Xin-Miao

doi:10.1002/mrc.2478

Cited by 59 publications

(40 citation statements)

References 22 publications

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“…Another group investigated the ethanolic extract of C. longa rhizomes . They isolated two new sesquiterpenes: 2‐methoxy‐5‐hydroxybisabola‐3,10‐diene‐9‐one, and 2,8‐epoxy‐5‐hydroxybisabola‐3,10‐diene‐9‐one; one new mono‐terpene: 2‐(2,5‐dihydroxy‐4‐methylcyclohex‐3‐enyl) propanoic acid; as well as five known sesquiterpenes.…”

Section: Chemical Composition Of Turmericmentioning

confidence: 99%

Curcumin‐free turmeric exhibits anti‐inflammatory and anticancer activities: Identification of novel components of turmeric

Aggarwal

Wei

et al. 2013

Molecular Nutrition Food Res

274

167

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Turmeric, a dried powder derived from the rhizome of Curcuma longa, has been used for centuries in certain parts of the world and has been linked to numerous biological activities including antioxidant, anti-inflammatory, anticancer, antigrowth, anti-arthritic, anti-atherosclerotic, antidepressant, anti-aging, antidiabetic, antimicrobial, wound healing, and memory-enhancing activities. One component of turmeric is curcumin, which has been extensively studied, as indicated by more than 5600 citations, most of which have appeared within the past decade. Recent research has identified numerous chemical entities from turmeric other than curcumin. It is unclear whether all of the activities ascribed to turmeric are due to curcumin or whether other compounds in turmeric can manifest these activities uniquely, additively, or synergistically with curcumin. However, studies have indicated that turmeric oil, present in turmeric, can enhance the bioavailability of curcumin. Studies over the past decade have indicated that curcumin-free turmeric (CFT) components possess numerous biological activities including anti-inflammatory, anticancer, and antidiabetic activities. Elemene derived from turmeric is approved in China for the treatment of cancer. The current review focuses on the anticancer and anti-inflammatory activities exhibited by CFT and by some individual components of turmeric, including turmerin, turmerone, elemene, furanodiene, curdione, bisacurone, cyclocurcumin, calebin A, and germacrone.

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Section: Chemical Composition Of Turmericmentioning

confidence: 99%

Curcumin‐free turmeric exhibits anti‐inflammatory and anticancer activities: Identification of novel components of turmeric

Aggarwal

Wei

et al. 2013

Molecular Nutrition Food Res

274

167

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“…In their structures, a bisabolone-type sesquiterpene substructure is combined with a curcuminoid moiety, connected via a CÀO bond. Two known compounds, (1E,4E)-1,5-bis(4-hydroxyphenyl)penta-1,4-dien-3-one (4) [12] and (1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one (5) [13], were also isolated.In this article, the isolation and structure determination of the three new compounds are described. …”

mentioning

confidence: 99%

Three New Bisabolocurcumin Ethers from the Rhizomes of Curcuma longa L.

Xiao¹,

Lei²,

Liu³

et al. 2012

Helvetica Chimica Acta

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Three new bisabolocurcumin ethers, named demethoxybisabolocurcumin ether (1), bisabolocurcumin ether (2), and didemethoxybisabolocurcumin ether (3), along with two known compounds, 4 and 5, were isolated from the AcOEt extract of the rhizomes of Curcuma longa L. Their structures were established by the analysis of NMR and MS data. The new compounds 1 -3, which possess a new 1,7-diarylheptanoid skeleton linked with a bisabolone-type sesquiterpene substructure by a CÀO bond, were found for the first time in a natural source. , and hypoglycemic properties [10]. Up to now, from C. longa, curcuminoids, sesquiterpenoids, and their derivatives were reported as components [11]. In our phytochemical investigation, three new bisabolocurcumin ethers, compounds 1 -3, were isolated from the title plant. In their structures, a bisabolone-type sesquiterpene substructure is combined with a curcuminoid moiety, connected via a CÀO bond. Two known compounds, (1E,4E)-1,5-bis(4-hydroxyphenyl)penta-1,4-dien-3-one (4) [12] and (1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one (5) [13], were also isolated.In this article, the isolation and structure determination of the three new compounds are described.

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“…From the comparison of these data with those reported in the literature by Li et al . (), the substance was identified as 5‐hydroxy‐1,7‐bis(4‐hydroxyphenyl)‐4,6‐heptadien‐3‐one (dihydrobisdemethoxycurcumin) (Fig. ).…”

Section: Resultsmentioning

confidence: 99%

“…() and Li et al . (), the substance was identified as 1‐(4‐hydroxy‐3‐methoxyphenyl)‐7‐(4‐hydroxyphenyl)hepta‐1,6‐diene‐3,5‐dione (demethoxycurcumin) (Fig. ).…”

Section: Resultsmentioning

confidence: 99%

Plant growth inhibitors in turmeric (Curcuma longa) and their effects on Bidens pilosa

Akter

Islam

Takara

et al. 2018

Weed Biology and Management

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Turmeric (Curcuma spp.) has numerous biological activities, including anticancer, antibacterial, antifungal and insecticidal properties. Here, we evaluated the plant growth-inhibitory activities of two cultivars of Curcuma longa (C. longa; Ryudai gold and Okinawa ukon) against radish, cress, lettuce and Bidens pilosa (B. pilosa). The methanol extracts of both turmeric varieties inhibited the seed germination and seedling growth of all the tested plants. Ryudai gold had a significantly higher inhibitory effect on the seed germination and root and shoot growth of the plants than Okinawa ukon. Therefore, Ryudai gold was chosen for the isolation of plant growth-inhibitory compounds using a silica gel column and high-performance liquid chromatography. The structural identification of the compounds was carried out using 1 H NMR, 13 C NMR and liquid chromatography-tandem mass spectrometry. The growth inhibitors were identified as four curcuminoids; dihydrobisdemethoxycurcumin (1), bisdemethoxycurcumin (2), demethoxycurcumin (3) and curcumin (4). The IC 50 of the curcuminoids against the root and shoot growth of B. pilosa ranged from 8.7 AE 1.7 to 12.9 AE 1.8 and from 15.5 AE 1.8 to 38.9 AE 2.8 μmol L −1 , respectively. Compound 1 showed the lowest IC 50 against the root and shoot growth of B. pilosa. These results suggested that Ryudai gold has a potential growth-inhibitory effect against B. pilosa. *P < 0.05 versus Okinawa ukon. Results are expressed as the mean AE standard error of three independent experiments in triplicate.

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Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa

Cited by 59 publications

References 22 publications

Curcumin‐free turmeric exhibits anti‐inflammatory and anticancer activities: Identification of novel components of turmeric

Curcumin‐free turmeric exhibits anti‐inflammatory and anticancer activities: Identification of novel components of turmeric

Three New Bisabolocurcumin Ethers from the Rhizomes of Curcuma longa L.

Plant growth inhibitors in turmeric (Curcuma longa) and their effects on Bidens pilosa

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