Crystal Structure of Curcumenol: Evidence of Asymmetric O–H...O (bridged) Hydrogen-Bonded Closed Dimer

Muangsin, Nongnuj; Ngamrojnavanich, Nattaya; Onanong, S.; Chaichit, Narongsak; Roengsumran, Sophon; Petsom, Amorn

doi:10.1023/b:jory.0000048881.57572.ef

Cited by 5 publications

(4 citation statements)

References 8 publications

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“…Curcuma zedoaria, also known as white turmeric, is a species that is a rich source of terpenoids.Curcumenol, isolated from Globba malaccensis Ridl, belongs to the monoclinic, space group C2, with a 16.8467 (4), b 7.6799 (2), c 11.8613 (10) Å and β 115.997 (1) °. This modification is less dense, as noted from its calculated density of 1.28 (Muangsin et al, 2004). The present modification (I), (Fig.…”

supporting

confidence: 41%

Curcumenol fromCurcuma zedoaria: a second monoclinic modification

et al. 2010

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.003 Å; R factor = 0.037; wR factor = 0.090; data-to-parameter ratio = 10.2.The title compound, systematic name 9-isopropylidene-2,6-dimethyl-11-oxatricyclo[6.2.1.0 1,5 ]undec-6-en-8-ol, C 15 H 22 O 2 , which crystallizes with two molecules of similar conformation in the asymmetric unit, features three fused rings, two of which are five-membered and the third six-membered. Of the two five-membered rings, the one with an O atom has a distinct envelope shape (with the O atom representing the flap). The six-membered ring is also envelope-shaped as it shares a common O atom with the five-membered ring. In the crystal, the two independent molecules are linked by a pair of O-HÁ Á ÁO hydrogen bonds, generating a dimer. Related literatureFor the C2 modification isolated from Globba malaccensis Ridl, see: Muangsin et al. (2004). ExperimentalCrystal data Data collectionBruker SMART APEX diffractometer 13257 measured reflections 3298 independent reflections 2882 reflections with I > 2(I) R int = 0.046

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supporting

confidence: 41%

Curcumenol fromCurcuma zedoaria: a second monoclinic modification

et al. 2010

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“…However, prior phytochemical studies on the genus Globba have revealed several contents as main compounds, among other the presence sesquiterpene and diarylheptanoid in G. malaccensis Ridl (A synonym for G. variabilis subsp. Variabilis) [22]; two new chemical compounds of lipids, three new labdane-type diterpenes and two new steroids from the rhizomes of G. reflexa [23]; triterpene and steroids from G. racemosa Sm; phenolic compound, steroid, labdane, diterpene and benzofuran from G. pendula Roxb. [24]; heptadecane, pinocarvone, l-linalool, alloaromadendrene, β -caryophyllene, α-humulene, terpineol, lavandulol, 2,6-dimethyl-1,5,7-octatrien-3-ol in methanol crude extract from G. marantina [25] and steroids, alkaloids, flavonoids, cardiac glycosides, saponins, tannins, terpenoids, phlobatinins, fatty acids, coumarins and phenols compounds from ethanolic tuber extract of G. bulbifera [26].…”

Section: The Phytochemical Compounds Of Ethanol Extract Of the Rhizommentioning

confidence: 99%

“…The presence of major chemical contents of Globba schomburgkii Hook. F. and Globba ophioglossa Wight had been detected by Raj et al [9] among others cyperene 3.1 % (Gs), 0.9% (Go), b-caryophyllene 31.7% (Gs), 1.0% (Go), aromadendrene 5.5% (Gs), a-humulene 5.3% (Gs), 0.7% (Go), caryophyllene oxide 10.3% (Gs), 21.8% (Go), (E)-nerolidol 5.7% (Go), humulene epoxide* 5.9 % (Go), zerumbone 22…”

Section: Introductionmentioning

confidence: 99%

Distribution and Phytocomponent in the Ethanol Extract of Globba candida Gagnep. (Zingiberaceae) by GC-MS Analysis

Andila

Tirta²

2019

JTLS

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Globba is the third largest genera in the Zingiberaceae family, distributed in tropical and subtropical regions with the center of biodiversity in Southeast Asia. The study about phytochemical contents Globba is an interesting especially Globba candida Gapnep which have been never reported. The aims of this study were to observe distribution and phytochemical compounds of ethanol extract of G. candida Gapnep. found on Bali Island. Hydrodistillation was used to determine the presence of its essential oil and a Gas Chromatography-Mass Spectrometry (GC-MS) was used to carry out the phytochemical analysis of the essential oil and ethanol extracts of G. candida Gapne. The phytochemical analysis of the rhizomes and leaves ethanol extracts of G. candida Gapnep revealed 36 and 8 identified chemical compounds representing 85,82% and 85,47% of the total analyzed extracts. However, there was no essential oil constituent found in G. candida Gapnep. The main compounds of the rhizome extract of G. candida Gapnep were levoglucosan 19.07%, allylhydrazone acetaldehyde 5.52%, trans-2,3-epoxybutane 6.30%, butan-3-enoic acid methyl ester 4.36%, 2-methylcyclopentanone 4.02%, and 2-n-propyl-oxetan 4.00%. While the dominant contents of the leaves extract of G. candida Gapnep were pinostrobin chalcone 75.63%.

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“…350 The structure of curcumenol has been confirmed by X-ray analysis. 351 This compound and furanodienone are the major active antiinflammatory constituents of Curcuma phaeocaulis. 352 Rotundone has been identified as the main responsible agent for the pepper aroma in grapes, wine, herbs and spices, including peppercorns.…”

Section: Eremophilane and Bakkanementioning

confidence: 99%