Oruwacin, a new iridoid ferulate from Morinda lucida

Adesogan, E. K.

doi:10.1016/s0031-9422(00)90940-3

Cited by 40 publications

(25 citation statements)

References 7 publications

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“…Our results leave no choice but to revise the absolute configurations not only of the iridoids above, but probably also of most of the related, more-condensed iridoids such as allamcin [15], allamandicin [11] [15] [18], plumieride coumarate [20], oruwacin [20] [37], and all of their respective glucosides. The question of absolute configuration could unambiguously be settled by X-ray structure analysis of one of the d-glucosides.…”

Section: 2mentioning

confidence: 99%

Revision of the Absolute Configuration of Plumericin and Isoplumericin fromPlumeria rubra

Elsässer

Krohn

Akhtar

et al. 2005

C&B

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The absolute configurations of plumericin (1) and isoplumericin (2), isolated from Plumeria rubra, were re-assigned based on a combination of X-ray crystal-structure determination and quantum-mechanical calculations of their circular dichroism (CD) spectra. The experimental CD spectra showed an excellent match with those calculated for the (1S,5R,8R,9R,10R) absolute configuration (corresponding to ent-1 and ent-2, resp.), opposite to that generally accepted and published in the literature. Since the (false) plumericin configuration has been often used to derive the absolute configuration of related iridoids by chemical correlation, their absolute configurations also have to be reconsidered.

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Section: 2mentioning

confidence: 99%

Revision of the Absolute Configuration of Plumericin and Isoplumericin fromPlumeria rubra

Elsässer

Krohn

Akhtar

et al. 2005

C&B

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“…However, this empirical rule should be carefully used in daily research. Stepehens pointed out that the very similar compounds oruwacin 63 [107] and plumericin 64 [103,104] have totally different absolute configuration [106]. Reassignments of some natural products using DFT methods have been reported.…”

Section: Or and Ord Computationsmentioning

confidence: 99%

Progression of Absolute Configuration Determination in Natural Product Chemistry Using Optical Rotation (Dispersion), Matrix Determinant and Electronic Circular Dichroism Methods

Sheng-Ding¹,

Shen²,

Luo³

et al. 2011

COC

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With the development of separation materials, more and more complex natural products with poly-stereogenic centers are obtained. However, due to small quantity of the isolated compounds, or no crystal formed, or complex 2D NMR correlation signals, absolute configuration identification for these compounds becomes difficult. Now, computational methods provide researchers many benefits in structural determinations for chiral natural products. Computational methods include (1) optical rotation (OR) and its dispersion (ORD) computations; (2) electronic circular dichroism (ECD or CD) calculations; (3) computations of determinant of matrix for stereogenic centers. In methods (1) to (2), the mostly used quantum theory contained density functional theory (DFT) with different basis sets, e.g. B3LYP/aug-cc-pVDZ//B3LYP/6-31G(d). Effects from solvents on OR value can be investigated using different corresponding software. In the cases, optimizations performed in the corresponding solution are helpful to obtain the correct predictions although it is not usual at present time. Matrix model as one of the mathematic methods is different from quantum methods, which is of easily being understood and effective in absolute configuration assignment for acyclic chiral compounds. In this review, necessary theory basis for the three methods are simply introduced for modern readers, the focus of which is the application of these methods in natural product chemistry by various examples reported in different journals from 1998 to the end of April of 2010 except for matrix method to the May of 2010 based on an experimental chemist's viewpoints.

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“…[11][12][13][14][15] The plant contains anthraquinones, [16][17][18] iridoids, [19] triterpenoids [20] and volatile oil. [21] Extracts from M. lucida have shown some biological activities, comprising antimalarial, [17,20,[22][23][24][25] trypanocidal, [23] purgative, [26] anti-inflammatory and analgesic [27] and antimicrobial [18,28,29] activities. Meanwhile, the leaf and root extracts exhibit anti-diabetic activities [30,31] .…”

Section: Blood Glucose Measurementsmentioning

confidence: 99%

Hypoglycaemic and Antioxidant Activities of the Stem Bark of Morinda Lucida Benth in Streptozotocin – Induced Diabetic Rats

Fleischer¹,

Sarkodie²,

Komlaga³

et al. 2011

Phcog Commn.

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Oruwacin, a new iridoid ferulate from Morinda lucida

Cited by 40 publications

References 7 publications

Revision of the Absolute Configuration of Plumericin and Isoplumericin fromPlumeria rubra

Revision of the Absolute Configuration of Plumericin and Isoplumericin fromPlumeria rubra

Progression of Absolute Configuration Determination in Natural Product Chemistry Using Optical Rotation (Dispersion), Matrix Determinant and Electronic Circular Dichroism Methods

Hypoglycaemic and Antioxidant Activities of the Stem Bark of Morinda Lucida Benth in Streptozotocin – Induced Diabetic Rats

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