Untersuchungen in der Saponinreihe. X. Mitteilung. Zur Kenntnis der Mono-oxy-triterpensäuren.

Winterstein, Alfred; Stein, Gertrud

doi:10.1515/bchm2.1932.208.1-3.9

Cited by 54 publications

(17 citation statements)

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“…Some of the major components of the resin were found to be the diterpenes incensole ( Figure 3) and isoincensole, their oxide or acetate derivatives ( Figure 3), and the triterpene boswellic acids, which are considered to be biomarkers of olibanum. [13] Due to their prevalence in the resin, the pentacyclic triterpenoid boswellic acids were reported as constituents of Boswellia resin relatively early (see Winterstein & Stein [16] ). In an attempt to identify the active components in the resin, boswellic acids were examined for their anti-inflammatory effects.…”

Section: The Active Constituents Of Boswellia Resinmentioning

confidence: 99%

<I>Boswellia</I> resin: from religious ceremonies to medical uses; a review of in-vitro, in-vivo and clinical trials

Moussaieff¹,

Mechoulam²

2009

j pharm pharmacol

102

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Section: The Active Constituents Of Boswellia Resinmentioning

confidence: 99%

<I>Boswellia</I> resin: from religious ceremonies to medical uses; a review of in-vitro, in-vivo and clinical trials

Moussaieff¹,

Mechoulam²

2009

j pharm pharmacol

102

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“…Acetyl-boswellic acids (Ac-BAs), as a mixture of acetylated derivatives of mainly /1-BA (c in Table 1) and 1 1-keto-,B-BA (b), were isolated from the resin of Boswellia carterii (olibanum) by extraction into ether, precipitation with barium hydroxide, acetylation to mixed anhydrides with acetic anhydride, cleavage of the mixed anhydrides and crystallization of the Ac-BAs from methanol British Journal of Pharmacology (1996) 117, 615-618 (Winterstein & Stein, 1932). BAs were obtained by the saponification of Ac-BAs.…”

Section: Chemicalsmentioning

confidence: 99%

Acetyl‐11‐keto‐β‐boswellic acid (AKBA): structure requirements for binding and 5‐lipoxygenase inhibitory activity

Sailer

Subramanian

Rall

et al. 1996

British J Pharmacology

160

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1 5-Lipoxygenase (5-LOX) products from endogenous arachidonic acid in ionophore-stimulated peritoneal polymorphonuclear leukocytes (PMNL) and from exogenous substrate (20 gM) in 105,000 g supernatants were measured. 2 The effects of natural pentacyclic triterpenes and their derivatives on 5-LOX activity were compared with the inhibitory action of acetyl-l -keto-p-boswellic acid (AKBA), which has been previously shown to inhibit the 5-LOX by a selective, enzyme-directed, non-redox and non-competitive mechanism. 3 The 5-LOX inhibitory potency of AKBA was only slightly diminished by deacetylation of the acetoxy group or reduction of the carboxyl function to alcohol in intact cells (ICs = 1.5 vs. 3 and 4.5 pM, respectively) and in the cell-free system (8 vs. 20 and 45 gM).5 fl-Boswellic acid (f-BA), lacking the 1 1-keto function, inhibited 5-LOX only partially and incompletely, whereas the corresponding alcohol from fl-BA, as well as amyrin, acetyl-ll-keto-amyrin, 1 l-keto-f-boswellic acid methyl ester had no 5-LOX inhibitory activity up to 50 pM in either system. 5 fl-BA only partially prevented the AKBA-induced 5-LOX inhibition, whereas the non-inhibitory compounds, amyrin and acetyl-1 l-keto-amyrin, almost totally antagonized the AKBA effect and shifted the concentration-inhibition curve for the incomplete inhibitor fl-BA to the right. In contrast, the noninhibitory 1 1-keto-fl-BA methyl ester exerted no antagonizing effect.6 The results demonstrate that the pentacyclic triterpene ring system is crucial for binding to the highly selective effector site, whereas functional groups (especially the 11 -keto function in addition to a hydrophilic group on C4 of ring A) are essential for 5-LOX inhibitory activity.

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“…Compared to other triterpenoic acids, such as betulinic, ursolic, oleanolic, glycyrrhetinic or maslinic acid, b-boswellic acids received less attention probably due their limited availability and high costs of the resin. Several years ago, J. Jauch et al [20,21] improved older extraction and purification techniques [22,23] significantly; this allowed a more convenient isolation of 3-acetyl-11-keto-b-boswellic acid (AKBA, 2), together with 11-keto-b-boswellic acid (KBA, 3) and 3-acetyl-b-boswellic acid (ABA, 4).…”

Section: Introductionmentioning

confidence: 99%

11-Keto-boswellic acid derived amides and monodesmosidic saponins induce apoptosis in breast and cervical cancers cells

Csuk

Barthel-Niesen

Barthel

et al. 2015

European Journal of Medicinal Chemistry

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Untersuchungen in der Saponinreihe. X. Mitteilung. Zur Kenntnis der Mono-oxy-triterpensäuren.

Cited by 54 publications

References 0 publications

<I>Boswellia</I> resin: from religious ceremonies to medical uses; a review of in-vitro, in-vivo and clinical trials

<I>Boswellia</I> resin: from religious ceremonies to medical uses; a review of in-vitro, in-vivo and clinical trials

Acetyl‐11‐keto‐β‐boswellic acid (AKBA): structure requirements for binding and 5‐lipoxygenase inhibitory activity

11-Keto-boswellic acid derived amides and monodesmosidic saponins induce apoptosis in breast and cervical cancers cells

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