Hepatoprotective Prenylaromadendrane-Type Diterpenes from the Gum Resin of <i>Boswellia carterii</i>

Wang, Yan-Gai; Ren, Jin; Wang, Aiguo; Yang, Jun; Ji, Tengfei; Ma, Qinge; Tian, Jin; Su, Ya‐Lun

doi:10.1021/np400526b

Cited by 41 publications

(30 citation statements)

References 22 publications

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“…For example, in Ethiopia, Fig. 28 Nine new boscarterols from Boswellia carteri (Wang et al 2013 ) Apharsemon, Myrrh and Olibanum: Ancient Medical Plants where some export of spices occurs, rehabilitation of these ancient spice crops could provide a new source of income for the local population. Currently, replanting projects in the wild are under way in Ethiopia and Somalia.…”

Section: Discussionmentioning

confidence: 99%

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RETRACTED CHAPTER: Apharsemon, Myrrh and Olibanum: Ancient Medical Plants

Ben-Yehoshua

Hanŭs

2014

Medicinal and Aromatic Plants of the World

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Among the most reputed ancient medical plants were the: olibanumfrankincense, derived from Boswellia spp., myrrh, derived from Commiphoras spp., both from southern Arabia and the Horn of Africa, and apharsemon of Judea, derived from Commiphora gileadensis that had its origin also in these territories. The demand for these medical plants that were also important spices was met by scarce and limited sources of supply. The incense trade and trade routes were developed to carry this precious cargo over long distances through many countries to the important foreign markets of Egypt, Mesopotamia, Persia, Greece, and Rome. The export of the frankincense and myrrh made Arabia extremely wealthy, so much so that Theophrastus, Strabo, and Pliny all referred to it as Felix (fortunate) Arabia . At present, this export hardly exists, and the spice trade has declined to around 1,500 t, coming mainly from Somalia; both Yemen and Saudi Arabia import rather than export these frankincense and myrrh.Apharsemon, known also as the Judaean balsam, grew only around the Dead Sea Basin in antiquity and achieved fame by its highly reputed aroma and medical properties but has been extinct in this area for many centuries. The resin of this crop was sold, by weight, at a price twice that of gold, the highest price ever paid for an agricultural commodity. This crop was an important source of income for the many rulers of ancient Judea; the farmers' guild that produced the apharsemon survived over 1,000 years. Currently there is interest in a revival based on related plants of similar origin. These three ancient plants now are under investigation in many countries for medicinal uses. Many publications and patents on these three plants appeared in recent years.

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Section: Discussionmentioning

confidence: 99%

“…All compounds (except compounds D and G) exhibited moderate hepatoprotective activity against D-galactosamine-induced toxicity in HL-7702 cells (Wang et al 2013 ) (Fig. 28 ).…”

Section: Boswellia Carteriimentioning

confidence: 96%

RETRACTED CHAPTER: Apharsemon, Myrrh and Olibanum: Ancient Medical Plants

Ben-Yehoshua

Hanŭs

2014

Medicinal and Aromatic Plants of the World

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“…The cneorubenoid diterpenoids, boscartols A–I and olibanumol D, can be considered to be prenylated aromadendranes ( Figure 2 ), and have been isolated from the oleo-gum resin of Boswellia carteri [ 21 ]. The absolute configuration of the C(15) of boscartol D was not experimentally determined [ 21 ]. Nevertheless, both diastereomers, (15 R )-boscartol D and (15 S )-boscartol D were used in the reverse docking.…”

Section: Resultsmentioning

confidence: 99%

“…Boswellia carteri oleo-gum resin is the source of several prenylated aromadendrane (cneorubenoid) diterpenoids ( Figure 2 ) [ 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Protein Targets of Frankincense: A Reverse Docking Analysis of Terpenoids from Boswellia Oleo-Gum Resins

Byler

Setzer

2018

Medicines

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Background: Frankincense, the oleo-gum resin of Boswellia trees, has been used in traditional medicine since ancient times. Frankincense has been used to treat wounds and skin infections, inflammatory diseases, dementia, and various other conditions. However, in many cases, the biomolecular targets for frankincense components are not well established. Methods: In this work, we have carried out a reverse docking study of Boswellia diterpenoids and triterpenoids with a library of 16034 potential druggable target proteins. Results: Boswellia diterpenoids showed selective docking to acetylcholinesterase, several bacterial target proteins, and HIV-1 reverse transcriptase. Boswellia triterpenoids targeted the cancer-relevant proteins (poly(ADP-ribose) polymerase-1, tankyrase, and folate receptor β), inflammation-relevant proteins (phospholipase A2, epoxide hydrolase, and fibroblast collagenase), and the diabetes target 11β-hydroxysteroid dehydrogenase. Conclusions: The preferential docking of Boswellia terpenoids is consistent with the traditional uses and the established biological activities of frankincense.

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“…The chemical structures of the isolated terpenoids were identified by ESI-MS, and detailed spectroscopic analyses, as well as comparison with the literatures. As a result, two new tirucallane-type triterpene acids (2 and 3) were isolated, together with one known prenylaromadendrane-type diterpene (Boscartol A, 1) [1] and two known β-boswellic acids, 11-keto-β-boswellic acid (4) [15] and acetyl-11-ketoboswellic acid (5) [15]. The three known compounds were identified by comparison of their spectroscopic data with the reported values, including ESI-MS, 1 H-NMR, and 13 C-NMR data.…”

Section: Structure Identification Of the Isolated Compoundsmentioning

confidence: 99%

Extraction and purification of five terpenoids from olibanum by ultrahigh pressure technique and high‐speed countercurrent chromatography

Zhao

Song

et al. 2017

J of Separation Science

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Five terpenoids, including two new ones, 3,7-dioxo-tirucalla-8,24-dien-21-oic acid (2) and 3α-acetoxyl-7-oxo-tirucalla-8,24-dien-21-oic acid (3), and three known ones, boscartol A (1), 11-keto-β-boswellic acid (4), and acetyl-11-keto-boswellic acid (5), have been extracted by the ultrapressure extraction and purified by pH-zone-refining countercurrent chromatography and high-speed countercurrent chromatography from olibanum. For ultrapressure extraction, the optimal condition including 200 MPa of extraction pressure, ethyl acetate of extraction solvent, 1:20 (g/mL) of solid/liquid ratio, and 2 min of extraction time were obtained. For the separation, from 1.5 g of the terpenoid extract, 220.1 mg of 4, 255.5 mg of 5, and 212.3 mg of the mixture of 1, 2, and 3 were obtained by pH-zone-refining countercurrent chromatography under the solvent system of chloroform/ethyl acetate/methanol/water (3:1:3:2, v/v/v/v) with aqueous ammonia and trifluoroacetic acid as retention and eluter agents. The enriched mixture (210 mg) was further separated by conventional high-speed countercurrent chromatography with petroleum ether/ethyl acetate/methanol/water (1:0.8:1.1:0.6, v/v/v/v), yielding 30.1 mg of 1, 35.5 mg of 2, 12.3 mg of 3. The structures of these five terpenoids were elucidated by extensive spectroscopic methods.

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Hepatoprotective Prenylaromadendrane-Type Diterpenes from the Gum Resin of Boswellia carterii

Cited by 41 publications

References 22 publications

RETRACTED CHAPTER: Apharsemon, Myrrh and Olibanum: Ancient Medical Plants

RETRACTED CHAPTER: Apharsemon, Myrrh and Olibanum: Ancient Medical Plants

Protein Targets of Frankincense: A Reverse Docking Analysis of Terpenoids from Boswellia Oleo-Gum Resins

Extraction and purification of five terpenoids from olibanum by ultrahigh pressure technique and high‐speed countercurrent chromatography

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