Synthetic access toward the diverse ginsenosides

“…Shown in Figure 2 are representative TCM-relevant triterpene glycosides we have synthesized; their occurrence and bioactivities are listed in Table 2. A collective synthesis of ginsenosides (35)(36)(37)(38) and a convergent synthesis of asiaticoside (46) are chosen to illustrate the synthetic approaches.…”

Section: Synthesis Of Triterpene Glycosides Occurring In Tcmmentioning

confidence: 99%

Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Zhu

2018

Chin. J. Chem.

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Traditional Chinese medicine (TCM) is a huge treasure trove for the discovery and development of modern pharmaceuticals. Indeed, numerous biologically and pharmacologically significant molecules have been identified from TCM; among them, a considerable portion belongs to glycosides. These glycosides are extremely diverse in structures, consisting of a large variety of aglycones, glycans, as well as glycosidic linkages. In addition, these glycosides occur frequently as a complicated mixture of congeners in the nature sources. This micro‐heterogeneity leads to the isolation of a homogeneous glycoside in an appreciable amount a formidable task. Therefore, development of synthetic approaches toward these nature glycosides has received great attention. In this account, we summarize our twenty‐year efforts spent on this topic. Fifty five representative TCM‐relevant glycosides synthesized by our group are highlighted. Based on the aglycone structure, these glycosides are categorized into three groups, i.e., steroid glycosides, triterpene glycosides, and flavonoid and phenolic glycosides. Typical synthetic approaches are discussed, showing the demanding tactics for regio‐ and stereo‐controlled installation of glycans and overall manipulation of protecting groups. These expedient and scalable synthetic approaches have provided practical alternatives to the accessibility of these TCM components and thus opportunities for their in depth biological and pharmacological studies.

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“…Before attempting to install the trisaccharide unit onto the hindered 2'-OH group in 26, [21] we tested the reaction with amonosaccharide donor;thus,the condensation of 26 with 2,3,4-tri-O-benzoyl-d-quinovosyl ortho-hexynylbenzoate (3 equiv) was complete within 30 min under the catalysis of [PPh 3 Au]OTf (0.1 equiv with respect to the donor) in the presence of 5 MS in CH 2 Cl 2 at room temperature,a nd the desired disaccharide was obtained in high yield (89 %; see the Supporting Information). Glycosylation of 3hydroxyholostane 2 with the protected xylosyl o-hexynylbenzoate 3 proceeded smoothly in the presence of [PPh 3 Au]NTf 2 (0.1 equiv with respect to the donor) in CH 2 Cl 2 at room temperature;s ubsequent removal of the 2-O-Azmb group with Me 3 Pi nT HF/H 2 Of acilitated the purification of the product to provide the b-xyloside 26 in good yield (73 %; J 1',2' = 5.2 Hz).…”

mentioning

confidence: 99%

Total Synthesis of Echinoside A, a Representative Triterpene Glycoside of Sea Cucumbers

Chen

Shao

et al. 2017

Angew Chem Int Ed

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Echinoside A, a sulfonylated holostane tetrasaccharide with potent anticancer and antifungal activity, was synthesized in a longest linear sequence of 35 steps and 0.6 % overall yield. The synthetic approach is adaptable to the synthesis of congeners and analogues, as exemplified by the ready synthesis of ds-echinoside A and echinoside B, and thus will facilitate in-depth studies on the promising biological effects of echinoside A. Moreover, the present synthesis demonstrates the feasibility of synthetic access to the characteristic complex triterpene glycosides that occur ubiquitously in sea cucumbers.

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Synthetic access toward the diverse ginsenosides

Cited by 60 publications

References 63 publications

Chapter 8. Recent advances in gold-catalyzed glycosylation

Chapter 8. Recent advances in gold-catalyzed glycosylation

Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Total Synthesis of Echinoside A, a Representative Triterpene Glycoside of Sea Cucumbers

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