Two new protostane-type triterpenoids from <i>Alisma orientalis</i>

Xin, Xiu‐Lan; Zhao, Xinyu; Huo, Xiaokui; Tian, Xiangge; Sun, Cheng‐Peng; Zhang, Hou-Li; Tian, Ye; Liu, Yong; Wang, Xun

doi:10.1080/14786419.2017.1344660

Cited by 21 publications

(16 citation statements)

References 21 publications

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“…Protostane triterpenes are natural plant products with distinct pharmacological activities, but their natural distribution is limited to a few plant families 33,34 . Squalene epoxidase (SE) is the rate-limiting enzyme in the triterpene biosynthesis pathway.…”

Section: Discussionmentioning

confidence: 99%

Methyl jasmonate promote protostane triterpenes accumulation by up-regulating the expression of squalene epoxidases in Alisma orientale

Tian

et al. 2019

Sci Rep

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Protostane triterpenes, which are found in Alisma orientale, are tetracyclic triterpenes with distinctive pharmacological activities. The natural distribution of protostane triterpenes is limited mainly to members of the botanical family Alismataceae. Squalene epoxidase (SE) is the key rate-limiting enzyme in triterpene biosynthesis. In this study, we report the characterization of two SEs from A. orientale. AoSE1 and AoSE2 were expressed as fusion proteins in E. coli, and the purified proteins were used in functional research. In vitro enzyme assays showed that AoSE1 and AoSE2 catalyze the formation of oxidosqualene from squalene. Immunoassays revealed that the tubers contain the highest levels of AoSE1 and AoSE2. After MeJA induction, which is the main elicitor of triterpene biosynthesis, the contents of 2,3-oxidosqualene and alisol B 23-acetate increased by 1.96- and 2.53-fold, respectively. In addition, the expression of both AoSE proteins was significantly increased at four days after MeJA treatment. The contents of 2,3-oxidosqualene and alisol B 23-acetate were also positively correlated with AoSEs expression at different times after MeJA treatment. These results suggest that AoSE1 and AoSE2 are the key regulatory points in protostane triterpenes biosynthesis, and that MeJA regulates the biosynthesis of these compounds by increasing the expression of AoSE1 and AoSE2.

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Section: Discussionmentioning

confidence: 99%

Methyl jasmonate promote protostane triterpenes accumulation by up-regulating the expression of squalene epoxidases in Alisma orientale

Tian

et al. 2019

Sci Rep

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“…In 2016 and 2017, Ma et al identified a library of new alisol derivatives, namely, alismanols M ( 24 ) and O‐Q ( 25–27 ), 16‐oxo‐11‐anhydroalisol A 24‐acetate ( 28 ), 13 β ,17 β ‐epoxy‐24,25,26,27‐tetranor‐alisol A 23‐oic acid ( 29 ), 16 β ‐acetoxy alisol B ( 30 ), and 16 α ‐acetoxy alisol B ( 31 ) from A. orientale (Cang et al, 2017; Huang et al, 2017; Ma et al, 2016). Furthermore, Xin et al isolated two new protostanes, 17‐ epi alisolide ( 32 ) and 24‐ epi alismanol D ( 33 ), from A. orientale (Xin et al, 2018). Li et al also investigated A. orientale and identified 12 new triterpenes, including alisol R ( 34 ), 25‐methoxyalisol F ( 35 ), 16 β ‐hydroperoxyalisol B 23‐acetate ( 36 ), alisol S 23‐acetate ( 37 ), 16 β ‐hydroperoxyalisol B ( 38 ), 16 β ‐methoxyalisol B ( 39 ), 16 β ‐methoxyalisol E ( 40 ), 16 β ,25‐ dimethoxyalisol E ( 41 ), 16 β ‐hydroperoxyalisol E ( 42 ), alisol T ( 43 ), and two natural triterpenoids alisols U ( 43 ) and V ( 44 ).…”

Section: Phytochemical Constituents Of the Genus Alismamentioning

confidence: 99%

“…5 β ,29‐Dihydroxy alisol A ( 59 ), obtained from A. orientale , inhibited CES 2 with an IC 50 value of 29.2 μM, and the underlying mechanism between 59 and CES 2 was studied by molecular docking, all of which revealing the presence of hydrogen bond interactions with Glu77, Ser80, IIe446, and Lys447 and a lowest binding free energy of −3.94 kcal/mol (Wang et al, 2019). Xin et al (2018) isolated two protostanes 17‐ epi alisolide A and 24‐ epi alismanol D ( 33 ) and found that 24‐ epi alismanol D ( 33 ) had an inhibitory effect against CES 2 with an IC 50 value of 23.1 μM. Twenty‐two protostanes were obtained from A. orientale by Mai et al, and the inhibitory effect of all the compounds on CES 2 was experimentally evaluated.…”

Section: Biological and Pharmacological Activitiesmentioning

confidence: 99%

Alisma genus: Phytochemical constituents, biosynthesis, and biological activities

Feng

Liu

Huo

et al. 2020

Phytotherapy Research

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The genus Alisma contains 11 species distributed worldwide, of which at least two species (A. orientale [Sam.] Juzep. and A. plantago‐aquatica Linn.) have been used as common herbal medicines. Secondary metabolites obtained from the genus Alisma are considered to be the material basis for the various biological functions and medicinal applications. In this review, we mainly focused on the recent investigations of secondary metabolites from plants of the genus Alisma and their biological activities, with the highlighting on the diversity of the chemical structures, the biosynthesis of interesting secondary metabolites, the biological activities, and the relationships between structures and bioactivities.

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“…Among C-2 may be submitted by carbanyl group (109) (Mai et al, 2015). The configuration of C-17 is determined (107, 108) (Xin et al, 2018).…”

Section: Nor-and Seco-protostanesmentioning

confidence: 99%

Triterpenoids From Alisma Species: Phytochemistry, Structure Modification, and Bioactivities

et al. 2020

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Plants from Alisma species belong to the genus of Alisma Linn. in Alismataceae family. The tubers of A. orientale (Sam.) Juzep, also known as Ze Xie in Chinese and Takusha in Japanese, have been used in traditional medicine for a long history. Triterpenoids are the main secondary metabolites isolated from Alisma species, and reported with various bioactive properties, including anticancer, lipid-regulating, anti-inflammatory, antibacterial, antiviral and diuretic activities. In this brief review, we aimed to summarize the phytochemical and pharmacological characteristics of triterpenoids found in Alisma, and discuss their structure modification to enhance cytotoxicity as well.

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Two new protostane-type triterpenoids from Alisma orientalis

Cited by 21 publications

References 21 publications

Methyl jasmonate promote protostane triterpenes accumulation by up-regulating the expression of squalene epoxidases in Alisma orientale

Methyl jasmonate promote protostane triterpenes accumulation by up-regulating the expression of squalene epoxidases in Alisma orientale

Alisma genus: Phytochemical constituents, biosynthesis, and biological activities

Triterpenoids From Alisma Species: Phytochemistry, Structure Modification, and Bioactivities

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