A new abietane diterpene from Glyptostrobus pensilis

Zhang, Yumei; Yin, Runsheng; Jia, Rui-Rui; Yang, En-Hu; Xu, Hong‐Xi; Tan, Ning‐Hua

doi:10.1016/j.fitote.2010.08.001

Cited by 10 publications

(10 citation statements)

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“…The contents of terpenoid natural products have been documented in many species of the Cupressaceae [17,44,45,46], but the investigation of the former family Taxodiaceae is incomplete. The terpenoid content of Glyptostrobus pensilis (Staunton) Koch (Chinese Water Pine) is limited [17], with only two trace diterpenoids, namely glypensin A and 12-acetoxy- ent -labda-8(17),13E-dien-15-oic acid, identified [37]. According to the merger of Cupressaceae and Taxodiaceae to the Cupressaceae s.l., G. pensilis was placed in the subfamily Taxodioideae [47].…”

Section: Resultsmentioning

confidence: 99%

“…Structure determinations and pharmacological potential studies of resin terpenoids isolated and purified from species of the Taxodioideae subfamily have been reported by numerous chemists and pharmacologists [24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42]. However, the connection of the known natural products isolated from these conifers with their application as tracers in other interdisciplinary sciences has been limited [7,8,14,43].…”

Section: Introductionmentioning

confidence: 99%

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Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS

2019

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The resins bled from stems and in seed cones and leaves of Cryptomeria japonica, Glyptostrobus pensilis, Taxodium distichum, and T. mucronatum were characterized to provide an overview of their major natural product compositions. The total solvent extract solutions were analyzed as the free and derivatized products by gas chromatography-mass spectrometry to identify the compounds, which comprised minor mono- and sesquiterpenoids, and dominant di- and triterpenoids, plus aliphatic lipids (e.g., n-nonacosan-10-ol). Ferruginol, 7α-p-cymenylferruginol, and chamaecydin were the major characteristic markers for the Taxodioideae conifer subfamily. The mass spectrometric data can aid polar compound elucidation in environmental, geological, archeological, forensic and pharmaceutical studies.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS

2019

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“…It is not only an important part of the phylogenetic research of Taxodiaceae plants but also a popular ornamental plant and a common tree species for windbreak and embankment reinforcement; it is also a good raw material for shipbuilding and bridge construction [31][32][33][34][35]. The secondary metabolites of G. pensilis bark can also inhibit the activity of human protein tyrosine phosphatase [36].…”

Section: Introductionmentioning

confidence: 99%

Prediction of Suitable Distribution of a Critically Endangered Plant Glyptostrobus pensilis

Zhang

Yang

et al. 2022

Forests

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Glyptostrobus pensilis is a critically endangered living fossil plant species of the Mesozoic era, with high scientific research and economic value. The aim of this study was to assess the impact of climate change on the potential habitat area of G. pensilis in East Asia. The MaxEnt (maximum entropy) model optimized by the ENMeval data package was used to simulate the potential distribution habitats of G. pensilis since the last interglacial period (LIG, 120–140 ka). The results showed that the optimized MaxEnt model has a high prediction accuracy with the area under the receiver operating characteristic curve (AUC) of 0.9843 ± 0.005. The current highly suitable habitats were found in the northeast of Jiangxi, the east of Fujian; the main climatic factors affecting the geographic distribution of G. pensilis are temperature and precipitation, with precipitation as the dominant factor. The minimum temperature of coldest month (Bio6) may be the key factor restricting the northward distribution of G. pensilis; during the LIG, it contracted greatly in the highly suitable habitat area. In the 2070s, the suitable distribution area will move northward and the area of highly suitable habitat will increase. Seasonal changes in temperature and precipitation may be important climatic factors causing the changes in geographic distribution. The results will provide a theoretical basis for the management and resource protection of G. pensilis.

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“…It consists of an ormald ecalin-type system, and au nique 1,4-quinoid moiety with as tereocenter (C-8), which is difficult to construct. This tricyclics keleton of bisnorditerpene (1)i safundamental skeleton of many diterpenoids, such as glypensin A, [2] piliferol, [3] and piliferalactone. [3] Due to the unique structure and potential biological activities, we designed as trategy to synthesize this bisnorditerpene.…”

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confidence: 99%

Concise Total Synthesis of the Bisnorditerpene (+)‐(5β,8α,10α)‐8‐hydroxy‐13‐methylpodocarpa‐9(11),13‐diene‐3,12‐dione

Zhang

et al. 2016

Asian J Org Chem

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The first enantioselective total synthesis of the bisnorditerpene( + +)-(5b,8a,10a)-8-hydroxy-13-methylpodocarpa-9(11),13-diene-3,12-dione (1)w as accomplished in 7s teps with 18.5 %o verall yield from known aldehyde and chiral epoxide. Key steps of the synthesis include ac ationic domino cyclization used to construct the [6,6,6] fused framework, and an oxidative dearomatization reaction used to form the 1,4-quinoid moiety.The bisnorditerpene rel-(5b,8a,10a)-8-hydroxy-13-methylpodocarpa-9(11),13-diene-3,12-dione (1) ( Figure 1) was isolated from Croton regelianus var.m atosii in 2010 by Pessoa et al. [1] This plant is used as traditionalm edicine in "Caatinga", Northeast region of Brazil, popularly known as "velame de cheiro". Bisnorditerpene (1)h as a[ 6,6,6] fused framework, three stereocenters, one of which is aq uaternary carbon. It consists of an ormald ecalin-type system, and au nique 1,4-quinoid moiety with as tereocenter (C-8), which is difficult to construct. This tricyclics keleton of bisnorditerpene (1)i safundamental skeleton of many diterpenoids, such as glypensin A, [2] piliferol, [3] and piliferalactone. [3] Due to the unique structure and potential biological activities, we designed as trategy to synthesize this bisnorditerpene. Ac ationic dominoc yclization [4] was employed to construct the fundamentalt ricyclic framework. The retrosynthetic analysis is outlined in Scheme 1. Bisnorditerpene (+ +)-1 couldb eo btained from intermediate 2 through an oxidatived earomatization reaction. The configuration of stereocenter( C-8) was also formed in this step. The phenol 2 couldb ed erived from 3 via several functional group transformations, including desulfurization, oxidation andd emethylation. It should be noted that the tricyclic skeleton 3 could be constructed from 4 by cationic domino cyclization in one step. To synthesizet he cyclization precursor 4 from 5 and 6,aCorey-Seebachu mpolungr eaction could be used.Our synthesis of bisnorditerpene(+ +)-1 commencedf rom the knownaldehyde 7. [5] Aldehyde 7 was treated with 1,3-propanedithiol, giving dithiane 5 [6] in 96 %y ield (Scheme 2). Lithiation of dithiane 5 under standard reactionc onditions followed by aC orey-Seebachu mpolung reaction [7] with epoxide 6,w hich was produced from geraniol derivative, according to the procedure outlined by Weimer and co-workers, [8] resulted in precursor 4 with ac hiral epxoide in good yield. The key precursor was prepared by two steps in this convergent way.Geraniol derivative 8 was treated with aS hi asymmetric epoxidation catalyst( the sugar-derived catalyst 9 [9] ), affording ep-Figure 1. Structure of bisnorditerpene (1), glypensin A, piliferol, and piliferalactone.Scheme1.Retrosynthetic analysis of (+ +)-(1).[a] S.

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A new abietane diterpene from Glyptostrobus pensilis

Cited by 10 publications

References 4 publications

Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS

Terpenoids of the Swamp Cypress Subfamily (Taxodioideae), Cupressaceae, an Overview by GC-MS

Prediction of Suitable Distribution of a Critically Endangered Plant Glyptostrobus pensilis

Concise Total Synthesis of the Bisnorditerpene (+)‐(5β,8α,10α)‐8‐hydroxy‐13‐methylpodocarpa‐9(11),13‐diene‐3,12‐dione

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