A new 3,4-seco-oleanane-type triterpenoid with an unusual enedione moiety from Hypericum ascyron
Chunmei ChenGuangzheng WeiHucheng ZhuYi GuoXiao‐Nian LiJinwen ZhangYanfei LiuGuangmin YaoZengwei LuoYongbo XueYonghui Zhang
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Oleanane
Friedelin
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Hypericum
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The methanolic extract from the flowers buds of Camellia japonica L. (Theaceae) were found to exhibit potent inhibitory activities on ethanol- or indomethacin-induced gastric mucosal lesions in rats. Through bioassay-guided separation, 28-noroleanane-type triterpene oligoglycosides, camelliosides A, B, and C, and an oleanane-type triterpene oligoglycoside, camellioside D, were isolated from the methanolic extract together with five known compounds. The absolute stereostructures of camelliosides were determined on the basis of chemical and physicochemical evidence, which included the structure revision of the nortriterpene aglycons (camellenodiol and camelledionol). The principal oligoglycosides, camelliosides A and B, showed platelet aggregation activity in addition to the gastroprotective effects on ethanol- or indomethacin-induced gastric mucosal lesions in rats.
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Two new oleanane-type triterpene saponins, named glomeruloside I (1) and glomeruloside II (2), were isolated from the leaves of Glochidion glomerulatum (Miq.) Boerl. Their structures were determined by extensive spectroscopic methods, including 1D- and 2D-NMR, MS data, and chemical methods.
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Objective To study the nor-oleanane triterpenoids and search the lead compounds to determine its specific bioavailability.Methods According to the related literatures of nor-oleanane triterpenoids and the investigation of our team,the characters of nor-oleanane triterpenoids were illustrated.Results All kinds of the aglycones of the nor-oleanane triterpenoids were analyzed,and their distribution in nature,pharmacological activity,structural diversity and the rules of spectrosocopy were summarized.The biosynthesis pathway of the 28-nor-oleanane triterpene saponins with double bond at C20(29) was introduced.Conclusions This article evaluates the nor-oleanane triterpenoids comprehensively,and provides the reference for searching the lead compounds with bioavailability.
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Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E–H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.
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Chemical investigation of the leaves of Putranjiva roxburghii has resulted in the isolation of two new triterpenoids, putralone, a novel 10alpha-hydroxy-25-nor D:A friedo-olean-9(11)-en-3 one and 3beta-acetoxy-cycloart-24-en-23-one, along with a rare hopanoid, adian-5-en-3beta,29-diol. Other known triterpenoids isolated from this plant are 3beta-acetoxy-adian-5-ene, putrol, putrone, putranjivadione, roxburghonic acid, friedelin, friedlan-3alpha-ol, oleanolic acid and erythrodiol. Interestingly, putralone is the first example of a naturally occurring nor friedo-oleanane triterpenoid having a hydroxyl functionality at the C-10 position.
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Celastraceae
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Four new oleanane-type triterpene saponins, named buddlejasaponins I (1), II (2), III (3) and IV (4) were isolated from the aerial parts of Buddleja japonica HEMSL., together with a known saponin saikosaponin a (5). Their structures were elucidated on the basis of the chemical and spectroscopic studies.
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The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B (6) one common triterpene, friedelin (7), and the steroidal triterpene stigmasterol (8). The structures of these compounds were established based on spectral evidence (1D and 2D NMR).
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