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New Jujubogenin Glycosides from Colubrina asiatica
Abstract
Three new jujubogenin glycosides, namely, 3' '-O-acetylcolubrin (1); 3' ',2' "-O-diacetylcolubrin (2), and 3' '-O-acetyl-6' '-O-trans-crotonylcolubrin (3), were isolated from the leaves of Colubrina asiatica, in addition to the known colubrin, rutin, and kaempferol 3-O-rutinoside. Compounds 1-3 were isolated and purified via a combination of chromatographic procedures, and determined structurally using spectroscopic methods.
... 3-Hydorpxymethyl-A-nor cholestane (117) was found in extracts of Cretaceous black shales of Upper Barremian age (115 Myr BP) and is believed to be a component of sea sponges [84]. ...
... A jujubogenin glycoside, namely 3-O-acetylcolubrin (174), was isolated from the leaves of Colubrina asiatica [117]. Ether extracts from the heartwood of Colubrina granulosa yielded the polyphenolic coumaranone maesopsin 3,7-O,O-dibenzoyl ceanothic acid methylester (175) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (176) [118]. ...
The main focus of this review is to introduce readers to the fascinating class of lipid molecules known as norsteroids, exploring their distribution across various biotopes and their biological activities. The review provides an in-depth analysis of various modified steroids, including A, B, C, and D-norsteroids, each characterized by distinct structural alterations. These modifications, which range from the removal of specific methyl groups to changes in the steroid core, result in unique molecular architectures that significantly impact their biological activity and therapeutic potential. The discussion on A, B, C, and D-norsteroids sheds light on their unique configurations and how these structural modifications influence their pharmacological properties. The review also presents examples from natural sources that produce a diverse array of steroids with distinct structures, including the aforementioned A, B, C, and D-nor variants. These compounds are sourced from marine organisms like sponges, soft corals, and starfish, as well as terrestrial entities such as plants, fungi, and bacteria. The exploration of these steroids encompasses their biosynthesis, ecological significance, and potential medical applications, highlighting a crucial area of interest in pharmacology and natural product chemistry. The review emphasizes the importance of researching these steroids for drug development, particularly in addressing diseases where conventional medications are inadequate or for conditions lacking sufficient therapeutic options. Examples of norsteroid synthesis are provided to illustrate the practical applications of this research.
... 3-Hydorpxymethyl-A-nor cholestane (117) was found in extracts of Cretaceous black shales of Upper Barremian age (115 Myr BP), which is believed to be a component of sea sponges [84]. ...
... The C-28 methyl ester of ceanothic acid (173) was detected in the bark of Zizyphus joazeiro [115] and in the seeds of Zizyphus jujube [116]. 19 A jujubogenin glycoside, namely 3"-O-acetylcolubrin (174), was isolated from the leaves of Colubrina asiatica [117]. Ether extracts from the heartwood of Colubrina granulosa yielded the polyphenolic coumaranone maesopsin 3,7-O,O-dibenzoyl ceanothic acid methylester (175), and 3-Oacetyl-7-O-benzoyl ceanothic acid methylester (176) [118]. ...
The main focus of this review is to introduce readers to the fascinating class of lipid molecules known as norsteroids, exploring their distribution across various biotopes and their biological activities. The review provides an in-depth analysis of various modified steroids, including A, B, C, and D-norsteroids, each characterized by distinct structural alterations. These modifications, which range from the removal of specific methyl groups to changes in the steroid core, result in unique molecular architectures that significantly impact their biological activity and therapeutic potential. The discussion on A, B, C, and D-norsteroids sheds light on their unique configurations and how these structural modifications influence their pharmacological properties. The review also presents examples from natural sources that produce a diverse array of steroids with distinct structures, including the aforementioned A, B, C, and D-nor variants. These compounds, sourced from marine organisms like sponges, soft corals and starfish, as well as terrestrial entities such as plants, fungi, and bacteria. The exploration of these steroids encompasses their biosynthesis, ecological significance, and potential medical applications, highlighting a crucial area of interest in pharmacology and natural product chemistry. The review emphasizes the importance of researching these steroids for drug development, particularly in addressing diseases where conventional medications are inadequate or for conditions lacking sufficient therapeutic options. Examples of norsteroid synthesis are provided to illustrate the practical applications of this research.
... A decoction of leaves and bark is traditionally used as a treatment for skin diseases, fruits as a fish poison and soap substitute, and the roots as a cure for inner fever and thirst (Mc Cormick 2007). Previous phytochemical studies of Colubrina species, including our recent investigation of the branches of C. asiatica (Sangsopha et al. 2018) demonstrated the presence of jujubogenin glycosides (Wagner et al. 1983;Seaforth et al. 1992;Oulad-Ali et al. 1994;ElSohly et al. 1999;Li et al. 1999;Lee et al. 2000), ceanothane triterpenes (Roitman and Jurd 1978), lupane triterpenes (Roitman and Jurd 1978;Baxter and Walkinshaw 1988) flavonoid glycosides (Guinaudeau et al. 1971;Guinaudeau et al. 1976;Guinaudeau et al. 1981), as well as the bisbenzylisoquinoline alkaloid O-methyldauricine (Tschesche et al. 1970). Further investigation of the EtOAc and MeOH extracts of the air-dried roots of C. asiatica gave two new triterpenoids, 3,7-O,O-dibenzoyl ceanothic acid methylester (1) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (2), together with nine known compounds, ceanothic acid (3) (Roitman and Jurd 1978), 24-hydroxyceanothic acid (4) (Lee et al. 1992), zizyberenalic acid (5) (Kundu et al. 1989), alphitolic acid (6) (Baxter and Walkinshaw 1988), betulinic acid (7) (Sharma et al. 2010), b-sitosterol-3-O-glucoside (8) (Faizi et al. 2001), squalene (9) (Huang et al. 2009), 3 00 ,2 000 -O-acetylcolubrin (10) and 3 00 -O-acetylcolubrin (11) (Lee et al. 2000) (Figure 1). ...
... Previous phytochemical studies of Colubrina species, including our recent investigation of the branches of C. asiatica (Sangsopha et al. 2018) demonstrated the presence of jujubogenin glycosides (Wagner et al. 1983;Seaforth et al. 1992;Oulad-Ali et al. 1994;ElSohly et al. 1999;Li et al. 1999;Lee et al. 2000), ceanothane triterpenes (Roitman and Jurd 1978), lupane triterpenes (Roitman and Jurd 1978;Baxter and Walkinshaw 1988) flavonoid glycosides (Guinaudeau et al. 1971;Guinaudeau et al. 1976;Guinaudeau et al. 1981), as well as the bisbenzylisoquinoline alkaloid O-methyldauricine (Tschesche et al. 1970). Further investigation of the EtOAc and MeOH extracts of the air-dried roots of C. asiatica gave two new triterpenoids, 3,7-O,O-dibenzoyl ceanothic acid methylester (1) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (2), together with nine known compounds, ceanothic acid (3) (Roitman and Jurd 1978), 24-hydroxyceanothic acid (4) (Lee et al. 1992), zizyberenalic acid (5) (Kundu et al. 1989), alphitolic acid (6) (Baxter and Walkinshaw 1988), betulinic acid (7) (Sharma et al. 2010), b-sitosterol-3-O-glucoside (8) (Faizi et al. 2001), squalene (9) (Huang et al. 2009), 3 00 ,2 000 -O-acetylcolubrin (10) and 3 00 -O-acetylcolubrin (11) (Lee et al. 2000) (Figure 1). Apart from 1 and 2, compounds 8 and 9 were also reported for the first time in the genus Colubrina. ...
Two new ceanothane triterpenes, 3,7-O,O-dibenzoyl ceanothic acid methylester (1) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (2), along with nine known compounds (3-11), were isolated from the roots of Colubrina asiatica. The isolated compounds were identified by spectroscopic evidence. Compounds 1 and 2 showed antimalarial activity against Plasmodium falciparum with IC50 values of 4.67 and 3.07 µg/mL, respectively. Compound 2 also showed antimycobacterial activity against Mycobacterium tuberculosis (MIC 6.25 µg/mL). In addition, compounds 1, 2, 10 and 11 showed cytotoxicity against three cancer cell lines (KB, NCI-H187 and MCF-7) with IC50 values ranging from 8.32 to 46.72 µg/mL.
... The leaves and bark are used traditionally as a decoction for the treatment of skin diseases and the roots as a cure for fever and thirst (Phonsena 2007). Previous reports of compounds from the leaves of C. asiatica and related Colubrina species led to the isolation of saponins (Wagner et al. 1983;Seaforth et al. 1992;Oulad-Ali et al. 1994;Lee et al. 2000;Li et al. 1999;ElSohly et al. 1999), triterpenes (Roitman & Jurd 1978;Baxter & Walkinshaw 1988) as well as alkaloids and phenolic compounds (Guinaudeau et al. 1976 As part of our research on Thai medicinal plants containing potential bioactive compounds, air-dried branches of C. asiatica were investigated. Both EtOAc and MeOH extracts showed activity against Plasmodium falciparum, Mycobacterium tuberculosis and cytotoxicity towards three cancer cell lines. ...
... (Al-Rawi & Jasim 1982); two phenylalanine derivatives: (-)-auranamide (13) and D-phenylalanine, N-benzoyl-(2R)-2-(acetylamino)-3phenylpropyl ester (14)(Jakupovic et al. 1987); a sesquiterpenoid: isointermedeol(15)(Thappa et al. 1979); and a jujubogenin glycoside: 3''-O-acetylcolubrin (16)(Lee et al. 2000) (Figure 1and supplementary material). ...
Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1-6), five steroids (7-11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1-15 have been isolated for the first time from this plant.
... revealed by resonances observed at δ C 165.6 (C-1''), 146.8 (C-3''), 122.9 (C-2''), 51.5 (OMe), and 18.0 (C-4'')[25]. The HMBC correlations observed from H-4 (δ H 5.55, dd, J = 3.2, 1.4 Hz) to C-1'' (δ C 165.6) and from the OMe (δ H 3.20, s) to C-7 (δ C 104.4) evidenced the linkage of the methoxy and the crotonyl groups at C-7 and C-4, respectively. ...
Massarilactones constitute a rare class of polyketides produced mainly by endophytic fungi. Given that semisynthetic derivatives often exhibit biological activities greater than those of the substrates, seven previously unreported derivatives of massarilactone D, compounds 2-8, were synthetized by acylation with methacryloyl chloride, cinnamoyl chloride, 4-bromobenzoyl chloride, trans-2-methyl-2-butenoyl chloride, and crotonyl chloride. These compounds were evaluated for their cytotoxic activity against the murine fibroblasts L929, human cervix carcinoma KB-3-1, human lung carcinoma A549, human prostate cancer PC-3, epidermoid carci-noma A431, ovarian carcinoma SKOV-3, and breast cancer MCF-7 cell lines. Compounds 2 and 3 exhibited significant cytotoxicity against all the tested cells. Some of the semisynthetic derivatives were also tested for their nematicidal activity and compound 4 displayed significant and selective nematicidal activity with LD 90 and LD 50 of 100 and 12.5 µg/mL, respectively. Since the parent compound was not active, the present study supports the fact that the acylation reaction can improve bioactivities of some natural products.
... Colubrina asiatica L. (Rhamnaceae) is a climbing shrub native to Southeast Asia, northern Australia, and the Pacific islands, reaching heights of up to 4 m and commonly found in wetlands and coastal areas. This plant has traditional medicinal applications wherein its leaves and bark are used to treat skin diseases, while the roots are utilized to alleviate fever and thirst [165][166][167]. A derivative of N-benzoyl-D-phenylalanine (33) has been found to possess weak cytotoxicity against various cancer cell lines, including HeLa cervical cancer (KB), small cell lung carcinoma (NCI-H187), and human breast cancer (MCF-7). ...
Cancer remains a significant medical challenge, necessitating the discovery of novel therapeutic agents. Ribosomally synthesized and post-translationally modified peptides (RiPPs) from plants have emerged as a promising source of anticancer compounds, offering unique structural diversity and potent biological activity. This review identifies and discusses cytotoxic RiPPs across various plant families, focusing on their absolute chemical structures and reported cytotoxic activities against cancer cell lines. Notably, plant-derived RiPPs such as rubipodanin A and mallotumides A–C demonstrated low nanomolar IC50 values against multiple cancer cell types, highlighting their therapeutic potential. By integrating traditional ethnobotanical knowledge with modern genomic and bioinformatic approaches, this study underscores the importance of plant RiPPs as a resource for developing innovative cancer treatments. These findings pave the way for further exploration of plant RiPPs, emphasizing their role in addressing the ongoing challenges in oncology and enhancing the repertoire of effective anticancer therapies.
Objective: A novel antifungal needs to be found to overcome fungal resistance to antifungal drugs. Medicinal plants contain biologically active compounds as antifungal agents. Peria Pantai (Colubrinaasiatica L. Brong) has been used as a folk medicine by the Acehnese community to treat skin disease. This research aim was to evaluate antifungal activity of C. asiatica leaf fraction against Candidaalbicans resistant fluconazole.Methode: The extraction was accomplished consecutively as solvent multistep using n-hexane, ethyl acetate, and methanol. Phytochemical investigation has done to each extract/fraction. The antifungal activity has been evaluated by Kirby-Bauer method.Result: The result of phytochemical investigation of n-hexane fraction contains steroid compound, ethyl acetate fraction contains saponin and steroid compounds, and the methanol fraction contains flavonoid, saponin, tannin, and steroid compounds. n-Hexane and ethyl acetate fraction of Peria Pantai leaf have not shown antifungal activity, while it has been shown on methanol fraction with inhibition zone 5,6; 7,17; 8,25; and 11,4 mm at 10%, 20%, 30% and 40%concentration.
Natural products (NPs) have been shown to be an extraordinary source of bioactive compounds and three-dimensionally complex frameworks that can be useful to produce high-value molecular collections able to address “undruggable” and difficult therapeutic targets. Bicyclic acetals are particularly relevant for these purposes, given their key role in several biological interactions and the structural and stereochemical diversity that comes from the many possible ring combinations. To investigate this topological diversity, we have systematically characterized in a systematic and detailed manner. fused, spiro and bridged bicyclic acetals in a large set of NPs, highlighting the great potential of bicyclic acetals in Diversity-Oriented Synthesis (DOS). Accordingly, a summary of some recent efforts on the development of acetal-containing small molecule collections through DOS approaches are herein reported.
AbstractA practical method for large‐scale preparation of acid‐labile aglycones including protopanaxadiol, protopanaxatriol, cycloastragenol, and jujubogenin from the corresponding glycoside containing fraction was developed. The key point of this improved method is to generate and maintain the critical reaction conditions, anhydrous and strongly basic, in situ. This effort over comes the weakness of the reported method for oxidative cleavage of glycones and scales up the preparation of these acid‐labile aglycones for further studies.
Epidemiological studies have revealed that a diet rich in plant-derived foods has a protective effect on human health. Identifying bioactive dietary constituents is an active area of scientific investigation that may lead to new drug discovery. Kaempferol (3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid found in many edible plants (e.g. tea, broccoli, cabbage, kale, beans, endive, leek, tomato, strawberries and grapes) and in plants or botanical products commonly used in traditional medicine (e.g. Ginkgo biloba, Tilia spp, Equisetum spp, Moringa oleifera, Sophora japonica and propolis). Some epidemiological studies have found a positive association between the consumption of foods containing kaempferol and a reduced risk of developing several disorders such as cancer and cardiovascular diseases. Numerous preclinical studies have shown that kaempferol and some glycosides of kaempferol have a wide range of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, cardioprotective, neuroprotective, antidiabetic, anti-osteoporotic, estrogenic/antiestrogenic, anxiolytic, analgesic and antiallergic activities. In this article, the distribution of kaempferol in the plant kingdom and its pharmacological properties are reviewed. The pharmacokinetics (e.g. oral bioavailability, metabolism, plasma levels) and safety of kaempferol are also analyzed. This information may help understand the health benefits of kaempferol-containing plants and may contribute to develop this flavonoid as a possible agent for the prevention and treatment of some diseases.
The major alkaloid from the bark of Colubrina asiatica was isolated and identified as O-methyl-dauricine (III).
Ten glycosides of kaempferol and quercetin, including the hitherto unknown kaempferol and quercetin 3-rutinoside-7-rhamnosides, have been isolated from Equisetum silvaticum L.
From the leaves of COLUBRINA ASIATICA B RONGEN (Rhamnaceae) two saponins have been isolated and structurally elucidated, mainly by (13)C-NMR-spectroscopic methods, as jujubogenin-3-O-[2-O-acetyl-3-O-(3-O-beta-D-xylopyranosyl-4-O-acetyl-beta-D-glucopyranosyl)-alpha-L-arabinoside] (colubrinoside) and jujubogenin-3-O- [2-O-acetyl -3-O- (2-O- beta -D- xylopyranosyl-beta-D-glucopyranosyl)-alpha-L-arabinoside] (colubrin) respectively. Both saponins inhibit the spontaneous motility of mice, even at low doses (1 mg/ kg), they show an antagonistic effect on amphetamine and exert a synergistic activity on chlordiazepoxide.
A new triterpenoid saponin, bacoside A3, a constituent of bacosides the saponin mixture of Bacopa monniera, was isolated and characterized. Its structure was established as 3-beta-[O-beta-D-glucopyranosyl(1-->3)-O- [alpha-L-arabinofuranosyl(1-->2) ]O-beta-D-glucopyranosyl)oxy]jujubogenin by chemical and spectral analyses. The cis-isomer of ebelin lactone was also obtained as one of the artefacts of the aglycone and its structure revised.
In The Flavonoids: Advance in Research
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