24-Methylpollinastanone, related triterpenoids and sterols from Costus tonkinensis

Böhme, Frank; Schmidt, Jürgen; Sung, Trần Văn; Adam, Günter

doi:10.1016/s0031-9422(97)00101-5

Cited by 13 publications

(3 citation statements)

References 13 publications

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“…This chloroform fraction was chromatographed over silica gel using hexane and eluted with solvents of increasing polarity. Further purification of a major sub-fraction by HPLC (hexane/chloroform, 1:9), followed by preparative TLC (chloroform/methanol, 9:1) yielded 24-methylenecycloartanone 4 (7 mg) [21,22].…”

Section: Resultsmentioning

confidence: 99%

Evaluation of Polygonum bistorta for Anticancer Potential Using Selected Cancer Cell Lines

Manoharan¹,

Yang²,

Hsu³

et al. 2007

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The chloroform and hexane fractions and their sub-fractions of Polygonum bistorta (Polygonaceae) were evaluated for their cytotoxic activity against P338 (Murine lymphocytic leukaemia), HepG2 (Hepatocellular carcinoma), J82 (Bladder transitional carcinoma), HL60 (Human leukaemia), MCF7 (Human breast cancer) and LL2 (Lewis lung carcinoma) cancer cell lines in culture. Both the chloroform and hexane fractions and a few of their sub-fractions showed moderate to very good activity against P388, HL60 and LL2 cancer cell lines. Both active and non-active fractions were further investigated for their chemical constituents. A total of nine compounds, viz. 24(E)-ethylidenecycloartanone (1), 24(E)-ethylidenecycloartan-3alpha-ol (2), cycloartane-3,24-dione (3), 24-methylenecycloartanone (4), friedelin (5), 3beta-friedelinol (6), beta-sitosterol (7), gamma-sitosterol (8) and beta-sitosterone (9) were isolated. One of the pure compounds, 24(E)-ethylidenecycloartanone 1, which was obtained in sufficient quantity, was tested for its cytotoxicity against P388, LL2, HL60 and WEHI164 (Murine fibrosarcoma) cancer cell lines but was found to have no activity even at a concentration of 100 microg/mL.

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Section: Resultsmentioning

confidence: 99%

Evaluation of Polygonum bistorta for Anticancer Potential Using Selected Cancer Cell Lines

Manoharan¹,

Yang²,

Hsu³

et al. 2007

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“…Based on the m/z of their molecular ions, one is likely its demethylated version, 24-methylene pollinastanol (metabolite 7) and the other differing from the previous by a reduced double bond, 24-methyl pollinastanol (metabolite 8). The identity of these metabolites was further supported by a shared fragment ion at m/z 269, representing the sterol backbone ([M-TMSiOH-SC] + ) and a fragment ion unique to 24-methyl pollinastanol at m/z 220 (Böhme et al ., 1997). Jointly, the accumulation of cycloeucalenol, and its aberrant metabolites 24-methylene pollinastanol and 24-methyl pollinastanol, suggests that clomiphene inhibits cycloeucalenol cycloisomerase (CPI) activity (Fig.…”

Section: Resultsmentioning

confidence: 96%

The selective estrogen receptor modulator clomiphene inhibits sterol biosynthesis inArabidopsis thaliana

Wang

Vriese

Desmet

et al. 2023

Preprint

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Sterols are produced via complex, multistep biosynthetic pathways involving similar enzymatic conversions in plants, animals and fungi, yielding a variety of sterol metabolites with slightly different chemical properties to exert diverse and specific functions. The role of plant sterols has been studied in the context of cell biological processes, signaling and overall plant development, mainly based on mutants. Due to their essential nature, genetic interference with their function causes pleiotropic developmental defects. An important alternative is to use a pharmacological approach. However, the current toolset for manipulating sterol biosynthesis in plants remains limited. Here, we probed a collection of inhibitors of mammalian cholesterol biosynthesis to identify new inhibitors of plant sterol biosynthesis. We provide evidence that imidazole-type fungicides, bifonazole, clotrimazole and econazole inhibit the obtusifoliol 14α-demethylase CYP51, that is highly conserved among eukaryotes. Surprisingly, we found that the selective estrogen receptor modulator, clomiphene, inhibits sterol biosynthesis, in part by inhibiting the plant-specific cyclopropyl-cycloisomerase CPI1. These results demonstrate that rescreening of the animal sterol biosynthesis pharmacology is an easy approach for identifying novel inhibitors of plant sterol biosynthesis. Such molecules can be used as entry points for the development of plant-specific inhibitors of sterol biosynthesis that can be used in agriculture.

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“…For its relative stereochemistry, see: Alves et al (2000); Ohta & Shimizu (1958). For general background the title compound and the plant Ainsliaea henryi, see: Anjaneyulu et al (1999); Boehme et al (1997); Chinese Materia Medica (2007); Ei-Dib et al (2004); Fiechi et al (1966); Gabrera & Seldes (1995); Jayasinghe et al (2001); Kojima et al (1985); Kolhe et al (1982); Lao et al (1984); Lawrie et al (1970); Li & Xue (1986); Manoharan et al (2005); Ohtsu et al (1998); Schulte et al (1979); Tachi et al (1971); Tandon & Rastogi (1976).…”

Section: Related Literaturementioning

confidence: 99%

24-Methylenecycloartanone

Xiong

Chen

et al. 2010

Acta Crystallogr E Struct Rep Online

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Key indicators: single-crystal X-ray study; T = 293 K, P = 0.0 kPa; mean (C-C) = 0.004 Å; R factor = 0.052; wR factor = 0.133; data-to-parameter ratio = 14.7.The title compound, C 31 H 50 O, a tetracyclic triterpene, was isolated from Ainsliaea henryi. The molecule contains a threemembered ring, a five-membered ring, which exhibits an envelope conformation, and three six-membered rings, which adopt chair conformations. Related literatureThe title compound was first isolated from rice bran oil, see: Ohta & Shimizu (1958)

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24-Methylpollinastanone, related triterpenoids and sterols from Costus tonkinensis

Cited by 13 publications

References 13 publications

Evaluation of Polygonum bistorta for Anticancer Potential Using Selected Cancer Cell Lines

Evaluation of Polygonum bistorta for Anticancer Potential Using Selected Cancer Cell Lines

The selective estrogen receptor modulator clomiphene inhibits sterol biosynthesis inArabidopsis thaliana

24-Methylenecycloartanone

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