Mass-spectrometric investigation of sterol and triterpenoid esters from leaves of the cotton plant

Rashkes, Ya. V.; Хидырова, Н. К.; Rashkes, A. M.; Shakhidoyatov, Kh. M.

doi:10.1007/bf00607535

Cited by 2 publications

(4 citation statements)

References 2 publications

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“…The known compounds were identified as myricetin 3-O-a-Lrhamnoside (3) Markham et al, 1978), myricetin 3-O-b-D-glucoside (4) (Agrawal and Bansal, 1989), quercetin 3-O-(3 00 -O-acetyl)-a-L-rhamnoside (5) , quercetin 3-O-a-L-rhamnoside (6) Markham et al, 1978), quercetin 3-O-b-D-glucoside (7) (Markham et al, 1978), (Masuda et al, 1991), kaempferol 3-O-b-D-glucoside (9) (Markham et al, 1978) naringenin (10) (Zhang et al, 2003), (S)-naringenin 5-O-b-D-glucoside (11) (Zhang et al, 2003;Gaffield, 1970), 2 0 ,4 0 ,6 0 ,4-tetrahydroxy- (Zhang et al, 2003), b-sitosterol (13) (Goad, 1991), b-sitosterol palmitate (14) (Nielsen and Kofod, 1963), 24-methylenecholesterol palmitate (15) (Rashkes et al, 1990), 4a-methyl-5a-ergosta-7,24(28)-diene3b,4b-diol (16) (Greca et al, 1991), ethyl gallate (17) (Hussain et al, 1979), gallic acid (18) (Hussain et al, 1979), p-coumaric acid (19) (Ji et al, 2005), and 4-methoxybenzoic acid (20) (Gadgoli and Mishra, 1999) by comparison of their physical and spectroscopic data with literature values (see Supporting Information).…”

Section: Resultsmentioning

confidence: 98%

“…In this paper, we have included the complete 1 H and 13 C NMR data for 5, along with HRESIMS, IR, UV, mp and specific rotation. Compound 15 was previously reported from the leaves of the cotton plant and identified on the basis of mass fragmentation (Rashkes et al, 1990). In this study, we have included additional spectroscopic data for compound 15.…”

Section: Resultsmentioning

confidence: 99%

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Antioxidant constituents of Nymphaea caerulea flowers

et al. 2008

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confidence: 98%

Section: Resultsmentioning

confidence: 99%

Antioxidant constituents of Nymphaea caerulea flowers

et al. 2008

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“…The compounds of 24-methylenecholesterol palmitate (3), cycloeucalenol (4), pollinastanol (5), 24-methylenecholesterol (6), linolenic acid (7), palmitic acid (8), monolinolein (9) and monopalmitin (10) were identified by comparing their 1 H-NMR and 13 C-NMR and MS data with those reported in literature. [5][6][7][8][9] Compound 1 was obtained as a colorless oil, and its molecular formula C 46 H 76 O 2 was established from HR-ESI-MS, which gave a pseudomolecular ion peak at m/z 681.5585 [MϩNa] ϩ . The 1 H-NMR, 13 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectrum (in CDCl 3 , Table 1) showed the presence of a 24-methylenecholesterol moiety compared with compound 6 and a unsatu-rated fat acid moiety.…”

Section: Resultsmentioning

confidence: 99%

“…In the following target screening the SFE-CO 2 extract showed potent 5a-reductase and aromatase inhibiting activity. Under bioactive guidance this extract was chromatographied by gel column and afforded two new phytosterol derivatives (1, 2) and eight known compounds (3)(4)(5)(6)(7)(8)(9)(10) (Fig. 1).…”

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5 Alpha-Reductase and Aromatase Inhibitory Constituents from Brassica rapa L. Pollen

Yang

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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401 Notes BPH (benign prostatic hyperplasia) is a prevalent syndrome in old man, about 40% men over 50 years suffered from BPH, but no definitive treatment. Pollens extracts have been reported having remarkable anti-BPH activity 1,2) and pollens have similar constitutes, including alkanes, alkenes, fatty acids, triterpene esters triglycerides, flavones, and so on.3,4) However the anti-BPH active components of pollen remain unknown. In our screening for anti-BPH pollen, Brassica rapa pollen exhibited a notable activity for reducing the volume of prostate in rat model with BPH (pϽ0.01, compared with model). In order to clarify the active principles of Brassica rapa pollen, water, 95% (v/v) ethanol, acetone and SFE-CO 2 (supercritical CO 2 fluid extract), four extracts were screened on anti-BPH activity. The SFE-CO 2 extract exhibited the remarkable bioactivity than other solvent extracts. In the following target screening the SFE-CO 2 extract showed potent 5a-reductase and aromatase inhibiting activity. Under bioactive guidance this extract was chromatographied by gel column and afforded two new phytosterol derivatives (1, 2) and eight known compounds (3-10) (Fig. 1). The structure of new compounds was determined using chemical and spectral methods. This report describes the isolation of the constitutes of Brassica rapa pollen and determination of their structure. We also report their 5a-reductase and aromatase inhibition bioactivities. Results and DiscussionAir-dried pollen of Brassica rapa L. was extracted with SFE-CO 2 two times. The concentrated extract was fractionated by SiO 2 c.c. (silica gel column chromatography) to afford fractions A-D. Fraction B showed potent 5a-reductase inhibition with inhibitory rate as 48.88Ϯ4.6%, fractions A and B showed potent aromatase inhibition with inhibitory rate as 79.6Ϯ6.9% and 84.0Ϯ0.1%, respectively. So the fractions A and B were successively separated by means of SiO 2 c.c. and HPLC using a reverse phase column to give two new compounds 1 and 2 along with eight known compounds 3-10. The compounds of 24-methylenecholesterol palmitate (3), cycloeucalenol (4), pollinastanol (5), 24-methylenecholesterol (6), linolenic acid (7), palmitic acid (8), monolinolein (9) and monopalmitin (10) Industry; 1320 West Beijing Road, Shanghai 200040, P. R. China. Received October 22, 2008 accepted January 10, 2009; published online January 14, 2009 In the screening of biologically active constituents from Brassica rapa pollen, the supercritical CO 2 fluid extract (SFE-CO 2 ) showed potent 5a a-reductase and aromatase inhibiting activity. The SFE-CO 2 extract was separated by various chromatographic methods to give two new phytosterol derivatives, 24-methylenecholesterol linolenate (1) and cycloeucalenol linolenate (2), as well as eight known compounds, 24-methylenecholesterol palmitate (3), cycloeucalenol (4), pollinastanol (5), 24-methylenecholesterol (6), linolenic acid (7), palmitic acid (8), monolinolein (9) and monopalmitin (10), compounds 7 and 9 showed potent 5a a-reductase in...

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Mass-spectrometric investigation of sterol and triterpenoid esters from leaves of the cotton plant

Cited by 2 publications

References 2 publications

Antioxidant constituents of Nymphaea caerulea flowers

Antioxidant constituents of Nymphaea caerulea flowers

5 Alpha-Reductase and Aromatase Inhibitory Constituents from Brassica rapa L. Pollen

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