Cytotoxic acetylenes from Panax quinquefolium.

Fujimoto, Yasuo; Satoh, Mitsuru; Takeuchi, Naoki; Kirisawa, Makoto

doi:10.1248/cpb.39.521

Cited by 50 publications

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“…As a continuing study, we have further isolated a new dammarane-type triterpene tetraglycoside called notoginsenoside-L (1) and two new dammarane-type triterpene triglycosides having an a-glucosidic linkage named notoginsenosides-M (2) and -N (3) together with ginsenoside-Rb 3 6) from the glycosidic fraction, whereas four known acetylenes, panaxynol, 7) panaxydol, 7) panaxytriol, 8) and 9) and a known sesquiterpene, 1b,6a-dihydroxy-4(15)-eudesmene, 10) were isolated from the ethyl acetate-soluble portion. In this paper, we describe the isolation and structure elucidation of three new notoginsenosides (1)(2)(3).…”

Section: )mentioning

confidence: 99%

Bioactive Saponins and Glycosides. XIX. Notoginseng (3): Immunological Adjuvant Activity of Notoginsenosides and Related Saponins: Structures of Notoginsenosides-L, -M, and -N from the Roots of Panax notoginseng (BURK.) F. H. CHEN.

Yoshikawa

Morikawa

Yashiro

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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The Araliaceae plant Panax notoginseng (BURK.) F. H. CHEN. is cultivated on a large scale in Yunnan and Guang-Xi provinces, China. The main roots of this plant, notoginseng ( or in Japanese), is used for treatment of trauma and bleeding due to internal and external injury. As the principal constituents of this plant, various dammarane-type triterpene saponins have been characterized from the roots, leaves, and buds.2) During the course of our chemical and pharmacological studies on the saponin constituents of natural medicines 1,3) and medicinal foodstuffs, 4) we found that the saponin fraction from notoginseng was found to show potent protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. 5) From the active saponin fraction, we have hitherto characterized ten dammarane-type triterpene saponins termed notoginsenosides-A (4), -B, -C (6), -D (7), -E, -G (11), -H (13), -I (8), -J (14), and -K (5) and an acetylenic fatty acid glycoside called notoginsenic acid b-sophoroside together with eighteen known saponins. 5)As a continuing study, we have further isolated a new dammarane-type triterpene tetraglycoside called notoginsenoside-L (1) and two new dammarane-type triterpene triglycosides having an a-glucosidic linkage named notoginsenosides-M (2) and -N (3) together with ginsenoside-Rb 3 6) from the glycosidic fraction, whereas four known acetylenes, panaxynol, 7) panaxydol, 7) panaxytriol, 8) and PQ-1, 9) and a known sesquiterpene, 1b,6a-dihydroxy-4(15)-eudesmene, 10) were isolated from the ethyl acetate-soluble portion. In this paper, we describe the isolation and structure elucidation of three new notoginsenosides (1-3). Furthermore, since notoginseng as well as ginseng (Panax ginseng C. A. MAYER, roots) and American ginseng (Panax quinquefolium L., roots) has been known to show tonic activity in Chinese traditional medicine, we examined the immunological adjuvant effect of the principal eleven notoginsenosides (1-8, 11, 13, 14), two ginsenosides (10, 18), 11) and five quinquenosides (9, 12, 15-17) 12) from notoginseng, ginseng, and American ginseng, respectively. . The carbon signals of the sapogenol part in the 13 C-NMR (Table 1) of 1 were found to be superimposable with those of 20(S)-protopanaxadiol glycosides, 5,11,12,15) while the carbon signals of the disaccharide moiety were similar to those of ginsenoside-Rb 1 (10) 11,15) except for the terminal 2Ј-O-b-D-xylopyranosyl moiety. The disaccharide structures bonding to the 3 and 20-hydroxyl groups in the 20(S)-protopanaxadiol part were determined by a heteronuclear multiple bond correlation (HMBC) experiment (J CH ϭ8 Hz) on 1. Namely, long-range correlations were observed between the 1Љ-proton and the 2Ј-carbon, between the 1Ј-proton and the 3-carbon, between the 1ЉЉ-proton and the 6ٞ-carbon, and between the 1ٞ-proton and the 20-carbon. On the basis of this New dammarane-type triterpene saponins, notoginsenosides-L, -M, and -N, were isolated from the glycosidic fraction of the dried roots of Panax notoginseng (BURK.) F. H. ...

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Section: )mentioning

confidence: 99%

Bioactive Saponins and Glycosides. XIX. Notoginseng (3): Immunological Adjuvant Activity of Notoginsenosides and Related Saponins: Structures of Notoginsenosides-L, -M, and -N from the Roots of Panax notoginseng (BURK.) F. H. CHEN.

Yoshikawa

Morikawa

Yashiro

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A few minor peaks that appeared in the HPLC chromatogram of the EtOAc extract (Fig. 2b) showed no characteristic UV absorption spectra except for the compound eluting at 65.5 min with k max at 240, 253, 267, and 280 nm, indicating that it could be a polyacetylene with a diyn-ene chromophore as found in panaxydiol [25]. This compound, which constituted below 8% of the total PA content in the fresh roots, was not subjected to further investigations.…”

Section: Resultsmentioning

confidence: 99%

“…Several PAs have been isolated from ginseng roots [5,8,[24][25][26] of which some exhibit anti-platelet-aggregatory action [5,22,23], and anti-inflammatory [5,9,27,28] and anticarcinogenic activity [5,9,25,29,30]. The most bioactive and abundant PAs in ginseng are falcarinol (= panaxynol) and panaxydol ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Biomass and content of ginsenosides and polyacetylenes in American ginseng roots can be increased without affecting the profile of bioactive compounds

Christensen

Jensen

2008

J Nat Med

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Fifty selected roots from a 7-year-old American ginseng (Panax quinquefolium L.) plant population grown in Denmark, with root weights varying from 191 to 490 g fresh weight (FW), were investigated for bioactive ginsenosides and polyacetylenes (PAs) in order to determine the correlation between the content of ginsenosides and PAs and root FW. PAs (falcarinol, panaxydol) and ginsenosides (Rb(1), Rb(2), Rb(3), Rc, Rd, Re, Rg(1)) were extracted from roots by sequential extraction with ethyl acetate and 80% methanol, respectively, and quantified in extracts by reverse-phase high-performance liquid chromatography (HPLC) using photodiode array detection. Total concentrations of PAs and ginsenosides varied between 150 and 780 mg/kg FW and 5,920 and 15,660 mg/kg FW, respectively. No correlation existed between the content of ginsenosides and PAs and root FW or between the total concentration of ginsenosides and PAs. Strong significant correlation was found between total content of ginsenosides and ginsenoside Rb(1) (r = 0.8190, P < 0.0001) and between total content of PAs and falcarinol (r = 0.9904, P < 0.0001). Based on the results of this study, it was concluded that it is possible to select large American ginseng roots for increased biomass production and concentration of bioactive ginsenosides and PAs without affecting the profile of bioactive compounds. Ginsenoside Rb(1) and falcarinol were found to be important selection parameters for identifying superior genotypes with the highest content of bioactive compounds.

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“…Unlike the fungal polyacetylene epoxyalcohols, 17 is a cissubstituted epoxide. Plant polyacetylenes are usually C 13 to C 17 1,3-disubstituted glycerols or 1,4-disubstituted tetritols, such as the 1,2,3-trihydroxyhepta-4,6-diyne 18 [24][25][26][27], the 1,2-epoxy-3-hydroxyhept-4,6-diynes 19a [28], 19b [25,29,30], and 19c [31], the 2,3-epoxy-1,4-dihydroxydeca-5,7,9-triynes 20 [32], and the 1,2:3,4-diepoxydeca-5,7,9-triynes 21a (annuadiepoxide) [33] and 21b (gummiferol) [34]. The (8R,9S,10R) configuration of 18 is based on chemical correlation [35] and is at variance with the (8S,9R,10S) configuration postulated earlier [36] on the basis of Horeau's method [37].…”

Section: 2mentioning

confidence: 99%