• Biomolecules & Therapeutics
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• v.7 no.2
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• pp.145-152
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• 1999

In an attempt to elucidate the anti-inflammatory action of ginseng total saponin, protopanaxadiol and protopanaxatriol, the anti-inflammatory activity of three compounds was investigated under various acute and chronic inflammatory models. The blood vessel permeability was slightly inhibited by total saponin and protopanaxatriol treatments. Granuloma formation induced by 2% carrageenan was inhibited by total saponin and protopanaxatriol. The cotton-pellet granuloma formation was significantly inhibited by intraperitoneal injection of total saponin. Total saponin and protopanaxadiol inhibited leukocyte emigration and protein exudation in CMC-induced pouch but protopanaxauiol increased leukocyte emigration. The swelling of rat hind paw induced by 1% carrageenan was significantly inhibited by total saponin, protopanaxadiol and protopanaxatriol both single and 2 weeks treatments. Total saponin, protopanaxadiol and protopanaxatriol decreased the anti-inflammatory activity in adrenalectomized rat. Our results suggest that total saponin, protopanaxadiol and protopanaxatriol have potent anti-inflammatory activity, this may be mediated in part through stimulation of adrenal glands.

• Journal of Ginseng Research
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• v.19 no.1
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• pp.45-50
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• 1995

(20S)- and (20R)-protopanaxadiol were prepared from crude ginseng saponin by chemical treatment. The $^{1}H$- and $^{13}C$-NMR signals of these compounds were fully assigned by various NMR techniques such as DEPT, 1H-1H COSY, HMQC, HMBC and NOESY.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1993.04a
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• pp.115-115
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• 1993

i) total ginsenoside의 분리 시판백삼(900g)을 상법에 따라 처리, 조 saponin을 얻었으며 (24g) 이를 20(S)-protopanaxadiol을 얻는 원료로 사용하였다. ii) 20(S)-protopanaxadiol의 분리연구 본 연구에서 가장 중요한 단계는 20(S)-protopanaxadiol을 다량 얻는 것이다. 그러나 인삼 saponin을 산으로 가수분해하면 진성 aglycone 인 20(S)-protopanaxadiol이 얻어지지 않고 artifact sapogenol인 panaxadiol이 얻어진다. 이를 해결하기 위하여 sodium ethoxide의 ethanol 용액, sodium butoxide의 butanol 용액, sodium methoxide의 pyridine 용액, sodium methoxide의 DMSO 용액등의 조건에서의 가수분해를 검토한 결과 aprotic polar splvent인 DMSO용매중에서의 분해가 가장 좋음을 알았다. iii) ginsenoside Rh$_2$의 합성연구 Koenigs-Knorr 법에 의하여 bromosugar와 20(S)-protopanaxadiol의 glycosidation 반응결과 약 40%의 수득률로 합성됨을 확인하였다.

• YAKHAK HOEJI
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• v.45 no.4
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• pp.328-333
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• 2001

Ginsenoside Rh$_2$, a minor glycoside constituent of the red ginseng is known as an unique antitumor compound. Several attempts to prepare it in a large scale including semisynthesis from betulafolientriol, an 3-epimer of 20(S)-protopanaxadiol, has been reported. We have previously reported a synthesis of ginsenoside Rh$_2$from 20(S)-protopanaxadiol obtained by alkaline hydrolysis of total ginsenoside. The regioselective synthesis of this compound was achieved by protection of 12-OH group.

• Journal of Ginseng Research
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• v.5 no.1
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• pp.49-55
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• 1981

The effects of total, protopanaxadiol-and protopanaxatriol-saponins on the in vitro activities of several enzymes in rat serum were observed Alkaline phosphatase activity was increased 61 % by total saponin and 46% by protopanaxatriol-saponin, compared to control group. While SCOT activity was slightly decreased by total saponin and protopanaxatriol- saponin, it was slightly increased by Protopanaxadiol-saponin And while SCPT activity was slightly decreased by total saponin, it was increased by protopanaxadiol-saponin and protopanaxatriol-saponin. Creatine phosphokinase activity had a tendency to be increased by protopanaxatriol-saponin. Lactate dehydrogenase activities were increased in three saponin treated groups, but those were nonignificant. Compared to the control group, lipase activity was increased by all saponin samples. It was increased 157% by total saponin The increase in lipase activity by total saponin corresponded with the decrease in serum t total lipid by total saponin .

• Proceedings of the Ginseng society Conference
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• 1993.09a
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• pp.74-83
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• 1993

In an attempt toward the synthesis of the difficulty accessible ginseng saponins the four dammarane glycosides identical to the natural $ginsenosides-Rh_2,$ - F2, compound K and chikusetsusaponin - LT8 have been prepared from betulafolienetriol(=dammar-24-ene-$3{\alpha},12{\beta}\;20(S)-triol).\;3-O-{\beta}-D-Glucopyranoside$ of 20(S) - protopanaxadiol $(=ginsenoside-Rh_2)$ have been obtained by the regio - and stereoselective glycosylation of the $12-O-acetyldammar-24-ene-3{\beta},\;12{\beta},$ 20(S)-triol. The 12-ketoderivative of 20(S)-protopanaxadiol has been used as aglycon in synthesis of chikusetsusaponin - LT8. Attempted regio - and stereoselective glycosylation of the less reactive tertiary C - 20 - hydroxyl group in order to synthesize the $20-O-{\beta}-D-glucopyranoside$ of 20(S)-protopanaxadiol(=compound K) using 3, 12 - di - O - acetyldammar - 24 - ene - $3{\beta},12{\beta},20(S)$-trial as aglycon was unsuccessful. Glycosylation of 3, 12 - diketone of betulafolienetriol followed by $NaBH_4$ reduction yielded the $20-O-{\beta}-D-glucopyranoside\;of\;dammar-24-ene-3{\beta},12{\alpha},$ 20(S)-triol, the $12{\alpha}-epimer$ of 20(S) - protopanaxadiol. Moreover, a number of semisynthetic ocotillol - type glucosides, analogs of natural pseudoginsenosides, have been prepared.

• Korean Journal of Pharmacognosy
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• v.26 no.4
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• pp.360-367
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• 1995

The metabolism of ginseng saponins by human intestinal bacteria was studied using human feces under anaerobic culture conditions. $Ginsenoside-Rb_1$, $-Rb_2$ and -Rc(protopanaxadiol type) were mainly metabolized to compound-K(C-K), $20-O-[{\alpha}-L-arabinopyranosyl(1{\rightarrow}6)-{\beta}-{_D}-glucopyranosyl]-20(S)-protopanaxadiol(compound-Y,\;C-Y)$, $20-O-[{\alpha}-L-arabinopyranosyl(1{\rightarrow}6)-{\beta}-{_D}-glucopyranosyll-20(S)-protopanaxadiol(ginsenosied-MC,{\;}MC)$, respectively, and $ginsenoside-Rg_1$ and -Re(protopanaxatriol type) to their aglycon, 20(S)-protopanaxatriol, though the pathway and rate of the metabolism were affected by fermentation medium. C-K was not decomposed any more, while C-Y and Mc were both gradually hydrolyzed to C-K.

• Korean Journal of Pharmacognosy
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• v.28 no.1
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• pp.35-41
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• 1997

Following ginsenoside-Rb1-hydrolyzing assay, strictly anaerobic bacteria were isolated from human feces and identified as Prevotella oris. The bacteria hydrolyzed ginsenoside Rb1 and Rd to $20-O-{\beta}-D-glucopyranosyl-20(S)-protopanaxadiol$ (I), ginsenoside Rb2 to $20-O-[{\alpha}-L-arabinofuranosyl (1{\rightarrow}6)-{\beta}-D-glucopyranosyl] - 20(S)-protopanaxadiol$ (ll) and ginsenoside Rc to $20-O-[{\alpha}-L-arabinofuranosyl (1{\rightarrow} 6){\beta}-D-g1ucopyranosyl]-20(S)-protopanaxadiol$ (III) like fecal microflora, but did not attack ginsenoside Re nor Rgl (Protopanaxatriol-type). Pharmacokinetic studies of ginseng saponins was also performed using specific pathogen free rats and demonstrated that the intestinal bacterial metabolites I-111, 20(S)- protopanaxatriol(IV) and 20(S)-protopanaxadiol(V) were absorbed from the intestines to $blood(0.4-5.1\;{\mu}g/ml)$ after oral administration with total saponin(1 g/kg/day).

• Journal of Ginseng Research
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• v.5 no.1
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• pp.41-48
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• 1981

Total saponin, protopanaxadiol-saponin and protopanaxatriol-saponin were isolated and purified from the side roots of red ginseng. After we administered them orally into rats during 5 weeks, we observed their effects on lipid and glucose content in rat serum. The change in body weight of protopanaxatriol- saponin treated group was slightly larger than those of other groups. Total lipid content in total saponin treated group showed an increase of about 20 % over that in control group. However, protopanaxadiol-saponin and protopanaxatriol- saponin treated groups showed no change. While triglyceride content in total saponin treated group decreased 29oyo compared to it s content in control group, its content in protopanaxatriol-saponin treated group increased 45%. Three saponin treated groups showed lower value than control group in total ant free cholesterol levels. While glucose content in total saponin treated group decreased slightly, that in Protopanaxadiol-saponin treated group decreased slightly compared to that in control group. And protopanaxatriol- saponin trented group showed the significant decrease of 25%. From these results, it is supposed that total saponin accelerates the conversion of lipid into glucose and that protopanaxatriol- saponin accelerates the conversion of glucose into lipid.

• YAKHAK HOEJI
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• v.29 no.4
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• pp.188-192
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• 1985

Protopanaxadiol (PD) fraction and protopanaxatriol (PT) fraction were separated from thebutanol fraction of panax ginseng roots. Each group of mice was injected with morphine hydrochloride (40 mg/kg s.c.) three times at 8 hr intervals for a period of 6 days. PD fraction and PT fraction were injected (25, 100 mg/kg i.p.) to mice 1 hr prior to the third morphine injection daily. Inhibition of morphine tolerance was evidenced by the increase in analgesic response to morphine hydrochloride (10mg/ kg i.p.) as estimated by the tail flick method. Inhibition of morphine tolerance by PT fraction was effective but there was no remarkable difference in inhibition of tolerance development between control group andPD fraction group.