Lentinan

Lentinan

Systematic (IUPAC) name
β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)β-D-glucopyranosyl-(1→3)]-β-D-glucopyranose
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	37339-90-5
ATC code	L03AX01 (WHO)
PubChem	CID 37723
ChemSpider	none
KEGG	D01695
Synonyms	(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-4-yl]oxyoxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Chemical data
Formula	C42H72O36
Molar mass	1152.99948 g/mol
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Lentinan is an intravenous anti-tumor polysaccharide isolated from the fruit body of shiitake (Lentinula edodes mycelium (LEM))). Lentinan has been approved as an adjuvant for stomach cancer in Japan since 1985. Lentinan is one of the host-mediated anti-cancer drugs which has been shown to affect host defense immune systems.

Chemistry

Lentinan is a β-1,3 beta-glucan with β-1,6 branching. Molecular weight of lentinan is 500,000 Da. Specific rotation +14-22° (NaOH).

Research

An in vitro experiment showed lentinan stimulated production of white blood cells in the human cell line U937.^[1] A pharmacological blend (MC-S) of lentinan, PSK, Ganoderma lucidum and Astragalus propinquus has also been shown to stimulate white blood cell production in vitro.^[2]

An in vivo experiment on mice, revealed lentinan is orally active (since clinical use of the drug is administered through an IV).^[3]

Limited clinical studies of cancer patients have associated lentinan with a higher survival rate, higher quality of life, and lower re-occurrence of cancer.^{[4][5][6][7][8][9][10][11]}

Lentinan may have been implicated in shiitake mushroom dermatitis.^[12]

Formulations containing Lentinan

Lentinex is a formulation featuring lentinan and is approved as a safe novel food in the EU.^[13]

See also

• Medicinal mushrooms

Notes

1. Sia GM, Candlish JK. (Mar 1999). "Effects of shiitake (Lentinus edodes) extract on human neutrophils and the U937 monocytic cell line.". Phytother Res. 13 (2): 133–7. doi:10.1002/(SICI)1099-1573(199903)13:2<133::AID-PTR398>3.0.CO;2-O. PMID 10190187.
2. Clark D, Adams M. (2007). "Using commercial nutraceutical mixes as immune stimulants: an in vitro proliferation study using Metabolic Cell-Support on non-stimulated human lymphocytes.". Austr. J. Med. Herbal. 19: 108–111.
3. Ng ML, Yap AT. (Oct 2002). "Inhibition of human colon carcinoma development by lentinan from shiitake mushrooms (Lentinus edodes).". J Altern Complement Med. (National University of Singapore) 8 (5): 581–9. doi:10.1089/107555302320825093. PMID 12470439.
4. Yang P, Liang M, Zhang Y, Shen B. (Aug 2008). "Clinical application of a combination therapy of lentinan, multi-electrode RFA and TACE in HCC.". Adv Ther. 25 (8): 787–94. doi:10.1007/s12325-008-0079-x. PMID 18670743.
5. Nimura H, Mitsumori N, Takahashi N, (Jun 2006). "[S-1 combined with lentinan in patients with unresectable or recurrent gastric cancer]". Gan to Kagaku Ryoho. 33 (1): 106–9. PMID 16897983.
6. Nakano H, Namatame K, Nemoto H, Motohashi H, Nishiyama K, Kumada K. (1999). "A multi-institutional prospective study of lentinan in advanced gastric cancer patients with unresectable and recurrent diseases: effect on prolongation of survival and improvement of quality of life. Kanagawa Lentinan Research Group.". Hepatogastroenterology. 46 (28): 2662–8. PMID 10522061.
7. Oba K, Kobayashi M, Matsui T, Kodera Y, Sakamoto J (July 2009). "Individual Patient Based Meta-analysis of Lentinan for Unresectable/Recurrent Gastric Cancer". Anticancer Res. 29 (7): 2739–45. PMID 19596954.
8. Hazama S, Watanabe S, Ohashi M, et al. (July 2009). "Efficacy of Orally Administered Superfine Dispersed Lentinan ({beta}-1,3-Glucan) for the Treatment of Advanced Colorectal Cancer". Anticancer Res. 29 (7): 2611–7. PMID 19596936.
9. Kataoka H, Shimura T, Mizoshita T, et al. (2009). "Lentinan with S-1 and paclitaxel for gastric cancer chemotherapy improve patient quality of life". Hepatogastroenterology 56 (90): 547–50. PMID 19579640.
10. Isoda N, Eguchi Y, Nukaya H, et al. (2009). "Clinical efficacy of superfine dispersed lentinan (beta-1,3-glucan) in patients with hepatocellular carcinoma". Hepatogastroenterology 56 (90): 437–41. PMID 19579616.
11. Shimizu K, Watanabe S, Watanabe S, et al. (2009). "Efficacy of oral administered superfine dispersed lentinan for advanced pancreatic cancer". Hepatogastroenterology 56 (89): 240–4. PMID 19453066.
12. Nakamura, T (1992). "Shiitake (Lentinus edodes) dermatitis". Contact Dermatitis 27 (2): 65–70. PMID 1395630. Retrieved August 18, 2015.
13. EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA). European Food Safety Authority (EFSA), Parma, Italy (2010), "Scientific Opinion on the safety of "Lentinus edodes extract" (Lentinex®) as a Novel Food ingredient" (PDF), EFSA Journal 7 (8): 1685, doi:10.2903/j.efsa.2010.1685

References

• Chihara, G. et al. ”Fractionation and purification of the polysaccharides with marked antitumor activity, especially lentinan, from Lentinus edodes (Berk.) Sing. (an edible mushroom)”, Cancer Research (1970),30(11):2776-2781.
• Ina, K. et al. “Lentinan prolonged survival in patients with gastric cancer receiving S-1-based chemotherapy”, World Journal of Clinical Oncology (2011),2(10):339-343.

External links

• Lentinan effects (antitumor and others)
• Memorial Sloan-Kettering Cancer Center's page for Lentinan.
• About Shiitake (by Solomon P. Wasser, 2005)
• Smith JE, Rowan NJ, Sullivan R Medicinal Mushrooms: Their Therapeutic Properties and Current Medical Usage with Special Emphasis on Cancer Treatments Cancer Research UK, 2001