Cryptoporic acid E

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Cryptoporic acid E
Category Enzyme inhibitors
Catalog number BBF-01086
CAS 120001-10-7
Molecular Weight 849.01
Molecular Formula C45H68O15

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Description

It is produced by the strain of Cryptoporus volvatus.

Specification

Synonyms (3S,4R)-3-((((1R,4aS,5S,8aR)-5-((((2R,3S)-3-(carboxymethyl)-1,4-dimethoxy-1,4-dioxobutan-2-yl)oxy)methyl)-1,4a-dimethyl-6-methylenedecahydronaphthalen-1-yl)methoxy)carbonyl)-4-(((1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)methoxy)-5-methoxy-5-oxopentanoic acid
IUPAC Name (3S,4R)-4-[[(1S,4aR,5R,8aS)-5-[[(2S,3R)-3-[[(1S,4aR,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methoxy]-2-(carboxymethyl)-4-methoxy-4-oxobutanoyl]oxymethyl]-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methoxy]-5-methoxy-3-methoxycarbonyl-5-oxopentanoic acid
Canonical SMILES CC1(CCCC2(C1CCC(=C)C2COC(C(CC(=O)O)C(=O)OCC3(CCCC4(C3CCC(=C)C4COC(C(CC(=O)O)C(=O)OC)C(=O)OC)C)C)C(=O)OC)C)CO
InChI InChI=1S/C45H68O15/c1-26-12-14-32-42(3,24-46)16-10-18-44(32,5)30(26)22-59-37(41(54)57-9)29(21-35(49)50)39(52)60-25-43(4)17-11-19-45(6)31(27(2)13-15-33(43)45)23-58-36(40(53)56-8)28(20-34(47)48)38(51)55-7/h28-33,36-37,46H,1-2,10-25H2,3-9H3,(H,47,48)(H,49,50)/t28-,29-,30-,31-,32-,33-,36+,37+,42-,43-,44+,45+/m0/s1
InChI Key PCFMECNNYYMDRS-VTRNTCPLSA-N

Properties

Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 860.6 °C at 760 mmHg
Melting Point 85-88 °C
Density 1.23 g/cm3

Reference Reading

1. Cryptoporic acid E from Cryptoporus volvatus inhibits influenza virus replication in vitro
Li Gao, Jiayuan Han, Jianyong Si, Junchi Wang, Hexiang Wang, Yipeng Sun, Yuhai Bi, Jinhua Liu, Li Cao Antiviral Res. 2017 Jul;143:106-112. doi: 10.1016/j.antiviral.2017.02.010. Epub 2017 Feb 21.
Influenza virus infection is a global public health issue. The efficacy of antiviral agents for influenza virus has been limited by the emergence of drug-resistant virus strains. Thus, there is an urgent need to identify novel antiviral therapies. Our previous studies have found that Cryptoporus volvatus extract can potently inhibit influenza virus replication in vitro and in vivo. However, the effective component of Cryptoporus volvatus, which mediates the antiviral activity, hasn't been identified. Here, we identified a novel anti-influenza virus molecule, Cryptoporic acid E (CAE), from Cryptoporus volvatus. Our results showed that CAE had broad-spectrum anti-influenza activity against 2009 pandemic strain A/Beijing/07/2009 (H1N1/09pdm), seasonal strain A/Beijing/CAS0001/2007(H3N2), mouse adapted strains A/WSN/33 (H1N1), and A/PR8/34 (H1N1). We further investigated the mode of CAE action. Time-course-analysis indicated that CAE exerted its inhibition mainly at the middle stages of the replication cycle of influenza virus. Subsequently, we confirmed that CAE inhibited influenza virus RNA polymerase activity and blocked virus RNA replication and transcription in MDCK cells. In addition, we found that CAE also impaired influenza virus infectivity by directly targeting virus particles. Our data suggest that CAE is a major effective component of Cryptoporus volvatus.
2. Update from Asia. Asian studies on cancer chemoprevention
T K Yun Ann N Y Acad Sci. 1999;889:157-92. doi: 10.1111/j.1749-6632.1999.tb08734.x.
In Asia, nontoxic dietary products are considered desirable primary prevention vehicles for conquering cancer. As early as 1978, investigators in Korea carried out extensive long-term anticarcinogenicity experiments using the mouse lung tumor model and observed an anticarcinogenic effect of Panax ginseng C.A. Meyer extract in 1980. The results showed that natural products can provide hope for human cancer prevention. A newly established nine-week medium-term model using mouse lung tumors (Yun's model) could confirm the anticarcinogenicity of ginseng that varies according to its type and age. Subsequently, the ginseng was shown by epidemiological studies to be a nonorgan-specific cancer preventive agent associated with a dose-response relationship. The anticarcinogenic effects of vegetarian foods common at every dining table in Korea and some synthetics were also studied using Yun's nine-week model. In brief, ascorbic acid, soybean lecithin, capsaicin, biochanin A, Ganoderma lucidum, caffeine, and a novel synthetic 2-(allylthio)pyrazine decrease the incidence of mouse lung tumors, whereas fresh ginseng (4 years old), carrot, spinach, Sesamum indicum, beta-carotene, and 13-cis retinoic acid do not. This result regarding beta-carotene is consistent with the ineffective findings of the ATBC trial, the CARET trial, and the Physicians' Health Study. In 1983, a cancer chemoprevention study group was first established in Japan. Subsequently, (-)-epigallocatechin gallate, cryptoporic acid E, and sarcophytol A from natural products, and synthetic acyclic retinoid and canventol were shown to be anticarcinogenic or chemopreventive in human subjects. Despite the frequent consumption of tea wordwide as a beverage and current experimental evidence of anticarcinogenesis, including controversial results of epidemiological studies, more systematic clinical trials for confirmation of preventive activity of tea against cancer are needed. Placebo-controlled intervention trials of dietary fiber are under study in Japan. In the past decade, new triterpenoids were isolated from various natural sources, and its biological activities were investigated in Asia. In the late 1970s a comprehensive chemoprevention program was established at the Institute of Materia Medica, Chinese Academy of Medical Sciences. Since then, many retinoid compounds have been synthesized and screened in the search for chemopreventive cancer agents. The National Cancer Institute (USA) and China are jointly engaged in the two-nutrition intervention in Linxian, China. The results of joint study of the general population and of dysplasia in China should stimulate further research to clarify the potential benefits of micronutrient supplements. We need to clarify if there is a connection between the lower rates of cancer mortality in Korea and the frequent consumption of anticarcinogenic vegetables or traditional foods, including ginseng and Ganoderma lucidum. The constituents of the nontoxic stable dietary products promise to be the future hope for conquering cancers in the coming years.
3. Chemical constituents from the fruiting bodies of Cryptoporus volvatus
Junchi Wang, Guangzhi Li, Na Lv, Li Gao, Li Cao, Liangang Shen, Jianyong Si Arch Pharm Res. 2016 Jun;39(6):747-54. doi: 10.1007/s12272-016-0754-4. Epub 2016 May 4.
New drimane-type sesquiterpene cryptoporol A (1), cryptoporic acid derivative 6'-cryptoporic acid E methyl ester (2), and pseudouridine derivative cryptoporine A (3), as well as a known ergosterol 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol (4), were isolated from a 90 % alcohol extract of the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established by spectroscopic analysis and circular dichroism. 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol (4) exhibited antiviral activity against porcine reproductive and respiratory syndrome virus, and all compounds showed weak antioxidant activities.

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