A fungal metabolite with diverse biological activities
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Sporogen-AO 1

Item No. 29576

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1aR,6R,7R,7aR,7bR)-4,5,6,7,7a,7b-hexahydro-6-hydroxy-7,7a-dimethyl-1a-(1-methylethenyl)-naphth[1,2-b]oxiren-2(1aH)-one
CAS Number
88418-12-6
Synonyms
  • (+)-Sporogen-AO 1
Molecular Formula
C15H20O3
Formula Weight
248.3
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1C=C2CC[C@@H](O)[C@H](C)[C@@]2(C)[C@]3([H])[C@@]1(C(C)=C)O3
InChi Code
InChI=1S/C15H20O3/c1-8(2)15-12(17)7-10-5-6-11(16)9(3)14(10,4)13(15)18-15/h7,9,11,13,16H,1,5-6H2,2-4H3/t9-,11+,13+,14+,15-/m0/s1
InChi Key
PCBDXYONDOCJPR-OANMRLRGSA-N
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $169

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    Product Description

    Sporogen-AO 1 is a fungal metabolite originally isolated from A. oryzae that has diverse biological activities.1,2,3,4,5 It inhibits HIV-1 Tat transactivation in a cell-based assay with an IC50 value of 15.8 µM.4 Sporogen-AO 1 is cytotoxic to HeLa, KB, and NCI H187 cancer cells (IC50s = 8.3, 9, and 5.1 µM, respectively).2,5 It is active against C. albicans (MIC = 4 mM).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tanaka, S., Wada, K., Marumo, S., et al. Structure of sporogen-ao 1, a sporogenic substance of Aspergillus oryzae. Tetrahedron Lett. 25(51), 5907-5910 (1984).

    2. Motohashi, K., Hashimoto, J., Inaba, S., et al. New sesquiterpenes, JBIR-27 and -28, isolated from a tunicate-derived fungus, Penicillium sp. SS080624SCf1. J. Antibiot. (Tokyo) 62(5), 247-250 (2009).

    3. Yurchenko, A., Smetanina, O.F., Kalinovsky, A., et al. Biologically active metabolites of the facultative marine fungus Penicillium citrinum. Chem. Nat. Compd. 48(6), 996-998 (2013).

    4. Jayasuriya, H., Zink, D.L., Polishook, J.D., et al. Identification of diverse microbial metabolites as potent inhibitors of HIV-1 Tat transactivation. Chem. Biodivers. 2(1), 112-122 (2005).

    5. Tansakul, C., Rukachaisirikul, V., Chalothorn, T., et al. Synthesis and cytotoxicity against KB and NCI-H187 cell lines of sporogen AO-1 analogues. Phytochem. Lett. 22, 128-132 (2017).