By means of 5α-reductase inhibitory activity-guided fractionation, a new lanostanoid, 15α-hydroxy-3-oxolanosta- 7, 9(11), 24(E)-trien-26-oic acid, named as ganoderic acid TR, was isolated from the ethanol extract of the fruiting bodies of Ganoderma lucidum (Fr.) Karst (Ganodermataceae). The compound showed potent inhibitory activity with an IC50 of 8.5 μM. Modified Mosher's method established the S-configuration of the secondary hydroxyl group at C-15. In addition, a carboxyl group on the side chain of ganoderic acid TR is essential to elicit the inhibitory activity because of the considerably lower activity of its methyl ester.
BartschG, RittmasterRS, KlockerH. (2002) Dihydrotestosterone and the concept of 5α-reductase inhibition in human benign prostatic hyperplasia. World Journal of Urology, 19, 413–425.
2.
WasserSP, WeisAL. (1999) Therapeutic effects of substances occurring in higher Basidiomycetes mushrooms: a modern perspective. Critical Reviews in Immunology, 19, 65–96.
3.
RussellDW, WilsonJD. (1994) Steroid 5α-reductase: two genes/two enzymes. Annual Review of Clinical Biochemistry, 63, 25–61.
4.
BartschG, RittmasterRS, KlockerH. (2000) Dihydrotestosterone and the concept of 5α-reductase inhibition in human benign prostatic hyperplasia. European Urology, 37, 367–380.
5.
KadotaA. (2005) Health foods containing Ganoderma lucidum (extracts) and Acanthopanax senticosus (extracts). Japan Kokai Tokyo Koho, 7 pp. JP 2005304422 A2 20051104
6.
BaoXF, WangXS, DongQ, FangJN, LiXY. (2002) Structural features of immunologically active polysaccharides from Ganoderma lucidum. Phytochemistry, 59, 175–181.
7.
HuH, AhnNS, YangX, LeeYS, KangKS. (2002) Ganoderma lucidum extract induces cell cycle arrest and apoptosis in MCF-7 human breast cancer cell. International Journal of Cancer, 102, 250–253.
8.
ShiaoMS. (2003) Natural products of the medicinal fungus Ganoderma lucidum: occurrence, biological activities, and pharmacological functions. Chemical Record, 3, 172–180.
9.
LinCN, TomeWP, WonSJ. (1991) Novel cytotoxic principles of formosan Ganoderma lucidum. Journal of Natural Products, 54, 998–1002.
10.
YangHL, ChenGH, LiYQ. (2005) A quantum chemical and statistical study of ganoderic acids with cytotoxicity against tumor cell. European Journal of Medicinal Chemistry, 40, 972–976.
11.
LiCH, ChenPY, ChangUM, KanLS, FangWH, TsaiKS, LinSB. (2005) Ganoderic acid X, a lanostanoid triterpene, inhibits topoisomerases and induces apoptosis of cancer cells. Life Sciences, 77, 252–265.
12.
KohdaH, TokumotoW, SakamotoK, FujiM, HiraiY, YamasakiK, KomodaY, NakamuraH, IshiharaS, UchidaM. (1985) The biologically-active constituents of Ganoderma lucidum (Fr.) Karst. histamine release-inhibitory triterpenes. Chemical & Pharmaceutical Bulletin, 33, 1367–1374.
13.
MorigiwaA, KitabatakeK, FujimotoY, IkekawaN. (1986) Angiotensin converting enzyme-inhibitory triterpenes from Ganoderma lucidum. Chemical & Pharmaceutical Bulletin, 34, 3025–3028.
14.
IwatsukiK, AkihisaT, TokudaH, UkiyaM, OshikuboM, KimuraY, AsanoT, NomuraA, NishinoH. (2003) Lucidenic acids P and Q, methyl lucidenate P, and other triterpenoids from the fungus Ganoderma lucidum and their inhibitory effects on Epstein-Barr virus activation. Journal of Natural Products, 66, 1582–1585.
15.
KomodaY, ShimizuM, SonodaY, SatoY. (1989) Ganoderic acid and its derivatives as cholesterol-synthesis inhibitors. Chemical & Pharmaceutical Bulletin, 37, 531–533.
16.
SonodaY, SekigawaY, SatoY. (1988) In vitro effects of oxygenated lanosterol derivatives on cholesterol-biosynthesis from 24, 25-dihydrolanosterol. Chemical & Pharmaceutical Bulletin, 36, 966–973.
OhtaniI, KusumiT, KashmanY, KakisawaH. (1991) High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. Journal of the American Chemical Society, 113, 4092–4096.
22.
ShimizuK, FukudaM, KondoR, SakaiK. (2000) The 5α-reductase inhibitory components from heartwood of Artocarpus incisus: structure-activity investigations. Planta Medica, 66, 16–19.
