Novel Phthalide Compounds from <i>Sparassis crispa</i> (Hanabiratake), Hanabiratakelide A&mdash;C, Exhibiting Anti-cancer Related Activity

Abstract

Sparassis crispa (SC), known as Hanabiratake in Japanese, is an edible mushroom with various medicinal properties. We isolated 3 novel phthalides, designated hanabiratakelide A (1), B (2), and C (3), from the SC fruit body. In this investigation, 3 known phthalides (4-6), ubiquinone-9, and 2 known unsaturated fatty acids were also isolated. Their structures were elucidated primarily through extensive NMR experiments. The isolated compounds 1-6 were tested for their anti-oxidant activity. The in vitro superoxide dismutase-like activity of the 3 hanabiratakelides was stronger than that of vitamin C. The compounds also exerted inhibitory effects on lipopolysaccharide-stimulated nitric oxide and prostaglandin E2 production by a murine macrophage cell line, RAW264. In addition, the growth of the colon cancer cell lines Caco-2 and colon-26 was significantly inhibited by treatment with the 3 hanabiratakelides. In vivo, the frequency of azoxymethane-induced aberrant crypt foci was reduced in SC-fed F344/N rats compared to rats fed a standard diet. In conclusion, 3 novel phthalides, hanabiratakelides, derived from SC were shown to possess anti-oxidant, anti-inflammatory, and anti-tumor activity.

Natural Products and Biological Activity of the Pharmacologically Active Cauliflower MushroomSparassis crispa

“…Yoshikawa et al isolated three novel phthalides, designated hanabiratakelide A (8), B (9), and C (10) in addition to three known phthalides, from the S. crispa fruiting body [34]. The 6 isolated compounds were tested for their antioxidant activity.…”

“…S. crispa feeding dose-dependently suppressed the malignant changes of ACF by 54% (0.3% group), 64% (1.0% group), and 75% (3.0% group). They concluded that the anticancer-related activity may originate from the aforementioned hanabiratakelides [34]. …”

Vegetative Development of &lt;i&gt;Sparassis crispa&lt;/i&gt; in Various Growth Conditions and Effect of Electric Pulse Simulation on Its Fruit Body Production

“…The results obtained from headspace analysis indicate that 3-octanone, DL-3-octanol, and 1-octen-3-ol contribute to the particular aroma of this mushroom [4]. Medicinal properties in S. crispa include anticancer activities‚ antiangiogenic‚ anti-metastatic, wound healing and immune stimulation effects [5]- [7]. It has been recorded that β-glucan content of S. crispa is about 43.6% as measured by enzyme method by Japan Food research laboratories.…”

Морфолого-культуральні властивості рідкісного лікарського гриба Sparassis crispa (Sparassidaceae, Polyporales)

“…Сучасні відомості щодо лікувальних властивостей S. crispa свідчать про широкий біологічний спектр дії цього гриба (Tada et al, 2007;Dalonso et al, 2015). Встановлено, що екстракти, отримані як з плодових тіл, так і міцеліальної маси даного виду, мають імуномодулюючий, онкостатичний і антиметастатичний ефекти (Woodward et al, 1993;Kwon et al, 2009;Yamamoto et al, 2009;Yoshikawa et al, 2010;Takashi, 2013). За умов глибинного і поверхневого культивування штами S. crispa здатні до біосинтезу антибіотиків і цитокінінів (Dyakov et al, 2011;Vedenicheva et al, 2016).…”