Hirsutanonol

Planta Med. 2013 Apr;79(6):499-505.

Diarylheptanoids from Alnus glutinosa bark and their chemoprotective effect on human lymphocytes DNA.[Pubmed: 23512500]

METHODS AND RESULTS:
A study of secondary metabolites from the bark of Alnus glutinosa led to the isolation of fourteen diarylheptanoids: oregonin (1), platyphylloside (2), rubranoside A (3), rubranoside B (4), Hirsutanonol (5), hirsutenone (6), Hirsutanonol-5-O-β-D-glucopyranoside (7), platyphyllonol-5-O-β-D-xylopyranoside (8), aceroside VII (9), alnuside A (10), alnuside B (11), 1,7-bis-(3,4-dihydoxyphenyl)-5-hydroxy-heptane-3-O-β-D-xylopyranoside (12), (5S)-1-(4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)-5-O-β-D-glucopyranosyl-heptan-3-one (13), and (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-O-β-D-[6-(3,4-dimethoxycinnamoylglucopyranosyl)]-heptan-3-one (14). All of the diarylheptanoids, except 1 and 5, were found in A. glutinosa for the first time, while 13 and 14 were new compounds. The structures were determined by spectroscopic techniques: 1D and 2D NMR, HR-ESI-MS, FTIR, UV, and CD. All isolated compounds were analyzed for an in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus assay.
CONCLUSIONS:
The majority of them, including the new compounds 13 and 14, exerted a pronounced effect in decreasing DNA damage in human lymphocytes. Diarylheptanoids 1, 2, 5, 13, and 14 at a concentration of 1 µg/mL decreased the frequency of micronuclei by 52.8 %, 43.8 %, 63.6 %, 44.4 %, and 56.0 %, respectively, exerting a much stronger effect than the synthetic protector amifostine (17.2 %, c = 1 µg/mL).

Arch Pharm Res. 2008 Oct;31(10):1287-9.

Cytotoxic activities of diarylheptanoids from Alnus japonica.[Pubmed: 18958419]

METHODS AND RESULTS:
The diarylheptanoids (1-10) 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranoside (1), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-O-beta-D-apiofuranosyl(1-->6)-beta-D-glucopyranoside (2), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-beta-D-glucopyranoside (3), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane (4), 1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-beta-D-glucopyranoside (5), oregonin (6), Hirsutanonol (7), hirsutenone (8), 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-O-beta-D-xylopyranoside (9), and platyphylloside (10), isolated from the bark of Alnus japonica, were analyzed for their cytotoxic activities on various human and mouse cancer cell lines. The cytotoxic activities of these ten compounds were evaluated against murine B16 melanoma, human SNU-1 gastric cancer, human SNU-354 hepatoma cancer and human SNU-C4 colorectal cell lines.
CONCLUSIONS:
The diarylheptanoids showed potent cytotoxic activities against murine B16 melanoma cells and human SNU-C1 gastric cancer cell when the cell viability was analyzed by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide) assay.

Korean J. Medicinal Crop Sci.,2005,13(2):85-90.

Constituents and their DPPH Scavenging Activities from the Leaves of Alnus hirsuta (Spach) Rupr.[Reference: WebLink]

METHODS AND RESULTS:
Phytochemical study on the EtOAc fraction from a MeOH extract of the leaves of Alnus hirsuta Rupr. led to the isolation of nine compounds betulin (1), betulinic acid (2), Hirsutanonol (3), hirsutenone (4), quercetin (5), avicularin (6), gallic acid (7), hyperin (8), and daucosterol (9). Among them, six compounds 1, 2, 57, and 9 are report from this plant for the first time. All isolated compounds were evaluated for their antioxidant activity using DPPH radical scavenging capacity and inhibition effect on mitochondrial lipid peroxidation.
CONCLUSIONS:
Six phenolic compounds 3-8 were found to have potent antioxidant activity. Of which, compounds 3, 4 and 5 showed significant free radical scavenging activity with the values of , respectively. In addition, the compounds 3-8 exhibited inhibition effect on the mitochondrial lipid peroxidation with the values of , respectively.

Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(6):1040-2.

Chemical constituents from roots of Chirita longgangensis var. hongyao.[Pubmed: 24956847]

METHODS AND RESULTS:
To study the chemical constituents from the roots of Chirita longgangensis var. hongyao. The methanol extract was isolated and purified by silica gel, Sephadex LH-20 and preparative HPLC. Their structures were elucidated by MS and spectral data (1H, 13C-NMR). Seven compounds were isolated and identified as plantainoside A (1), plantainoside B (2), calcedarioside C (3), calcedarioside D (4), platyphylloside (5), Hirsutanonol (6), and Hirsutanonol-5-O-beta-D-glucopyranoside (7).
CONCLUSIONS:
Compounds 5-7 were isolated for the first time from the family Gesneriaceae.

Phytomedicine. 2013 Jan 15;20(2):124-32.

Antifilarial diarylheptanoids from Alnus nepalensis leaves growing in high altitude areas of Uttarakhand, India.[Pubmed: 23219341]

Lymphatic filariasis continues to be a major health problem in tropical and subtropical countries. A macrofilaricidal agent capable of eliminating adult filarial parasites is urgently needed. Platyphyllenone (A), alusenone (B), hirustenone (C) and Hirsutanonol (D) are important biologically active diarylheptanoids present in Alnus nepalensis. In the present study, we report the antifilarial activity in diarylheptanoids isolated from the leaves of A. nepalensis.
METHODS AND RESULTS:
Out of four compounds (A-D) tested in vitro one has shown promising anti-filarial activity both in vitro and in vivo studies. This is the first ever report on antifilarial efficacy of a compound of the plant and warrants further studies around this scaffold. In addition, a sensitive, selective and robust densitometric high-performance thin-layer chromatographic method was developed and validated for the above four biomarker compounds. The separation was performed on silica gel 60F(254) high-performance thin layer chromatography plates using chloroform:methanol (9:1, v/v) as mobile phase.
CONCLUSIONS:
The quantitation of marker compounds was carried out using densitometric reflection/absorption mode at 600 nm after post-chromatographic derivatization using vanillin-sulfuric acid reagent. The method was validated for peak purity, precision, robustness, limit of detection (LOD) and quantitation (LOQ) etc., as per the International Conference on Harmonization (ICH) guidelines.

Biol Pharm Bull. 2000 Apr;23(4):517-8.

Inhibition of cyclooxygenase-2 expression by diarylheptanoids from the bark of Alnus hirsuta var. sibirica.[Pubmed: 10784440]

METHODS AND RESULTS:
Two known diarylheptanoids, oregonin (1), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-heptane-3-one-5-O-beta-D-xylopyranosi de and Hirsutanonol (2), (5S)-1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxyheptane-3-one isolated from the bark of Alnus hirsuta var. sibirica, showed significant inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced cyclooxygenase-2 (COX-2) expression in immortalized human breast epithelial MCF10A cells.