Home / Articles / Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity.

Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity.

Alexander Genrikhovich Tolstikov 1
Alexander Genrikhovich Tolstikov
, 
Genrikh Alexandrovich Tolstikov 2
Genrikh Alexandrovich Tolstikov
1 Boreskov Institute of Catalysis SB RAS, Novosibirsk
2 Novosibirsk Institute of Organic Chemistryof the Siberian Branch of Russian Academy of Sciences
10.1070/RC1996v065n05ABEH000219
Published 30 November 1995
Communication , Volume 65, Issue 5, 441-459
2
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Tolstikov A. G., Tolstikov G. A. Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity. // Russian Chemical Reviews. 1996. Vol. 65. No. 5. pp. 441-459.
GOST all authors (up to 50)
Copy cite
Tolstikov A. G., Tolstikov G. A. Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity. // Russian Chemical Reviews. 1996. Vol. 65. No. 5. pp. 441-459.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC1996v065n05ABEH000219
UR - https://rcr.colab.ws/publications/10.1070/RC1996v065n05ABEH000219
TI - Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity.
T2 - Russian Chemical Reviews
AU - Tolstikov, Alexander Genrikhovich
AU - Tolstikov, Genrikh Alexandrovich
PY - 1996
DA - 1995/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 441-459
IS - 5
VL - 65
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1996_Tolstikov,
author = {Alexander Genrikhovich Tolstikov and Genrikh Alexandrovich Tolstikov},
title = {Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity.},
journal = {Russian Chemical Reviews},
year = {1996},
volume = {65},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1996v065n05ABEH000219},
number = {5},
pages = {441--459},
doi = {10.1070/RC1996v065n05ABEH000219}
}
MLA
Cite this
MLA
Copy cite
Tolstikov, Alexander Genrikhovich, and Genrikh Alexandrovich Tolstikov. “Natural aliphatic oxygenated unsaturated acids. Synthesis and biological activity..” Russian Chemical Reviews, vol. 65, no. 5, Nov. 1996, pp. 441-459. https://rcr.colab.ws/publications/10.1070/RC1996v065n05ABEH000219.
Views / Visits / Downloads
16 / 16 / 3

Abstract

The review is devoted to natural unsaturated acyclic acids containing oxygen functions. Compounds of the aceto-genin and propiogenin types containing hydroxy, oxo, and epoxy groups as well as ether, hydrofuran, and hydropyran fragments are considered. Data are given on the biological activities of the acids themselves or of natural compounds whose structural elements are unsaturated acids. The methodology and strategy of the synthesis of both linear unsaturated hydroxy and alkoxy acids and those containing a heterocyclic fragment are discussed. The bibliograhy includes 172 references.

References

1.
Natürliche Fette und Öle – nachwachsende Rohstoffe für die chemische Industrie
Baumann H., Bühler M., Fochem H., Hirsinger F., Zoebelein H., Falbe J.
Angewandte Chemie , 1988
2.
Baumann H., Bühler M., Fochem H., Hirsinger F., Zoebelein H., Falbe J.
1988
4.
A New Glycosphingolipid from the Red AlgaCorallina pilulifera
Ishida R., Shirahama H., Matsumoto T.
Chemistry Letters , 1993
5.
Lesquerolic Acid. A New Hydroxy Acid from Lesquerella Seed Oil1a
SMITH C.R., WILSON T.L., MIWA T.K., ZOBEL H., LOHMAR R.L., WOLFF I.A.
Journal of Organic Chemistry , 1961
6.
Hydroxymonoenoic Acids of Lesquerella densipila Seed Oil
Binder R.G., Lee A.
Journal of Organic Chemistry , 1966
7.
Four fungitoxic C-18 hydroxy unsaturated fatty acids from stromata of
Koshino H., Togiya S., Yoshihara T., Sakamura S., Shimanuki T., Sato T., Tajimi A.
Tetrahedron Letters , 1987
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
11
T. T. Bannister
Diss. Abstr. , 1959
13.
Stereoselective Synthesis of Octadecapolyenoic Esters as an Insecticide
Tsuboi S., Wu X.H., Maeda S., Ono S., Kuroda A., Kawazu K., Takeda A.
Bulletin of the Chemical Society of Japan , 1987
14.
Dimorphecolic Acid—A Unique Hydroxydienoid Fatty Acid2
Smith C.R., Wilson T.L., Melvin E.H., Wolff I.A.
Journal of the American Chemical Society , 1960
15.
15
A. S. Holt
"Research in Photosynthesis" , 1957
16.
Phytoalexines et réactions de défense de la tomate aux infections par Phytophthora parasitica et Verticillium albo-atrum
Vernenghi A., Einhorn J., Kunesch G., Malosse C., Ramiandrasoa F., Ravisé A.
Canadian Journal of Botany , 1986
17.
Expeditious synthesis of the four isomers of methyl dimorphecolate
Duffault J., Einhorn J., Alexakis A.
Tetrahedron Letters , 1991
18.
Densipolic Acid: a Unique Hydroxydienoid Acid from Lesquerella densipila Seed Oil1a
Smith C.R., Wilson T.L., Bates R.B., Scholfield C.R.
Journal of Organic Chemistry , 1962
19.
Synthesis and physiological activities of both enantiomers of coriolic acid and their geometric isomers
Kobayashi Y., Okamoto S., Shimazaki T., Ochiai Y., Sato F.
Tetrahedron Letters , 1987
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
21.
Derivatives of α-D-Glucothiopyranose1
Rowell R.M., Whistler R.L.
Journal of Organic Chemistry , 1966
22.
Convergent stereocontrolled synthesis of 13-hydroxy-9Z, 11E-octadecadienoic acid (13-HODE)
Chan C., Cox P.B., Roberts S.M.
Journal of the Chemical Society Chemical Communications , 1988
23.
Synthesis of 12(R),13(S)-oxido-9-octadecenoic (vernolic) and 13(S)-hydroxy-9, 11-octadecadienoic (coriolic) acids
Moustakis C.A., Weerasinghe D.K., Mosset P., Falck J.R., Mioskowski C.
Tetrahedron Letters , 1986
24.
Short and efficient syntheses of coriolic acid
Rao A.V., Reddy S.P., Reddy E.R.
Journal of Organic Chemistry , 1986
25.
25
G. W. Robinson
J. Chem. Phys. , 1955
28.
Structure elucidation of liposidomycins, a class of complex lipid nucleoside antibiotics
Ubukata M., Kimura K., Isono K., Nelson C.C., Gregson J.M., McCloskey J.A.
Journal of Organic Chemistry , 1992
30.
UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE
Kato T., Yamaguchi Y., Hirano T., Yokoyama T., Uyehara T., Namai T., Yamanaka S., Harada N.
Chemistry Letters , 1984
32.
Synthesis and Structure Confirmation Of Compound D, A Proinflammatory Arachidonate Metabolite
Shin D., Yadagiri P., Falck J.R., Masferrer J.L., Schwartzman M.L.
Tetrahedron Letters , 1989
35.
Marine eicosanoids: Occurrence of 8-(R)-HETE in the starfishPatiria miniata
D'Auria M.V., Minale L., Riccio R., Uriarte E.
Cellular and Molecular Life Sciences , 1988
41.
Dioxamycin, a new benz(a)anthraquinone antibiotic.
SAWA R., MATSUDA N., UCHIDA T., IKEDA T., SAWA T., NAGANAWA H., HAMADA M., TAKEUCHI T.
Journal of Antibiotics , 2012
42.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
47.
Structure and synthesis of unsaturaded trihydroxy c18 fatty
Kato T., Yamaguchi Y., Abe N., Uyehara T., Namai T., Kodama M., Shiobara Y.
Tetrahedron Letters , 1985
48.
Total synthesis of unsaturated trihydroxy C18 fatty acids
Gossé-Kobo B., Mosset P., Grée R.
Tetrahedron Letters , 1989
49.
Unsaturated Polyhydroxy Acids having Prostaglandin-Like Activity from Bryonia alba II. Major Components
Panossian A., Avetissian G., Mnatsakanian V., Batrakov S., Vartanian S., Gabrielian E., Amroyan E.
Planta Medica , 1983
50.
50
G. Glacomello
Gazzetta. , 1935
52.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
53.
(−)-trans-7(S)-Methoxytetradec-4-enoic acid and related amides from the marine cyanophyte Lyngbya majuscula
Cardellina J.H., Dalietos D., Marner F., Mynderse J.S., Moore R.E.
Phytochemistry , 1978
55.
Synthesis of unsaturated trihydroxy C18 fatty acids
Quinton P., Le Gall T.
Tetrahedron Letters , 1991
57.
57
R. Livingston
"Research in Photosynthesis" , 1957
58.
58
N. E. Khomutov
1953
60.
Novel Monounsaturated Fatty Acids from the Sponges Amphimedon compressa and Mycale laevis
Carballeira N.M., Negrón V., Reyes E.D.
Journal of Natural Products , 1992
62.
7-keto-octadec-cis-11-enoic acid from Gardenia lucida seed oil
Mahmood C., Daulatabad J.D., Mohaddin M. Mulla G., Mirajkar A.M., Hosamani K.M.
Phytochemistry , 1991
66.
The macrolactins, a novel class of antiviral and cytotoxic macrolides from a deep-sea marine bacterium
Gustafson K., Roman M., Fenical W.
Journal of the American Chemical Society , 1989
68.
Plant Anticancer Agents, XLIII. (E,E)-7,12-Dioxo-octadeca-8,10-dien-1-oic Acid (Ostopanic Acid), a Cytotoxic Fatty Acid from Ostodes paniculata
Hamburger M., Handa S.S., Cordell G.A., Kinghorn A.D., Farnsworth N.R.
Journal of Natural Products , 1987
69.
70
N. Bubnov
Biofizika , 1960
70.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
71.
STRUCTURE AND SYNTHESIS OF 11,12,13-TRIHYDROXY-9Z,15Z-OCTADECADIENOIC ACIDS FROM RICE PLANT SUFFERING FROM RICE BLAST DISEASE
Kato T., Yamaguchi Y., Ohnuma S., Uyehara T., Namai T., Kodama M., Shiobara Y.
Chemistry Letters , 1986
74.
Total synthesis of colneleic acid
Corey E.J., Wright S.W.
Journal of Organic Chemistry , 1990
76.
Biosynthesis of the meroterpenoid metabolite, andilesin A, by Aspergillus variecolor: origins of the oxygen atoms
Mclntyre C.R., Scott F.E., Simpson T.J., Trimble L.A., Vederas J.C.
Journal of the Chemical Society Chemical Communications , 1986
77.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
78.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
79.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
80.
Absolute Stereochemistry and Novel Ring-Opening Oxidation of Methyl (R)-2-Hydroxysterculate
Nakatani M., Hase T.
Bulletin of the Chemical Society of Japan , 1991
81.
82
G. P. Brin
Biokhimiya , 1957
82.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
83.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
Acyclic diterpenes from Bifurcaria bifurcata
Semmak L., Zerzouf A., Valls R., Banaigs B., Jeanty G., Francisco C.
Phytochemistry , 1988
89.
L-687,781, a new member of the papulacandin family of beta-1,3-D-glucan synthesis inhibitors. I. Fermentation, isolation, and biological activity.
VANMIDDLESWORTH F., OMSTEAD M.N., SCHMATZ D., BARTIZAL K., FROMTLING R., BILLS G., NOLLSTADT K., HONEYCUTT S., ZWEERINK M., GARRITY G., WILSON K.
Journal of Antibiotics , 2012
90.
Mer-WF3010, a new member of the papulacandin family. II. Structure determination.
CHIBA H., KANETO R., AGEMATU H., SHIBAMOTO N., YOSHIOKA T., NISHIDA H., OKAMOTO R.
Journal of Antibiotics , 2012
91.
Structure elucidation of L-687,781, a new β-1,3-D-glucan synthesis inhibitor.
VanMiddlesworth F., Dufresne C., Smith J., Wilson K.E.
Tetrahedron , 1991
92.
(2E,4Z,6E)-, (2E,4E,6E)- and (2E,4E,6Z)-
Crombie L., Horsham M.A., Jarrett S.R.
Tetrahedron Letters , 1989
93.
Structure of AF-toxin II, one of the host-specific toxins produced by alternaria alternata strawberry pathotype
Nakatsuka S., Ueda K., Goto T., Yamamoto M., Nishimura S., Kohmoto K.
Tetrahedron Letters , 1986
94.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
96.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
97.
98
W. Franke
Chem. Zentr. , 1954
98.
Novel sponge-derived amino acids. 11. The entire absolute stereochemistry of the bengamides
Adamczeski M., Quinoa E., Crews P.
Journal of Organic Chemistry , 1990
99.
Novel sponge-derived amino acids. 5. Structures, stereochemistry, and synthesis of several new heterocycles
Adamczeski M., Quinoa E., Crews P.
Journal of the American Chemical Society , 1989
100.
Total synthesis and absolute configuration of bengamide A
Chida N., Tobe T., Okada S., Ogawa S.
Journal of the Chemical Society Chemical Communications , 1992
103.
Trowitzsch-Kienast W., Forche E., Wray V., Reichenbach H., Jurkiewicz E., Hunsmann G., Höfle G.
1992
105.
106
F. Fichter
Helv. Chim. Acta , 1927
106.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
107.
108
F. Fichter
Helv. Chim. Acta , 1924
108.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
109.
Tropical Marine Algae, VII. The Chemical Composition of Marine Algae from North Queensland Waters
Wright A.D., Coll J.C., Price I.R.
Journal of Natural Products , 1990
111.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
112.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
115.
Absolute configuration of A-32'287 [conocandin] and total synthesis of its methyl and tert-butyl esters
Banfi L., Cabri W., Poli G., Potenza D., Scolastico C.
Journal of Organic Chemistry , 1987
116.
Structure and biosynthesis of phomenoic acid, an antifungal compound isolated from Phoma lingam Tode
Devys M., Férézou J., Topgi R.S., Barbier M., Bousquet J., Kollmann A.
Journal of the Chemical Society Perkin Transactions 1 , 1984
117.
Biosynthesis of the fungal polyketide, cubensic acid from Xylaria cubensis.
O'Hagana D., Rogers S.V., Duffin G.R., Edwards R.L.
Tetrahedron Letters , 1992
118.
Studies on the biosynthesis of radiclonic acid
Seto H., Sasaki T., Yonehara H.
Tetrahedron Letters , 1977
119.
Antibiotic 1233A: a fungal β-lactone
Aldridge D.C., Giles D., Turner W.B.
Journal of the Chemical Society C Organic , 1971
120.
Structure of isobongkrekic acid, a novel .DELTA.2-E isomer of the antibiotic bongkrekic acid
Chatterjee S., Vijayakumar E.K., Roy K., Rupp R.H., Ganguli B.N.
Journal of Organic Chemistry , 1988
121.
Calbistrins, novel antifungal agents produced by Penicillium restrictum. II. Isolation and elucidation of structure.
BRILL G.M., CHEN R.H., RASMUSSEN R.R., WHITTERN D.N., MCALPINE J.B.
Journal of Antibiotics , 1993
122.
Tara, Jarvis B.B., Comezoglu S.N., Rao M.M., Pena N.B., Boettner F.E.
Journal of Organic Chemistry , 1987
123.
New Macrocyclic Trichothecenes from Baccharis megapotamica
Jarvis B.B., Cämezoglu S.N., Ammon H.L., Breedlove C.K., Miller R.W., Woode M.K., Streelman D.R., Sneden A.T., Dailey R.G., Kupchan S.M., Bryan R.
Journal of Natural Products , 1987
124.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
125.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
126.
Isolation and structure elucidation of viridiofungins A, B and C
Harris G.H., Turner Jones E.T., Meinz M.S., Nallin-Omstead M., Helms G.L., Bills G.F., Zink D., Wilson K.E.
Tetrahedron Letters , 1993
128.
129
J. Wiemann
Bull. Soc. chim. France , 1955
130.
Pseudomonic acid. Part 1. The structure of pseudomonic acid A, a novel antibiotic produced by Pseudomonas fluorescens
Chain E.B., Mellows G.
Journal of the Chemical Society Perkin Transactions 1 , 1977
132.
Pseudomonic acid derivatives from a marine bacterium
Stierle D.B., Stierle A.A.
Cellular and Molecular Life Sciences , 1992
134.
The total synthesis of zincophorin
Danishefsky S.J., Selnick H.G., DeNinno M.P., Zelle R.E.
Journal of the American Chemical Society , 1987
135.
Herboxidiene: a potent phytotoxic polyketide from Streptomyces sp. A7847
Isaac B.G., Ayer S.W., Elliott R.C., Stonard R.J.
Journal of Organic Chemistry , 1992
137.
138
S. Ono
J. Chem. Soc. Japan , 1957
138.
Synthesis of ring A of ambruticin and proof of its absolute stereochemistry
Just G., Potvin P.
Canadian Journal of Chemistry , 1980
140.
New congeners of swinholides from the okinawan marine sponge Theonella sp.
Tsukamoto S., Ishibashi M., Sasaki T., Kobayashi J.
Journal of the Chemical Society Perkin Transactions 1 , 1991
141.
Polycavernoside A: a novel glycosidic macrolide from the red alga Polycavernosa tsudai (Gracilaria edulis)
Yotsu-Yamashita M., Haddock R.L., Yasumoto T.
Journal of the American Chemical Society , 1993
142.
A novel type secoiridoid glucoside, hydrangenoside a from Hydrangea macrophylla
Inouye H., Takeda Y., Uesato S., Uobe K., Hashimoto T., Shingu T.
Tetrahedron Letters , 1980
143.
L-681,217, a new and novel member of the efrotomycin family of antibiotics.
KEMPF A.J., WILSON K.E., HENSENS O.D., MONAGHAN R.L., ZIMMERMAN S.B., DULANEY E.L.
Journal of Antibiotics , 2012
145.
Macrocyclic trichothecenes
Grove J.F.
Natural Product Reports , 1993
147.
Didemnaketals A and B, HIV-1 protease inhibitors from the ascidian Didemnum sp
Potts B.C., Faulkner D.J., Chan J.A., Simolike G.C., Offen P., Hemling M.E., Francis T.A.
Journal of the American Chemical Society , 1991
148.
The zaragozic acids : structure elucidation of a new class of squalene synthase inhibitors
Hensens O.D., Dufresne C., Liesch J.M., Zink D.L., Reamer R.A., VanMiddlesworth F.
Tetrahedron Letters , 1993
149.
The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity.
DAWSON M.J., FARTHING J.E., MARSHALL P.S., MIDDLETON R.F., O''NEILL M.J., SHUTTLEWORTH A., STYLLI C., TAIT R.M., TAYLOR P.M., WILDMAN H.G., BUSS A.D., LANGLEY D., HAYES M.V.
Journal of Antibiotics , 2012
150.
The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. III. Biosynthesis.
SIDEBOTTOM P.J., HIGHCOCK R.M., LANE S.J., PROCOPIOU P.A., WATSON N.S.
Journal of Antibiotics , 2012
151.
HMG-CoA reductase inhibitors for treatment of hypercholesterolemia.
Oates J.A., Wood A.J., Grundy S.M.
New England Journal of Medicine , 1988
152.
Squalestatin 1, a potent inhibitor of squalene synthase, which lowers serum cholesterol in vivo.
Baxter A., Fitzgerald B.J., Hutson J.L., McCarthy A.D., Motteram J.M., Ross B.C., Sapra M., Snowden M.A., Watson N.S., Williams R.J.
Journal of Biological Chemistry , 1992
153.
Structurally simplified squalestatins: A convenient route to a 67-unsubstituted derivative
Lester M.G., Giblin G.M., Inglis G.G., Procopiou P.A., Ross B.C., Watson N.S.
Tetrahedron Letters , 1993
155.
The squalestatins: C-3 Decarboxylation studies and rearrangement to the 6,8-dioxabicyclo[3.2.1]octane ring system
Chan C., Inglis G.G., Procopiou P.A., Ross B.C., Srikantha A.R., Watson N.S.
Tetrahedron Letters , 1993
156.
Zaragozic Acids D and D2: Potent Inhibitors of Squalene Synthase and of Ras Farnesyl-Protein Transferase
Dufresne C., Wilson K.E., Singh S.B., Zink D.L., Bergstrom J.D., Rew D., Polishook J.D., Meinz M., Huang L., Silverman K.C., Lingham R.B., Mojena M., Cascales C., Pelaéz F., Gibbs J.B., et. al.
Journal of Natural Products , 1993
157.
158
Friedl.
158.
Synthesis of (±)-zearalenone
Rama Rao A.V., Deshmukh M.N., Sharma G.V.
Tetrahedron , 1987
160.
A stereoselective synthesis of coriolic acid and dimorphecolic acid
Rama Rao A.V., Rajarathnam Reddy E., Sharma G.V., Yadagiri P., Yadav J.S.
Tetrahedron , 1986
164.
Total synthesis of bongkrekic acid
Corey E.J., Tramontano A.
Journal of the American Chemical Society , 1984
166.
Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin
Guindon Y., Yoakim C., Gorys V., Ogilvie W.W., Delorme D., Renaud J., Robinson G., Lavallee J.-., Slassi A.
Journal of Organic Chemistry , 1994
167.
Nicolaou K.C., Yue E.W., Naniwa Y., De Riccardis F., Nadin A., Leresche J.E., La Greca S., Yang Z.
1994
168.
Nicolaou K.C., Nadin A., Leresche J.E., Yue E.W., Greca S.L.
1994
169.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
171.
178
1946