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St. John's Wort (Hypericum Perforatum L.): A Review

© 1996 Christopher Hobbs L.Ac., A.H.G. 
(Excerpted from HerbalGram)

(9 of 9)  


Ideally, the commercial drug should consist mostly of flowering tops, but in common practice the whole above-ground plant with a considerable quantity of stem may be present. Flowers that are present should consist of 70-90% (or more) with immature capsules, otherwise the plants may have been harvested too late in the season. The hypericin content declines immediately after anthesis (flower maturity and pollination).

The leaves, when observed with a 10X hand lens, should be characterized by many punctate glands, clearly distinguishable by holding them up to a light source. The flowers will all contain fragments of the persistent dried petals, which may have red glands (appearing black) around the perimeter.

The taste (and smell) of St. John's wort is characteristicly slightly sweet, bitter, and astringent.

A commercial oil or tincture of Hypericum should be vivid, almost fluorescent red. If the preparation is pale red to pink, the hypericin content, and thus the quality of the product, is suspect.

Several methods are given in the literature for the TLC and HPLC identification of hypericin (130, 131, 132, 133, 134, 135, 136, 137, 138), and Katalin et al (1982) report on the histological examination of St. John's wort leaves (139).

Since tannins play a role in the therapeutic action of St. John's wort extracts, standardization with this fraction has been recommended (liquid extract containing 1% tannins) (140).


Literature

Review: An earlier review (1969) covers the history, development and photodynamic effect, chemical constituents, synthesis of hypericin, pharmacology and uses with 127 references (in German) 141.


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4. Hickey, M. & C. King. 1981. 100 Families of flowering plants, Cambridge University Press, Cambridge.
5. Wichtl, M. 1986. "Hypericum perforatum L. --Das Johanniskraut", Zeitschrift fur Phytotherapie 3: 87-90.
6. Campbell, M.H., et al. 1979. "Effect of time of application of herbicides on the long-term control of St. John's wort (Hypericum perforatum var. angustifolium)," Aust. J. Exp. Agric. Anim. Husb. 101: 746-8.
7. Pickering, C. 1879. Chronological History of Plants, Little, Brown & Co., Boston.
8. Jones, W.H.S. 1964. Pliny--Natural History v. VI: 8, 53. Harvard University Press, Cambridge.
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10. Fernie, W.T. 1897. Herbal Simples, John Wright & Co., Bristol.
11. Jaeger, E.C. 1972. A Source-Book of Biological Names and Terms. Charles C. Thomas, Springfield, IL.
12. Vickery, A.R. 1981. "Traditional uses and flolklore of Hypericum in the British Iles", Economic Botany 35: 289-295.
13. Fernie, Herbal Simples.
14. Gunther, R.T. 1933. The Greek Herbal of Dioscorides, Hafner Pub. Co. (1968).
15. Pickering, op cit.
16. Vickery, op cit.
17. Alleyne, J. 1733. A New English Dispensatory, Tho. Astley, London.
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19. Vickery, op cit.
20. Gerard, J. 1633. The Herbal. Revised and enlarged by T. Johnson, reprinted by Dover Publications, NY (1975).
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22. Fernie, op cit.
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29. Griffith, R.E. 1847. Medical Botany, Lea & Blanchard, Philadelphia.
30. King, J. 1876. The American Dispensatory, 10th ed., Wilstach, Baldwin & Co., Cincinnati.
31. Felter, H.W. & J.U. Lloyd. 1898. King's American Dispensatory, 18th ed., reprinted by Eclectic Medical Publications, Portland, OR.
32. Lust, J. 1974. The Herb Book. Bantam, NY.
33. Moore, M. 1979. Medicinal Plants of the Mountain West, Museum of New Mexico Press, Sante Fe.
34. Kitanov, G.M. & K.F. Blinova. 1987. "Modern state of the chemical study of species of the genus Hypericum." Chemistry of natural compounds 23: 151-66.
35. Brockmann, H., et al. 1974. "Zur isolierung und konstitution des pseudohypericins," Tetrahedron Lett. 23: 1991-4.
36. Dorossiev, I. 1985. "Determination of flavonoids in Hypericum perforatum," Pharmazie 40: 585-6.
37. Mathis, C. & G. Ourisson. 1963. "Etude chimio-taxonomique du genre Hypericum," Phytochemistry 2: 157-171.
38. Okpanyi, S.N. & M.L. Weischer. 1987. "Experimental animal studies of the psychotropic activity of a Hypericum extract," Arzneim.-Forsch 37: 10-13.
39. Meruelo, D., et al. 1988. "Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: Aromatic polycyclic diones hypericin and pseudohypericin," Proc. Ntl. Acad. Sci. 85: 5230-34.
40. Kitanov, G. 1983. "Determination of the absolute configuration of ctechins isolated from Hypericum perforatum," Farmatsiya (Sofia) 33: 19-22 (CA 99:50290j).
41. Wichtl, op cit.
42. Derbentseva, et al. 1972. "Effect of tannins from Hypericum perforatum on influenza viruses," Mikrobiol. Zh. (Kiev) 34: 768-72.
43. Karryev, M.O. & N.F. Komissarenko. 1980. Izv. Akad. Nauk Turkm. SSR, Ser. Biol. Nauk 1980: 52-7. (CA 93: 182809w).
44. Dorossiev, I, op cit.
45. Stoyanova, A., et al. 1987. "Thin-layer chromatography of extracts of Hypericum perforatum," Farmatsiya 1: 8-13 (CA 107:205272q).
46. Hoelzl, J. & E. Ostrowski. 1987. "St. John's wort (Hypericum perforatum L.) HPLC analysis of the main components and their variability in a population," Dtsch. Apoth. Ztg. 127: 1227-30 (CA 107:112686).
47. Berghoefer, R. & J. Hoelzl. 1987. "Biflavonoids in Hypericum perforatum. Part 1. Isolation of 13,II8- biapigenin," Planta Med. 53: 216-17.
48. Koget, T.A. 1972. "Determination of the amount of quercitrin in Hypericum perforatum," Khim. Prir. Soedin. (2): 242-3 (CA 77:45514b).
49. Maksyutina, N.P. & T.A. Koget. 1971. "Polyphenols from the grass Hypericum perforatum and the preparation novoimanin," Khim. Prir. Soedin. 7: 363-7 (CA 75:115923u).
50. Holzl, J. & E. Ostrowski. [d.m.]. "Analysis of the essential compounds of Hypericum perforatum," Planta Medica [v.m.]: 531.
51. Vasil'chenko, et al. 1986. "Analgesic action of flavonoids of Rhododendron luteum Sweet, Hypericum perforatum L., Lespedeza bicolor Turoz. and L. hedysaroides (Pall.) Kitag," Rastit. Resur. 22: 12-21 (CA 104:142140k).
52. Dittmann, J., et al. 1971. "Normalizing glucose metabolism in brain tumor slices by hyperoside," Arzneim.-Forsch. 21: 1999-2002.
53. National Academy of Sciences. 1975. "Herbal Pharmacology in the People's Republic of China," N.A.S., Washington.
54. Vasilchenko, E.A., et al. 1986. "The analgesic effect of flavonoids of Rhododendron luteum Sweet, Hypericum perforatum, Lespedeza bicolor Turoy and L. hedysaroides (Pall)," Kitaz. Rastit. Resur. 22: 12-21.
55. Nielsen, M. & P. Arends. 1978. Phytochemistry 17: 2040.
56. Suzuki, O., et al. 1984. Planta Med. 50: 272.
57. Hostettmannn, K. & H. Wagner. 1977. Phytochemistry 16: 821.
58. Denisova-Dyatlova, O.A. & V.I. Glyzin. 1982. Glyzin. Usp. Khim. 51: 1753.
59. Karryev, op cit.
60. Ayuga, C. & Rebuelta, M. 1986. "Comparative study of phenolic acids of Hypericum caprifolium Boiss. and Hypericum perforatum L.," An. R. Acad. Farm. 52: 723-7 (CA 107: 74319k).
61. Ollivier, B., et al. 1985. "Separation and identification of phenolic acids by high-performance liquid chromatography and ultraviolet spectroscopy. Application to Parietaria officinalis L. and to Saint-John's-wort (Hypericum perforatum L.)." J. Pharm. Belg. 40: 173-7.
62. Guevich, A.I., et al. 1971. "Hyperforin, an antibiotic from Hypericum perforatum," Antibiotiki 16: 510-2.
63. Brondz, I., et al. 1983. "The absolute configuration of hyperforin, an antibiotic from Hypericum perforatum L., based on the crystal structure determination of its p-bromobenzoate ester," Acta Chem. Scand., Ser. A A37: 263-5 (in English).
64. Gurevich, A.I., et al. 1971. "Hyperforin, an antibiotic from Hypericum perforatum," Antibiotiki (Moscow) 16: 510-13 (CA 75:95625t).
65. Negrash, A.K. & P.Ya. Pochinok. 1972. "Comparative study of chemotherapeutic and pharmacological properties of antimicrobial preparations from common St. John's wort," Fitonotsidy, Mater. Soveshch. 6th, Meeting date 1969, 198-200 (CA 78:66908u).
66. Sticher, O. 1977. "Plant mono-, di- and sesquiterpenoids with pharmacological or therapeutical activity," in New Natural Products and Plant Drugs with Pharmacological, Biological or Therapeutical Activity, ed. by H. Wagner & P. Wolff, Springer-Verlag, NY.
67. Khosa, R.L. & N. Bhatia. 1982. "Antifungal effect of Hypericum perforatum,: J. Sci. Res. Plants Med. 3: 49-50.
68. Chialva, F., et al. 1981. "Study on the composition of the essential oil from Hypericum perforatum L. and Teucrium chamaedrys L.," Riv. Ital. EPPOS 63: 286-8 (CA 96:11497a).
69. Mathis, C. & G. Ourisson. 1964. Phytochemistry 3: 133.
70. Mathis, C. & G. Ourisson. 1964. "Etude chimio-taxonomique du genre Hypericum-IV," Phytochemistry 3: 377-8.
71. Brondz, I., et al. 1983. "n-Alkanes of Hypericum perforatum: a revision", Phytochemistry 22: 295-6.
72. Mathis, C. & G. Ourisson. 1964. "Etude Chimio-taxonomique du genre hypericum-III," Phytochemistry 3: 133-141.
73. Brondz, I. & T. Greibrokk. [d.m.]. "n-1-alkanols of Hypericum perforatum", Journal of Natural Products 46: 940-1.
74. Snider, S.R. 1984. "Octacosanol in Parkinsonism [letter]," Ann. Neurol. 16: 723.
75. Yamashita, M, et al. 1986. "Aqeuous compositions containing octacosanol," Japanese patent: JP 86263937, date: 861121.
76. Hohnen oil co., Ltd. 1985. "Encapsulated health food supplements," Japanese patent: JP 85149367 A2, date: 850806.
77. Mori, M. 1982. "n-hexacosanol and n-octacosanol: feeding stimulants on the larvae of the silkworm, Bombyx mori," J. of Insect Physiology 28: 969-73.
78. Tandan, R. & W.G. Bradley. 1985. "Amyotrophic lateral sclerosis: part I. Clinical features, pathology, and ethical issues in management," Ann. Neurol. (USA) 18/3: 271-80.
79. Gonsette, R.E. 1982. "Treatment of multiple sclerosis," Bull. Soc. Belge. Ophtalmol 199-200: 275-80.
80. Noris, F.H., et al. 1986. "Trial of octacosanol in amyotrophic lateral sclerosis," Neurology (USA) 36/9: 1263-64.
81. Costes, C. & T. Chantal. 1967. "Carotenoid pigments of the petals of the inflorescence of St.-John's- wort (Hypericum perforatum)," Ann. Physiol. Veg. 9: 157-77 (CA 68:66335y).
82. Kitanov, op cit.
83. Mathis C., & G. Ourisson. 1964. "Etude Chimio-taxonomique du genre Hypericum-V.", Phytochemistry 3: 379.
84. Prokosheva, L.I. & L.V. Shatunova. 1985. "Content of active substances in the aboveground parts of Hypericum perforatum," Rastit. Resur. 21: 461-3.
85. Gozin, A.A. & V.S. Yasnetsov. 1979. "Effect of mineral fertilizers on the content levels of biologically active substances in common St.-John's-wort," Depositied Doc., VINITI 1108-79, 8 pp. Avail. VINITI (CA 92:127708s).
86. Razinskaite, D. 1970. "Active substances of St.-Joh's-wort. 1. Dynamics of the level of tannins," Liet. TSR Mokslu Akad. Darb., Ser. C (1): 47-53 (CA 73:127742f).
87. Zhebeleva, T.I. 1973. "Effect of ecological conditions on the morphology and flavonoid accumulation of Hypericum perforatum," Rast. Resur. 9: 402-4 (CA 80:12660e).
88. Razinskaite, D. 1971. "Active substances of Hypericum perforatum St. John's wort). 2. Flavonoids and dynamics of their content", Liet. TSR Mokslu Akad. Darb., Ser. C (1): 89-100 (CA 75:72427r).
89. Tsitsina, S.I. "Results of studying some medicinal plants containing flavone compounds," Tr. Bot. Sadov, Akad. Nauk Kaz SSR 11: 111-14 (CA 73:32345q).
90. Morelli, I., et al. 1983. "Selected Medicinal Plants," FAO Plant Production and Protection Paper 53/1, Rome.
91. [author missing]. 1981. "Uterotonic action of extracts from a group of medicinal plants," Vet. Med. Nauki 18: 94-8.
92. [author missing]. 1988. Fitoterapia 59: 165.
93. Vander, A.J., et al. 1970. Human Physiology, McGraw-Hill Book Co., NY.
94. American Medical Association. 1983. AMA Drug Evaluations, AMA, Chicago.
95. Suzuki, O., et al. 1980. "Inhibition of type A and type B monoamine oxidase by isogentisin and its 3-0- glucoside," Planta Medica 39: 19-23.
96. Suzuki, et al. 1981. "Inhibition of type A and type B monoamine oxidases by naturally occurring xanthones," Planta Medica 42: 17-21.
97. Suzuki, O., et al. 1984. "Inhibition of monoamine oxidase by hypericin," Planta Medica 50: 272-4.
98. Okpanyi, Von S.N. & M.L. Weishcer. 1987. "Tierexperimentelle Untersuchungen zur psychotropen wirksamkeit eines Hypericum-extraktes," Arzneim.-Forsch. 37: 10-13.
99. Muldner, Von H. & M. Zoller. 1984. "Antidepressive wirkung eines auf den wirkstoffkomplex hypercin standardisierten hypericum-extraktes," Arzneim.-Forsch. 34: 918.
100. Negrash, A.K., op cit.
101. Aizenman, B.E. 1969. "Antibiotic preparations from Hypericum perforatum," Mikrobiol. Zh. (Kiev) 31: 128-33, (CA 70: 118006e).
102. Derbentseva, N.A. & A.S. Rabinovich. 1968. "Isolation, purification, and study of some physicochemical properties of novoimanin," in Novoimanin Ego Lech. Svoistva, 15-18, Edited by: Solov'eva, A.I., "Naukova Dumka": Kiev, USSR.
103. Gurevich, A.I., op cit.
104. Saljic, J. 1975. "Ointment for the treatment of burns," Ger. Offen. 2,406,452 (CL. A61K), 21 Aug 1975 (CA 83: 197797).
105. [author missing]. 1981. "Anti-inflammatory action of a group of plant extracts," Vet. Med. Nauki 18: 87-94.
106. Proserpio, G. 1976. "Natural sunscreens: vegetable derivatives as sunscreens and tanning agents," Cosmet. Toiletries 91: 34, 39-44, 46.
107. Morelli, I., op cit.
108. Meruelo, D., G. Lavie & D. Lavie. 1988. "Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: aromatic polycyclic diones hypericin and pseudohypericin," Proc. Natl. Acad. Sci. 85: 5230-5234.
109. Scheel, L.D. 1972. "Photosensitizing agents," in Toxicants Occuring Naturally in Food, National Academy of Sciences, Washington.
110. Weiss, R.F. 1988. Herbal Medicine, Beaconsfield Publishers Ltd, Beaconsfield, England.
111. Scheel, L.D., op cit.
112. Marsh, C.D. 1930. "Toxic effect of St. Johnswort (Hypericum perforatum) on cattle and sheep," USDA Technical bulletin No. 202.
113. Araya, O.S., op cit.
114. Garrett, B.J., et al. 1982. "Consumption of poisonous plants (Senecio jacobaea, Symphytum officinale, Pteridium aquilinum, Hypericum perforatum) by rats: chronic toxicity, mineral metabolism, and hepatic drug-metabolizing enzymes," Toxicology Letters 10: 183-88.
115. Pace, N. & G. MacKinney. 1941. "Hypericin, the photodynamic pigment from St. John's wort," Journal of the Am. CHem Soc. 63: 2570-74.
116. Clare, N.T. 1952. "Photosensitization in diseases of domestic animals," Review Sweries No. 3 of the Commonwealth Bureau of Animal Health, Commonwealth Agricultural Bureaux, Bucks, England.
117. James, L.F. & A.E. Johnson. 1976. "Some major plant toxicities of the western United States," J. of Range Manag. 29: 356-63.
118. Araya, O.S., op cit.
119. Zaichikova, S.G., et al. 1985. "Study of the healing properties and determination of the upper parameters of toxicity of Hypericum," Farmatsiya 1: 62.
120. Roth, L., et al. 1984. Giftpflanzen--Pflanzengifte, ecomed, Munich.
121. Weiss, R.F., op cit.
122. Merck 1907 Index. Merck & Co., Rahway, NJ.
123. Todd, R.G. 1967. Martindale's Extra Pharmacopoeia, The Pharmaceutical Press, London.
124. Georgiev, E., et al. 1985. Effect of solvent and moisture of St. John's wort on extraction of some biologically active substances. II. Extraction of hypericin with glycol," Nauchni Tr. - Vissh Inst. Khranit. Vkusova Prom-st., Plovdiv 32: 257-63 (CA 105:29872h).
125. Georgiev, E., et al. 1985. "Effect of solvent and moisture of St. John's Wort on extraction of some biologically active substances. I. Extraction of hypericin with glycerides and ethyl alcohol," Nauchni Tr. Vissh Inst. Khranit. Vkusova Promst., Plovdiv 32: 251-6 (CA 105:29871g).
126. Georgiev, E., et al. 1983. "Extraction of Hypericum perforatum L.," Nauchni Tr. - Vissh Inst. Khranit. Vkusova Prom-st., Plovdiv 30: 175-83 (CA 101: 197996n).
127. Adamski, R. & E. Styp-Rekowska. 1971. "Stability of hypericin in juice, dry extract, and tablets from Hypericum perforatum plants," Farm. Pol. 27: 237-41 (CA 75:91286k).
128. Araya, O.S. & E.J.H. Ford. 1981. "An investigation of the type of photosensitization caused by the ingestion of St. John's wort (Hypericum perforatum) by calves," J. COmp. Path. 91: 135-41.
129. Todd, R.G. (ed.). 1977. Martindale's Extra Pharmacopoeia, The Pharmaceutical Press, London.
130. Hoelzl, op cit.
131. Dorosiev, I. 1985. "Determination of flavonoids in Hypericum perforatum," Pharmazie 40: 585-6 (in English).
132. Ollivier, op cit.
133. Pachaly, P. 1984. "Thin layer chromatography in the pharmacy: Practical examples," Dtsch. Apoth. Ztg. 124: 2153-61.
134. Freytag, W.E. 1984. "Determination of hypericin and pseudohypericin in Hypericum perforatum L. with HPLC," Dtsch. Apoth. Ztg 124: 2383-6.
135. Vanhaelen, M. & R. Vanhaelen-Fastre. 1983. "Quantitative determination of biologically active constituents in medicinal plant crude extracts by thin-layer chromatography-densitometry. I. .....Hypericum perforatum...Silybum marianum..(and others)," J. Chromatogr. 281: 263-71 (in English).
136. Chialva, F. , et al. 1983. "Direct headspace gas chromatographic analysis with glass capillary columns in quality control of aromatic herbs," J. Chromatogr. 279: 333-40 (in English).
137. Holzl, J. & E. Ostrowski, op cit.
138. Steinbach, R.A. 1981. "Problems in the purification and standardization of plant drugs, for example, Hypericum," Z. Angew. Phytother. 2:221-4 (CA 98: 113563c)
139. Katalin, L., et al. 1982. "Ultrastructural Examination of leaf differentiation in St. John's wort", Herba Hung. 21: 21-37.
140. Azaryan, R.A. 1985. "Standardization of [quality indexes for the medicinal] herb Hypericum perforatum," Farmatsiya (Moscow) 34: 18-21 (CA 104: 56271x).
141. Schilling, W. 1969. "A Review.....," Praep. Pharm. 5: 125-34.

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