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Progress in the Chemistry of Organic Natural Products

A. Douglas Kinghorn · Heinz Falk

Simon Gibbons · Jun’ichi Kobayashi
Yoshinori Asakawa · Ji-Kai Liu Editors

108
Progress in the
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Organic Natural
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Progress in the Chemistry of Organic Natural
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Founded by László Zechmeister

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Heinz Falk, Linz, Austria
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Yoshinori Asakawa, Tokushima, Japan
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A. Douglas Kinghorn • Heinz Falk •
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Editors

Progress in the Chemistry of

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Volume 108

With contributions by

R. Mata
M. Figueroa
A. Navarrete
I. Rivero-Cruz

S. Fiorito
F. Epifano
F. Preziuso
V. A. Taddeo
S. Genovese

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R. G. de Souza Berlinck
Editors
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College of Pharmacy Institute of Organic Chemistry
The Ohio State University Johannes Kepler University
Columbus, OH, USA Linz, Austria

Simon Gibbons Jun’ichi Kobayashi

UCL School of Pharmacy Grad. School of Pharmaceutical Science
University College London, Research Hokkaido University
London, UK Fukuoka, Japan

Yoshinori Asakawa Ji-Kai Liu

Faculty of Pharmaceutical Sciences School of Pharmaceutical Sciences
Tokushima Bunri University South-Central Univ. for Nationalities
Tokushima, Japan Wuhan, China

ISSN 2191-7043 ISSN 2192-4309 (electronic)

Progress in the Chemistry of Organic Natural Products
ISBN 978-3-030-01098-0 ISBN 978-3-030-01099-7 (eBook)
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Contents

Chemistry and Biology of Selected Mexican Medicinal Plants . . . . . . . 1

Rachel Mata, Mario Figueroa, Andrés Navarrete, and Isabel Rivero-Cruz
Biomolecular Targets of Oxyprenylated Phenylpropanoids and
Polyketides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 143
Serena Fiorito, Francesco Epifano, Francesca Preziuso,
Vito Alessandro Taddeo, and Salvatore Genovese
Secondary Metabolites of Endophytic Actinomycetes: Isolation,
Synthesis, Biosynthesis, and Biological Activities . . . . . . . . . . . . . . . . . 207
Darlon Irineu Bernardi, Fernanda Oliveira das Chagas, Afif Felix Monteiro,
Gabriel Franco dos Santos, and Roberto Gomes de Souza Berlinck

v
Chemistry and Biology of Selected Mexican
Medicinal Plants

Rachel Mata, Mario Figueroa, Andrés Navarrete, and Isabel Rivero-Cruz

Contents
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
2 Mexican Medicinal Plants Employed for Treating Major National Health Problems . . . . . . 3
2.1 Diabetes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
2.1.1 Swietenia humilis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
2.1.2 Mexican “Copalchis”: Hintonia latiflora, Hintonia standleyana,
and Exostema caribaeum . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9
2.1.3 Salvia circinata . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18
2.2 Smooth Muscle-Relaxant Agents for Gastrointestinal and Cardiovascular Illnesses . 22
2.2.1 Scaphyglottis livida, Maxillaria densa, and Nidema boothii . . . . . . . . . . . . . . . . . . 22
2.3 Antiulcer Agents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
2.3.1 Amphipterygium adstringens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
2.3.2 Ligusticum porteri . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
2.3.3 Hippocratea excelsa . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40
2.4 Analgesic and Anti-inflammatory Agents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
2.4.1 Hofmeisteria schaffneri . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46
2.4.2 Artemisia ludoviciana . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
2.5 Antiparasitics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
2.5.1 Dysphania graveolens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 65
2.5.2 Geranium niveum . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
2.6 Cytotoxic Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72
2.6.1 Annona mucosa . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
2.6.2 Annona purpurea . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
2.7 Anxiolytic and Sleep-Aid Agents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81
2.7.1 Valeriana procera . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82

R. Mata (*) · M. Figueroa (*) · A. Navarrete · I. Rivero-Cruz

Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México,
Ciudad de México, México
e-mail: [email protected]; mafi[email protected]; [email protected]; [email protected]

© Springer Nature Switzerland AG 2019 1

A. D. Kinghorn, H. Falk, S. Gibbons, J. Kobayashi, Y. Asakawa, J.-K. Liu (eds.),
Progress in the Chemistry of Organic Natural Products, Vol. 108,
https://doi.org/10.1007/978-3-030-01099-7_1
2 R. Mata et al.

2.8 Antiasthmatic Agents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87

2.8.1 Pseudognaphalium liebmannii . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88
3 Concluding Remarks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92
Appendix . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 93
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 118

1 Introduction

Mexico is a multifaceted and heterogeneous country with high cultural richness and
10–12% of the world’s biodiversity. This country ranks 4th in the variety of vascular
plants with about 31,000 different species; of this stock more than 3350 form part of
the medicinal flora. When the Spanish conquerors arrived to ancient Mexico, they
found existing civilizations with a holistic view of illnesses and healing. These early
Mesoamericans inhabitants used religious, magic rituals and a variety of plant-based
remedies to improve health. The abundance and variety of Mexican medicinal flora
can be traced from published work written from the sixteenth century to modern
times. Crucial and most important sources of information about traditional Mexican
medicine were recently reviewed [1].
The use of herbal medicines survives to this day in modern Mexico; the original
Aztec beliefs and practices are interlaced with strands of the European medicine
introduced by the Spaniards in the sixteenth century. They are an integral element of
alternative medical care and the best testimony of their efficacy and cultural value is
the persistence of medicinal plants in present-day Mexican markets, where the
highest percentage of medicinal and aromatic plants is sold.
For more than 100 years, researchers have explored Mexican medicinal flora from
the ethnobotanical, anthropological, chemical, pharmacological, and biotechnolog-
ical points of view; in a few cases some clinical investigations have been pursued.
The most important investigations have been carried out at the Instituto Nacional de
Antropología, Instituto Mexicano del Seguro Social, Universidad Autónoma de
Nuevo León, Universidad Autónoma del Estado de Morelos, Instituto Tecnológico
y de Estudios Superiores de Monterrey, Universidad Autónoma Metropolitana,
Centro de Investigación y Estudios Avanzados del Instituto Politécnico Nacional,
and Universidad Nacional Autónoma de México. The no-longer existing Instituto
Médico Nacional and Instituto Mexicano de Plantas Medicinales deserve special
mention since they were devoted to the study of Mexican medicinal plants in
different periods of the twentieth century. Both are good examples of important
institutions dedicated to the comprehensive analysis of the national Materia Medica,
and were pioneering institutions in bioprospecting matters.
In the twenty-first century, the commerce of medicinal plants in Mexico has grown
due to a global resurgence of herbal-based remedies. Furthermore, according to a
recent survey, 54% of health professionals and 49% of physicians have used medicinal
plants as an alternative therapy for several diseases. Twenty-eight percent of health
professionals and 26% of physicians, have recommended or prescribed medicinal
plants to their patients, in particular for digestive and respiratory ailments; finally, 73%
Chemistry and Biology of Selected Mexican Medicinal Plants 3

of health professionals would agree to receiving academic information regarding the

use and prescribing of medicinal plants [2].
Concomitantly, a loss of biodiversity, over-exploitation, biopiracy, and weak
regulations on the use of medicinal plants are the major impediments to the growth
of herbal medicine as an important national industry [3]. Therefore, current research
on medicinal plants should also involve conservation issues and the sustainable
search for bioactive natural products based on traditional knowledge, regulation, and
quality control of the most important species; these are essential issues for the
growth of a rational herbal medicine usage.
In the following sections, some work from the authors’ laboratories will be
highlighted. The most relevant phytochemical and pharmacological profiles of a
selected group of plants widely used for treating major national health problems will
be discussed.

2 Mexican Medicinal Plants Employed for Treating Major

National Health Problems

2.1 Diabetes

The global prevalence of diabetes in adults has been increasing over recent decades,
making this disease a major public health threat in countries all over the world. The
International Diabetes Federation estimated the global prevalence to be 425 million in
2017, which implied a health expenditure of 673 billion USD [4]. The prevalence of
diabetes in adults aged 20–79 years is predicted to rise to 10.4% in 2040. Of the total
diabetics, about 95% have type 2 diabetes mellitus (T2DM). Mexico is one of the
countries most affected by this metabolic disease, in particular indigenous people
owing to changes in their traditional lifestyle and the effects of industrialization on
both environmental and sociocultural norms. In 2017, there were more than 12 million
people affected by diabetes, representing a prime cause of mortality. In Mexico as in
other regions of the world, people use plants to treat the symptoms of diabetes. More
than 300 different plants have been described as reputedly beneficial for the diabetic
patient [5–7], but most claims are subjective and few have received any suitable
scientific evaluation. So far, about 200 plants have been investigated scientifically in
Mexico in order to establish their antidiabetic potential. Most studies have been
limited to the preclinical evaluation of extracts prepared with selected solvents using
different pharmacological models [6]; the depth of their analysis is variable since some
authors have reported in detail the mode of action of the extracts while others just
measured their hypoglycemic activity. Other studies have determined both the active
principles and the preclinical efficacy of the traditional preparations. Finally, only a
very few studies have pursued in-depth clinical observations. Most of the work of the
present author group falls into the second category, involving detailed phytochemical
work coupled with substantial preclinical biological observations.
Some examples of our work on antidiabetic plants are described in the following
sections. In addition, other investigations, from other authors and ourselves, carried out
4 R. Mata et al.

after a survey on diabetic plants was published in 2005 [6], are summarized in the
Appendix Table.

2.1.1 Swietenia humilis

Swietenia humilis Zuccarini (Meliaceae), locally known as “zopilote”, “cobano”,

“flor de venadillo” and “caoba”, is a medium-sized deciduous tree (Fig. 1). The
species is regarded as one of the three true American mahogany species. It grows in a
very wide ecological range within its native Pacific watershed of Central America
and Mexico. The seeds are wind dispersed and highly valued for medicinal purposes.
The plant is also a much appreciated hardwood species in the neotropics and is
seriously threatened owing to overexploitation and habitat destruction. Therefore, a
multilateral treaty called the Convention on International Trade in Endangered
Species of Wild Fauna and Flora lists S. humilis in Appendix II (all parts and
derivatives except the seeds) [8]. Also, it is categorized in the International Union
for Conservation of Nature Red List of Threatened Species as “vulnerable” [9].
The medicinal use of the seeds of S. humilis can be traced to the sixteenth century;
the Spanish royal physician Francisco Hernández, in his magnificent manuscript
“Four Books on the Nature and Virtues of Plants and Animals for Medicinal
Purposes in New Spain”, described the antiulcer, astringent, antitussive, and emol-
lient properties of these seeds. In the middle of the twentieth century, their astringent
effects were also described [10]. In the present day, decoctions of the seeds of
S. humilis (SHD), alone or in combination with other plants, are valued for treating
indigestion, stomachache, amebic dysentery, and diarrhea. The ground raw seeds or
their decoctions are also ingested as a blood depurative and antidiabetic agent [5, 6].
In general, for conducting our studies focused on the determination of any
pharmacological properties of traditional extracts, first acute preclinical toxicity
using the Lorke procedure is assessed [11]. This method measures acute toxicity
for 14 days in mice using a range of doses between 10 and 5000 mg/kg, in two
phases. The dried seeds and SHD (10–5000 mg/kg) showed no acute toxic effects
when assessed by the Lorke procedure. The calculated LD50 values of the prepar-
ation and crude drug were higher than 5000 mg/kg.

Fig. 1 Leaves, stems (A), and seeds (A and B) of Swietenia humilis

murder

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